2-Chloro-5-iodobenzoic acid Chemical Properties

Melting point:

157-161 °C (lit.)

Boiling point:

353.1±27.0 °C(Predicted)

Density 

2.077±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.53±0.25(Predicted)

color 

Yellow to light brown crystals or crystalline powder (light sensitive)

Sensitive 

Light Sensitive

BRN 

2254110

InChI

InChI=1S/C7H4ClIO2/c8-6-2-1-4(9)3-5(6)7(10)11/h1-3H,(H,10,11)

InChIKey

GEBYSTBEDVQOTK-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(I)=CC=C1Cl

CAS DataBase Reference

19094-56-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T,N,Xi

Risk Statements 

25-41-50/53

Safety Statements 

26-39-45-60-61

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Irritant

PackingGroup 

III

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-5-iodobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

2-Chloro-5-iodobenzoic Acid is a useful synthetic intermediate. It is used to prepare metabotropic glutamate receptor subtype-??2 (mGluR2) positive allosteric modulator (PAM). It is also used to synthesize quinolone carboxylic acids as cell-permeable inhibitors of protein tyrosine phosphatase.

Synthesis

The general procedure for the synthesis of 2-chloro-5-iodobenzoic acid from 5-amino-2-chlorobenzoic acid was as follows: 123 g of 2-chloro-5-aminobenzoic acid was added to 2000 g of 20% aqueous sulfuric acid solution, and the temperature of the reaction was maintained at 0 to 10 °C. An aqueous sodium nitrite solution (51 g sodium nitrite dissolved in 200 g water) was prepared and added drop by drop to the reaction system, and the progress of the reaction was monitored by TLC (unfolding agent ratio of petroleum ether/ethyl acetate = 1:3) during the reaction. Upon completion of the reaction, 1.2 g of urea was added and cooled to 0 °C with stirring, potassium iodide solution (130 g KI dissolved in 500 g of water) was quickly added and stirring was continued until no bubbles were produced and then stirred for 30 min. The reaction mixture was filtered and washed with 200 g of water to give a brown solid. The solid was dissolved in 400 g of ethyl acetate and washed sequentially with 300 mL of 1N hydrochloric acid, 300 mL of 10% sodium bisulfite solution and 400 mL of saturated brine, and the organic phase was dried with magnesium sulfate. After drying, the crude product was obtained by concentration under reduced pressure at 50 °C. The crude product was dissolved in 400 mL of toluene and heated at 80 °C for 1 hour, then cooled to 0-5 °C for 1 hour for crystallization. Finally, it was dried under reduced pressure at 50 °C to give 191 g of 2-chloro-5-iodobenzoic acid as a pale yellow solid with 99.6% purity and 93.7% yield.

References

[1] Patent: CN106748721, 2017, A. Location in patent: Paragraph 0031; 0032
[2] RSC Advances, 2017, vol. 7, # 86, p. 54881 - 54891

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