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HomeProduct name listAtropic acid

Atropic acid

  • CAS NO.:492-38-6
  • Empirical Formula: C9H8O2
  • Molecular Weight: 148.16
  • MDL number: MFCD00046531
  • EINECS: 207-753-6
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-05 11:59:05
Atropic acid Structural

What is Atropic acid?

Chemical properties

White to Off-White Solid.

The Uses of Atropic acid

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.
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.

Properties of Atropic acid

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
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)

Safety information for Atropic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for Atropic acid

InChIKey ONPJWQSDZCGSQM-UHFFFAOYSA-N

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