2-Butynoic acid, 98%, Thermo Scientific Chemicals

Name: 2-Butynoic acid, 98%, Thermo Scientific Chemicals
SKU: A15542.03

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Catalog number A15542.03

also known as A15542-03

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Chemical Identifiers

CAS590-93-2

IUPAC Namebut-2-ynoic acid

Molecular FormulaC4H4O2

InChI KeyLUEHNHVFDCZTGL-UHFFFAOYSA-N

SMILESCC#CC(O)=O

Specifications

Specification Sheet

Assay (GC)≥97.5%

FormCrystals or powder or crystalline powder

Melting Point (clear melt)73.0-80.0?C

Appearance (Color)White to pale cream

Assay (Aqueous acid-base Titration)≥97.5 to ≤102.5%

2-Butynoic acid is used as an intermediate in organic synthesis and pharmaceuticals. It is used as a synthon in various reactions, which includes cylcoalkylation of phenols to flavones and chromones. It is involved in the cyclization of gamma-butyrolactones. It is also used in the synthesis of Z-trisubstituted olefins through μ-alkylation. It plays an important role in the preparation of chirally pure 1,2,3,4-tetrahydroisoquinoline analogs, which finds application as anti-cancer agents.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
2-Butynoic acid is used as an intermediate in organic synthesis and pharmaceuticals. It is used as a synthon in various reactions, which includes cylcoalkylation of phenols to flavones and chromones. It is involved in the cyclization of gamma-butyrolactones. It is also used in the synthesis of Z-trisubstituted olefins through µ-alkylation. It plays an important role in the preparation of chirally pure 1,2,3,4-tetrahydroisoquinoline analogs, which finds application as anti-cancer agents.

Solubility
Soluble in water. Slightly soluble in methanol and chloroform.

Notes
Store in a cool place. Incompatible with strong oxidizing agents, strong bases and strong reducing agents.

RUO – Research Use Only

General References:

For Diels-Alder reactions with dienes, see: Chem. Ber., 114, 1793 (1981); Liebigs Ann. Chem., 1089 (1981).
The dilithio derivative can be alkylated at the 4-position. The resulting Li salts can, if required, be converted directly to their TMS or methyl esters by reaction with TMS chloride or MeI: Tetrahedron Lett., 83 (1979).
Yan, H.; Mao, J.; Rong, G.; Liu, D.; Zheng, Y.; He, Y. Facile synthesis of (E)-beta-nitroolefinic alkoxyamines via silver-catalyzed decarboxylative nitroaminoxylation of phenylpropiolic acids. Green Chem. 2015, 17 (5), 2723-2726.
Zheng, Y.; Mao, J.; Rong, G.; Xu, X. A NCS mediated oxidative C-H bond functionalization: direct esterification between a C(sp³)-H bond and carboxylic acids. Chem. Commun. 2015, 51 (42), 8837-8840.