o-Acetotoluidide

Base Information

• Chemical Name: o-Acetotoluidide
• CAS No.: 120-66-1
• Molecular Formula: C9H11 N O
• Molecular Weight: 149.192
• Hs Code.: 29242990
• European Community (EC) Number: 204-414-4
• NSC Number: 3365
• UNII: 425I3L2A81
• DSSTox Substance ID: DTXSID1024413
• Nikkaji Number: J5.330I
• Wikidata: Q27258494
• Metabolomics Workbench ID: 123650
• ChEMBL ID: CHEMBL1568309
• Mol file: 120-66-1.mol

Synonyms:N-acetyl-2-toluidine;N-acetyl-o-toluidine

Chemical Property of o-Acetotoluidide

Chemical Property:

• Appearance/Colour: off white to brown flake
• Melting Point: 110 C
• Refractive Index: 1.5279 (estimate)
• Boiling Point: 296 C
• PKA: 15.13±0.70(Predicted)
• Flash Point: 247.3°C
• PSA: 29.10000
• Density: 1.111g/cm³
• LogP: 2.02640
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: It is slightly soluble in acetone, chloroform, toluene, benzene.
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 149.084063974
• Heavy Atom Count: 11
• Complexity: 145

Purity/Quality:

99.5% ^*data from raw suppliers

o-Methylacetanilide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: CC1=CC=CC=C1NC(=O)C
• Uses: o-Methylacetanilide is a substituted acetanilide that is used as precursor for various pharmaceuticals including their intermediates. Acetanilide is used as an inhibitor of peroxides and?stabilizer for cellulose ester varnishes.?It is used as an intermediate for the synthesis of?rubber accelerators, dyes and dye intermediate and camphor. It is used as a precursor in penicillin synthesis and other pharmaceuticals including painkillers and intermediates.

Technology Process of o-Acetotoluidide

There total 83 articles about o-Acetotoluidide 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: 99.0%

acetic anhydride (108-24-7) + o-toluidine (95-53-4) → N-(2-methylphenyl)acetamide (120-66-1)

Guidance literature:

In ethyl acetate; for 0.5h; Cooling with ice;

Reference yield: 99.0%

acetamide (60-35-5) + ortho-methylphenyl iodide (615-37-2) → N-(2-methylphenyl)acetamide (120-66-1)

Guidance literature:

With aluminum oxide; potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; In toluene; at 110 ℃; for 8h;

DOI:10.1055/s-2004-829099

Reference yield: 98.0%

acetic acid (64-19-7,77671-22-8) + o-toluidine (95-53-4) → N-(2-methylphenyl)acetamide (120-66-1)

Guidance literature:

at 150 ℃; microwave irradiation;

DOI:10.1080/00397910701860372

upstream raw materials:

acetic anhydride

o-toluidine

benzene

1,3-di-o-tolyltriazene

Downstream raw materials:

4-oxo-4-(4-acetylamino-3-methyl-phenyl)-trans-crotonic acid

N-(2-methylphenyl)-N-phenylacetamide

N-(4-methoxyphenyl)-2-methylbenzenamine

acetic acid-(2-methyl-4-trityl-anilide)

Refernces

• 1、 Wang, Biying,Jiang, Chengfei,Qian, Jiasheng,Zhang, Shuwei,Jia, Xiaodong,Yuan, Yu. "Synthesis of 2-methylbenzoxazoles directly from: N -phenylacetamides catalyzed by palladium acetate". . p. 101 - 107. Retrieved 2017.
• 2、 Swaminathan,K.,Venkatasubramanian,N.. "-". . p. 1161 - 1166. Retrieved 1975.
• 3、 Liang, Yuxue,Gao, Shuang,Wan, Huihui,Wang, Junwei,Chen, Huilin,Zheng, Zhuo,Hu, Xinquan. "Syntheses and resolutions of new chiral biphenyl backbones: 2-Amino-2′-hydroxy-6,6′-dimethyl-1,1′-biphenyl and 2-amino-2′-hydroxy-4,4′,6,6′-tetramethyl-1,1′- biphenyl". . p. 1267 - 1273. Retrieved 2003.
• 4、 Zeynizadeh, Behzad,Mohammad Aminzadeh, Farkhondeh,Mousavi, Hossein. "Chemoselective reduction of nitroarenes, N-acetylation of arylamines, and one-pot reductive acetylation of nitroarenes using carbon-supported palladium catalytic system in water". . p. 3289 - 3312. Retrieved 2021/05/11.
• 5、 Patel, Anuj P.,Shaikh, Mohammedumar M.,Gurjar, Kamlesh K.,Chikhalia, Kishor H.. "Synthesis of indenoquinolinone through aryne-mediated Pd(II)-catalysed remote C–H activation". . p. 2049 - 2061. Retrieved 2021/02/01.