2-Iodobenzoic acid Chemical Properties

Melting point:

160-162 °C(lit.)

Boiling point:

313.9±25.0 °C(Predicted)

Density 

2.25

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in dimethyl sulfoxide and methanol

pka

2.85(at 25℃)

form 

Powder, Crystals or Flakes

color 

Light yellow to orange-brown

Water Solubility 

sparingly soluble

Sensitive 

Light Sensitive

Merck 

14,5030

BRN 

1861406

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

InChIKey

CJNZAXGUTKBIHP-UHFFFAOYSA-N

CAS DataBase Reference

88-67-5(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 2-iodo-(88-67-5)

EPA Substance Registry System

Benzoic acid, 2-iodo- (88-67-5)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-37/38-41-36/37/38-20/21/22

Safety Statements 

26-39-24/25-22-36

WGK Germany 

3

RTECS 

DH2975000

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29163900

MSDS

• Language:English Provider:2-Iodobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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2-Iodobenzoic acid Usage And Synthesis

Description

2-iodobenzoic acid and its derivatives are important pharmaceutical and chemical raw materials, which are necessary for the synthesis of various high-iodine reagents. It is commonly used as a precursor for the synthesis of 2-Iodoxybenzoic acid (IBX) and Dess-Martin peridinane, which are used as mild oxidants. It is also used in Suziki reaction.

Chemical Properties

white crystal powder. Soluble in alcohol and ether, insoluble in water.

Uses

Reagent for detection of sulfhydryl groups in proteins. 2-Iodobenzoic acid acts as a precursor in the preparation of 2-Iodoxybenzoic acid (IBX) and Dess-Martin periodinane, which finds application as an oxidizing agent in synthetic chemistry. It is also used in Suzuki reaction.

Preparation

2-Iodobenzoic acid is obtained from Anthranilic acid by diazotization and substitution. Diazotization of Anthranilic acid with sodium nitrite in the presence of sulfuric acid, control the temperature below 10℃, filter the diazotization solution, add the mixture of potassium iodide and sulfuric acid, stir for 10min after addition, and boil. Filter, wash with sodium thiosulfate solution, 2-Iodobenzoic acid can be recrystallized from water.

Definition

ChEBI: An iodobenzoic acid with a single iodo substituent placed at the 2-position.

Application

2-Iodobenzoic acid can be used as a reactant in the synthesis of oligo(m-phenylene ethynylenes), (±)-lycoricidine and various detoxifiers of organophosphorus nerve agents. Additionally, it is used as a precursor in the preparation of oxidizing reagents like 2-iodoxybenzoic acid (IBX) and Dess-Martin periodinane (DMP).

Synthesis Reference(s)

Journal of the American Chemical Society, 93, p. 4841, 1971 DOI: 10.1021/ja00748a029

Purification Methods

Crystallise the acid repeatedly from water and EtOH. Sublime it under vacuum at 100o. [Beilstein 9 IV 1030.]

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