2-Chloromandelic acid Chemical Properties

Melting point:

90-93 °C(lit.)

Boiling point:

266.91°C (rough estimate)

Density 

1.3245 (rough estimate)

refractive index 

1.5250 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly, Sonicated), Methanol (Slightly)

form 

Crystalline Powder

pka

3.30±0.10(Predicted)

color 

White to pale cream

Water Solubility 

Very soluble in water.

BRN 

2367070

Stability:

Hygroscopic

InChI

InChI=1S/C8H7ClO3/c9-6-4-2-1-3-5(6)7(10)8(11)12/h1-4,7,10H,(H,11,12)

InChIKey

RWOLDZZTBNYTMS-UHFFFAOYSA-N

SMILES

C(C1C=CC=CC=1Cl)(O)C(=O)O

CAS DataBase Reference

10421-85-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

HS Code 

29181990

MSDS

• Language:English Provider:o-Chloromandelic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Chloromandelic acid Usage And Synthesis

Chemical Properties

White to pale cream crystalline powder

Uses

2-Chloromandelic acid, is used as a pharmaceutical intermediate as well as in the medicine industry. It is used as a intermediate of clopidrogrel.

General Description

2-Chloromandelic acid (2-ClMA) is a mandelic acid derivative. A report based on its solid state-NMR, X-ray powder diffraction (XPRD) and Fourier transform infrared spectroscopy (FTIR) data reveals that in solid state 2-ClMA exists as a racemic compound. The study also suggests that the crystals of racemic 2-ClMA belongs the monoclinic space group P21/c. The efficiency of (R)-(+)-N-benzyl-1-phenylethylamine in resolving racemate 2-ClMA has been investigated.

Synthesis

First, 150 mL of toluene was added to a flask equipped with a stirrer and an internal thermometer. Under stirring conditions, 0.09 g (0.08 x 10^-3 mol) of the (R,R)-VO salen complex from Example 1 and 21.1 g (0.15 mol) of freshly prepared 2-chlorobenzaldehyde were added sequentially. Subsequently, 10.1 g (0.375 mol) of hydrocyanic acid was added all at once. The resulting dark green homogeneous solution was stirred for 24 h at room temperature in a closed apparatus. The conversion was analyzed by gas chromatography (GC) to be 98% and the enantiomeric excess (ee) value of (S)-2-chloromandelate cyanohydrin was 73%.

References

[1] Patent: US2004/236129, 2004, A1. Location in patent: Page 4
[2] Patent: US2004/236129, 2004, A1. Location in patent: Page 4
[3] Patent: US2004/236129, 2004, A1. Location in patent: Page 4
[4] Patent: US2004/236129, 2004, A1. Location in patent: Page 4
[5] Patent: US2004/236129, 2004, A1. Location in patent: Page 4

2-Chloromandelic acid(10421-85-9)Related Product Information

• 2-Chloroaniline
• Ethyl 2-(Chlorosulfonyl)acetate
• DL-Malic acid
• Mandelic acid
• Folic acid
• Stearic acid
• 2-Chlorotoluene
• 2-(Chloromethyl)benzonitrile
• (S)-(+)-Mandelic acid
• Hyaluronic acid
• Sodium cloxacillin monohydrate
• 2-Chlorobenzotrifluoride
• Citric acid
• α-Lipoic Acid
• Ascoric Acid
• 2-Fluoropropiophenone
• 2-Chlorobenzyl alcohol
• 2-Fluorobenzaldehyde