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Methyl 5-bromovalerate

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Methyl 5-bromovalerate Basic information
Product Name:Methyl 5-bromovalerate
Synonyms:5-broMo-Methyl E;Methyl 5-broMovalerate, 97% 10GR;Methyl 5-broMovalerate 97%;5-broMo-pentanoate;METHYL 5-BROMOVALERATE;METHYL 5-BROMVALERATE;METHYL 5-BROMOPENTANOATE;5-bromo-pentanoicacimethylester
CAS:5454-83-1
MF:C6H11BrO2
MW:195.05
EINECS:226-709-7
Product Categories:C6 to C7;Carbonyl Compounds;Esters;bc0001
Mol File:5454-83-1.mol
Methyl 5-bromovalerate Structure
Methyl 5-bromovalerate Chemical Properties
Boiling point 79-80°C 4mm
density 1.363 g/mL at 25 °C (lit.)
refractive index n20/D 1.463(lit.)
Fp 211 °F
storage temp. Sealed in dry,Room Temperature
form Liquid
color Clear colorless to brown
Specific Gravity1.363
Water Solubility Slightly soluble in water.
BRN 1749649
InChIInChI=1S/C6H11BrO2/c1-9-6(8)4-2-3-5-7/h2-5H2,1H3
InChIKeyRAVVJKCSZXAIQP-UHFFFAOYSA-N
SMILESC(OC)(=O)CCCCBr
CAS DataBase Reference5454-83-1(CAS DataBase Reference)
EPA Substance Registry SystemMethyl 5-bromovalerate (5454-83-1)
Safety Information
Safety Statements 23-24/25
WGK Germany 3
TSCA TSCA listed
HS Code 29159080
Storage Class10 - Combustible liquids
MSDS Information
ProviderLanguage
Methyl 5-bromovalerate English
ACROS English
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ALFA English
Methyl 5-bromovalerate Usage And Synthesis
Chemical PropertiesCLEAR COLOURLESS TO BROWN LIQUID
UsesIt is employed as an intermediate in the production of Apixaban .
Synthesis
Methanol

67-56-1

5-Bromovaleric acid

2067-33-6

Methyl 5-bromovalerate

5454-83-1

5-Bromovaleric acid (2.01 g, 10.0 mmol) was dissolved in methanol (10 mL) and the solution was subsequently transferred into a syringe. The syringe was mounted on a syringe pump and the methanol solution was pumped at a flow rate of 0.177 mL/min into a stainless steel column (4.0 mm ID x 50 mm length, 0.53 mL internal volume) filled with HO-SAS (334 mg). The stainless steel column was immersed in an oil bath preheated to 110°C and connected to a back pressure regulator (set pressure 75 psi). As the reaction mixture flowed out of the column outlet, the fraction collected during the first 10 min was discarded. The reaction mixture was then collected over the next 3 minutes and n-decane was added as an internal standard for gas chromatography (GC) analysis. The reaction mixture was continued to be collected in a glass flask for 30 min, after which the solvent was removed by rotary evaporation. The crude product was purified by fast column chromatography on silica gel (SiO2) with an eluent ratio of hexane/ethyl acetate (5:1), resulting in methyl 5-bromovalerate (1.13 g, 99% yield).

References[1] Journal of Materials Chemistry B, 2013, vol. 1, # 34, p. 4225 - 4230
[2] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 5, p. 607 - 612
[3] Organic Letters, 2015, vol. 17, # 1, p. 138 - 141
[4] Synlett, 2004, # 10, p. 1735 - 1738
[5] New Journal of Chemistry, 2001, vol. 25, # 9, p. 1182 - 1184
Methyl 5-bromovalerate Preparation Products And Raw materials
Raw materialsMethanol-->5-Bromovaleric acid
Preparation ProductsCIS-9,10-METHYLENEOCTADECANOIC ACID
Tag:Methyl 5-bromovalerate(5454-83-1) Related Product Information
Methyl acetate Pivalic acid Bensulfuron methyl METHYL VALERATE METHYL THIOPHENE-2-CARBOXYLATE Methyl formate Methyl isovalerate Methyl trimethylacetate Methylparaben Estradiol valerate Chloromethyl pivalate MAGNESIUM DIPROPYLACETATE HYDRATE Kresoxim-methyl Methyl 2-bromo-2-methylpropionate Methyl 2-bromobenzoate Methyl bromoacetate 2-Propylpentanoic acid Thiophanate-methyl

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