36847-51-5

Basic information

• Product Name: Ethyl 2,4-dibromobutyrate
• Synonyms: ETHYL 2,4-DIBROMOBUTYRATE;ETHYL-ALPHA,GAMMA-DIBROMOBUTYRATE;2,4-DIBROMO-BUTYRIC ACID ETHYL ESTER;2,4-Dibromobutanoic acid ethyl ester;Butanoic acid, 2,4-dibromo-, ethyl ester;2,4-dibromo-butanoicaciethylester;ETHYL 2,4-DIBROMOBUTANOATE
• CAS NO: 36847-51-5
• Molecular Formula: C₆H₁₀Br₂O₂
• Molecular Weight: 273.95
• EINECS: 253-240-5
• Mol File: 36847-51-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 222.5°C (rough estimate)
• Flash Point: 106.632 °C
• Appearance: /
• Density: 1.6987
• Vapor Pressure: 0.019mmHg at 25°C
• Refractive Index: 1.4960 (estimate)
• CAS DataBase Reference: Ethyl 2,4-dibromobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2,4-dibromobutyrate(36847-51-5)
• EPA Substance Registry System: Ethyl 2,4-dibromobutyrate(36847-51-5)

Safety Data

• Hazardous Substances Data: 36847-51-5(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

InChI:InChI=1/C6H10Br2O2/c1-2-10-6(9)5(8)3-4-7/h5H,2-4H2,1H3

Upstream product

• 64-17-5 ethanol 
• 63164-16-9 2,4-dibromo-butyric acid 
• 52412-07-4 2,4-dibromo-butyryl bromide 
• 1759-53-1 cyclopropanecarboxylic acid 
• 96-48-0 4-butanolide 
• 82820-87-9 2,4-dibromobutanoyl chloride 

Downstream Products

• 67706-74-5 isoxazolidine-2,5-dicarboxylic acid 2-benzyl ester 5-ethyl ester 
• 72081-67-5 N-(2-p-Methoxy-phenethyl)-2-carbethoxyazetidine 
• 71556-64-4 N-Benzhydryl-2-carbethoxyazetidine 
• 2969-81-5 Ethyl 4-bromobutyrate 
• 4606-07-9 ethyl cyclopropylcarboxylate 
• 105-54-4 butanoic acid ethyl ester 
• 107-92-6 butyric acid 
• 1004985-70-9 ethyl 4-bromo-2-phenylbutanoate 
• 1606993-73-0 N-(4-methoxyphenyl)-2-ethoxycarbonyl-2-methylazetidine 
• 1047988-11-3 ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate 
• 459426-36-9 ethyl 1-((S)-1-phenylethyl)azetidine-2-carboxylate 
• 1158445-88-5 C₁₇H₂₃NO₂ 
• 1606993-72-9 N-(4-trifluoromethylphenyl)-2-ethoxycarbonylazetidine 
• 1606993-71-8 N-(4-methylphenyl)-2-ethoxycarbonylazetidine 

Relevant articles and documents

Base-promoted diastereoselective α-alkylation of borane: N -((S)-1′-phenylethyl)azetidine-2-carboxylic acid ester complexes

The base-promoted α-alkylation of N-((S)-1-phenylethyl)azetidine-2-carboxylic acid esters 1 was investigated. The use of diastereomerically pure borane complexes 3 as substrates, which are easily prepared from 1, dramatically improved the yields and diastereoselectivities of α-alkylated products 2. For example, the treatment of tert-butyl ester (1S,2S,1′S)-3a with 2.4 equivalents of lithium bis(trimethysilyl)amide (LiHMDS) at 0 °C followed by 2.6 equivalents of benzyl bromide afforded α-benzylated (2S,1′S)-2aa in 90% yield as almost a single diastereomer. Our method enables the production of optically active α-substituted azetidine-2-carboxylic acid esters starting from commercially available (S)-1-phenylethylamine, which is one of the least expensive chiral compounds.

Synthesis of the cytotrienin A core via metal catalyzed C-C coupling

A synthetic approach to the C17-benzene ansamycins via metal catalyzed C-C coupling is described. Key bond formations include direct iridium catalyzed carbonyl crotylation from the alcohol oxidation level followed by chelation-controlled Sakurai-Seyferth dienylation to form the stereotriad, which is attached to the arene via Suzuki cross-coupling. The diene-containing carboxylic acid is prepared using rhodium catalyzed acetylene-aldehyde reductive C-C coupling mediated by gaseous hydrogen. Finally, ring-closing metathesis delivers the cytotrienin core.

Preparation of β-lactams from azetidine-2-carboxylic acids and esters

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