55831-56-6

Basic information

• Product Name: 3-Chloro-2-butenoic acid
• Synonyms: 2-Butenoic acid, 3-chloro-;3-Chloro-2-butenoic acid;3-Chlorocrotonic acid
• CAS NO: 55831-56-6
• Molecular Formula: C₄H₅ClO₂
• Molecular Weight: 120.5343
• Mol File: 55831-56-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 94°C
• Boiling Point: 148.96°C (rough estimate)
• Flash Point: 76.4°C
• Appearance: /
• Density: 1.2094 (rough estimate)
• Vapor Pressure: 0.187mmHg at 25°C
• Refractive Index: 1.4350 (estimate)
• PKA: pK1: 3.84 (25°C)
• CAS DataBase Reference: 3-Chloro-2-butenoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-2-butenoic acid(55831-56-6)
• EPA Substance Registry System: 3-Chloro-2-butenoic acid(55831-56-6)

Safety Data

• Hazardous Substances Data: 55831-56-6(Hazardous Substances Data)

Usage

General Description

3-Chloro-2-butenoic acid is an organic compound with the chemical formula C4H5ClO2. It is a colorless, corrosive liquid with a pungent odor. 3-Chloro-2-butenoic acid is mostly used in the synthesis of pharmaceutical compounds. Its primary application is in the manufacturing of anti-inflammatory drugs and herbicides. It is also used as a precursor in the synthesis of other organic compounds due to its reactivity and ability to participate in various chemical reactions. However, it is important to handle this chemical with caution due to its corrosive nature and potential health hazards.

InChI:InChI=1/C4H5ClO2/c1-3(5)2-4(6)7/h2H,1H3,(H,6,7)/b3-2-

Upstream product

• 38624-62-3 ethyl 3-chloro-2-butenoate 
• 590-93-2 2-Butynoic acid 

Downstream Products

• 4593-90-2 3-phenylbutyric acid 
• 103385-16-6 3,3-diphenylbutanoic acid 

Relevant articles and documents

Decarbonylation of phenylacetic acids by high valent transition metal halides

Triphenylacetic acid underwent unusual decarbonylation when allowed to react with a series of halides of group 4-6 metals in their highest oxidation state, in dichloromethane at ambient temperature. Thus, the reaction of CPh3COOH with MoCl5, in 1:1 molar ratio, afforded the trityl salt [CPh3][MoOCl4], 1, in 79% yield, while the 1:2 reaction of CPh3COOH with NbF5 afforded [CPh3][NbF6], 2, in 70% yield, NbOF3 being the metal co-product. CPh3COOH reacted with NbCl5, TiF4 and WOCl4 to give mixtures of compounds, however the cation [CPh3]+ was NMR identified in each case. [CPh3][NbCl6], 3, was isolated from NbCl5 and CPh3COCl, prior to being generated from CPh3COOH and PCl5. The reaction of CPh3COOH with TiCl4 was non-selective, and the salt [CPh3][Ti2Cl8(μ-κ2-O2CCPh3)], 4, was obtained in 18% yield. The decarbonylation reactions of CMePh2COCl and CMe2PhCOCl by means of NbCl5 led to the indanes 5a-b, which were isolated in 79-97% yields after hydrolysis of the mixtures and subsequent alumina filtration of the organic phases. The reactions of CH(Ph)2COOH with NbCl5 and WCl6 afforded NbCl4(OOCCHPh2), 6, and CHPh2COCl, respectively, as the prevalent species. CPh2(CH2CH2Br)COOH did not undergo CO release when allowed to interact with WCl6, instead selective intramolecular condensation to C(Ph)2C(O)OCH2CH2, 7, occurred. MeCCCOOH underwent hydrochlorination by WCl6 to give MeC(Cl)CHCOOH, 8, in 72% yield. All the products were fully characterized by elemental analysis, IR and multinuclear NMR spectroscopy. In addition, the solid state structures of 1, 2, 4, 7, and 8 were elucidated by X-ray diffraction.

A New Method for the Preparation of γ,δ-Unsaturated Ketones via Claisen Rearrangement

Thermal rearrangement of monosodium salts of 3-(allyloxy)crotonates derived from primary and secondary allylic alcohols and of disodium salts of 3-(allyloxy)-2-alkenoic acids affords γ,δ-unsaturated ketones.