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

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

Uses

Used in Pharmaceutical Industry:
METHYL 2,4-DIBROMOBUTYRATE is used as an intermediate in the synthesis of pharmaceutical compounds for its ability to contribute to the development of new drugs and enhance the properties of existing ones.
Used in Perfume and Flavor Industry:
METHYL 2,4-DIBROMOBUTYRATE is used as a precursor for the creation of esters, which are essential in the formulation of fragrances and flavors, adding to the richness and complexity of scents and tastes.
Used in Agrochemical Production:
METHYL 2,4-DIBROMOBUTYRATE is utilized in the production of agrochemicals, contributing to the development of effective pest control and crop protection solutions.
Used as a Solvent:
METHYL 2,4-DIBROMOBUTYRATE is employed as a solvent in various chemical processes, facilitating reactions and improving the efficiency of industrial applications.

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

• 18085-37-5 methyl 1-benzyl-2-azetidinecarboxylate 
• 220364-79-4 methyl 1,4-dibenzyl-1,4-diazepane-5-carboxylate 
• 96999-01-8 1-(1-bromocyclopropyl)formic acid methyl ester 
• 76799-57-0 methyl 2-acetoxy-4-bromobutyrate 
• 98485-43-9 1-Methylmercapto-cyclopropan-carbonsaeure-⁽¹⁾-methylester 

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.

Method for preparing methyl 2,4-dibromobutyrate under catalysis of brominated sulfonic acid resin

The invention discloses a method for preparing methyl 2,4-dibromobutyrate under the catalysis of a brominated sulfonic acid resin. The method comprises the following steps: adding a brominated sulfonic acid resin catalyst with a mass fraction of 2-5% into gamma-butyrolactone; heating to 80-90 DEG C, adding a certain amount of liquid bromine in a dropwise manner, keeping the temperature at 90-100 DEG C, and reacting for 3-5 hours; cooling to room temperature, adding methanol in a dropwise manner, and reacting for 10-15 hours; filtering to remove the catalyst, washing the catalyst with a detergent, drying, and repeatedly using; and distilling the filtrate to obtain the target product. According to the invention, the catalyst is high in catalytic activity, short in reaction time and high in raw material utilization rate, and can be repeatedly used; and with the method, the damage of phosphorus-containing wastewater to the environment is avoided, the wastewater amount is less, the production cost is reduced, the post-treatment is convenient, links of extraction, water washing, drying and the like are reduced, operation is easy, product quality is high, and the environment-friendly thought is met.

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.

Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil

A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.

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.

SYNTHESIS OF CYCLIC AMIDINES

The invention relates to an innovative method for synthesis of cyclic amidines. The synthesis starts from a β-, γ- or δ-lactone which is twofold brominated. After esterification of the carboxyl function, the bromine atoms are nucleophilically substituted and the corresponding diamino compound is obtained. The ring closure to the cyclic amidine is accomplished subsequently by reaction with orthoester, imidate or thioimidate. Owing to interposing additional steps for recovery of the diamino compound in enantiomerically pure form, the enantiomers of the cyclic amidines can be stereoselectively synthesized.

NHC-Catalyzed intramolecular redox amidation for the synthesis of functionalized lactams

A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.

Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates

Enantiopure 1-phenylethylazetidine-2-carboxylates and 2-acylazetidines were prepared and reacted with chloroformates to yield α-chloro-γ-amino butyric acid esters and ketones from ring opening reaction of azetidinium ion intermediate in a completely regio- and stereoselective manner.

Enzymatic resolution of methyl N-alkyl-azetidine-2-carboxylates by Candida antarctica lipase-mediated ammoniolysis

A facile method for the synthesis of optically active azetidine-2- carboxylic acid derivatives is presented Racemic N-alkylated azetidine esters are resolved by lipase from Candida antarctica in an ammoniolysis reaction, and both the S-amide and the R-ester are obtained with excellent stereoselectivity.