590-92-1 Usage
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/ja01176a061Organic 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.]
Check Digit Verification of cas no
The CAS Registry Mumber 590-92-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,9 and 0 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 590-92:
(5*5)+(4*9)+(3*0)+(2*9)+(1*2)=81
81 % 10 = 1
So 590-92-1 is a valid CAS Registry Number.
InChI:InChI=1/C3H5BrO2/c4-2-1-3(5)6/h1-2H2,(H,5,6)/p-1
590-92-1Relevant articles and documents
METHOD OF MAKING ACRYLIC ACID FROM LACTIC ACID OR LACTIDE USING MOLTEN SALT CATALYSTS
-
Page/Page column 42-54, (2018/09/28)
A method of making acrylic acid in liquid phase by contacting a feed stream containing lactic acid, lactide, or mixtures thereof with a molten salt catalyst comprising a protic ionic liquid (PIL), which contains a bromide anion (Br-), is provided.
Catalytic Bromination of Alkyl sp3C-H Bonds with KBr/Air under Visible Light
Zhao, Mengdi,Lu, Wenjun
supporting information, p. 5264 - 5267 (2018/09/12)
Alkyl sp3C-H bonds of cycloalkanes and functional branch/linear alkanes have been successfully brominated with KBr using air or O2 as an oxidant at room temperature to 40 °C. The reactions are carried out in the presence of catalytic NaNO2 in 37% HCl (aq)/solvent under visible light, combining aerobic oxidations and photochemical radical processes. For various alkane substrates, CF3CH2OH, CHCl3, or CH2Cl2 is employed as an organic solvent, respectively, to enhance the efficiency of bromination.
METHODS OF MAKING ACRYLIC ACID FROM LACTIC ACID OR ITS DERIVATIVES IN LIQUID PHASE
-
Page/Page column 67, (2018/02/28)
Methods for making acrylic acid, acrylic acid derivatives, or mixtures thereof by contacting a feed stream containing lactic acid, lactic acid derivatives, or mixtures thereof with a molten salt catalyst comprising an ionic liquid (IL) and an acid in liquid phase are provided.