4-Chlorocinnamic acid Chemical Properties

Melting point:

248-250 °C(lit.)

Boiling point:

260.71°C (rough estimate)

Density 

1.2377 (rough estimate)

refractive index 

1.5426 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

4.41(at 25℃)

form 

Fine Crystalline Powder

color 

White

BRN 

1365308

InChI

InChI=1S/C9H7ClO2/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6H,(H,11,12)

InChIKey

GXLIFJYFGMHYDY-ZZXKWVIFSA-N

SMILES

C(O)(=O)C=CC1=CC=C(Cl)C=C1

CAS DataBase Reference

1615-02-7(CAS DataBase Reference)

NIST Chemistry Reference

p-Chlorocinnamic acid(1615-02-7)

EPA Substance Registry System

2-Propenoic acid, 3-(4-chlorophenyl)- (1615-02-7)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38-20/21/22

Safety Statements 

36-28A-26-24/25

WGK Germany 

3

RTECS 

GD8490000

Hazard Note 

Irritant

HS Code 

29163990

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

MSDS

• Language:English Provider:4-Chlorocinnamic acid
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4-Chlorocinnamic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

4-Chlorocinnamic Acid is a derivative of Cinnamic Acid (C442030) and plays an important role in the development of plants. 4-Chlorocinnamic Acid may also show potential antimicrobial, antioxidant, anti-inflammatory, and antitumoral activity.

Definition

ChEBI: 4-chlorocinnamic acid is an organochlorine compound comprising trans-cinnamic acid having a chloro substituent at the 4-position on the phenyl ring. It is functionally related to a trans-cinnamic acid.

Synthesis

To a 100mL three-necked round-bottomed flask, 1.41g (0.01mol) of p-chlorobenzaldehyde, 1.27g (0.011mol) of malonic acid, and 0.77g (0.01mol) of ammonium acetate were added and mixed well. A thermometer and a spherical condenser tube were connected and the reaction was carried out in a microwave reactor. After the reaction was completed, 5 mL of water was heated into the flask and the unreacted p-chlorobenzaldehyde was removed by distillation with water vapor. Add 10% sodium hydroxide solution 5mL to 6mL, add activated carbon to remove the color, extract filtration, transfer the filtrate to a beaker, acidify with concentrated hydrochloric acid until the Congo red paper turns blue or pH = 3 to 4. Cool to precipitate the crystals, extract filtration, wash the precipitate with a small amount of water, extract dry, and dry the crude product. Recrystallize with water-ethanol (1:3 v/v) and dry. The yield was calculated, and the optimal synthesis conditions were: material ratio of n(p-chlorobenzaldehyde):n(malonic acid):n(ammonium acetate) = 1.0:1.1:1.0, reaction time of 13 min, power of 800 W, and a yield of 85.8% under these conditions. Melting point determination and infrared spectral analysis were carried out. Compared with the traditional method, it has the advantages of short time, high yield and less pollution.

Purification Methods

Recrystallise the acid from EtOH or aqueous EtOH (charcoal). UV has max at 275nm (EtOH). [Walling & Wolfstirn J Am Chem Soc 69 852 1947, Beilstein 9 H 596, 9 II 395, 9 III 2727, 9 IV 2033.]

4-Chlorocinnamic acid(1615-02-7)Related Product Information

• Ethyl cinnamate
• 3-(Trifluoromethyl)cinnamic acid
• Cinnamic acid
• Propyl cinnamate
• Stearic acid
• Octyl 4-methoxycinnamate
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Methyl cinnamate
• trans-Cinnamic acid
• Citric acid
• 4-Methoxycinnamic acid
• Ascoric Acid
• 3,4-Dichlorocinnamic acid
• 3-Nitro-4-chlorocinnamic acid
• TRANS-2,4-DICHLOROCINNAMIC ACID
• 2-Chlorocinnamic acid
• 5-Nitro-2-chlorocinnamic acid