2-Iodo-4-methylbenzoic acid

Base Information

• Chemical Name: 2-Iodo-4-methylbenzoic acid
• CAS No.: 1829-21-6
• Molecular Formula: C8H7IO2
• Molecular Weight: 262.047
• Hs Code.: 2916399090
• DSSTox Substance ID: DTXSID10401569
• Wikidata: Q82204744
• Mol file: 1829-21-6.mol

Synonyms:2-iodo-4-methylbenzoic acid;1829-21-6;Benzoic acid, 2-iodo-4-methyl-;MFCD01312232;3-iodo-4-toluic acid;2-iodo-4-methylbenzoicacid;4-methyl-2-iodobenzoic acid;SCHEMBL9741686;WNVUYAMRIXEZAT-UHFFFAOYSA-;DTXSID10401569;WNVUYAMRIXEZAT-UHFFFAOYSA-N;BAA82921;SC5074;AKOS027252479;AS-10131;SY245079;CS-0041338;InChI=1/C8H7IO2/c1-5-2-3-6(8(10)11)7(9)4-5/h2-4H,1H3,(H,10,11)

Chemical Property of 2-Iodo-4-methylbenzoic acid

Chemical Property:

• Melting Point: 134-136 °C
• Boiling Point: 335.2±30.0 °C(Predicted)
• PKA: 3.03±0.10(Predicted)
• PSA: 37.30000
• Density: 1.867±0.06 g/cm3(Predicted)
• LogP: 2.29780
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 261.94908
• Heavy Atom Count: 11
• Complexity: 158

Purity/Quality:

98%Min ^*data from raw suppliers

2-Iodo-4-methylbenzoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C(C=C1)C(=O)O)I

Technology Process of 2-Iodo-4-methylbenzoic acid

There total 9 articles about 2-Iodo-4-methylbenzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

2-bromo-4-methylbenzoic acid (7697-27-0) → 4-methyl-2-iodobenzoic acid (1829-21-6)

Guidance literature:

2-bromo-4-methylbenzoic acid; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

With iodine; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201900242 DOI:10.1002/cmdc.201900618

Reference yield: 74.0%

p-Toluic acid (99-94-5) → 4-methyl-2-iodobenzoic acid (1829-21-6)

Guidance literature:

With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; iodine; silver(I) acetate; triethylamine; at 23 ℃; for 2h; regioselective reaction; Sealed tube;

DOI:10.1002/chem.202002204

Reference yield: 64.0%

(2-iodo-4-methylphenyl)methanol (126156-20-5) → 4-methyl-2-iodobenzoic acid (1829-21-6) + 2-iodo-4-methylbenzaldehyde (126156-28-3)

Guidance literature:

With potassium permanganate; tetrabutylammomium bromide; In water; benzene; for 3h; Ambient temperature;

DOI:10.1021/jo00305a011

upstream raw materials:

4-methylanthranilic acid

2-iodo-4-methylbenzaldehyde

(2-iodo-4-methylphenyl)methanol

2-iodo-4-methylbenzonitrile

Downstream raw materials:

methyl 2-iodo-4-methylbenzoate

4-methyl-2-(phenylamino)benzoic acid

C₁₅H₁₅NO

C₁₅H₁₇NO

Refernces

• 1、 Bolli, Martin H.,Boss, Christoph,Brotschi, Christine,Gatfield, John,Heidmann, Bibia,Jenck, Francois,Roch, Catherine,Sifferlen, Thierry,Treiber, Alexander,Williams, Jodi T.. "From Oxadiazole to Triazole Analogues: Optimization toward a Dual Orexin Receptor Antagonist with Improved in vivo Efficacy in Dogs". supporting information. . Retrieved 2020/01/25.
• 2、 Wang, Junliang,Dong, Cong,Wu, Liangfei,Xu, Mingkai,Lin, Jun,Wei, Kun. "Palladium-Catalyzed β-C?H Arylation of Ketones Using Amino Amide as a Transient Directing Group: Applications to Synthesis of Phenanthridinone Alkaloids". supporting information. p. 3709 - 3715. Retrieved 2018/09/14.