96-32-2

Basic information

• Product Name: Methyl bromoacetate
• Synonyms: Methyl broMoacetate, 99% 100GR;Methyl broMoacetate, 99% 25GR;Methyl BroMoacetate(Methyl 2-BroMoacetate;Methyl broMoacetate 97%;BroMine Methyl acetate;BAM;BROMO METHYLACETATE;BROMOACETIC ACID METHYL ESTER
• CAS NO: 96-32-2
• Molecular Formula: C₃H₅BrO₂
• Molecular Weight: 152.97
• EINECS: 202-499-2
• Product Categories: Building Blocks;C2 to C5;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;Organics;C2 to C5;Carbonyl Compounds;Esters;500 Series Drinking Water Methods;BromoEPA;Chemical Class;Halogenated;Method 552
• Mol File: 96-32-2.mol
• Article Data: 25

Chemical Properties

• Melting Point: -50°C
• Boiling Point: 51-52 °C15 mm Hg(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless to slightly yellow/Liquid
• Density: 1.616 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.25mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Storage Temp.: Store at R.T.
• Water Solubility: Miscible with methanol, ether and acetone. Slightly miscible with water
• BRN: 506256
• CAS DataBase Reference: Methyl bromoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl bromoacetate(96-32-2)
• EPA Substance Registry System: Methyl bromoacetate(96-32-2)

Safety Data

• Hazard Codes: T,Xi,F
• Statements: 25-34-37-23/24/25-40-36/37/38-38
• Safety Statements: 26-36/37/39-45-28A-36-16
• RIDADR: UN 2643 6.1/PG 2
• WGK Germany: 3
• RTECS: AF6300000
• F: 19
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 96-32-2(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 96-32-2 differently. You can refer to the following data:
1. Methyl bromoacetate was used in the synthesis of novel coumarins. It was also employed in the synthesis of cis-cyclopropanes
2. Methyl bromoacetate is used in the synthesis of coumarins and cis-cyclopropanes. It reacts with the conjugate base of (methylmethoxycarbene)pentacarbonylchromium(0) to prepare alkylated carbene complexes. Further, it is used to make vitamins and pharmaceuticals.

Application

Methyl Bromoacetate is an organic building block that has been used as a reactant in the preparation of isoquinolinone indole acetic acid derivatives as antagonists of chemoattractant receptor homologous molecule expressed on Th2 cells (CRTH2) for the treatment of allergic inflammatory diseases.

General Description

A colorless to straw-colored liquid with a sharp penetrating odor. Denser than water and soluble in water. Severly irritates skin and eyes. Toxic by ingestion and inhalation. Used to make vitamins and pharmaceuticals.

Reactivity Profile

Methyl bromoacetate is a halogenated ester. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Hazard

Vapor is strong irritant to eyes.

Safety Profile

Poison by intravenous route. When heated to decomposition it emits toxic fumes of Br-. See also ESTERS.

InChI:InChI=1/C3H5BrO2/c1-6-3(5)2-4/h2H2,1H3

Upstream product

• 20688-29-3 dimethyl 2-bromofumarate 
• 6832-16-2 methyl diazoacetate 
• 67-56-1 methanol 
• 79-08-3 bromoacetic acid 
• 201230-82-2 carbon monoxide 
• 74-95-3 1,1-dibromomethane 
• 79-37-8 oxalyl dichloride 
• 60-29-7 diethyl ether 
• 77-78-1 dimethyl sulfate 
• 109-87-5 Dimethoxymethane 
• 598-21-0 2-Bromoacetyl bromide 
• 79-20-9 acetic acid methyl ester 
• 186581-53-3 diazomethane 
• 358-98-5 1,2-dibromo-1-fluoro-ethene 

Downstream Products

• 74356-96-0 (2-[2]pyridyl-benzimidazol-1-yl)-acetic acid methyl ester 
• 34850-99-2 methoxycarbonylmethyl-hexamethylenetetraminium; bromide 
• 14399-63-4 2-(1-hydroxycyclohexyl)acetic acid 
• 24254-64-6 methyl 3-(4-fluorophenyl)butanoate 
• 24254-65-7 3-(4-chlorophenyl)butyric acid methyl ester 
• 72039-44-2 Sodium; [(2-hydroxy-ethyl)-(4-morpholin-4-yl-7-phenyl-pyrido[3,4-d]pyridazin-1-yl)-amino]-acetate 
• 72039-43-1 4--1-morpholino-7-phenylpyrido<3,4-d>pyridazine sodium salt 
• 109-11-5 morpholine-3-one 
• 7367-87-5 3-hydroxyoctanoic acid methyl ester 
• 19078-76-3 methyl 4-bromo-4-phenylbutanoate 
• 62000-57-1 methyl 3-nitro-3-phenyl-2-hydroxycarboxylate 
• 24254-67-9 β-Methyl<1,1'-biphenyl>-4-propansaeuremethylester 
• 1883-13-2 3-hydroxydodecanoic acid 
• 28254-78-6 (3R)-(-)-3-Hydroxydodecanoic acid 

Relevant articles and documents

Enantioselective Allenoate-Claisen Rearrangement Using Chiral Phosphate Catalysts

Herein we report the first highly enantioselective allenoate-Claisen rearrangement using doubly axially chiral phosphate sodium salts as catalysts. This synthetic method provides access to β-amino acid derivatives with vicinal stereocenters in up to 95percent ee. We also investigated the mechanism of enantioinduction by transition state (TS) computations with DFT as well as statistical modeling of the relationship between selectivity and the molecular features of both the catalyst and substrate. The mutual interactions of charge-separated regions in both the zwitterionic intermediate generated by reaction of an amine to the allenoate and the Na+-salt of the chiral phosphate leads to an orientation of the TS in the catalytic pocket that maximizes favorable noncovalent interactions. Crucial arene-arene interactions at the periphery of the catalyst lead to a differentiation of the TS diastereomers. These interactions were interrogated using DFT calculations and validated through statistical modeling of parameters describing noncovalent interactions.

Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones

A phosphine-catalyzed domino process of benzofuranones with allenoates has been developed which furnishes highly functionalized unsymmetrical 3,3-disubstituted benzofuranones in synthetically useful yields. The mechanism for the transformation is a tandem β-umpolung/γ-umpolung process.

Cross-dehydrogenative coupling reactions by transition-metal and aminocatalysis for the synthesis of amino acid derivatives

The direct approach: The title coupling reactions of N-aryl glycine esters with unmodified ketones occurred smoothly in the presence of tert-butyl hydroperoxide (TBHP) or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under mild conditions (see scheme). The oxidant used for C-H activation determined the selectivity of the reactions for a particular type of ketone substrate. Copyright