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Click Chemistry “Click Chemistry” is a term which was first described by K. B. O Sharpless of the Scripps Research Institute in 2001 to describe reactions R O HN that afford products in high yields and in excellent selectivities by O Ph R= Ph N N N / H2O (1 : 1), 50 C°, 5 days joining molecular pieces as easily as clicking together the two pieces Cl N N t BuOH N3 O Ph CuSO4, Cu Ph carbon-hetero bond formation reactions. The term “Click” means HN (36 Alkynes) K i = 23 nM (minimum) R O of a seat belt buckle. In general, the definition of click chemistry is HN described as follows: nBuLi, O Ph (CH2O)n Ph N N N THF, -78 C° to 0 C° CH2OH N N K i = 8 nM Cl 1 1. give very high chemical yields of desired products 2. combination of readily available simple building blocks b) Research of Mycobacterium Tuberculosis Cell Wall Synthetase3) 3. generate almost no byproducts Dondoni et al. have reported the synthesis of a set of 4. simple product isolation by non-chromatographic methods C-oligomannosides (2a-f) through click chemistry using a 5. reaction proceeds in water, as well as in organic solvents 1,2,3-triazole ring as the interglycosidic linker. The compounds 2a-f inhibit mannosyltransferases, which are involved in the biosynthesis of the cell envelope of Mycobacterium tuberculosis cell wall synthase. While there are a number of reactions that fulfill this criteria, the 1) Huisgen 1,3-dipolar [3 + 2] cycloaddition of azides and alkynes has Among them, the hexamer (n = 4) 2c and octamer (n = 6) 2f show the highest activities IC50 = 0.14 and 0.22 mM, respectively. emerged as the frontrunner. In general, the 1,2,3-triazole ring is not almost oxidized or reduced, which makes it possible to strongly connect two substrates. H 3C BnO BnO HO OBn O N3 OBn O BnO BnO N3 OBn O BnO BnO BnO BnO OBn O OMOM OH N + N + Metal (cat.) N N N H 3C N OH O HO HO N N N HO HO This reaction system affords desired products in almost 100% yield OH O n N with no need of repurification, such as recrystallization or column N N chromatography. Thus, this methodology is an eco-friendly reaction. HO HO 2a (n = 0) OH O 2b (n = 2) 2c (n = 4) 2d (n = 6) Moreover, the combination of various alkynes and azides allows it to 2e (n = 8) OH rapidly construct large compound libraries, and 1,2,3-triazole itself exhibits various kinds of biological activities, such as anti-allergenic or anti-bacterial activities. In addition, the reaction proceeds even in ● 2f (n = 14) Synthesis of Functional Materials water, and thus, click chemistry has been widely used in many research fields as below: Click chemistry have been also successfully applied into polymer synthesis or material science. For example, Kang and Jin et al. have ● Research of Various Pharmaceutical Lead Candidates reported the synthesis of side-chain liquid-crystal polymers 3 and 4 by using click chemistry. According to their results, the dye-sensitized solar-cell fabricated from 3 gives a power-conversion efficiency of 4.11%.4) a) Application of Anti-HIV Agent