609-11-0

Basic information

• Product Name: ETHYL 2,3-DIBROMOBUTYRATE
• Synonyms: 2,3-dibromo-butanoicaciethylester;Butanoic acid, 2,3-dibromo-, ethyl ester;Butyric acid, 2,3-dibromo-, ethyl ester;Ethyl 2,3-dibromobutanoate;Ethyl alpha,beta-dibromobutyrate;ETHYL A,B-DIBROMOBUTYRATE;ETHYL 2,3-DIBROMOBUTYRATE;ETHYL 2,3-DIBROMO-N-BUTYRATE
• CAS NO: 609-11-0
• Molecular Formula: C₆H₁₀Br₂O₂
• Molecular Weight: 273.95
• EINECS: 210-177-8
• Mol File: 609-11-0.mol

Chemical Properties

• Melting Point: 58.5°C
• Boiling Point: 104 °C / 17mmHg
• Flash Point: 90.9°C
• Appearance: /
• Density: 1,69 g/cm3
• Vapor Pressure: 0.0809mmHg at 25°C
• Refractive Index: 1.4940-1.4970
• CAS DataBase Reference: ETHYL 2,3-DIBROMOBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,3-DIBROMOBUTYRATE(609-11-0)
• EPA Substance Registry System: ETHYL 2,3-DIBROMOBUTYRATE(609-11-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 1760
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 609-11-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2,3-DIBROMOBUTYRATE is used as a chemical intermediate for the synthesis of pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL 2,3-DIBROMOBUTYRATE serves as an intermediate in the production of various agrochemicals, aiding in the creation of pesticides and other agricultural chemicals to protect crops and enhance yields.
Used in Food Industry:
ETHYL 2,3-DIBROMOBUTYRATE is utilized as a flavoring agent, adding specific tastes and aromas to food products, thereby enhancing their sensory appeal to consumers.
Used in Fragrance Industry:
As a fragrance ingredient, ETHYL 2,3-DIBROMOBUTYRATE is employed to create and enhance the scent profiles of various products, such as perfumes, cosmetics, and household items, due to its fruity odor.

InChI:InChI=1/C6H10Br2O2/c1-3-10-6(9)5(8)4(2)7/h4-5H,3H2,1-2H3

Upstream product

• 10544-63-5 ethyl crotonate 
• 623-70-1 ethyl (E)-crotonate 
• 6776-19-8 ethyl (Z)-crotonate 
• 533-68-6 2-bromobutyric acid ethyl ester 
• 600-30-6 erythro-2,3-dibromobutanoic acid 

Downstream Products

• 67770-59-6 3-methyl-2,3-dihydro-benzo[1,4]dioxin-2-carboxylic acid ethyl ester 
• 600-18-0 2-Oxobutyric acid 
• 707-19-7 (+/-)-3t-methyl-cyclopropane-1,1,2r-tricarboxylic acid 
• 10544-63-5 ethyl crotonate 
• 103668-27-5 ethyl 2,3-bis<(benzoylthio)acetamido>butanoate 
• 103668-26-4 ethyl 2,3-bis<(benzoylthio)acetamido>butanoate 
• 21759-74-0 ethyl (Z)-3-(benzylamino)-2-butenoate 
• 89529-96-4 3-benzylsulfanylbutyric acid ethyl ester 
• 100608-91-1 1-benzyl-3-methyl-aziridine-2-carboxylic acid ethyl ester 

Relevant articles and documents

Aziridines as templates: A general strategy for the stereospecific synthesis of 2-azetidinones

Various routes to a variety of azridine-2-carboxylates have been described and the stereochemistry of these compounds has been determined by spectroscopic methods. Further, greater diversity of β-lactams via ring expansion of these azridines-2-carboxylates were obtained by a general, efficient and direct stereospecific approach.

