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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.

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  • 18698-96-9 Structure
  • Basic information

    1. Product Name: 2-Iodophenylacetic acid
    2. 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+%
    3. CAS NO:18698-96-9
    4. Molecular Formula: C8H7IO2
    5. Molecular Weight: 262.04
    6. EINECS: -0
    7. Product Categories: Aromatic Phenylacetic Acids and Derivatives;Phenylacetic acid;Miscellaneous;C8;Carbonyl Compounds;Carboxylic Acids
    8. Mol File: 18698-96-9.mol
  • Chemical Properties

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

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-37
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT, LIGHT SENSITIVE
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 18698-96-9(Hazardous Substances Data)

18698-96-9 Usage

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).

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)

18698-96-9 Well-known Company Product Price

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  • Alfa Aesar

  • (L15116)  2-Iodophenylacetic acid, 98+%   

  • 18698-96-9

  • 1g

  • 211.0CNY

  • Detail
  • Alfa Aesar

  • (L15116)  2-Iodophenylacetic acid, 98+%   

  • 18698-96-9

  • 5g

  • 704.0CNY

  • Detail

18698-96-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(2-iodophenyl)acetic acid

1.2 Other means of identification

Product number -
Other names 2-(2-Iodophenyl)acetic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:18698-96-9 SDS

18698-96-9Relevant articles and documents

Gold-catalyzed intermolecular [4+1] spiroannulation: via site-selective aromatic C(sp2)-H functionalization and dearomatization of phenol derivatives

Li, Yongfeng,Liu, Lu,Tang, Zhiqiong,Zhang, Junliang

supporting information, p. 8202 - 8205 (2020/08/17)

Herein, we have developed a novel and simple protocol to realize the C-H bond functionalization/dearomatization of naphthols and phenols with ortho-alkynylaryl-α-diazoesters under gold(i) catalysis. In this protocol, various spirocyclic molecules could be obtained in good yields with excellent chemo- and regio-selectivity and moderate to good diastereoselectivity. This journal is

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.

Stereospecific Synthesis of Tetrahydronaphtho[2,3-b]furans Enabled by a Nickel-Promoted Tandem Reductive Cyclization

Peng, Yu,Xiao, Jian,Xu, Xiao-Bo,Duan, Shu-Ming,Ren, Li,Shao, Yong-Liang,Wang, Ya-Wen

supporting information, p. 5170 - 5173 (2016/10/14)

A Ni-mediated cascade to a stereoselective synthesis of trans-tetrahydronaphtho[2,3-b]furans is efficiently achieved for the first time. The mild reductive system can be easily generated from inexpensive and air-stable materials and shows a broad positional tolerance of substituents that were previously difficult or impossible to access by other methods. Facile syntheses toward new analogues of therapeutic agents (iso)deoxypodophyllotoxin are also reported. In addition, the inherent substrate control is disclosed for the observed unique stereoselectivities during cyclizations.

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.

Silver nanocluster redox-couple-promoted nonclassical electron transfer: An efficient electrochemical wolff rearrangement of α-diazoketones

Sudrik, Surendra G.,Chaki, Nirmalya K.,Chavan, Vilas B.,Chavan, Sambhaji P.,Chavan, Subhash P.,Sonawane, Harikisan R.,Vijayamohanan

, p. 859 - 864 (2007/10/03)

In this work we report the unique electrocatalytic role of benzoic acid protected silver nanoclusters (Agn, mean core diameter 2.5 nm) in the Wolff rearrangement (Scheme 1) of α-diazoketones. More specifically, the presence of a Agn0/Agn+ redox couple facilitates a nonclassical electron-transfer process, involving chemical reaction(s) interposed between two electron-transfer steps occurring in opposite directions. Consequently, the net electron transfer between the electron mediator (Agn) and α-diazoketone is zero. In-situ UV-visible studies using pyridine as a nucleophilic probe indicate the participation of α-ketocarbene/ketene as important reaction intermediates. Controlled potential coulometry of α-diazoketones using Agn as the anode results in the formation of Wolff rearranged carboxylic acids in excellent yield, without sacrificing the electrocatalyst.

