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492-86-4

Basic Information
CAS No.: 492-86-4
Name: 4-Chloromandelic acid
Article Data: 54
Molecular Structure:
Molecular Structure of 492-86-4 (4-Chloromandelic acid)
Formula: C8H7ClO3
Molecular Weight: 186.595
Synonyms: Mandelicacid, p-chloro- (6CI,7CI,8CI);(4-Chlorophenyl)(hydroxy)acetic acid;(p-Chlorophenyl)hydroxyacetic acid;2-(4-Chlorophenyl)-2-(hydroxy)acetic acid;2-Hydroxy-2-(4-chlorophenyl)aceticacid;4-Chloro-DL-mandelic acid;DL-4-Chloromandelicacid;DL-p-Chloromandelic acid;NSC 31400;NSC 8112;p-Chloromandelic acid;7138-34-3;
EINECS: 207-764-6
Density: 1.468 g/cm3
Melting Point: 114-118 °C
Boiling Point: 361.4 °C at 760 mmHg
Flash Point: 172.4 °C
Appearance: white crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-36-26
PSA: 57.53000
LogP: 1.45800
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Specification

The CAS registry number of Benzeneacetic acid,4-chloro-a-hydroxy- is 492-86-4. Its EINECS registry number is 207-764-6. The IUPAC name is 2-(4-chlorophenyl)-2-hydroxyacetic acid. In addition, the molecular formula is C8H7ClO3 and the molecular weight is 186.59. It is also called Benzeneacetic acid,4-chloro-a-hydroxy-. What's more, it is a kind of white crystalline powder and belongs to the classes of Fine Chemical & Intermediates; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts.

Physical properties of Benzeneacetic acid,4-chloro-α-hydroxy- are: (1)ACD/LogP: 1.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.22; (4)ACD/LogD (pH 7.4): -2.18; (5)ACD/BCF (pH 5.5): 1; (6)ACD/KOC (pH 5.5): 1; (7)#H bond acceptors: 3; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 3; (10)Polar Surface Area: 35.53 Å2; (11)Index of Refraction: 1.605; (12)Molar Refractivity: 43.79 cm3; (13)Molar Volume: 127 cm3; (14)Surface Tension: 62.2 dyne/cm; (15)Density: 1.468 g/cm3; (16)Flash Point: 172.4 °C; (17)Enthalpy of Vaporization: 64.07 kJ/mol; (18)Boiling Point: 361.4 °C at 760 mmHg; (19)Vapour Pressure: 7.43E-06 mmHg at 25°C.

Preparation of Benzeneacetic acid,4-chloro-a-hydroxy-: it can be prepared by p-chloroacetophenone through bromination, hydrolysis and acidification reaction. Mix chlorobenzene, carbon bisulfide with aluminium trichloride at first. Then add ethylanhydride into the mixture with stirring. The reaction should reflux for 2 hours. And then after a series of washing, drying and vacuum distillation you can get 4-chloroacetophenone. Then add bromine into 4-chloroacetophenone at reaction temperature of 36-40 °C. Then go through washing by water and sodium hydrogen sulfite to get 4-ω,ω'-dibromoacetophenone. At last, you can get the desired product by means of hydrolysis, neutralization, extraction by ethyl ether, drying and crystallization.

Uses of Benzeneacetic acid,4-chloro-a-hydroxy-: it can be used as pharmaceutical intermediates. In addition, it can react with methanol to get 4-chloro-mandelic acid-methyl ester. This reaction will need reagent 2,2-Dimethoxypropane and catalyst p-Toluenesulfonic acid. The yield is about 68% at reaction temperature of 55 °C.

Benzeneacetic acid,4-chloro-a-hydroxy- can react with methanol to get 4-chloro-mandelic acid-methyl ester

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing and avoid contact with skin and eyes and do not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=CC(=CC=C1C(C(=O)O)O)C
(2)InChI: InChI=1S/C8H7ClO3/c9-6-3-1-5(2-4-6)7(10)8(11)12/h1-4,7,10H,(H,11,12)
(3)InChIKey: BWSFWXSSALIZAU-UHFFFAOYAU