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Atropic acid

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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
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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
pka
3.86±0.11(Predicted)
color 
White to Off-White
Water Solubility 
1.3g/L(20 ºC)
Merck 
14,874
Stability:
Light Sensitive
InChIKey
ONPJWQSDZCGSQM-UHFFFAOYSA-N
CAS DataBase Reference
492-38-6(CAS DataBase Reference)
NIST Chemistry Reference
Benzeneacetic acid, «alpha»-methylene-(492-38-6)
EPA Substance Registry System
Benzeneacetic acid, .alpha.-methylene- (492-38-6)
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Safety Information

Risk Statements 
36/37/38
Safety Statements 
26-36/37/39
HS Code 
29163990
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Atropic acid Usage And Synthesis

Chemical Properties

White to Off-White Solid.

Uses

Atropic acid is an Impurity of Ipratropium bromide and Atropine Sulfate. Atropic acid and β,β-dimethylatropic acid are plant growth regulators.

Preparation

The 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.

Reactions

Atropic 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.

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.

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