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.)

Flash point:

211 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

Specific Gravity

1.363

color 

Clear colorless to brown

Water Solubility 

Slightly soluble in water.

BRN 

1749649

InChI

InChI=1S/C6H11BrO2/c1-9-6(8)4-2-3-5-7/h2-5H2,1H3

InChIKey

RAVVJKCSZXAIQP-UHFFFAOYSA-N

SMILES

C(OC)(=O)CCCCBr

CAS DataBase Reference

5454-83-1(CAS DataBase Reference)

EPA Substance Registry System

Methyl 5-bromovalerate (5454-83-1)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29159080

MSDS

• Language:English Provider:Methyl 5-bromovalerate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Methyl 5-bromovalerate Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO BROWN LIQUID

Uses

It is employed as an intermediate in the production of Apixaban .

Synthesis

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(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