Discovery 2) Whiting and Sharpless et al. have reported the synthesis of a series of 1,4-disubstituted-1,2,3-triazoles as potential candidates for HIV protease inhibitors in a combination of azide-containing fragments N3 N3 C 8H 17 + O(H2C)6O2C R CO 2(CH 2)6O R C8 H17 with a diverse array of functionalized alkyne-containing building blocks by using click chemistry. After further optimization, it was revealed that 1 has the highest activity, exhibiting 8 nM of Ki value. N N N3 CuSO4 5H2O, Et3N Na-L-ascorbate C 8H 17 N C8 H17 THF, 35 C°, 48 h R O(H2C)6O2C n CO 2(CH 2)6O 3 (R = OMe) 4 (R = CN) 2 Please inquire for pricing and availability of listed products to our local sales representatives. R Click Chemistry amines in a short time to afford the corresponding diazo compounds ●Bioscience in high yields.13) In these reactions, the by-products can be removed by conventional extraction procedures due to their high solubility in Bioconjugation (example: surface modification of virus)5) water. In general, viruses are made up of a number of protein subunits, and N capsids, which enclose DNA or RNA, are formed as protein shells. In N particular, in the case of spherical viruses, the capsids have an CH3 N3 PF6 + 9 CH3 DMAP R NH2 R N3 CH2Cl2 A2457 (9) icosahedral symmetry form with sixty protein subunits. Finn and Sharpless et al. have reported the modification of the exterior surface Entry R 9 (eq.) DMAP (eq.) Temp. Time (h) Yield (%) of a spherical virus, cowpea mosaic virus by azides or alkynes, followed 1 Ph 1.15 1.1 rt 2.5 87 2 4-MeC 6H4 1.15 1.1 rt 1.5 94 3 4-AcC6H4 1.15 3 50 °C 5 83 4 4-O 2NC6H4 2 3 50 °C 4 61 5 1-naphthyl 1.3 1.1 50 °C 1.5 92 6 PhCH2CH2 1.15 5a) rt 0.25 74 7 1-adamantyl 1.15 1.1 rt 0.33 71 by the labeling of these species using fluorescein dye-azide or alkyne by click chemistry. H N H N O Virus capsid HO N3 O O 60 O a) CO2H 5 H N H N O O 60 O N H R 7 (R = -C CH ) 8 (R = -CH2CH2N3) 6 ● Et 3N is used instead of DMAP. Ethynylation Reagents A number of ethynylation reagents have been developed for the synthesis of terminal acetylenes. For example, ethynyl(phenyl) N 5 + 7 Cu(I) N 6 + 8 N Cu(I) iodonium tetrafluoroborate (E0467) (10) is an electrophilic O N HN Dye n ethynylation reagent developed by Ochiai et al., which reacts with active methylene compounds to afford the corresponding a-ethynylated products in high yields under mild conditions. As for N N O HN Dye n Thus, click chemistry has been widely used as a methodology of other existing electrophilic ethynylation reagents, ethyl lead triacetate has been exploited, which is prepared ethynyl(trimethyl)stannane and lead tetraacetate. from However, preparation of this reagent requires the use of heavy metal synthesizing novel molecules in a number of research fields. Other compounds, which make it an unattractive procedure. than these applications, click chemistry also has been applied in ethynylation procedure using this reagent requires careful control of various fields, such as the synthesis of dendrimers,6) dendrons,7) the reaction conditions. The ethynylation