Methyl 3-bromopropionate Chemical Properties

Melting point:

75°C

Boiling point:

64-66 °C/18 mmHg (lit.)

Density 

1.53 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.458(lit.)

Flash point:

167 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid

color 

Clear colorless to slightly yellow

Water Solubility 

Immiscible

BRN 

1742949

CAS DataBase Reference

3395-91-3(CAS DataBase Reference)

NIST Chemistry Reference

Propanoic acid, 3-bromo-, methyl ester(3395-91-3)

EPA Substance Registry System

Propanoic acid, 3-bromo-, methyl ester (3395-91-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-37/39-24/25

WGK Germany 

3

RTECS 

UA2451790

TSCA 

Yes

HS Code 

29159080

MSDS

• Language:English Provider:Methyl 3-bromopropionate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Methyl 3-bromopropionate Usage And Synthesis

Chemical Properties

Very slightly yellow liquid

Uses

Methyl 3-bromopropionate was used in the synthesis of spiroanellated γ-lactones, pinacols and unprecedented 3-(1-hydroxycycloalkyl)-l-oxaspiro[n,m]alkan-2-ones.

Synthesis

Methyl propiolate (52 mL, 0.583 mol) was mixed with recrystallized N-bromosuccinimide (120 g, 0.674 mol) in 1,700 mL of acetone under nitrogen protection. Pure silver nitrate (9.9 g, 0.0583 mol) was added to the solution in a single addition and the reaction mixture was stirred at room temperature for 6 hours. Upon completion of the reaction, the acetone was evaporated under reduced pressure (25 °C bath temperature) to give a gray slurry. The slurry was washed with hexane (2 x 200 mL), filtered to remove the gray solid, and the filtrate was concentrated under vacuum to give 95 g of a pale yellow oily crude product. The crude product was passed through a short distillation under reduced pressure (65 °C, ca. 25 mmHg) and the fractions were collected with a receiver cooled with dry ice/acetone to give 83.7 g (88% yield) of methyl 3-bromopropynoate as a pale yellow oil. Calculated values for elemental analysis of [C4H3BrO2]: C, 29.48; H, 1.86. Measured values: C, 29.09; H, 1.97.

References

[1] Patent: WO2004/13137, 2004, A1. Location in patent: Page 76
[2] Tetrahedron Letters, 2010, vol. 51, # 13, p. 1793 - 1796

Methyl 3-bromopropionate(3395-91-3)Related Product Information

• 3-BROMOISONICOTINIC ACID METHYL ESTER
• Methyl 3-bromobenzoate
• methyl 3-bromopicolinate
• Methyl 3-bromobutyrate
• Ethyl 3-bromopropionate
• Ethyl 2,3-dibromopropionate
• ETHYL 2,3-DIBROMO-3-PHENYLPROPIONATE
• Methyl 3-bromopropionate
• Methyl 2-(bromomethyl)acrylate
• METHYL 3-BROMO-2-(BROMOMETHYL)PROPIONATE
• Ethyl bromopyruvate
• METHYL (R)-(+)-3-BROMO-2-METHYLPROPIONATE
• ETHYL 2-(BROMOMETHYL)ACRYLATE
• ETHYL 2,3-DIBROMOBUTYRATE
• METHYL 2-BROMOPROPIONATE,Methyl alpha-bromopropionate,Methyl2-bromopropionate,97%
• 3-Bromopropionic acid
• Methyl propionate
• Metaclazepam