o-Toluic acid

Base Information

• Chemical Name: o-Toluic acid
• CAS No.: 118-90-1
• Molecular Formula: C8H8O2
• Molecular Weight: 136.15
• Hs Code.: 29163900
• European Community (EC) Number: 204-284-9
• NSC Number: 2193
• UNII: 9NR3033Y0U
• DSSTox Substance ID: DTXSID6026161
• Nikkaji Number: J10.074I
• Wikipedia: O-Toluic_acid
• Wikidata: Q3291707
• Metabolomics Workbench ID: 52164
• ChEMBL ID: CHEMBL114957
• Mol file: 118-90-1.mol

Synonyms:o-Toluate;2-Methylbenzoic acid;o-Methylbenzoic acid;o-Methylbenzoate;2-methylbenzoate;Orthotoluic acid;Benzoic acid, 2-methyl-;Toluic acid;2-Methylbenzoic acid;o-Toluic acid;

Chemical Property of o-Toluic acid

Chemical Property:

• Appearance/Colour: Pale yellow crystals or off-white flaky solid.
• Vapor Pressure: 0.00603mmHg at 25°C
• Melting Point: 103-105 ºC
• Refractive Index: 1.512
• Boiling Point: 260.9 ºC at 760 mmHg
• PKA: 3.91(at 25℃)
• Flash Point: 118.8 ºC
• PSA: 37.30000
• Density: 1.151 g/cm³
• LogP: 1.69320
• Storage Temp.: Store below +30°C.
• Solubility.: 1.2g/l
• Water Solubility.: <0.1 g/100 mL at 19℃
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 136.052429494
• Heavy Atom Count: 10
• Complexity: 131

Purity/Quality:

≥99% ^*data from raw suppliers

o-Toluic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: CC1=CC=CC=C1C(=O)O
• Uses: Bacteriostat. o-Toluic acid is part of a group of Benzoic acid (B203900) derivatives that possess inhibitory activity against mushroom tyrosinases. o-Toluic acid is also used as a reagent to synthesize halogen-substituted benzoic acids (such as 2,4-Dichlorobenzoic acid [D431955]), which have potential muscle stimulating effects.

Technology Process of o-Toluic acid

There total 307 articles about o-Toluic 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: 89.3%

o-xylene (95-47-6) → ortho-methylbenzoic acid (118-90-1) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5)

Guidance literature:

o-xylene; With manganese(IV) oxide; C₃₂H₁₆N₈O₄Ru; C₄₆H₃₉CrN₁₂O₂; oxygen; at 195 ℃; for 0.2h; under 14251.4 Torr;

With manganese(IV) oxide; C₃₂H₁₆N₈O₄Ru; C₄₆H₃₉CrN₁₂O₂; oxygen; acetic acid; at 150 ℃; for 4h; under 4500.45 Torr; Temperature; Pressure; Reagent/catalyst;

Reference yield: 74.0%

carbon monoxide (201230-82-2) + 1-iodyl-2-methylbenzene (16825-70-0) → ortho-methylbenzoic acid (118-90-1) + ortho-methylphenyl iodide (615-37-2)

Guidance literature:

With sodium tetrachloropalladate; sodium carbonate; In water; at 40 ℃; for 10h; Yields of byproduct given;

DOI:10.1021/jo00070a008

Reference yield: 73.0%

o-xylene (95-47-6) → ortho-methylbenzoic acid (118-90-1) + 2-(hydroxymethyl)benzoic acid (612-20-4) + benzene-1,2-dicarboxylic acid (88-99-3,73607-73-5) + o-carboxybenzaldehyde (119-67-5)

Guidance literature:

o-xylene; With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate; In acetic acid; at 150 ℃; for 3h; under 22801.5 Torr;

With sodium hydroxide; at 90 ℃; Further stages.;

DOI:10.1002/1615-4169(20010226)343:2<220::aid-adsc220>3.0.co;2-n

upstream raw materials:

ortho-tolylmagnesium bromide

2-benzofuran-1(3H)-one

phthalic anhydride

1-oxo-1H-isochromene-3-carboxylic acid

Downstream raw materials:

2-Methyl-benzoic acid methyl ester

3-methyl-1-(o-tolyl)butan-1-one

2-phenyl-1-o-tolylethanone

6,6'-dimethyl-3,3'-methanediyl-di-benzoic acid

Refernces

Rh-Catalyzed cascade C-H activation/C-C cleavage/cyclization of carboxylic acids with cyclopropanols

10.1039/d1cc01778k

The research focuses on the development of a novel Rh(III)-catalyzed cascade reaction involving C–H activation, ring-opening C–C bond cleavage, and cyclization of carboxylic acids with cyclopropanols to synthesize 3-substituted phthalides and a,b-butenolides. This reaction exhibits excellent functional group tolerance and operates under relatively mild conditions, which is significant for the late-stage functionalization of bioactive compounds. The experiments involved optimizing the reaction conditions using ortho-methylbenzoic acid and 1-phenylcyclopropan-1-ol as model substrates, with the best yield achieved using [Cp*RhCl2]2/AgOAc, Cs2CO3, and 4 ? MS in CH3CN solvent at 80°C. The scope of the reaction was explored with various aryl- and alkyl-substituted cyclopropanols and carboxylic acids, yielding the desired products in modest to good yields. Mechanistic studies included kinetic isotope effect experiments, deuterium incorporation experiments, and the examination of potential intermediates, leading to a proposed mechanism involving rhodacycle formation, β-C elimination, β-H elimination, and migratory insertion steps.