18698-96-9 Usage
Chemical Properties
Cream powder
Uses
2-Iodophenylacetic acid is a synthetic intermediate that is widely used in the chemical, pharmaceutical and cosmetic industries. 2-Iodophenylacetic acid is also used as a reagent to synthesize Cepharanone B, a natural and potentially antineoplastic aristolactam that is found in Piper longum (a medicinal plant native to India).
Application
2-Iodophenylacetic acid may be used in the preparation of:2-iodophenylacetyl chloride3,4-dimethoxyphenyl 2-iodophenylacetateN-{2-[2-(2-iodophenyl)-acetylamino]-ethyl}-2-(3,4- dichlorophenyl)-acetamide
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).
General Description
2-Iodophenylacetic acid is a substituted acetic acid that can be prepared from 2-iodobenzyl cyanide. It undergoes palladium-catalyzed reaction with allenes to form 1,3-butadienes. 2-Iodophenylacetic acid also undergoes photolysis in carbon tetrachloride to form the corresponding chloro compound.
Check Digit Verification of cas no
The CAS Registry Mumber 18698-96-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,8,6,9 and 8 respectively; the second part has 2 digits, 9 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 18698-96:
(7*1)+(6*8)+(5*6)+(4*9)+(3*8)+(2*9)+(1*6)=169
169 % 10 = 9
So 18698-96-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H7IO2/c9-7-4-2-1-3-6(7)5-8(10)11/h1-4H,5H2,(H,10,11)
18698-96-9Relevant articles and documents
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Dippy,Lewis
, p. 644,648 (1936)
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Ruthenium-catalyzed umpolung carboxylation of hydrazones with CO2
Yan, Si-Shun,Zhu, Lei,Ye, Jian-Heng,Zhang, Zhen,Huang, He,Zeng, Huiying,Li, Chao-Jun,Lan, Yu,Yu, Da-Gang
, p. 4873 - 4878 (2018/06/07)
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
Mei, Tian-Sheng,Wang, Dong-Hui,Yu, Jin-Quan
supporting information; experimental part, p. 3140 - 3143 (2010/09/03)
(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.