method using 10 has been calyxarenes,8) rotaxanes,9) catenanes,10) the development of chemical at the center of attention in many fields, as this method does not use 11) 12) The highly toxic heavy metal compounds, and the reaction proceeds sensors, and the labeling of DNA. under mild conditions. TCI offers a variety of azide and terminal acetylene compounds readily available in the field of click chemistry as below. In addition, HC C I azidation and ethynylation reagents are also listed in this brochure. O O BF4 R 10 + R Base C CH O O E0467 (10) ● Azidation Reagent ex.) O O C CH Organic azide compounds can be synthesized in a simple manner O Y. 74% C O CH 3 CH O Y. 93% by the reaction of sodium azide with halogenated alkyl compounds, or the reaction with trifluoromethanesulfonyl azide and primary amines, however, these azide sources potentially have highly explosive Additionally, (1-diazo-2-oxopropyl)phosphonate (D3546) (11) is 2-Azido-1,3- a reagent for the synthesis of terminal alkynes, which was developed dimethylimidazolinium hexafluorophosphate (A2457) (9), which was by Ohira and Bestmann et al.15,16) 11 reacts with aldehydes in the developed by Kitamura et al., is a crystalline diazotransfer reagent presence of potassium carbonate and methanol to give the one having high thermal stability and low explosibility. The differential homologated terminal alkynes in high yields. 11 is widely known as scanning calorimetry (DSC) experiment of 9 has revealed that the the “Ohira-Bestmann reagent” after its discoverers, and the reaction exothermic decomposition temperature was approximately 200 °C. proceeds in mild conditions without using strong bases. character, which makes it difficult to handle. Moreover, 9 has tested negative for the impact and friction-sensitivity tests.13) Under basic conditions, 9 reacts with several kinds of primary Please inquire for pricing and availability of listed products to our local sales representatives. 3 Click Chemistry Org. Chem. 2010, 75, 6326. (Application 1)16) O O P CH3 4) J. S. Park, Y. H. Kim, M. Song, C. -H. Kim, M. A. Karim, J. W. Lee, Y. -S. Gal, P. Kumar, S. -W. Kang, S. -H. Jin, Macromol. Chem. Phys. 2010, 211, 2464. OCH3 OCH3 N2 Cl D3546 (11) + R CHO CHO OHC 11 K2CO3 Product R CHO R MeOH, rt, 4-16 h CHO Chem. Soc. 2003, 125, 3192. 97 Cl 6) M. Malkoch, K. Schleicher, E. Drockenmuller, C. J. Hawker, T. P. Russell, P. Wu, V. V. Fokin, Macromolecules, 2005, 38, 3663. 74 CHO S 5) Q. Wang, T. R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless, M. G. Finn, J. Am. Yield (%) 7) G. Franc, A. Kakkar, Chem. Commun. 2008, 5267. S 8) S. P. Bew, R. A. Brimage, N. L. Hermite, S. V. Sharma, Org. Lett. 2007, 9, 3713. 80 9) W. R. Dichtel, O. S. Miljanić, J. M. Spruell, J. R. Heath, J. F. Stoddart, J. Am. Chem. Soc. 2006, 128, 10388. 