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419869

Sigma-Aldrich

Ethynyl p-tolyl sulfone

98%

Synonym(s):

p-Toluenesulfonylacetylene, Tosylacetylene

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About This Item

Linear Formula:
CH3C6H4SO2C≡CH
CAS Number:
13894-21-8
Molecular Weight:
180.22
Beilstein/REAXYS Number:
2556169
MDL number:
MFCD00191647
UNSPSC Code:
12352100
PubChem Substance ID:
24866282
NACRES:
NA.22

assay

98%

mp

73-74 °C (lit.)

solubility

organic solvents: soluble(lit.)

SMILES string

Cc1ccc(cc1)S(=O)(=O)C#C

InChI

1S/C9H8O2S/c1-3-12(10,11)9-6-4-8(2)5-7-9/h1,4-7H,2H3

InChI key

FTHKWIMQNXVEHW-UHFFFAOYSA-N

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Related Categories

Application

Ethynyl p-tolyl sulfone (Tosylacetylene) may be used in the synthesis of 2-(4-methylphenylsulfonyl)ethenyl (tosvinyl, Tsv) protected derivatives. It may be used as starting reagent for the synthesis of optically active indan-2-ols.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Takeshi Hanazawa et al.
The Journal of organic chemistry, 68(12), 4980-4983 (2003-06-07)
An efficient and practical synthesis of optically active indan-2-ols 1 has been developed starting from readily accessible optically active 4-siloxy-1,6-alkadiynes 2 and ethynyl p-tolyl sulfone, where the metalative Reppe reaction mediated by an economical divalent titanium reagent, Ti(O-i-Pr)(4)/2 i-PrMgCl, is
A Simplified Method for the Preparation of Ethynyl P-Tolyl Sulfone and Ethynyl Phenyl Sulfone.
Chen Z and Trudell ML.
Synthetic Communications, 24(21), 3149-3155 (1994)
David Tejedor et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 25(66), 15046-15049 (2019-09-26)
A universal, practical and scalable organocatalytic hydrocyanation manifold to provide β-substituted acrylonitriles bearing an electron-withdrawing functionality has been implemented. The catalytic manifold operates under the reactivity generation principle "a good nucleophile generates a strong base", and it uses 1,4-diazabicyclo[2.2.2]octane (DABCO)
Elena Petit et al.
The Journal of organic chemistry, 79(18), 8826-8834 (2014-08-28)
The use of the 2-(4-methylphenylsulfonyl)ethenyl (tosvinyl, Tsv) group for the protection of the NH group of a series of imides, azinones (including AZT), inosines, and cyclic sulfonamides has been examined. The Tsv-protected derivatives are obtained in excellent yields by conjugate
Hao Chen et al.
Bioorganic & medicinal chemistry letters, 17(7), 1979-1983 (2007-02-16)
A library of potential antifungal triazole-modified beta-methoxyacrylate analogues was designed and synthesized via a Cu(I)-catalyzed 1,3-dipolar alkyne-azide coupling reaction or 'click chemistry'. Subsequent biological screening revealed that some compounds displayed low to moderate antifungal activity toward pathogenic fungi and low

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