3-Iodobenzoic acid

3-Iodobenzoic acid Property

Melting point:

185-187 °C(lit.)

Boiling point:

337.2±25.0 °C(Predicted)

Density 

2.2170 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Powder

pka

3.8(at 25℃)

color 

White to beige

Water Solubility 

Soluble in Chloroform and Methanol. Insoluble in water.

Sensitive 

Light Sensitive

BRN 

971088

InChI

InChI=1S/C7H5IO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4H,(H,9,10)

InChIKey

KVBWBCRPWVKFQT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

618-51-9(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3-iodo-(618-51-9)

EPA Substance Registry System

Benzoic acid, 3-iodo- (618-51-9)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

T

HazardClass 

IRRITANT, LIGHT SENSITIVE

HS Code 

29163990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

3-Iodobenzoic acid Chemical Properties,Usage,Production

Description

3-Iodobenzoic acid is added as UV absorbing background electrolyte in separation of uncharged cyclodextrins and their derivatives by capillary electrophoresis.3-Iodobenzoic acid was used in solid phase synthesis of γ-turn mimetic library.

Chemical Properties

white to beige powder

Uses

suzuki reaction

Uses

3-Iodobenzoic acid is used in solid phase synthesis of γ-turn mimetic library. It is used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Uses

3-Iodobenzoic acid was used in solid phase synthesis of γ-turn mimetic library.

Definition

ChEBI: 3-iodobenzoic acid is an iodobenzoic acid with a single iodo substituent placed at the 3-position.

General Description

3-Iodobenzoic acid is added as UV absorbing background electrolyte in separation of uncharged cyclodextrins and their derivatives by capillary electrophoresis.

Synthesis

The general procedure for the synthesis of 3-iodobenzoic acid from 3-carboxyphenylboronic acid was as follows: arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0 mg) were added to a 20 mL Schlenk tube fitted with a non-magnetic stir bar. The Schlenk tube was evacuated twice and backfilled with N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg) were added to the tube at room temperature. The Schlenk tube was sealed and placed in a preheated oil bath at 80 °C for 8-12 h under a stream of N2 gas. After completion of the reaction, the resulting solution was cooled to room temperature. H2O (10 mL) was added, and for the product 3-iodobenzoic acid, 1 M HCl was added to the aqueous solution until the pH reached 2 prior to extraction.The aqueous layer was extracted with EtOAc (3 x 5 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated by rotary evaporation. Finally, the residue was purified by silica gel column chromatography to obtain the target product 3-iodobenzoic acid.

Purification Methods

Crystallise the acid repeatedly from water and EtOH. Sublime it under vacuum at 100o. [Beilstein 9 IV 1033.]

References

[1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000
[2] Chemistry - A European Journal, 2011, vol. 17, # 20, p. 5652 - 5660