10) O. S. Miljanić, W. R. Dichtel, S. I. Khan, S. Mortezaei, J. R. Heath, J. F. Stoddart, (Application 2)17) J. Am. Chem. Soc. 2007, 129, 8236. CHO 11) Y. H. Lau, P. J. Rutledge, M. Watkinson, M. H. Todd, Chem. Soc. Rev. 2011, 40, 11 (2.64 eq.) K2CO3 (3.5 eq.) CO2Me 2848. CO2Me 12) G. A. Burley, J. Gierlich, M. R. Mofid, H. Nir, S. Tal, Y. Eichen, T. Carell, J. Am. MeOH, rt, 2 h OTIPS OTIPS Chem. Soc. 2006, 128, 1398. Yield 84% 13) M. Kitamura, M. Yano, N. Tashiro, S. Miyagawa, M. Sando, T. Okauchi, Eur. J. Org. Chem. 2011, 458. 14) M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani, Y. Nagao, J. Chem. References Soc. Chem. Commun. 1990, 118; M. Ochiai, TCIMAIL, 1999, number 104, 2. 1) R. Huisgen, Proc. Chem. Soc.1961, 357. 15) S. Ohira, Synth. Commun.1989, 19, 561. 2) M. Whiting, J. C. Tripp, Y. -C. Lin, W. Lindstrom, A. J. Olson, J. H. Elder, K. B. 16) S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521. Sharpless, V. V. Fokin, J. Med. Chem. 2006, 49, 7697. 17) J. D. White, P. R. Blakemore, C. C. Browder, J. Hong, C. M. Lincoln, P. A. Nagornyy, L. A. Robarge, D. J. Wardrop, J. Am. Chem. Soc. 2001, 123, 8593. 3) M. L. Conte, A. Marra, A. Chambery, S. S. Gurcha, G. S. Besra, A. Dondoni, J. A1540 Metal Catalysts T2665 5g 25g C2346 O 25g 500g 1g 5g O O Cu2 CH3 C O CH3 T1442 2 OCu . H2O CF3 . S OCu O 2 Copper(I) Acetate [598-54-9] Copper(II) Acetate Monohydrate [6046-93-1] Copper(I) Trifluoromethanesulfonate Benzene Complex [42152-46-5] A2457 D1672 T0801 5g (CH3CN)4Cu PF6 Tetrakis(acetonitrile) copper(I) Hexafluorophosphate [64443-05-6] 5g N Azidation Reagents N N3 O P O N3 CH3 N3 (CH2)3CH3 Tetrabutylammonium [993-22-6] Azide 4 CH3 Si N3 CH3 Diphenylphosphoryl Azide Trimethylsilyl Azide [26386-88-9] [4648-54-8] (CH2)3CH3 (CH2)3CH3 CH3 O PF6 5g 25g CH3(CH2)3 N 25g CH3 2-Azido-1,3-dimethylimidazolinium Hexafluorophosphate [1266134-54-6] T0920 5g 25g 250g Please inquire for pricing and availability of listed products to our local sales representatives. Click Chemistry E0467 HC C I 25mL 500mL T1239 5mL 25mL 250mL BF4 CH3 CH3 Ethynylation Reagents D3546 M0180 1g CH3 HC C C OH Ethynyl(phenyl)iodonium Tetrafluoroborate [Ethynylating Reagent] [127783-34-0] Si C CH CH3 CH3 2-Methyl-3-butyn-2-ol [115-19-5] A0930 A0971 Trimethylsilylacetylene [1066-54-2] 1g 5g O O P CH3 OCH3 OCH3 N2 Dimethyl (1-Diazo-2oxopropyl)phosphonate (Ohira-Bestmann Reagent) [90965-06-3] 5g 25g 5g O Azide Compounds A1786 A2052 5g 25g 1g 5g A2290 O NH C CH3 A2474 A2524 100mg 4-Azidocinnamaldehyde [22736-78-3] N3 OH O O HN O O CH3 CH3 O 3'-Azido-3'-deoxythymidine 4-Azidosalicylic Acid [30516-87-1] [66761-27-1] 25g CH3 CH3 O 2-Azido-1,3-bis[(2,2dimethyl-1,3-dioxan-5-yl)oxy]propane N3 B1110 B1111 100mg 25g NH H H S O N H (CH2)4 HC CH N3 N3 HC CH N3 N-(3-Azidopropyl) biotinamide[908007-17-0] B3693 100mg O O N3 C OH N N3 4-Acetamidobenzenesulfonyl Azide [2158-14-7] 4-Azidobenzoic Acid [6427-66-3] O O O CH CH C H N3 100mg 1g CH3 HN HO O N3 O O SO2N3 C OH Organic Azides N3 N3CH2 O OCH3 CH3 N3CH2 O CH3 OCH3 2,6-Bis(4-azidobenzylidene)cyclohexanone (wetted with ca. 30% Water, containing 25g on a dry weight basis) [Research for Photosensitive Material] [20237-98-3] 2,6-Bis(4-azidobenzylidene)-4-methylcyclohexanone (wetted with ca. 30% Water, containing 25g on a dry weight