Ethyl bromoacetate

Base Information

• Chemical Name: Ethyl bromoacetate
• CAS No.: 105-36-2
• Deprecated CAS: 679806-14-5,2374896-00-9
• Molecular Formula: C4H7BrO2
• Molecular Weight: 167.002
• Hs Code.: 29159080
• European Community (EC) Number: 203-290-9
• NSC Number: 8832
• UN Number: 1603
• UNII: D20KFB313W
• DSSTox Substance ID: DTXSID4020587
• Nikkaji Number: J45.013H
• Wikipedia: Ethyl_bromoacetate
• Wikidata: Q413962
• Pharos Ligand ID: YL5ZF62WBJQD
• ChEMBL ID: CHEMBL1085948
• Mol file: 105-36-2.mol

Synonyms:ethyl bromoacetate

Chemical Property of Ethyl bromoacetate

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid
• Vapor Pressure: 2.6 mm Hg ( 25 °C)
• Melting Point: -38 °C
• Refractive Index: n20/D 1.451(lit.)
• Boiling Point: 168.499 °C at 760 mmHg
• Flash Point: 47.778 °C
• PSA: 26.30000
• Density: 1.501 g/cm³
• LogP: 0.94440
• Storage Temp.: Store below +30°C.
• Solubility.: water: insoluble
• Water Solubility.: Miscible with ethanol, acetone, benzene and ethyl ether. Immiscible with water.
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 165.96294
• Heavy Atom Count: 7
• Complexity: 62.7
• Transport DOT Label: Poison Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Ethyl bromoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+
• Hazard Codes: T+
• Statements: 26/27/28
• Safety Statements: 26-45-7/9-1/2

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CCOC(=O)CBr
• Uses: Ethyl bromoacetate is widely used as an alkylating reagent involved in the Reformatsky reaction to prepare the beta-hydroxy esters by reacting with carbonyl compounds. It is also used for the syntheses of witting reagent, artificial diethylstilbestrol antigen, 3-phenyl-1-naphthol and steroidal thiazolidinone derivatives. It finds applications in the preparation of reversibly photoresponsive coumarin-stabilized polymeric nanoparticles in an aqueous medium which act as a detectable drug carrier.

Technology Process of Ethyl bromoacetate

There total 57 articles about Ethyl 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: 95.0%

ethanol (64-17-5) + bromoacetic acid (79-08-3) → ethyl bromoacetate (105-36-2)

Guidance literature:

With thionyl chloride; In diethyl ether; at 0 - 20 ℃;

DOI:10.1002/ejoc.200300410

Reference yield: 78.0%

diazoacetic acid ethyl ester (623-73-4) → ethyl bromoacetate (105-36-2)

Guidance literature:

With 1-bromo-butane; [HB(3,5-(CF₃)2Pz)3]Ag(THF);

DOI:10.1021/ja034801o

Reference yield: 65.0%

ethyl vinyl ether (109-92-2,25104-37-4) → ethyl bromoacetate (105-36-2)

Guidance literature:

With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; at 20 ℃; for 0.166667h; regioselective reaction;

DOI:10.1055/s-0030-1259090

upstream raw materials:

bromoacetic anhydride

ethanol

diazoacetic acid ethyl ester

ethyl bromide

Downstream raw materials:

piperidin-1-yl-acetic acid ethyl ester

ethyl 2-(1-hydroxycyclopentyl)acetate

imidazo[1,2-a]pyridin-2-one

imidazo[1,2-a]pyridin-2(3H)-one hydrobromide

Refernces

• 1、 Maury, Catherine,Petrissans, Jean. "Analyse structurale des derives fonctionnels des acides carboxyliques Partie III. Acetate d'ethyle et derives α-halogenes". . p. 221 - 232. Retrieved 1991.
• 2、 Vojtko, Jan,Tomcik, Peter. "A method for esterification reaction rate prediction of aliphatic monocarboxylic acids with primary alcohols in 1,4-dioxane based on two parametrical taft equation". . p. 189 - 196. Retrieved 2014.
• 3、 Chen, Jijun,Long, Wenhao,Zhao, Yanwei,Li, Haiyan,Zheng, Yonggao,Lian, Pengcheng,Wan, Xiaobing. "In Situ Generation of Oxazole Ylide and Interception with Sulfonamide: Construction of Amidines Using Two Diazo Molecules". . p. 857 - 865. Retrieved 2018.
• 4、 Gold,Sommer,Whitmore. "-". . p. 2874. Retrieved 1948.
• 5、 -. "Synthesis process of thiazole medical intermediate". Paragraph 0013. . Retrieved 2021/06/09.
• 6、 -. "Synthesis method of ethyl 3-hydroxyhexanoate". Paragraph 0017; 0019; 0021; 0023; 0025; 0027; 0029; 0031. . Retrieved 2020/02/27.