A radical based addition-elimination route for the preparation of indoles

Indoles, including tricyclic derivatives, are produced by cyclisations of aryl radicals onto vinyl halides followed by elimination of halide radical and tautomerism of the resulting product; the aryl radicals are produced using "clean methodology" either by reaction of iodide ions with arenediazonium salts or by reaction of phosphorus-centred radicals with aryl iodides. The Royal Society of Chemistry 2000.

Carbonylation of silylated hydroxymethyl aziridines to β-lactams

Functionalized β-lactams are synthesized by carbonylative ring expansion of silylated hydroxymethyl aziridines catalyzed by dicobalt octacarbonyl, a process that proceeds with inversion of configuration. Ring opening and elimination occurs on attempted carbonylation of aziridine carboxylates.

A new synthesis of indoles

Aryl radical cyclisation onto appropriate vinyl bromides leads to a new route to indoles.

Perfluorohexane as a novel reaction medium for bromination reactions

Perfluorohexane is shown to be a good alternative to carbon tetrachloride as a non-toxic, non-ozone-depleting, inert reaction medium for bromination reactions. Yields of brominated products were nearly quantitative and the reaction work-up was easier.

1,2-asymmetric induction in radical reactions. Deuteration and allylation reactions of β-oxy-α-bromo esters

Chiral radicals were generated by halogen abstraction reactions of β-oxy-α-bromo esters and their asymmetric deuteration and allylation reactions were studied.

An Improved Synthesis of 3-(1-Imidazolyl)-2-alkenoic Acid Derivatives and Related Compounds

The preparative method of 3-(1-imidazolyl)-2-alkenoic acid derivatives and the related compounds was improved by the use of strong bases such as sodium hydride in DMF.By this improved method, the preparation of 2-substituted 3-(1-imidazolyl)-2-alkenoic acid derivatives was accomplished in good yields.

Tissue Distribution Properties of Technetium-99m-Diamide-Dimercaptide Complexes and Potential Use as Renal Radiopharmaceuticals

A series of new ligands and the corresponding technetium-99m chelates based on diamide dimercaptide donor groups were synthesized as derivatives of technetium-99m 1,2-bis(2-thioacetamido)ethane, a complex shown to be excreted by renal tubular secretion. Chelation with 99mTc resulted in single radiochemical products or the expected numbers of stereoisomers. They were purified by high-performance liquid chromatography (HPLC) and evaluated in mice as potential renal tubular function agents. The in vivo properties were sensitive to the presence of functional groups, the positional isomerism of the carboxylate group functionality, and the chelate ring stereochemistry of the ligand. The presence of methyl groups slowed renal transit and decreased renal specificity. Cyclohexyl rings fused to the ethylene bridge of the center chelate ring decreased renal excretion while aromatic rings essentially abolished renal excretion. Slow hepatobiliary clearance was observed as an alternate mode of excretion. Polar groups, such as hydroxyl, carboxylate, and carboxamide, increased renal excretion rates and specificity in a stereochemically dependent manner. 99mTc chelates of 1,3-bis(2-thioacetamido)-2-hydroxypropane, 3,4-bis(2-thioacetamido)butanoate and 1,8-dimercapto-2,7-dioxo-3,6-diazanonanoate were identified as promising new renal radiopharmaceuticals.

Kinetics and Mechanism of Bromine Addition to Derivatives of Unsaturated Aliphatic Carboxylic Acids in Aqueous Solution

This paper deals with the kinetics of bromine addition to unsaturated compounds in presence of added bromide ions at 22, 30, 38, 46, and 54 deg C.The substrates used were acrylamide (AAm), methyl acrylate (MA), ethyl acrylate (EA), butyl acrylate (BA), t-butyl acrylate (tBA), methacrylamide (MAAm), methyl methacrylate (MMA), ethyl methacrylate (EMA), methyl crotonate (MC), and ethyl crotonate (EC).The kinetics was followed potentiometrically.The activation parameters (ΔH*, ΔS*, and ΔG*) were calculated and compared.Estimation of product ratio of bromohydrin to dibromide showed the absence of any correlation of the product formation with reactivity of the substrates.The observed parameters are discussed in relation to the proposed reaction mechanisms.