29547-04-4

Basic information

• Product Name: METHYL 2,4-DIBROMOBUTYRATE
• Synonyms: METHYL 2,4-DIBROMOBUTANOATE;BUTANOIC ACID, 2,4-DIBROMO-METHYL ESTER;Nsc167181;2,4-Dibromobutyric acid methyl ester;>=97.0%
• CAS NO: 29547-04-4
• Molecular Formula: C₅H₈Br₂O₂
• Molecular Weight: 259.92
• Mol File: 29547-04-4.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 71℃ (5 Torr)
• Flash Point: 97.1 °C
• Appearance: /
• Density: 1.840 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0463mmHg at 25°C
• Refractive Index: 1.5084 (589.3 nm 20℃)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: METHYL 2,4-DIBROMOBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 2,4-DIBROMOBUTYRATE(29547-04-4)
• EPA Substance Registry System: METHYL 2,4-DIBROMOBUTYRATE(29547-04-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3334
• WGK Germany: 3
• F: 19
• Hazardous Substances Data: 29547-04-4(Hazardous Substances Data)

Usage

General Description

Methyl 2,4-dibromobutyrate is a chemical compound with the molecular formula C5H7Br2O2. It is a clear, colorless liquid with a fruity aroma and is commonly used in the production of pharmaceuticals and perfumes. METHYL 2,4-DIBROMOBUTYRATE is primarily used as an intermediate in the synthesis of other organic compounds, particularly in the creation of esters, which are commonly used in the fragrance and flavor industries. Additionally, it can also be used as a solvent and in the production of agrochemicals. Methyl 2,4-dibromobutyrate is considered a hazardous substance and should be handled with care, as it may cause skin and eye irritation upon contact.

InChI:InChI=1/C5H8Br2O2/c1-9-5(8)4(7)2-3-6/h4H,2-3H2,1H3

Upstream product

• 67-56-1 methanol 
• 52412-07-4 2,4-dibromo-butyryl bromide 
• 96-48-0 4-butanolide 
• 82820-87-9 2,4-dibromobutanoyl chloride 

Downstream Products

• 62664-91-9 N-(2-Phenethyl)-2-(carbomethoxy)azetidine 
• 18085-37-5 methyl 1-benzyl-2-azetidinecarboxylate 
• 204274-30-6 methyl (2R,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 
• 204274-29-3 methyl (2S,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylate 
• 205443-19-2 1-(4-Methoxy-benzyl)-azetidine-2-carboxylic acid methyl ester 
• 186096-46-8 methyl (2R,αR)-N-α-methylbenzylazetidine-2-carboxylate 
• 249734-39-2 methyl (2S,αR)-N-α-methylbenzylazetidine-2-carboxylate 
• 17330-25-5 methyl 1-p-tosylazetidine-2-carboxylate 
• 220364-79-4 methyl 1,4-dibenzyl-1,4-diazepane-5-carboxylate 
• 18085-35-3 1-tert-Butyl-2-(methoxycarbonyl)azetidine 
• 70288-65-2 (R)-methyl 2,4-dibromobutyrate 
• 70288-65-2 (S)-methyl 2,4-dibromobutyrate 
• 1353160-88-9 methyl N-benzyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate 
• 1376574-08-1 methyl N-tosyl-2-(2-methoxycarbonylethyl)azetidine-2-carboxylate 

Relevant articles and documents

Trispirododecane-4,8,12-trione and Other Oligomers of Carbonylcyclopropane. The Organozinc Route

1-Bromocyclopropanecarboxylic acid (8) and its chloride (9) were prepared from γ-butyrolactone on a 20-100-g scale.Dehalogenation of 9 with zinc-copper couple in acetonitrile gave not only the known dispiro octane-4,8-dione (3) but also the aesthetically pleasing title compound 10 and 6-cyclopropylidene-5-oxaspirohexan-4-one (11) as well as tetracyclic α-alkylidene-γ-butyrolactone 12, i.e., 3-(oxodispirooctan-4-ylidene)tetrahydro-2-furanone. "Zinc carbon enolate" 13a is considered to be an important intermediate en route to 10 in solventacetonitrile.The X-ray crystal structure of 10 shows the molecule to be nearly planar with very short distal cyclopropane carbon-carbon bonds .

Synthesis of optically active 2-substituted azetidine-2-carbonitriles from chiral 1-arylethylamineviaα-alkylation ofN-borane complexes

The base-promoted α-alkylation ofN-((S)-1-arylethyl)azetidine-2-carbonitriles3viaformation of theirN-borane complexes4was investigated. For example, treatment of diastereomerically pure boraneN-((S)-1′-(4′′-methoxyphenyl)ethyl)azetidine-2-carbonitrile complex (1S,2S,1′S)-4bwith 1.2 equivalents of LDA at ?78 °C followed by 1.3 equivalents of benzyl bromide at ?78 °C and warming to room temperature produced α-benzylated (2S,1′S)-5bain 72% yield and (2R,1′S)-5bain 2% yield. A mechanism for this diastereoselective α-alkylation was proposed. Our method enables the production of optically active 2-substituted azetidine-2-carbonitriles, such as α-benzylated (S)-10aand (R)-10a, starting from commercially available (S)-(1-(4-methoxyphenyl)ethyl)amine.

Synthesis method of 5-fluoro-2-(1-bromocyclopropyl) pyridine

The invention relates to a synthesis method of 5-fluoro-2-(1-bromocyclopropyl) pyridine. 1,4-butyrolactone, ethyl 4-bromobutyrate and 5-fluoro-2-mercaptopyridine are used as raw materials to prepare 5-fluoro-2-(1-bromocyclopropyl) pyridine through eleven steps of reaction. A synthetic route of the 5-fluoro-2-(1-bromocyclopropyl) pyridine is as follows: (as described in the specification). The invention has the advantages that the synthesis method of 5-fluoro-2-(1-bromocyclopropyl) pyridine improves the yield and provides an efficient synthesis method for the synthesis of the compound.

An efficient synthesis of 1-bromo-1-cyanocyclopropane

An efficient process for the synthesis of 1-bromo-1-cyanocyclopropane has been developed starting from inexpensive γ-butyrolactone via bromination, cyclisation, ammoniation and dehydration reaction. The sequence proceeds in good yield.