2-Iodo-3-methylbenzoic acid

Base Information

• Chemical Name: 2-Iodo-3-methylbenzoic acid
• CAS No.: 108078-14-4
• Molecular Formula: C8H7IO2
• Molecular Weight: 262.047
• Hs Code.: 29163990
• European Community (EC) Number: 675-836-8
• DSSTox Substance ID: DTXSID50374763
• Wikidata: Q82163328
• Mol file: 108078-14-4.mol

Synonyms:2-Iodo-3-methylbenzoic acid;108078-14-4;2-IODO-M-TOLUIC ACID;MFCD00079764;2-iodo-3-methyl-benzoic Acid;Benzoic acid,2-iodo-3-methyl-;2-Iodo-3-methylbenzoicacid;3-methyl-2-iodobenzoic acid;SCHEMBL350506;2-Iodo-3-methyl benzoic acid;DTXSID50374763;PZUXUOZSSYKAMX-UHFFFAOYSA-N;AMY28378;2-Iodo-3-methylbenzoic acid, 97%;AKOS000140314;CS-W007789;AS-20027;SY025091;FT-0600047;EN300-39534;A801804;J-002053;Z239685230

Chemical Property of 2-Iodo-3-methylbenzoic acid

Chemical Property:

• Vapor Pressure: 0.000107mmHg at 25°C
• Melting Point: 150-153 °C(lit.)
• Refractive Index: 1.645
• Boiling Point: 323.512 °C at 760 mmHg
• PKA: 2.93±0.10(Predicted)
• Flash Point: 149.455 °C
• PSA: 37.30000
• Density: 1.868 g/cm³
• LogP: 2.29780
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• 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%,99%, ^*data from raw suppliers

2-Iodo-3-methylbenzoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=CC=C1)C(=O)O)I
• Uses: 2-Iodo-3-methylbenzoic acid may be used in the synthesis of:methyl 2-iodo-3-methylbenzoate 10,11-dihydro-10-oxodibenz[b,f]oxepin-4-acetic acid5-methyl-3-pentyl-1H-isochromen-1-one

Technology Process of 2-Iodo-3-methylbenzoic acid

There total 7 articles about 2-Iodo-3-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: 92.0%

3-methylantranilic acid (4389-45-1) → 2-iodo-3-methylbenzoic acid (108078-14-4)

Guidance literature:

3-methylantranilic acid; With hydrogenchloride; In water; at 0 ℃; for 0.25h;

With sodium nitrite; In water; at 0 ℃; for 1.66667h;

With potassium iodide; In water; at 0 - 20 ℃; for 24.33h;

DOI:10.1002/adsc.201901356

Reference yield:

3-methyl-2-nitrobenzoic acid (5437-38-7) → 2-iodo-3-methylbenzoic acid (108078-14-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

2.1: H₂SO₄ / H₂O / 1 h / 20 °C

2.2: NaNO₂ / H₂O / 1.5 h / 10 °C

2.3: 84 percent / KI; Cu powder / H₂O / 30 °C

With sulfuric acid; hydrogen; palladium on activated charcoal; In ethanol; water;

DOI:10.1021/jo0302408

Reference yield:

m-Toluic acid (99-04-7) → 2-iodo-3-methylbenzoic acid (108078-14-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 46 percent / HNO₃ / 1 h / -10 °C

2.1: 99 percent / H₂ / Pd/C / ethanol / 20 °C / 760 Torr

3.1: H₂SO₄ / H₂O / 1 h / 20 °C

3.2: NaNO₂ / H₂O / 1.5 h / 10 °C

3.3: 84 percent / KI; Cu powder / H₂O / 30 °C

With sulfuric acid; hydrogen; nitric acid; palladium on activated charcoal; In ethanol; water;

DOI:10.1021/jo0302408

upstream raw materials:

3-methylantranilic acid

3-methyl-2-nitrobenzoic acid

m-Toluic acid

3-Methyl-2-nitrobenzenecarboxamide

Downstream raw materials:

methyl 2-iodo-3-methylbenzoate

2-iodo-3-methylbenzoyl chloride

(2-iodo-3-methylphenyl)methanol

2-iodo-3-methylbenzoic acid ethyl ester

Refernces

• 1、 Boelke, Andreas,Caspers, Lucien D.,Kuczmera, Thomas J.,Lork, Enno,Nachtsheim, Boris J.. "Iodolopyrazolium Salts: Synthesis, Derivatizations, and Applications". supporting information. p. 7261 - 7266. Retrieved 2020/10/05.
• 2、 Dang, Pan,Zheng, Zhilei,Liang, Yun. "Copper-Catalyzed C(sp3)-S Bond and C(sp2)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds". . p. 2263 - 2268. Retrieved 2017/02/26.