N-Methyl-o-toluidine

Base Information

• Chemical Name: N-Methyl-o-toluidine
• CAS No.: 611-21-2
• Molecular Formula: C8H11N
• Molecular Weight: 121.182
• Hs Code.: 2921430090
• European Community (EC) Number: 210-260-9
• NSC Number: 9395
• UNII: E41NZ1ZY58
• DSSTox Substance ID: DTXSID4060600
• Wikidata: Q1959580
• Mol file: 611-21-2.mol

Synonyms:N-Methyl-o-toluidine;N,2-Dimethylaniline;611-21-2;2,N-Dimethylaniline;o-Toluidine, N-methyl-;Benzenamine, N,2-dimethyl-;N,o-Dimethylaniline;o,N-Dimethylaniline;n-methyl-o-methylaniline;n,n'-dimethylaniline;2-(Methylamino)toluene;N,2-Dimethylbenzenamine;2-Methyl-N-methylaniline;UNII-E41NZ1ZY58;E41NZ1ZY58;NSC 9395;NSC-9395;EINECS 210-260-9;N-methyltoluidine;NSC9395;methyl-o-tolyl-amine;n-methyl-2-toluidine;2,N-dimethyl-aniline;methyl-(o-tolyl)-amine;n-methyl-ortho-toluidine;Benzenamine,2-dimethyl-;n-methyl-2-methylaniline;METHYL(O-TOLYL)AMINE;SCHEMBL172153;DTXSID4060600;GUAWMXYQZKVRCW-UHFFFAOYSA-;N-Methyl-o-toluidine, >=95%;N-METHYL-N-(O-TOLYL)AMINE;N-METHYL-2-METHYLBENZENAMINE;MFCD00025627;STK503780;N-(2-METHYLPHENYL)METHYLAMINE;AKOS000258549;NC-0217;CS-0152952;FT-0632549;M0445;EN300-59029;D78237;Q1959580;W-105191;Z335283244;2,3,4,5-TETRAHYDRO-PYRROLO[1,2-A][1,4]DIAZEPIN-1-ONE

Chemical Property of N-Methyl-o-toluidine

Chemical Property:

• Appearance/Colour: Clear liquid, darkening on storage
• Vapor Pressure: 0.225mmHg at 25°C
• Melting Point: -10.08°C (estimate)
• Refractive Index: 1.562-1.565
• Boiling Point: 207.5 °C at 760 mmHg
• PKA: 4.72±0.10(Predicted)
• Flash Point: 76.4 °C
• PSA: 12.03000
• Density: 0.968 g/cm³
• LogP: 2.10970
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility.: Practically insoluble in water
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 121.089149355
• Heavy Atom Count: 9
• Complexity: 80.6

Purity/Quality:

99.9% ^*data from raw suppliers

N-Methyl-o-toluidine >95.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 52/53-33-23/24/25
• Safety Statements: 61-45-36/37-28A-28

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=CC=C1NC
• Uses: Reactant for:Palladium-catalyzed coupling reactionsPalladium-catalyzed amination of bromoindazoles

Technology Process of N-Methyl-o-toluidine

There total 83 articles about N-Methyl-o-toluidine 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: 96.0%

1,3,5-tris(o-tolyl)-hexahydro-s-triazine (54043-60-6) → N,2-dimethylaniline (611-21-2)

Guidance literature:

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; at 20 ℃; for 12h;

Reference yield: 93.0%

2'-methylformanilide (94-69-9) + dimethyl sulfate (77-78-1) → N'-methyl-N-(2-methylphenyl)formanilide (131840-54-5) + N,2-dimethylaniline (611-21-2)

Guidance literature:

With hexamethylenetetramine hydrobromide; potassium carbonate; In benzene; at 8 - 10 ℃; for 0.75h;

DOI:10.1080/00397919208021146

Reference yield: 93.0%

→ N,2-dimethylaniline (611-21-2)

Guidance literature:

With hydrogen; In 1,4-dioxane; at 60 ℃; for 24h; under 7500.75 Torr; Sealed tube; Green chemistry;

upstream raw materials:

methyl magnesium iodide

diethyl ether

1-methyl-2-nitrobenzene

toluene-4-sulfonic acid-(N-methyl-o-toluidide)

Downstream raw materials:

N-methyl-N-(2-methylphenyl)acetamide

N-(2-methylphenyl)-N-methylbenzylamine

N-methyl-N-(o-methylphenyl)benzamide

N-methyl-2-methylchloroacetanilide

Refernces

• 1、 Feng, Xinshu,Huang, Ming. "Effect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols". . . Retrieved 2021/06/21.
• 2、 Falk, Eric,Gasser, Valentina C. M.,Morandi, Bill. "Synthesis of N-Alkyl Anilines from Arenes via Iron-Promoted Aromatic C-H Amination". supporting information. p. 1422 - 1426. Retrieved 2021/03/08.