590-93-2

Basic information

• Product Name: 2-Butynoic acid
• Synonyms: 1-Propynecarboxylic acid;3-Methylpropiolic acid;2-BUTYNOIC ACID;BUT-2-YNOIC ACID;TETROLIC ACID;2-Butynoicacid,98%;2-BUTYNOIC ACID 98%;Methylacetylenecarboxylic acid
• CAS NO: 590-93-2
• Molecular Formula: C₄H₄O₂
• Molecular Weight: 84.07
• EINECS: 209-695-7
• Product Categories: Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives;Building Blocks;C1 to C5;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 590-93-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 78-80 °C(lit.)
• Boiling Point: 200-203°C
• Flash Point: 200-203°C
• Appearance: White to yellow/Powder
• Density: 0,9641 g/cm3
• Vapor Pressure: 0.117mmHg at 25°C
• Refractive Index: 1.3918 (estimate)
• Storage Temp.: 2-8°C
• Solubility: water: soluble50mg/mL, clear to very slightly hazy, colorless to
• PKA: 2.62(at 25℃)
• Water Solubility: Soluble in water. Slightly soluble in methanol and chloroform.
• BRN: 1740205
• CAS DataBase Reference: 2-Butynoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butynoic acid(590-93-2)
• EPA Substance Registry System: 2-Butynoic acid(590-93-2)

Safety Data

• Hazard Codes: C
• Statements: 34-20/21/22
• Safety Statements: 26-27-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 590-93-2(Hazardous Substances Data)

Usage

Description

2-Butynoic acid, also known as 4-octyn-3-one, is an organic compound characterized by its unique structure containing a triple bond and a carboxylic acid group. It is a white to yellow powder with distinct chemical properties that make it a versatile compound in various applications.

Uses

Used in Organic Synthesis:
2-Butynoic acid is used as an intermediate in organic synthesis and pharmaceuticals. It serves as a synthon in various reactions, including cycloacylation of phenols to flavones and chromones. This versatile compound is also involved in the cyclization of gamma-butyrolactones, which are important in the synthesis of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-butynoic acid plays a crucial role in the preparation of chirally pure 1,2,3,4-tetrahydroisoquinoline analogs. These analogs find application as anti-cancer agents, making 2-butynoic acid an essential component in the development of potential cancer treatments.
Used in Synthesis of Z-trisubstituted Olefins:
2-Butynoic acid is also utilized in the synthesis of Z-trisubstituted olefins through μ-alkylation. This process is significant in the creation of various chemical compounds with specific properties and applications in different industries.
Overall, 2-butynoic acid is a valuable compound in the fields of organic synthesis and pharmaceuticals, contributing to the development of new compounds and potential treatments for various conditions, including cancer.

InChI:InChI=1/C4H4O2/c1-2-3-4(5)6/h1H3,(H,5,6)/p-1

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Downstream Products

• 2809-69-0 2,4-hexadiyne 
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• 50418-39-8 3-Methylbicyclo<2.2.1>hepta-2,5-dien-2-carbonsaeure 
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• 78822-89-6 phenyl but-2-ynoate 
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• 164468-30-8 (1'S)-phenyl 2'-propenyl 2-butynoate 
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• 169131-88-8 (1'R)-phenyl 2'-propenyl 2-butynoate 

Relevant articles and documents

Thermal Stability of 2-Butynoic Acid (Tetrolic Acid)

Work to assess the thermal properties of 2-butynoic acid (a precursor to acalabrutinib) has revealed the potential for thermal runaway on heating; testing using accelerated rate calorimetry (ARC) showed exothermic onset from 135 °C, precluding short-path distillation as a means of purification. Recrystallization was shown to be effective as an alternative technique to purify the compound and avoid the distillation procedure.

Rh-Catalyzed Asymmetric Hydrogenation of Unsaturated Medium-Ring NH Lactams: Highly Enantioselective Synthesis of N-Unprotected 2,3-Dihydro-1,5-benzothiazepinones

A straightforward method to prepare 1,5-benzothiazepines was reported. Catalyzed by a Rh/Zhaophos complex, unsaturated cyclic NH lactams with a medium-size ring were hydrogenated smoothly, giving remarkably high enantioselectivities. The sulfur atom in the substrates did not bring an inhibition which was observed with commercially available bisphosphine ligands. This method was successfully applied in the scale-up synthesis of (R)-(-)-thiazesim.

Preparation method of 2-butynoic acid

The invention relates to the technical field of preparation of 2-butynoic acid, in particular to a preparation method of 2-butynoic acid. The preparation method provided by the invention comprises thefollowing steps: mixing 2-butyn-1-ol, a catalyst, hypochlorite, an alkaline substance and water, carrying out an oxidation reaction, and adding an acid to obtain the 2-butyne acid. On the basis of not using a phase transfer catalyst, high yield and purity of 2-butynoic acid are ensured. According to the embodiment, the high performance liquid chromatography (HPLC) purity of the 2-butynoic acid prepared by the preparation method is more than or equal to 99.6%, and the yield is more than or equal to 52.7%.