Benzyl 2-bromoacetate

Base Information

• Chemical Name: Benzyl 2-bromoacetate
• CAS No.: 5437-45-6
• Molecular Formula: C9H9BrO2
• Molecular Weight: 229.073
• Hs Code.: 29159080
• European Community (EC) Number: 226-611-4
• NSC Number: 23980,16114
• UNII: 64U2RK18D3
• DSSTox Substance ID: DTXSID4040343
• Nikkaji Number: J7.983I
• Wikidata: Q27263791
• ChEMBL ID: CHEMBL3184596
• Mol file: 5437-45-6.mol

Synonyms:Aceticacid, bromo-, benzyl ester (6CI,7CI,8CI);Acetic acid, bromo-, phenylmethylester (9CI);Benzyl bromoacetate;Bromoacetic acidbenzyl ester;Merbac 35;NSC 16114;NSC 23980;Phenylmethyl bromoacetate;Benzyl 2-bromoacetate;

Chemical Property of Benzyl 2-bromoacetate

Chemical Property:

• Appearance/Colour: Colorless or light yellow liquid
• Vapor Pressure: 0.00243mmHg at 25°C
• Melting Point: 199-201 °C(Solv: water (7732-18-5))
• Refractive Index: n20/D 1.544(lit.)
• Boiling Point: 287.773 °C at 760 mmHg
• Flash Point: 116.485 °C
• PSA: 26.30000
• Density: 1.474 g/cm³
• LogP: 2.12470
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Methanol
• Water Solubility.: Not miscible or difficult to mix in water.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 227.97859
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

98% ^*data from raw suppliers

2-BromoaceticAcidPhenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: C1=CC=C(C=C1)COC(=O)CBr
• Uses: It is employed in biological research purpose. Benzyl bromoacetate was used in the alkylation of (-)-2,3-O-isopropylidene-D-threitol that afforded lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid.

Technology Process of Benzyl 2-bromoacetate

There total 12 articles about Benzyl 2-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: 100.0%

bromoacetic acid (79-08-3) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl bromoacetate (5437-45-6)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 120 ℃; for 24h;

DOI:10.1016/j.tet.2007.11.097

Reference yield: 98.0%

2-Bromoacetyl bromide (598-21-0) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl bromoacetate (5437-45-6)

Guidance literature:

With sodium hydrogencarbonate; In acetonitrile; at 0 ℃; for 0.916667h; Sealed tube; Inert atmosphere;

DOI:10.15227/orgsyn.089.0501

Reference yield: 85.0%

bromoacetic acid methyl ester (96-32-2) + benzyl alcohol (100-51-6,185532-71-2) → Benzyl bromoacetate (5437-45-6)

Guidance literature:

With 1,3-bis(2,4,6-trimethylphenyl)imidazole hydrochloride; potassium tert-butylate; In benzene; at 80 ℃; for 10h; Inert atmosphere;

DOI:10.1039/b910162d

upstream raw materials:

bromoacetic acid

benzyl alcohol

ethyl bromoacetate

1-ethoxy-1-cyclopropanol

Downstream raw materials:

Trimethylammoniumessigsaeurebetain-benzylester-bromid

benzyl 2-(dimethoxyphosphoryl)acetate

benzyl morpholino-acetate

N-(Benzyloxycarbonylmethyl)pyridinium bromide

Refernces

• 1、 Grob, Nathalie M.,Schibli, Roger,Béhé, Martin,Valverde, Ibai E.,Mindt, Thomas L.. "1,5-Disubstituted 1,2,3-Triazoles as Amide Bond Isosteres Yield Novel Tumor-Targeting Minigastrin Analogs". supporting information. p. 585 - 592. Retrieved 2021/04/12.
• 2、 Song, Yang,Zhang, Hao,Guo, Jiabao,Shao, Yifei,Ding, Yuzhou,Zhu, Li,Yao, Xiaoquan. "Visible-Light-Induced Oxidative α-Alkylation of Glycine Derivatives with Ethers under Metal-Free Conditions". . p. 5914 - 5921. Retrieved 2021/11/22.