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: 2024-11-19 20:33:22
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.
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) |
 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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