basis) [5284-79-7] (2R,3R,5S,6S)-5,6Bis(azidomethyl)-2,3dimethoxy-2,3-dimethyl1,4-dioxane [832117-79-0] B3694 D1606 S0860 N3CH2 N3CH2 100mg O OCH3 CH3 O CH3 OCH3 (2S,3S,5R,6R)-5,6Bis(azidomethyl)-2,3dimethoxy-2,3-dimethyl1,4-dioxane PEG Azides Sugar Azides B3790 N3 10mg H N O S S OH O 25g N3 OH N H CH3 25g 10mg N3 N3 CH CH O O .4H2O SO3Na NaO3S N3 D2580 C O N Bis[2-(4azidosalicylamido)ethyl] Disulfide [199804-21-2] Disodium 4,4'-Diazidostilbene-2,2'disulfonate Tetrahydrate [2718-90-3] Dodecylbenzenesulfonyl Azide (soft type) (mixture) [79791-38-1] N-Succinimidyl 5-Azido-2nitrobenzoate[60117-35-3] A2293 A2363 A2500 A2523 1g 1g 5g 100mg NO2 O 100mg O O N3 O O O OH N3 O O O NH2 N3 O O O O HN H OH NH H S O (CH2)4 N H O O O N3 11-Azido-3,6,9trioxaundecanoic Acid [172531-37-2] 11-Azido-3,6,9trioxaundecan-1-amine [134179-38-7] 14-Azido-3,6,9,12tetraoxatetradecanol [86770-68-5] N-[2-[2-[2-(2-Azidoethoxy)ethoxy]ethoxy]ethyl]biotinamide[875770-34-6] A1616 A1678 A1811 A1812 AcO AcO 1g 5g OAc O N3 AcHN BnO BnO 1g 5g OBn O Ph N3 AcHN 1g 5g O O HO 1g Ph O N3 NHAc O O O O N3 NHAc 2-Acetamido-4,6O-benzylidene-2-deoxy-bD -glucopyranosyl Azide [168397-51-1] 2-Acetamido-3-O-allyl-4,6O-benzylidene-2-deoxy-bD -glucopyranosyl Azide Please inquire for pricing and availability of listed products to our local sales representatives. 5 2-Acetamido-3,4,6-triO-acetyl-2-deoxy-bD -glucopyranosyl Azide [6205-69-2] 2-Acetamido-3,4,6-triO-benzyl-2-deoxy-bD -glucopyranosyl Azide [214467-60-4] Click Chemistry A1813 1g A1832 100mg A1833 100mg Ph Ph O O BnO O O Ph O O O N3 N3 O NHAc O O HO HO O CH3 O N3 O OC(CH3)3 OC(CH3)3 HN 2-Acetamido-3-O-benzyl4,6-O-benzylidene-2-deoxyb-D -glucopyranosyl Azide [80887-27-0] D -galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]- L-threonine tert-Butyl Ester [195976-07-9] O-(2-Azido-4,6-O-benzylidene-2-deoxy-aD -galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]- L-serine tert-Butyl Ester [878483-02-4] A2172 A2267 G0257 500mg OH O HO HO O N3 AcHN 2-Azidoethyl 2-Acetamido-2deoxy-b-D -glucopyranoside [142072-12-6] G0330 1g 5g HN O-(2-Azido-4,6-O-benzylidene-2-deoxy-a- AcO OAc O AcO 1g OH O HO HO O N3 HO AcO N3 O AcO OAc OBn O O HO NaO3SO COONa HO O O HO OH O HO O HO O HO HO OH O AcHN HO HO HO HO O O HO O M1637 Ph O OCH3 O O HO 1g 5g M1638 Price on request OH O HO OH O O O AcHN N3 GlcA[3S]b(1-3)Gal b(1-4)GlcNAc b(1-2)Man a-Ethylazide N3 Ph O O O O N3 AcHN GalNAc b(1-3)GlcNAc b-Ethylazide 1g OCH3 O O OCH3 4-Methoxyphenyl 2-Azido4,6-O-benzylidene-2-deoxyb-D -glucopyranoside 4-Methoxyphenyl 3-O-Allyl-2azido-4,6-O-benzylidene2-deoxy-b-D -glucopyranoside [889453-78-5] T1732 T1733 T2196 OAc O AcO AcO AcO N3 OAc 1,3,4,6-Tetra-O-acetyl2-azido-2-deoxy-a- D glucopyranose [56883-33-1] 100mg N3 O AcO AcO HO NaO3SO COONa HO O O HO 1g 5mL 25mL CH CH3 C C CH OH HO O O O HO AcHN O OH O HO O HO OH O O HO N3 T1731 100mg OAc O AcO O N3 OCH3 OAc 4-Methoxyphenyl 3-O-Allyl2-azido-4,6-O-benzylidene2-deoxy-b-D -galactopyranoside [889453-83-2] 1,3,4,6-Tetra-O-acetyl2-azido-2-deoxy-a- D galactopyranose [67817-30-5] B1114 D0037 OAc O OAc 1,3,4,6-Tetra-O-acetyl-2-azido2-deoxy-b-D -glucopyranose [80321-89-7] 5mL D1723 5g C CH CH3 CH 10mL 100mL 5mL 25mL CH3 Hydrocarbons C HO N3 1,3,4,6-Tetra-O-acetyl2-azido-2-deoxy-a- D mannopyranose [68733-20-0] D1326 OH O O N3 OCH3 200mg 1g OAc Terminal Acetylenes D0997 O Price on request AcO O N3 4-Methoxyphenyl 2-Azido3,6-di-O-benzyl-2-deoxy-bD -glucopyranoside [1272755-25-5] AcO AcO O N3 HNK-1 Ethylazide M1643 O O N3 N3 100mg O O H1333 Price on request Ph HO BnO O G0373 GlcNAc b(1-2)Man a1-Ethylazide 1g N3 OAc Ph O AcO O O G0372 100mg O M1617 O OAc OH O OCH3 Gal[2346Ac]b(1-3) GalN3[46Bzd]-b-MP OAc O AcO 1g 5g G0337 O N3 AcO G0309 Gal[2346Ac]b(1-3) GlcN3[46Bzd]-b-MP AcHN HO OAc OAc O AcO AcO 1g 5g 2-Azidoethyl b- D -Glucopyranoside [165331-08-8] HO HO O 1g 5g 2-[2-(2-Azidoethoxy)ethoxy] ethyl 2,3,4,6-Tetra-O-acetylD -galactopyranoside [381716-33-2] O O A2377 Fmoc 2-Azidoethyl 2,3,4,6-Tetra-Oacetyl-b-D -glucopyranoside [140428-81-5] Ph O Fmoc CH3 H3C C C CH C CH CH3 3,3-Dimethyl-1-butyne [917-92-0] 1-Decyne D1724 H0048 1mL 5mL CH3 C CH [764-93-2 ] 25mL CH3(CH2)4C CH 1,4-Decadiyne 1-Dodecyne H0140 [765-03-7] 25mL 250mL (50% in Hexane, ca. 2.7mol/L) 1,9-Decadiyne [1720-38-3] H0433 H0440 5mL [929-53-3] 1g 1,5-Decadiyne[53963-03-4] 1-Heptyne H0483 M0269 5mL [628-71-7] 5mL CH3 CH3(CH2)3C CH 1-Hexyne 6 [693-02-7] CH3(CH2)13C CH CH3(CH2)14C CH 1-Hexadecyne [629-74-3] 1-Heptadecyne[26186-00-5] HC C(CH2)3C CH 1,6-Heptadiyne[2396-63-6] Please inquire for pricing and availability of listed products to our local sales representatives. CH3 CH CH2C CH 4-Methyl-1-pentyne [7154-75-8] Click Chemistry M0271 5mL CH3 N0301 5mL 10mL CH3 CH3 C C CH 5-Methyl-1-hexyne [2203-80-7] 1-Nonyne O0147 P0068 HC C 5mL 25mL 25mL 1,7-Octadiyne [871-84-1] 1-Pentyne T0761 U0033 CH3(CH2)11 C CH [3452-09-3] CH3CH2CH2C CH (CH2)4 C CH 5mL 25mL CH [627-19-0] HC 5mL C C CH CH3 C CH 1-Undecyne [2243-98-3] D2496 D4233 200mg 1g O0050 25mL 250mL CH3 C 1,8-Nonadiyne[2396-65-8] 1-Octyne P0356 P1881 5mL CH3(CH2)15C CH CH [629-05-0] 200g 1-Octadecyne [629-89-0] T0760 5mL CH3(CH2)10 C CH 1-Pentadecyne [765-13-9] Propyne (ca. 3% in Heptane) [74-99-7] 1-Tridecyne [26186-02-7] B2301 D2151 Hydrocarbons having Benzene Ring E0196 25mL 500mL 5g 25g C CH 1g 5g C CH (CH2)3CH3 C CH 1-Butyl-4-ethynylbenzene [79887-09-5] 1,4-Diethynylbenzene [935-14-8] E0563 E0564 C CH 5g 25g C CH 5g 25g C CH C CH HC C (CH2)4CH3 1,3-Diethynylbenzene [1785-61-1] 4,4'-Diethynylbiphenyl [38215-38-2] E0603 E0654 1g 5g 5mL CH3C CH C CH C CH O0128 CH3(CH2)12C CH 5mL 1-Tetradecyne [765-10-6] 1g 5g N0406 5g Ethynylbenzene[536-74-3] 1-Ethynyl-4-hexylbenzene [79887-11-9] E0655 E0665 E0749 C CH OCH3 (CH2)5CH3 1-Ethynyl-4-pentylbenzene [79887-10-8] 5g 25g 1g 5g 25g CH2CH3 CH3 C CH 5g 25g F C CH C CH CH3 C CH 4-Ethynylanisole[768-60-5] 1-Ethynyl-2-fluorobenzene [766-49-4] 4-Ethynyltoluene[766-97-2] 3-Ethynyltoluene[766-82-5] 1-Ethyl-4-ethynylbenzene [40307-11-7] E0750 E0933 F0470 P0358 P1956 5g 25g 100mg C CH 1g 5g C CH 5mL CH2CH2C 1g 5g CH C CH CH2C CH CH2CH2CH3 1-Ethynyl-4-propylbenzene [62452-73-7] Carboxylic Acids & Their Derivatives P0497 