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:

ethyl 2-methylbenzoate

2-methyl-benzoic acid-(4-bromo-phenacyl ester)

2-methyl-N-m-tolylbenzamide

4-hydroxyphenyl 2-methylphenyl ketone

Refernces

• 1、 Khaibulova, T. Sh.,Boyarskaya,Boyarskii. "Steric effect of substituents in haloarenes on the rate of cross-coupling reactions". . p. 360 - 365. Retrieved 2013.
• 2、 Battaglia, Luigi Pietro,Nardelli, Mario,Pelizzi, Corrado,Predieri, Giovanni,Chiusoli, Gian Paolo. "ARYL RADICALS FROM ORGANOMETALLIC SOURCES. PREFERENTIAL ATTACK ON THE SIDE CHAIN OF TOLUENES BY THE o-TOLYL RADICALS.". . p. C19 - C22. Retrieved 1986.
• 3、 Wei, Benmei,Zhang, Zhiyong,Dai, Zhiqun,Guan, Jintao. "An efficient approach for the deprotection of esters using ionic liquid as nucleophile". . p. 6404 - 6406. Retrieved 2013.
• 4、 Foerster, Tobias,Schunk, Stephan A.,Jentys, Andreas,Lercher, Johannes A.. "Co and Mn polysiloxanes as unique initiator-catalyst-systems for the selective liquid phase oxidation of o-xylene". . p. 3254 - 3256. Retrieved 2011.
• 5、 Wei, Ben-Mei,Zhang, Zhi-Yong,Dai, Zhi-Qun,Zhang, Kai-Cheng. "Application of chloroaluminate ionic liquid as catalyst and medium for the dealkylation of esters". . p. 1029 - 1033. Retrieved 2011.
• 6、 STEVENS,HOLLAND. "Synthesis of anthracene-9-C114.". . p. 718 - 719. Retrieved 1950.
• 7、 Mallia, Carl J.,Walter, Gary C.,Baxendale, Ian R.. "Flow carbonylation of sterically hindered ortho-substituted iodoarenes". . p. 1503 - 1511. Retrieved 2016.
• 8、 Fichter,Rinderspacher. "-". . p. 40. Retrieved 1927.
• 9、 Shibahara, Fumitoshi,Kinoshita, Shinsuke,Nozaki, Kyoko. "Palladium(II)-catalyzed sequential hydroxylation-carboxylation of biphenyl using formic acid as a carbonyl source". . p. 2437 - 2439. Retrieved 2004.
• 10、 Linn, Kathleen,Kuethe, Jeffrey T.,Peng, Zhihui,Yasuda, Nobuyoshi. "Practical preparation of benzyloxyacetic acids". . p. 3762 - 3765. Retrieved 2008.