79232-66-9

Basic information

• Product Name: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)-
• Synonyms: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(Z)-; (Z)-4-Bromo-3-oxo-2-methoxyiminobutyric acid
• CAS NO: 79232-66-9
• Molecular Formula: C5H6 Br N O4
• Molecular Weight: 224.011
• Mol File: 79232-66-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)-(79232-66-9)
• EPA Substance Registry System: Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)-(79232-66-9)

Safety Data

• Hazardous Substances Data: 79232-66-9(Hazardous Substances Data)

Usage

General Description

Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)- is a compound with the molecular formula C6H7BrNO3. It is also known as 4-Bromo-2-(methoxyimino)-3-oxo-butanoic acid, and is a chemical used in the Agrochemical market. It is a derivative of the herbicide cyhalofop and is used as an intermediate for the synthesis of pharmaceuticals and other organic compounds. Butanoic acid, 4-bromo-2-(methoxyimino)-3-oxo-,(2Z)- is a pale yellow to yellow powder with a molecular weight of 228.03 g/mol. It is important to handle and store this chemical with care, following all safety precautions and guidelines for handling hazardous materials.

Synthetic route

2-Methoxyiminoacetoacetic acid-tert-butyl ester (79232-65-8) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9)

Conditions	Yield
With chloro-trimethyl-silane; bromine; triethylamine; trifluoroacetic acid In tetrachloromethane; hexane; dichloromethane; nitrogen; water; acetonitrile	70.5%
With bromine In 5,5-dimethyl-1,3-cyclohexadiene; di-isopropyl ether; water	42.4%

(Z)-2-methoxyimino-3-oxo-butyric acid (77361-12-7) + 2-Methoxyiminoacetoacetic acid-tert-butyl ester (79232-65-8) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9)

Conditions	Yield
With hydrogen bromide; bromine In dichloromethane; water; acetic acid; trifluoroacetic acid

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride (77361-11-6)

Conditions	Yield
With phosphorus pentachloride In hexane; dichloromethane	96%
With phosphorus pentachloride In dichloromethane at -20 - -5℃; Product distribution / selectivity;
With phosphorus pentachloride In dichloromethane

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + N,N-dimethylformiminium chloride chlorosulphate → 4-bromo-2(Z)-methoxyimino-3-oxo butyric acid-N,N-dimethyl formiminium chloride chlorosulfate

Conditions	Yield
In dichloromethane at -25 - 10℃; for 2.5h;

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) → 4-bromo-2-methoxyimino-3-oxo butyric acid chloride (1056123-64-8)

Conditions	Yield
With phosphorus pentachloride In dichloromethane at -25 - -20℃; for 0.666667h;

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + oxalyl dichloride (79-37-8) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride (77361-11-6) + 4-bromo-2-methoxyimino-3-oxobutyrl chloride

Conditions	Yield
In dichloromethane

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + phosphorus pentachloride (10026-13-8, 874483-75-7) → (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride (77361-11-6)

Conditions	Yield
In dichloromethane

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + phosphorus oxy chloride + 2-Mercapto-5-phenyl-1,3,4-oxadiazole (3004-42-0) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-mercapto-5-phenyl-1,3,4-oxadiazolyl-(Z)-4-bromo-2-methoxyimino-3-oxo-butyrate

Conditions	Yield
With pyridine In acetonitrile

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + Benzhydryl 7-amino-3-vinyl-3-cephem-4-carboxylate hydrochloride + trimethylsilylacetamide → benzhydryl 7-(4-bromo-2-methoxyiminoacetoacetamido)-3-vinyl-3-cephem-4-carboxylate

Conditions	Yield
With trichlorophosphate In water; ethyl acetate; N,N-dimethyl-formamide
With trichlorophosphate In water; ethyl acetate; N,N-dimethyl-formamide

(Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid (79232-66-9) + C24H28N2O6S2Si → 7-[2-(syn)methoxyimino-3-oxo-4-bromobutyrylamino]-3-[(fur-2-ylcarbonyl)thiomethyl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester

Conditions	Yield
Stage #1: (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid With phosphorus pentachloride In dichloromethane at -30℃; for 0.5h; Stage #2: C24H28N2O6S2Si In dichloromethane at -30℃; for 0.25 - 0.333333h;

Upstream product

• 79232-65-8 2-Methoxyiminoacetoacetic acid-tert-butyl ester 
• 77361-12-7 (Z)-2-methoxyimino-3-oxo-butyric acid 

Downstream Products

• 77361-11-6 (Z)-4-bromo-2-methoxyimino-3-oxo-butyric acid chloride 
• 1056123-64-8 4-bromo-2-methoxyimino-3-oxo butyric acid chloride 

Relevant articles and documents

Process for producing 4-halogeno-2-alkoxyimino-3-oxo fatty acid

4-Halogeno-2-alkoxyimino-3-oxo fatty acid can be produced by one-pot and one-step by reacting a halogenating agent with a 2-alkoxyimino-3-oxo fatty acid ester in an ether solvent or a mixed solvent of an ether solvent and an inert organic solvent such as carbon tetrachloride, benzene, toluene, etc.

4-halogeno-2-oxyimino-3-oxobutyric acids and derivatives

A method of producing a 4-halo-2-(substituted or unsubstituted)hydroxyimino-3-oxobutyric acid ester or amide, which is a synthetic intermediate of value for the production of cephalosporins containing an aminothiazole group, characterized by reacting a 2-(substituted or unsubstituted)-hydroxyimino-3-oxobutyric acid or an ester or amide thereof with a silylating agent and reacting the resulting novel 2-(substituted)hydroxyimino-3-silyloxy-3-butenoic acid ester or amide with a halogenating agent.