TERT-BUTYL 2,4-DIBROMOBUTYRATE

Base Information

• Chemical Name: TERT-BUTYL 2,4-DIBROMOBUTYRATE
• CAS No.: 77629-96-0
• Molecular Formula: C8H14Br2O2
• Molecular Weight: 302.006
• Hs Code.: 2915900090
• Mol file: 77629-96-0.mol

Synonyms:TERT-BUTYL 2,4-DIBROMOBUTANOATE;TERT-BUTYL 2,4-DIBROMOBUTYRATE

Chemical Property of TERT-BUTYL 2,4-DIBROMOBUTYRATE

Chemical Property:

• Vapor Pressure: 0.00516mmHg at 25°C
• Refractive Index: n20/D 1.486
• Boiling Point: 275.2°C at 760 mmHg
• Flash Point: 107 °C
• PSA: 26.30000
• Density: 1.562 g/mL at 20 °C(lit.)
• LogP: 2.87660
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

tert-Butyl 2,4-dibromobutyrate technical, ≥85% (GC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: tert-Butyl 2,4-dibromobutyrate was employed as building block in reaction with primary amines to yield azetidine-2-carboxylates.

Technology Process of TERT-BUTYL 2,4-DIBROMOBUTYRATE

There total 4 articles about TERT-BUTYL 2,4-DIBROMOBUTYRATE 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: 91.0%

2,4-dibromobutanoyl chloride (82820-87-9) + tert-butyl alcohol (75-65-0) → 2,4-dibromobutyric acid tert-butyl ester (77629-96-0,71725-02-5)

Guidance literature:

With pyridine; In dichloromethane; at -25 - 10 ℃; for 1.25h;

DOI:10.1021/acs.orglett.7b00707

Reference yield: 53.0%

4-butanolide (96-48-0) + tert-butyl alcohol (75-65-0) → 2,4-dibromobutyric acid tert-butyl ester (77629-96-0,71725-02-5)

Guidance literature:

4-butanolide; With phosphorus tribromide; at 100 ℃; Inert atmosphere;

With bromine; for 7h;

tert-butyl alcohol; Further stages;

Reference yield: 51.0%

4-butanolide (96-48-0) + isobutene (115-11-7,15220-85-6) → 2,4-dibromobutyric acid tert-butyl ester (77629-96-0,71725-02-5)

Guidance literature:

4-butanolide; With bromine; phosphorus tribromide; at 100 ℃; for 0.583333h; Inert atmosphere;

isobutene; With sulfuric acid; In dichloromethane; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/ejoc.201600611

upstream raw materials:

4-butanolide

isobutene

2,4-dibromo-butyric acid

tert-butyl alcohol

Downstream raw materials:

N-(2-Phenylethyl)-2-(carbo-tert-butoxy)azetidine

tert-butyl N-benzylazetidine-2-carboxylate

tert-butyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate

3-(1,1-dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate

Refernces

• 1、 Tayama, Eiji,Nishio, Ryotaro,Kobayashi, Yoshiaki. "Base-promoted diastereoselective α-alkylation of borane: N -((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes". supporting information. p. 5833 - 5845. Retrieved 2018/08/22.
• 2、 Tayama, Eiji,Watanabe, Kazutoshi,Matano, Yoshihiro. "Ring-Strain Effects in Base-Induced Sommelet–Hauser Rearrangement: Application to Successive Stereocontrolled Transformations". supporting information. p. 3631 - 3641. Retrieved 2016/07/29.