Methyl bromoacetate

Base Information

• Chemical Name: Methyl bromoacetate
• CAS No.: 96-32-2
• Molecular Formula: C3H5BrO2
• Molecular Weight: 152.975
• Hs Code.: 29159080
• European Community (EC) Number: 202-499-2
• NSC Number: 2642
• UN Number: 2643
• UNII: LI6481MCM6
• DSSTox Substance ID: DTXSID7052737
• Nikkaji Number: J2.844D
• Wikipedia: Methyl_2-bromoacetate
• Wikidata: Q27894374
• Mol file: 96-32-2.mol

Synonyms:Methyl bromoacetate;96-32-2;methyl 2-bromoacetate;Bromoacetic acid methyl ester;ACETIC ACID, BROMO-, METHYL ESTER;Methyl monobromoacetate;Methyl alpha-bromoacetate;NSC 2642;Acetic acid, 2-bromo-, methyl ester;Methylester kyseliny bromoctove;2-bromoacetic acid methyl ester;Methyl-2-bromoacetate;EINECS 202-499-2;UN2643;Methyl .alpha.-bromoacetate;Methylester kyseliny bromoctove [Czech];bromo-acetic acid methyl ester;LI6481MCM6;EC 202-499-2;methylbromacetate;methylbromoacetat;methylbromacetat-;methyl bromacetate;methvl bromoacetate;methyl-bromoacetate;methylbromo-acetate;methyl brornoacetate;methyl -bromoacetate;methyl bromo-acetate;BrCH2COOMe;1-Methyl bromoacetate;BrCH2COOCH3;Bromoacetic acid methyl;methyl 2-bromo-acetate;methyl 2-bromoethanoate;bromoacetic methyl ester;carbomethoxymethyl bromide;methyl 2-bromanylethanoate;Methyl bromoacetate, 97%;bromoacetic acid methylester;bromoaceticacid methyl ester;UNII-LI6481MCM6;WLN: E1VO1;SCHEMBL26568;bromo acetic acid methyl ester;Bromo acetic acid, methyl ester;DTXSID7052737;HSDB 8463;2-bromo-acetic acid methyl ester;METHYL.ALPHA.-BROMOACETATE;NSC2642;monobromo acetic acid methyl ester;BCP06456;MFCD00000189;NA2643;AKOS009158462;UN 2643;AS-18626;Methyl bromoacetate [UN2643] [Poison];Methyl bromoacetate [UN2643] [Poison];B0533;FT-0628707;EN300-59820;A845577;Q-100976;Q27894374;F2190-0277

Chemical Property of Methyl bromoacetate

Chemical Property:

• Appearance/Colour: clear to slightly yellow liquid
• Vapor Pressure: 3.25mmHg at 25°C
• Melting Point: -50°C
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 154 °C at 760 mmHg
• Flash Point: 62.8 °C
• PSA: 26.30000
• Density: 1.615 g/cm³
• LogP: 0.55430
• Storage Temp.: Store at R.T.
• Water Solubility.: Miscible with methanol, ether and acetone. Slightly miscible with water
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 151.94729
• Heavy Atom Count: 6
• Complexity: 52.8
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

BAM ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi,F
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: COC(=O)CBr
• Uses: Methyl bromoacetate was used in the synthesis of novel coumarins. It was also employed in the synthesis of cis-cyclopropanes 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.

Technology Process of Methyl bromoacetate

There total 19 articles about Methyl bromoacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

Dimethoxymethane (109-87-5) + 2-Bromoacetyl bromide (598-21-0) → bromoacetic acid methyl ester (96-32-2)

Guidance literature:

at 0 ℃; for 11h;

DOI:10.1081/SCC-120002510

Reference yield: 81.0%

methanol (67-56-1) + bromoacetic acid (79-08-3) → bromoacetic acid methyl ester (96-32-2)

Guidance literature:

bromoacetic acid; With oxalyl dichloride; at 60 ℃; for 3h;

methanol; at 20 ℃; for 0.5h;

DOI:10.1002/(sici)1099-0690(199911)1999:11<2909::aid-ejoc2909>3.0.co;2-5

Reference yield: 80.0%

→ bromoacetic acid methyl ester (96-32-2)

Guidance literature:

upstream raw materials:

dimethyl 2-bromofumarate

methyl diazoacetate

methanol

bromoacetic acid

Downstream raw materials:

(2-[2]pyridyl-benzimidazol-1-yl)-acetic acid methyl ester

methoxycarbonylmethyl-hexamethylenetetraminium; bromide

2-(1-hydroxycyclohexyl)acetic acid

benzyl-methoxycarbonylmethyl-dimethyl-ammonium; bromide

Refernces

• 1、 Huang, Zhusheng,Yang, Xiuqin,Yang, Fulai,Lu, Tao,Zhou, Qingfa. "Phosphine-Catalyzed Domino β/γ-Additions of Benzofuranones with Allenoates: A Method for Unsymmetrical 3,3-Disubstituted Benzofuranones". supporting information. p. 3524 - 3527. Retrieved 2017/07/17.
• 2、 Pecak, Wiktoria H.,Son, Jongwoo,Burnstine, Amy J.,Anderson, Laura L.. "Synthesis of 1,4-enamino ketones by [3,3]-rearrangements of dialkenylhydroxylamines". supporting information. p. 3440 - 3443. Retrieved 2014/07/21.