Benzyl 2-bromoacetate Chemical Properties

Melting point:

199-201 °C(Solv: water (7732-18-5))

Boiling point:

166-170 °C22 mm Hg(lit.)

Density 

1.446 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.544(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Liquid

Specific Gravity

1.446

color 

Clear colorless to light yellow

Water Solubility 

Not miscible or difficult to mix in water.

BRN 

973658

LogP

2.368 (est)

CAS DataBase Reference

5437-45-6(CAS DataBase Reference)

NIST Chemistry Reference

Benzyl 2-bromoacetate(5437-45-6)

EPA Substance Registry System

Benzyl bromoacetate (5437-45-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

RIDADR 

2810

WGK Germany 

3

RTECS 

AF5957215

F 

19

HS Code 

29159080

MSDS

• Language:English Provider:Benzyl 2-bromoacetate
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Benzyl 2-bromoacetate Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

It is employed in biological research purpose. Benzyl bromoacetate was used in the alkylation of (-)-2,3-O-isopropylidene-D-threitol that afforded lipopeptide, 2-[(4R,5R)-5-({[(9H-fluoren-9-yl)methoxy]carbonylaminomethyl}-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]acetic acid.

Synthesis

General method: A mixture of acid 2 (0.033 g), 2-bromoacetic acid (3a) (0.137 g, 0.988 mmol) adsorbed on silica gel and benzyl alcohol (4a) (0.108 g, 1.000 mmol) was stirred and reacted at 80°C for 24 h under argon protection. After completion of the reaction, the mixture was cooled to room temperature, ether (5 mL x 5) was added for extraction, and the organic layer was separated by decantation from the silica gel adsorbed acid 2. The organic layer was concentrated under reduced pressure to remove the solvent, and then purified by silica gel column chromatography to afford benzyl 2-bromoacetate (5aa) (0.189 g, 83% yield) using hexane/ethyl acetate (v/v = 10/1) as eluent. The silica gel adsorbed acid 2 was recovered by vacuum drying at room temperature to give a white powder (0.033 g, 99% recovery).

Purification Methods

Dilute the ester with Et2O, wash it with 10% aqueous NaHCO3, H2O, dry (MgSO4) and fractionate it using a Fenske (glass helices packing) column. [Bergmann & Szinai J Chem Soc 1521 1956, Beilstein 6 IV 2265.] LACHRYMATORY.

References

[1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 367, p. 116 - 120

Benzyl 2-bromoacetate(5437-45-6)Related Product Information

• Benzyl alcohol
• Benzyl acetate
• Benzyl 2-chloroacetate
• Benzyl nicotinate
• BENZYL PHENYLACETATE
• Bromoacetic acid
• Ethyl bromoacetate
• Methyl bromoacetate
• tert-Butyl bromoacetate
• VINYL NEONONANOATE
• GLYCIDYL NEODECANOATE, MIXTURE OF BRANCHED ISOMERS
• Decanoyl/octanoyl-glycerides
• Phenyl bromoacetate
• Bronopol
• Acetic acid
• Ethyl acetate
• 1-Bromo-2-methoxyethane
• Benzyl formate