5g 25g O F 2-Ethynylnaphthalene [2949-26-0] 1-Ethynyl-4-fluorobenzene [766-98-3] 4-Phenyl-1-butyne [16520-62-0] 3-Phenyl-1-propyne (stabilized with BHT) [10147-11-2] H0823 H0882 H0905 H0964 HC 1g O C HC O CH3 5g 25g O C 100mg 1g O OH O OH 5g 25g HC C CH C OH CH3 OH OH C CH Ethyl 2-Hydroxy3-butynoate [18418-08-1] 5-Hexynoic Acid [53293-00-8] 2-Hydroxy-3-butynoic Acid [38628-65-8] 2-Hexyl-4-pentynoic Acid [96017-59-3] P0528 P0529 P1038 U0054 5mL 25mL O CH C C OH CH C C OCH3 Propiolic Acid [471-25-0] Methyl Propiolate [922-67-8] 5mL 25mL O 5g 25g O CH3 HC C C OCH2CH3 CH C C O C CH3 Ethyl Propiolate[623-47-2] tert-Butyl Propiolate [13831-03-3] 1g 5g O HC C OH CH3 Please inquire for pricing and availability of listed products to our local sales representatives. 10-Undecynoic Acid [2777-65-3] 7 Click Chemistry B0750 25mL 500mL B0799 5mL 25mL CH3 Alcohols B1001 5mL 25mL OH HC C 3-Butyn-2-ol (55% in Water, [2028-63-9] 3-Butyn-1-ol D0737 D1266 25mL 500mL OH CH3 CH3 CHCH2 C C CH HC C CH3 OH CH3 HC C HC C OH OH ca. 7.5mol/L) 1g 1g CH3 HC C OH B2910 B2909 CH3 CH3 CH3 [927-74-2] 5mL 3-Butyn-2-ol [2028-63-9] (R)-(+)-3-Butyn-2-ol [42969-65-3] D1276 D2495 CH3 CH3 CH3 CH C CH CHCH2CH2 10mL OH CH3 5g 25g HC C C CH OH OH (S)-(-)-3-Butyn-2-ol [2914-69-4] 3,5-Dimethyl-1-hexyn-3-ol [107-54-0] 3,6-Dimethyl-1-heptyn-3-ol [19549-98-5] 3,4-Dimethyl-1-pentyn-3-ol [1482-15-1] 1,1-Diphenyl-2-propyn-1-ol [3923-52-2] D3710 E0270 E0272 E0273 E0297 5g 25mL 500mL 5mL CH3 C 25g 500g HO OH HC C(CH2)8OH 5mL 25mL CH2CH3 CH HC C OH HC C (CH2)3CH3 CH3 C CH CH2CH3 OH CH2CH3 9-Decyn-1-ol[17643-36-6] 4-Ethyl-1-octyn-3-ol [5877-42-9] 3-Ethyl-1-heptyn-3-ol [5396-61-2] 3-Ethyl-1-pentyn-3-ol [6285-06-9] 1-Ethynyl-1-cyclohexanol [78-27-3] E0548 H0141 H0455 H0462 H0687 5g 5mL 25mL 1mL 5mL OH OH CH3CH2CH2CHC CH HC C 5mL HC CH3(CH2)3 CH C CH HC C CH3 5mL 25mL C OH OH OH 9-Ethynyl-9-fluorenol [13461-74-0] 1-Hexyn-3-ol [105-31-7] 1-Heptyn-3-ol [7383-19-9] 5-Hexyn-3-ol[19780-84-8] 5-Hexyn-1-ol [928-90-5] H0823 H0905 100mg 1g M0180 M0396 M0860 HC 1g O C 25mL 500mL OH O O CH3CH2 C C CH HC C C OH OH 5mL 25mL OH CH3 HC C CH C OH CH3 25mL 500mL CH3OCH2 C CH CH3 CH3 Ethyl 2-Hydroxy3-butynoate [18418-08-1] 2-Hydroxy-3-butynoic Acid [38628-65-8] 2-Methyl-3-butyn-2-ol [115-19-5] 3-Methyl-1-pentyn-3-ol [77-75-8] Methyl Propargyl Ether [627-41-8] M0961 M1312 O0196 25mL 250mL O0235 P0069 CH3 C 5mL 5mL 25mL CH3 OH CH3 C CH3 HC C C CH CH2 CH 5-Methyl-1-hexyn-3-ol [61996-79-0] 3-Methyl-1-penten-4-yn-3-ol [3230-69-1] 1-Octyn-3-ol P0220 P0817 P0818 5mL 25mL HC HC HC OH C OH 4-Pentyn-1-ol [5390-04-5] T2046 U0055 CH3 SO3CH2CH2C CH 3-Butynyl p-Toluenesulfonate [23418-85-1] 8 HC C C CH3CH2 CH C CH (S)-1-Octyn-3-ol [w Side- [818-72-4] 5mL Chain Unit for PG Synthesis] [32556-71-1] 1-Pentyn-3-ol [4187-86-4] T1224 5g T1455 CH CH3 OH C OH CH O CH3 CH3 5g OH 10-Undecyn-1-ol [2774-84-7] 4-Pentyn-2-ol [2117-11-5] Other Functional Terminal Acetylenes 5g O CH3 S O CHC S OCH2C O 1-Phenyl-2-propyn-1-ol [4187-87-5] 5g CH3 10g OH OH OH 5g 25g CH 1g 5g CH O 1-Butyn-3-yl p-Toluenesulfonate [53487-52-8] Propargyl p-Toluene[6165-76-0] sulfonate A1122 B2393 10g 5g NH2 O HC C C CH3 C CH 3-Ethynylaniline [54060-30-9] Please inquire for pricing and availability of listed products to our local sales representatives. 