3-Bromopropionic acid Chemical Properties

Melting point:

58-62 °C(lit.)

Boiling point:

140-142 °C (45 mmHg)

Density 

1.48 g/mL at 25 °C(lit.)

refractive index 

1.4753 (estimate)

Flash point:

150 °F

storage temp. 

2-8°C

solubility 

H₂O: 0.1 g/mL, clear

form 

Crystals or Crystalline Powder

pka

4.00(at 25℃)

color 

White to slightly yellow

Water Solubility 

0.1 g/mL

Merck 

14,1433

BRN 

1071333

Dielectric constant

11.0（20℃）

CAS DataBase Reference

590-92-1(CAS DataBase Reference)

NIST Chemistry Reference

Propanoic acid, 3-bromo-(590-92-1)

EPA Substance Registry System

Propanoic acid, 3-bromo- (590-92-1)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

RTECS 

UE7875000

Hazard Note 

Corrosive/Highly Flammable

TSCA 

Yes

HazardClass 

4.1

PackingGroup 

III

HS Code 

29159080

Hazardous Substances Data

590-92-1(Hazardous Substances Data)

MSDS

• Language:English Provider:3-Bromopropionic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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3-Bromopropionic acid Usage And Synthesis

Chemical Properties

white to pale yellow or orange crystalline. soluble in water, alcohol, ether, chloroform, benzene. Hydrolysis in alkaline solution generates hydroxypropionic acid. Corrosive. for organic synthesis.

Uses

3-Bromopropionic acid used as quaternization agent in amperometric biosensors.

Application

3-Bromopropionic acid is a widely used chemical intermediate. It can be used as a starting material to synthesize derivatives such as esters, acid halides and amides; the active group bromine can undergo a series of reactions, and is mainly used in the fields of pesticides and medicines. Such as the pesticides diflufenacil, furalax and so on.

Preparation

3-Bromopropionic acid is prepared by reacting acrylonitrile with hydrogen bromide to obtain bromopropionitrile and then hydrolyzing it. Add acrylonitrile to boiling hydrobromic acid, reflux at 130°C for 6 hours, extract the solid obtained by filtration with ethanol, and obtain the crude product after recovering ethanol by distillation under reduced pressure. By heating 2-cyanoethanol and 40% hydrobromic acid to reflux for 2h, 3-bromopropionic acid can also be produced with a yield of over 80%.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2807, 1949 DOI: 10.1021/ja01176a061
Organic Syntheses, Coll. Vol. 1, p. 131, 1941

Safety Profile

Moderately toxic by intraperitoneal route. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of Br-. See also BROMIDES.

Purification Methods

The acid crystallises as plates from CCl4. It is soluble in organic solvents and H2O. Its methyl ester has b 65o/18mm and 80o/27mm. The S-benzylisothiouronium salt has m 136o. [Kendall & McKenzie Org Synth Coll Vol I 131 1941, Beilstein 2 IV 764.]

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