Atropic acid

Atropic acid Basic information
Product Name:Atropic acid
Synonyms:2-Phenylpropenoic acid;2-PHENYLPROP-2-ENOIC ACID;Ipratropium EP Impurity D;Ipratropium Bromide EP Impurity D (2-Phenyl Acrylic Acid);Ipratropium Bromide EP Impurity D;2-Phenylacrylic acid 95%;2-PHENYLACRYLIC ACID;ALPHA-PHENYLACRYLIC ACID
CAS:492-38-6
MF:C9H8O2
MW:148.16
EINECS:207-753-6
Product Categories:Aromatics, Impurities;Pharmaceutical Intermediates
Mol File:492-38-6.mol
Atropic acid Structure
Atropic acid Chemical Properties
Melting point 106-107°
Boiling point bp ~267° with partial decompn
density 1.0061 (rough estimate)
refractive index 1.5049 (estimate)
storage temp. 2-8°C
solubility DMSO (Slightly), Methanol (Slightly)
form Solid
pka3.86±0.11(Predicted)
color White to Off-White
Water Solubility 1.3g/L(20 ºC)
Merck 14,874
Stability:Light Sensitive
InChIKeyONPJWQSDZCGSQM-UHFFFAOYSA-N
CAS DataBase Reference492-38-6(CAS DataBase Reference)
NIST Chemistry ReferenceBenzeneacetic acid, «alpha»-methylene-(492-38-6)
EPA Substance Registry SystemBenzeneacetic acid, .alpha.-methylene- (492-38-6)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36/37/39
HS Code 29163990
MSDS Information
Atropic acid Usage And Synthesis
Chemical PropertiesWhite to Off-White Solid.
UsesAtropic acid is an Impurity of Ipratropium bromide and Atropine Sulfate. Atropic acid and β,β-dimethylatropic acid are plant growth regulators.
PreparationThe synthesis of atropic acid involves several steps. Firstly, tropic acid is oxidized with hot KMnO4 to form benzoic acid. Secondly, tropic acid reacted with HBr to produce C9H9O2Br. Thirdly, C9H9O2Br is reacted with alcoholic KOH to yield atropic acid, C9H8O2. Finally, atropic acid is catalytically hydrogenated to form hydratropic acid, C9H10O2.
ReactionsAtropic acid is formed by the dehydration of tropic acid. Hence addition of water to atropic acid gives tropic acid.
Atropic acid, on oxidation yields benzoic acid. The formation of benzoic acid reveals that atropic acid and tropic acid contain atleast one benzene nucleus with a side chain containing carboxylic acid in their structure.
atropic acid reaction
As atropic acid is an unsaturated acid it mean atropic acid may be either structure (I) or (II) .
Hence, the structure (II) is atropic acid which is confirmed by oxidation with KMnO4 to form phenylglyoxal.
Atropic acid Preparation Products And Raw materials
Preparation Products(R)-(-)-2-Phenylpropionic acid-->(S)-(+)-2-Phenylpropionic acid-->3-(4-methoxyphenyl)-2-phenylacrylic acid
Hyaluronic acid Phenylmaleic anhydride ALPHA-CARBOXY-4-BROMO-4'-NITRO STILBENE Atropic acid 4-CHLORO-(ALPHA-PHENYL)-CINNAMIC ACID RARECHEM AL BO 2387 Butyl acrylate FERRIC BENZOYLACETONATE alpha-Phenylcinnamic acid Acrylic acid 1-Phenyl-2-nitropropene Atropic acid, ethyl ester 3,4-DIHYDRO-1,2-NAPHTHALENEDICARBOXYLIC ANHYDRIDE Ethyl acrylate 4-HYDROXY-3-PHENYLCOUMARIN Poly(acrylic acid) Methacrylic acid OTAVA-BB BB7020252434

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