Wolff rearrangement of α-diazoketones using in situ generated silver nanoclusters as electron mediators

Sudrik, Surendra G.,Sharma, Jadab,Chavan, Vilas B.,Chaki, Nirmalya K.,Sonawane, Harikisan R.,Vijayamohanan, Kunjukrishna P.

, p. 1089 - 1092 (2007/10/03)

We report Wolff rearrangement of α-diazoketones by in situ generated silver nanoclusters (Agn, 2-4 nm) from silver(I) oxide (Ag 2O) involving a nonclassical electron-transfer process. Our results show that Agn+/Agn0 redox couple allows the initial removal of an electron from α-diazoketone and its back-donation after chemical reaction(s). Controlled potential coulometry (CPC) of various α-diazoketones results in the realization of Wolff-rearranged carboxylic acids in excellent yields.

Copper(I) mediated intramolecular cyclization of 2-(2-amino-phenylethynyl)benzoic and [2-(2-aminophenylethynyl)phenyl]acetic acid esters: A new synthetic step towards isoindolo[2,1-a]indoles and 5H-indolo[2,1-a]isoquinolines

Reboredo, Francisco J.,Treus, Mónica,Estévez, Juan C.,Castedo, Luis,Estévez, Ramón J.

, p. 1603 - 1606 (2007/10/03)

We describe herein parallel synthetic routes to isoindolo[2,1-a]indoles and 5H-indolo[2,1-a]isoquinolines from 2-(2-aminophenylethynyl)benzoic acid esters and [2-(2-aminophenylethynyl)phenyl]acetic acid esters, respectively.

Regioselective synthesis of isoquino[1,2-b][3]benzazepines (homoprotoberberines) through 11-membered-ring stilbene lactams obtained by radical macrocyclization

Rodriguez, Gema,Castedo, Luis,Dominguez, Domingo,Saa, Carlos,Adam, Waldemar

, p. 4830 - 4833 (2007/10/03)

Silylated 11-membered-ring stilbene lactams 3 (E and Z) were easily prepared by intramolecular addition of an aryl radical to a trimethylsilylacetylene. Oxidation of their hindered stilbene double bonds with dioxiranes gave oxidative cleavage of their electron-rich aromatic rings. However, reduction of the amide to an amine functionality in both lactams (E and Z) triggers a regioselective [7,6]-transannular cyclization to isoquino[1,2-b][3]benzazepines (homoprotoberberines).

Controlled double-bond migration in palladium-catalyzed intramolecular arylation of enamidines

Ripa, Lena,Hallberg, Anders

, p. 7147 - 7155 (2007/10/03)

Palladium-catalyzed intramolecular cyclization of N-(N′-tert-butylformimidoyl)-6-[2-(2-iodophenyl)-ethyl]-1,2,3,4- tetrahydropyridine (1a) and N-(N′-tert-butylformimidoyl)-6-[3-(2-iodophenyl)propyl]-1,2,3,4- tetrahydropyridine (1b) respectively results in formation of spiro compounds 1′-(N-tert-butylformimidoyl)-3′,4′-dihydrospiro[indan-1, 2′(1′H)-pyridine] (4a), 1′-(N-tert-butylformimidoyl)-1′,6′-dihydrospiro[indan-1, 2′(3′H)-pyridine] (5a), and 1′-(N-tert-butylformimidoyl)-5′,6′-dihydrospiro[indan-1, 2′(1′H)-pyridine] (6a) and 1′-(N-tert-butylformimidoyl)-3,3′,4,4′- tetrahydrospiro[naphthalene-1(2H),2′(1′H)-pyridine] (4b), 1′-(N-tert-butylformimidoyl)-1′,3,4,6′- tetrahydrospiro[naphthalene-1(2H),2′(3′H)-pyridine] (5b), and 1′-(N-tert-butylformimidoyl)-3,4,5′,6′- tetrahydrospiro[naphthalene-1(2H),2′(1′H)-pyridine] (6b). The double-bond migration process can be controlled, and any of the three double-bond isomers can be prepared by employing proper ligands. A combination of BINAP and the amidine function was required to obtain the isomers 5a and 5b with the double bond in the homoallylic position relative to the aryl group. An electrospray ionization mass spectrometric study was conducted to support suggested reaction intermediates.

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