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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:
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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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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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