55831-56-6

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-2-butenoic acid is used as a key intermediate in the synthesis of anti-inflammatory drugs, contributing to the development of medications that help alleviate inflammation and associated pain or discomfort.
Used in Agrochemical Industry:
3-Chloro-2-butenoic acid also serves as a precursor in the manufacturing of herbicides, playing a crucial role in the production of chemicals that control, mitigate, or kill unwanted plants in agricultural settings.
Used in Organic Synthesis:
Due to its reactivity, 3-Chloro-2-butenoic acid is utilized as a precursor in the synthesis of other organic compounds, broadening its applications across various chemical and industrial processes.
It is important to handle 3-Chloro-2-butenoic acid with care due to its corrosive nature and potential health hazards, ensuring safety measures are in place during its use in research, production, and application.

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 academic research and scientific papers

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.

Total Syntheses of Atrovenetin and Atrovenetinone: A Naphthalene-Annulation Approach to a Discoid Tricycle Using Allenic Acid

A total synthesis of atrovenetin has been achieved. The discoid tricyclic motif was constructed by a novel three-carbon annulation of naphthalene derivative and allenic acid under acidic conditions. An effective protocol for the conversion of atrovenetin

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.