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HomeProduct name list3-Bromopropionic acid

3-Bromopropionic acid

  • CAS NO.:590-92-1
  • Empirical Formula: C3H5BrO2
  • Molecular Weight: 152.97
  • MDL number: MFCD00002763
  • EINECS: 209-694-1
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-09-03 12:56:46
3-Bromopropionic acid Structural

What is 3-Bromopropionic acid?

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.

The Uses of 3-Bromopropionic acid

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

What are the applications of 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.]

Properties of 3-Bromopropionic acid

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
pka 4.00(at 25℃)
form  Crystals or Crystalline Powder
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 for 3-Bromopropionic acid

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
GHS Hazard Statements H314:Skin corrosion/irritation
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P363:Wash contaminated clothing before reuse.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 3-Bromopropionic acid

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