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2-Chlorocinnamic acid

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2-Chlorocinnamic acid Basic information

Product Name:
2-Chlorocinnamic acid
Synonyms:
  • AKOS BBS-00006452
  • AKOS B004073
  • AKOS BBB/195
  • 3-(2-CHLOROPHENYL)PROPENOIC ACID
  • 3-(2-CHLORO-PHENYL)-ACRYLIC ACID
  • RARECHEM BK HC T319
  • OTAVA-BB BB0125160239
  • O-CHLOROCINNAMIC ACID
CAS:
3752-25-8
MF:
C9H7ClO2
MW:
182.6
EINECS:
223-154-2
Product Categories:
  • Aromatic Cinnamic Acids, Esters and Derivatives
  • Cinnamic acid
  • Acids & Esters
  • Chlorine Compounds
  • 3752-25-8
Mol File:
3752-25-8.mol
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2-Chlorocinnamic acid Chemical Properties

Melting point:
208-210 °C(lit.)
Boiling point:
260.71°C (rough estimate)
Density 
1.2377 (rough estimate)
refractive index 
1.5426 (estimate)
storage temp. 
Room temperature.
solubility 
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Water Solubility 
Insoluble in water
form 
powder to crystal
pka
4.23(at 25℃)
color 
White to Almost white
BRN 
1365198
InChIKey
KJRRTHHNKJBVBO-AATRIKPKSA-N
CAS DataBase Reference
3752-25-8(CAS DataBase Reference)
NIST Chemistry Reference
2-Chlorocinnamic acid(3752-25-8)
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Safety Information

Hazard Codes 
Xn,Xi
Risk Statements 
20/21/22-36/37/38-22
Safety Statements 
36-26-36/37
WGK Germany 
3
RTECS 
GD8450000
Hazard Note 
Irritant
HS Code 
29124990

MSDS

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2-Chlorocinnamic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder. Insoluble in water, soluble in ethanol, ethyl acetate and other organic solvents.

Uses

2-Chlorocinnamic acid is a kind of trans-cinnamate. It is used in organic synthesis.

Biological Functions

2-Chlorocinnamic acid is a cinnamic acid derivative that inhibits the hydroxylation of phenylpropanoids. It has been shown to inhibit the activity of cinnamic acid derivatives and their hydroxylation in cell lines, which is linked to the inhibition of cellulose acetate synthesis. 2-Chlorocinnamic acid also has an inhibitory effect on the chloride ion and water molecule. The chloride ion may be needed for the formation of hydrochloric acid, which is necessary for cellulose acetate hydrolysis, while water molecules are involved in many biochemical reactions. 2-Chlorocinnamic acid affects human cell lines at temperatures between 10°C and 37°C and at regiospecific sites. This oxidative dehalogenation reaction catalyzed by R. rubra was found to be regiospecific for 2-chlorocinnamic acid; the chloride ion was probably removed after the ring fission reaction.

Synthesis

O-chlorocinnamic acid is prepared by reacting o-phthalaldehyde with malonic acid.

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