Download Click Chemistry

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
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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
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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.
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R-5106E 20130314 Printed in Japan