3-Butyn-2-one[1423-60-5] Click Chemistry B3242 5g B3701 1g 5g C1195 1g 5g C1493 5mL 25mL C1522 5mL 25mL Br Cl HC CCH2CH2Br HC CH3 C Cl CH HC C Cl C CH 4-Bromo-1-butyne [38771-21-0] 1-Bromo-4-ethynylbenzene [766-96-1] 3-Chloro-1-butyne [21020-24-6] 6-Chloro-1-hexyne [10297-06-0] 5-Chloro-1-pentyne [14267-92-6] C1984 D2817 E0037 E0040 E0340 5g 25g 5mL CH C CH3 1g 5g H3C N CH3 H Cyclopropylacetylene [6746-94-7] 3-Dibutylamino-1-propyne [6336-58-9] E0466 E0505 1g 5g 10g OH C CH H3C N H HO O Ethynylestradiol [57-63-6] Ethisterone E0560 E0561 1g 5g [434-03-7] 100mg 500mg NH2 C CH 2-Ethynylpyridine [1945-84-2] E0579 1g 5g C CH O C CH O O S C CH CH3 1mL 5mL OH C CH H3C H C CH 1g 5g N O N HC C CH C O Ethynyl p-Tolyl Sulfone [13894-21-8] 4-Ethynylaniline [14235-81-5] 3-Ethynylpyridine [2510-23-8] 4-Ethynylpyridine [2510-22-7] 4-Ethynylphthalic Anhydride [73819-76-8] E0892 E0894 E0915 L0246 M0728 1g 5g 1g 1g 5g 1g 1g 5g C CH H3C C CH H N S S C CH 2-Ethynylthiophene [4298-52-6] Lynestrenol N0449 N0450 P0484 P0810 25g 500g OH C CH H H H H CH3O 4-Ethynyltriphenylamine [205877-26-5] 100mg 1g H3C H H 3-Ethynylthiophene [67237-53-0] 100mg 1g OH C CH [52-76-6] 25mL Mestranol [72-33-3] P0911 5mL 25mL O OH C CH H3C H H3C H H H C CH3 C CH H H H O O O HC CCH2Br HC CCH2Cl HC CCH2NH2 H Norethisterone [68-22-4] Norethisterone Acetate [51-98-9] with MgO) Propargyl Bromide (stabilized [106-96-7] Propargyl Chloride [624-65-7] Propargylamine [2450-71-7] P0990 P1173 P1272 P1273 P1438 5g 25g HC CCH2NH2 . HCl 5mL 25mL Propargylaldehyde Diethyl Acetal [10160-87-9] P1469 P1624 25g [106-96-7] Toluene, ca. 9.2mol/L) Triphenylpropargylphosphonium Bromide [2091-46-5] Q0091 100mg 1g T1239 T1683 H3C O O T2387 OCH2 C CH 2-(2-Propynyloxy)tetrahydropyran [6089-04-9] H H O Quinestrol Propargyl Chloride (70% in [624-65-7] OH C CH H 4-Propargylthiomorpholine 1,1-Dioxide [10442-03-2] CH Br Toluene, ca. 9.2mol/L) CH O CH2C HC CCH2Cl Propargyl Bromide (80% in N S 5g 25g P HC CCH2Br Propargylamine Hydrochloride[15430-52-1] CH2C 25g 250g OCH2CH3 HC C OCH2CH3 5g 25g 25g 500g [152-43-2] 5mL 25mL 250mL CH(CH3)2 CH3 CH3 Si 5mL 25mL C CH CH3 Trimethylsilylacetylene [1066-54-2] (CH3)2CH Si C CH CH(CH3)2 Triisopropylsilylacetylene [89343-06-6] 1g 5g CH2CH3 CH3CH2 Si C CH CH2CH3 Triethylsilylacetylene [1777-03-3] Please inquire for pricing and availability of listed products to our local sales representatives. 9 Click Chemistry 10 Please inquire for pricing and availability of listed products to our local sales representatives. Click Chemistry Please inquire for pricing and availability of listed products to our local sales representatives. 11 • Availability, price or specification of the listed products are subject to change without prior notice. • Reproduction forbidden without the prior written consent of Tokyo Chemical Industry Co., Ltd. R-5106E 20130314 Printed in Japan