18698-96-9

Basic information

• Product Name: 2-Iodophenylacetic acid
• Synonyms: RARECHEM AL BO 1302;O-IODOPHENYLACETIC ACID;2-IODOPHENYLACETIC ACID;2-(2-IODOPHENYL)ACETIC ACID;BENZENEACETIC ACID, 2-IODO-;2-Iodo-benzeneacetic acid;2-IODOPHENYLACETIC ACID, 98+%;2-IODOPHENYLACETIC ACID, 97+%
• CAS NO: 18698-96-9
• Molecular Formula: C₈H₇IO₂
• Molecular Weight: 262.04
• EINECS: -0
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Phenylacetic acid;Miscellaneous;C8;Carbonyl Compounds;Carboxylic Acids
• Mol File: 18698-96-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 116-119 °C(lit.)
• Boiling Point: 344.5 °C at 760 mmHg
• Flash Point: 162.1 °C
• Appearance: Cream/Powder
• Density: 1.885 g/cm³
• Vapor Pressure: 2.5E-05mmHg at 25°C
• Refractive Index: 1.643
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: pK1:4.038 (25°C)
• Sensitive: Light Sensitive
• BRN: 2086800
• CAS DataBase Reference: 2-Iodophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Iodophenylacetic acid(18698-96-9)
• EPA Substance Registry System: 2-Iodophenylacetic acid(18698-96-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• HazardClass: IRRITANT, LIGHT SENSITIVE
• Hazardous Substances Data: 18698-96-9(Hazardous Substances Data)

Usage

Description

2-Iodophenylacetic acid is a substituted acetic acid that can be prepared from 2-iodobenzyl cyanide. It is a synthetic intermediate with a cream powder appearance, and it undergoes palladium-catalyzed reactions with allenes to form 1,3-butadienes. Additionally, it undergoes photolysis in carbon tetrachloride to form the corresponding chloro compound.

Uses

Used in Chemical Industry:
2-Iodophenylacetic acid is used as a synthetic intermediate for the production of various chemical compounds.
Used in Pharmaceutical Industry:
2-Iodophenylacetic acid is used as a reagent to synthesize Cepharanone B, a natural and potentially antineoplastic aristolactam found in Piper longum, a medicinal plant native to India.
Used in Cosmetic Industry:
2-Iodophenylacetic acid is used in the preparation of various cosmetic products.
Used in Research and Development:
2-Iodophenylacetic acid may be used in the preparation of:
2-iodophenylacetyl chloride
3,4-dimethoxyphenyl 2-iodophenylacetate
N-2-[2-(2-iodophenyl)-acetylamino]-ethyl-2-(3,4-dichlorophenyl)-acetamide
These applications highlight the versatility of 2-Iodophenylacetic acid in different industries, from chemical synthesis to pharmaceutical research and cosmetic product development.

Preparation

synthesis of 2-Iodophenylacetic acid: The anthranilic acid solution was acidified with sulfuric acid to pH = 1 followed by a diazotization reaction. The diazonium was added dropwise to the potassium iodide-sulfuric acid solution (3.5 g KI, 1.0 mL concentrated H2SO4, 5 mL water) preheated to 60-70 °C, stirred for 30 min, placed overnight, and filtered to obtain the product. Recrystallization with 50% ethanol aqueous solution gave 3.83 g of 2-iodophenylacetic acid, the yield was 73% (calculated as o-nitrophenylacetic acid), and the melting point was 113-115 °C (117 °C reported in the literature).

InChI:InChI=1/C8H7IO2/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4H,5H2,(H,10,11)

Upstream product

• 40400-13-3 2-Iodobenzyl bromide 
• 151-50-8 potassium cyanide 
• 40400-15-5 2-(2-iodophenyl)acetonitrile 
• 143-33-9 sodium cyanide 
• 66370-75-0 methyl (2-iodophenyl)acetate 
• 103-82-2 phenylacetic acid 
• 59-48-3 2-oxoindole 
• 52470-94-7 (2-iodophenyl)diazomethyl ketone 
• 59473-45-9 2-(chloromethyl)iodobenzene 
• 615-37-2 ortho-methylphenyl iodide 
• 95-53-4 o-toluidine 
• 5344-90-1 2-Aminobenzyl alcohol 
• 88-67-5 2-Iodobenzoic acid 
• 5159-41-1 2-iodobenzyl alcohol 

Downstream Products

• 90794-29-9 ethyl 2-(2-iodophenyl)acetate 
• 2005-16-5 (2-carboxymethyl-phenyl)-dichloro-λ³-iodane 
• 54997-35-2 2-(4-Cyclopropylphenylthio)phenylessigsaeure 
• 40400-30-4 2-(4-Methylselenphenylthio)-phenylessigsaeure 
• 54920-95-5 [2-(2-amino-5-chloro-phenylsulfanyl)-phenyl]-acetic acid 
• 26059-40-5 2-(2-iodophenyl)ethan-1-ol 
• 20904-50-1 2-(4-Amino-phenylmercapto)-phenylessigsaeure 
• 13420-57-0 (2-(2-Chlorophenylthio)phenyl)acetic Acid 
• 111400-25-0 (2-(4-dimethylaminophenylthio)phenyl)acetic acid 
• 84964-61-4 <2-(3-Methylphenylthio)phenyl>acetic Acid 
• 16175-07-8 2-<2-(4-methylthiophenylthio)phenyl>acetic acid 
• 16174-91-7 <2-(3-trifluoromethylphenylthio)phenyl>acetic acid 
• 80709-55-3 <2-(3,4-dimethoxyphenylthio)phenyl>acetic acid 
• 76242-88-1 <2-(3-fluorophenylthio)phenyl>acetic acid 

Relevant articles and documents

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Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2

The first ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2 to generate important aryl acetic acids is reported. Besides aldehyde hydrazones, a variety of ketone hydrazones, which have not been successfully applied in previous umpolung reactions with other reactive electrophiles, also show high reactivity and selectivity under mild conditions. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and offers easy derivation of important structures, including bioactive felbinac and adiphenine. Computational studies reveal that this umpolung reaction proceeds through the generation of a Ru-nitrenoid followed by concerted [4 + 2] cycloaddition with CO2.

Expedient drug synthesis and diversification via ortho-C-H iodination using recyclable PdI2 as the precatalyst

(Figure Presented) Pd(II)-catalyzed ortho-C-H iodination reactions of phenylacetic acid substrates have been achieved using recyclable PdI2 as the precatalyst. This class of substrates is incompatible with the classic amide formation/ortho-lithiation/iodination sequence. The power of this new technology is demonstrated by facile drug functionalization and drastically shortened syntheses of the drugs diclofenac and lumiracoxib.