2-Iodobenzoic acid

Synonym(s):o-Iodobenzoic acid;IBA

CAS NO.：88-67-5
Empirical Formula: C7H5IO2
Molecular Weight: 248.02
MDL number: MFCD00002419
EINECS: 201-850-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-19 23:02:33

What is 2-Iodobenzoic acid?

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.

The Uses of 2-Iodobenzoic acid

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.

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.]

Properties of 2-Iodobenzoic acid

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
form	Powder, Crystals or Flakes
pka	2.85(at 25℃)
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.
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 for 2-Iodobenzoic acid

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H302:Acute toxicity,oral H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.