tert-Butyl bromoacetate

Base Information

• Chemical Name: tert-Butyl bromoacetate
• CAS No.: 5292-43-3
• Deprecated CAS: 2676972-35-1
• Molecular Formula: C6H11BrO2
• Molecular Weight: 195.056
• Hs Code.: 29159080
• European Community (EC) Number: 226-133-6
• NSC Number: 82470
• UNII: LY42AF89SN
• DSSTox Substance ID: DTXSID2063763
• Nikkaji Number: J254.923I
• Wikidata: Q72514090
• Mol file: 5292-43-3.mol

Synonyms:tert-Butyl bromoacetate;5292-43-3;tert-butyl 2-bromoacetate;t-Butyl bromoacetate;Acetic acid, bromo-, 1,1-dimethylethyl ester;Bromoacetic Acid tert-Butyl Ester;tert-Butylbromoacetate;bromo-acetic acid tert-butyl ester;MFCD00000188;Acetic acid, bromo-, tert-butyl ester;tert-ButylBromoacetate-13C;LY42AF89SN;BrCH2C(O)OC(CH3)3;1,1-dimethylethyl 2-bromoacetate;1,1-Dimethylethyl monobromoacetate;Acetic acid, 2-bromo-, 1,1-dimethylethyl ester;2-bromoacetic acid tert-butyl ester;EINECS 226-133-6;NSC 82470;Bromoacetic acid 1,1-dimethylethyl ester;t-butylbromoaceate;t-butylbromoacteate;t-Butylbromoacetate;t-Butyl-bromoacetate;tert butylbromoacetate;tertbutyl bromoacetate;tert-butyl bromacetate;tert butyl bromoacetate;tert-butyl-bromoacetate;tert.-butylbromoacetate;tert.butyl bromoacetate;Tert. butylbromoacetate;BrCH2CO2-t-Bu;t-butyl 2-bromoacetate;t-butyl-2-bromoacetate;tert-butyl-bromo-acetate;tert-butyl2-bromoacetate;tert.-butyl bromoacetate;dimethylethyl bromoacetate;tertiarybutyl bromoacetate;t-buty alpha-bromoacetate;bromoacetate t-butyl ester;t-butyl alpha-bromoacetate;tert-Butyl-2-bromoacetate;tertiary butyl bromoacetate;T-BUTYL BROMOACTATE;UNII-LY42AF89SN;tert-Butyl |A-bromoacetate;tert-butyl 2-bromo-acetate;NCIOpen2_001241;SCHEMBL38493;tert-butyl alpha-bromoacetate;2-bromoacetate t-butyl ester;bromoacetic acid t-butyl ester;tert-butyl 2-bromanylethanoate;1,1-dimethylethyl bromoacetate;tert-Butyl bromoacetate, 98%;bromoacetic acid tert-butylester;DTXSID2063763;BNWCETAHAJSBFG-UHFFFAOYSA-;bromoacetic acid-tert-butyl ester;2-bromoacetic acid-t butyl ester;bromoacetic acid tert.-butyl ester;AMY28710;BCP24432;bromo-acetic acid tert.-butyl ester;CS-D1664;NSC82470;STR02323;AB6559;NSC-82470;2-bromoacetic acid tert.-butyl ester;AKOS009159099;TERT-BUTYL .ALPHA.-BROMOACETATE;BP-20407;bromo-acetic acid 1,1-dimethylethyl ester;2-bromoacetic acid 1,1-dimethylethyl ester;B1473;FT-0623217;EN300-61309;tert-Butyl bromoacetate, purum, >=97.0% (GC);A829312;Q-201798;F0001-1365

Chemical Property of tert-Butyl bromoacetate

Chemical Property:

• Appearance/Colour: slightly yellow transparent liquid
• Vapor Pressure: 2.01mmHg at 25°C
• Melting Point: 44-47 °C
• Refractive Index: 1.457
• Boiling Point: 163.999 °C at 760 mmHg
• Flash Point: 59.101 °C
• PSA: 26.30000
• Density: 1.352 g/cm³
• LogP: 1.72300
• Storage Temp.: 0-6°C
• Sensitive.: Lachrymatory
• Water Solubility.: Miscible with ethanol, chloroform and ethyl acetate. Immiscible with water.
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 193.99424
• Heavy Atom Count: 9
• Complexity: 104

Purity/Quality:

99%, ^*data from raw suppliers

tert-Butyl bromoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F
• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 26-24/25-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Esters
• Canonical SMILES: CC(C)(C)OC(=O)CBr
• Uses: tert-Butyl Bromoacetate is a halogenated t-butyl acetate commonly used as an alkylating agent. tert-Butyl Bromoacetate is used in the synthesis of collagenase inhibitors. tert-Butyl bromoacetate is used as an intermediate in the production of dyes, pharmaceuticals, agrochemicals and in organic compounds. It finds application as an alkylating agent. It plays an important role to prepare (2-oxo-4-vinyl-azetidin-1-yl)-acetic acid tert-butyl ester and in collagenase inhibitors synthesis.

Technology Process of tert-Butyl bromoacetate

There total 12 articles about tert-Butyl 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: 97.6%

bromoacetic acid (79-08-3) + isobutene (115-11-7,15220-85-6) → bromoacetic acid tert-butyl ester (5292-43-3)

Guidance literature:

With Amberlyst-15; at -78 - 20 ℃; for 24h; Autoclave;

DOI:10.1039/c2cc17339e

Reference yield: 96.0%

2-Bromoacetyl bromide (598-21-0) + tert-butyl alcohol (75-65-0) → bromoacetic acid tert-butyl ester (5292-43-3)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.10.074

Reference yield: 88.4%

aqueous potassium carbonate + bromoacetic acid (79-08-3) + isobutene (115-11-7,15220-85-6) → bromoacetic acid tert-butyl ester (5292-43-3)

Guidance literature:

With sulfuric acid; In dichloromethane;

upstream raw materials:

bromoacetic acid

isobutene

2-Bromoacetyl bromide

tert-butyl alcohol

Downstream raw materials:

cyanoacetic acid tert-butyl ester

3-hydroxydodecanoic acid

(3R)-(-)-3-Hydroxydodecanoic acid

(3S)-3-hydroxydodecanoic acid

Refernces

• 1、 Das, Sanju,De Sarkar, Suman,Mandal, Tanumoy. "Acridine Orange Hemi(Zinc Chloride) Salt as a Lewis Acid-Photoredox Hybrid Catalyst for the Generation of α-Carbonyl Radicals". supporting information. . Retrieved 2021/12/10.
• 2、 Bi, Hong-Yan,Liu, Feng-Ping,Liang, Cui,Su, Gui-Fa,Mo, Dong-Liang. "A Tunable Route to Prepare α,β-Unsaturated Esters and α,β-Unsaturated-γ-Keto Esters through Copper-Catalyzed Coupling of Alkenyl Boronic Acids with Phosphorus Ylides". supporting information. p. 1510 - 1516. Retrieved 2018/03/05.