N,N-Dimethyl-2-(methylthio)aniline

Base Information

• Chemical Name: N,N-Dimethyl-2-(methylthio)aniline
• CAS No.: 2388-50-3
• Molecular Formula: C9H13NS
• Molecular Weight: 167.275
• Hs Code.: 2930909090
• DSSTox Substance ID: DTXSID70507556
• Nikkaji Number: J80.468A
• Wikidata: Q82363838
• Mol file: 2388-50-3.mol

Synonyms:2388-50-3;N,N-Dimethyl-2-(methylthio)aniline;SCHEMBL3145793;DTXSID70507556;BMVUVEYWVYKKNB-UHFFFAOYSA-N;o-(methylthio)-N,N-dimethyl-aniline;2-Aminothiophenol, N,N,S-trimethyl-;N, N-dimethyl-2-methylsulfanylaniline;N,N-Dimethyl-2-(methylsulfanyl)aniline

Chemical Property of N,N-Dimethyl-2-(methylthio)aniline

Chemical Property:

• PSA: 28.54000
• LogP: 2.47450
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 167.07687059
• Heavy Atom Count: 11
• Complexity: 114

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)C1=CC=CC=C1SC

Technology Process of N,N-Dimethyl-2-(methylthio)aniline

There total 9 articles about N,N-Dimethyl-2-(methylthio)aniline 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%

formic acid (64-18-6) + 2-(Methylthio)aniline (2987-53-3) → o-(N,N-dimethylamino)phenyl methyl thioether (2388-50-3)

Guidance literature:

With platinum on carbon; phenylsilane; In toluene; at 80 ℃; for 15h;

DOI:10.1039/c6cy00674d

Reference yield: 84.0%

methanethiosulfonic acid S-methyl ester (2949-92-0,31761-75-8) + 2-bromo-N,N-dimethylaniline (698-00-0) → o-(N,N-dimethylamino)phenyl methyl thioether (2388-50-3)

Guidance literature:

2-bromo-N,N-dimethylaniline; With N,N,N,N,-tetramethylethylenediamine; C₄H₉Mg⁽¹⁺⁾*2C₈H₁₇O^(1-)*Li⁽¹⁺⁾; In toluene; at 25 ℃; Schlenk technique; Inert atmosphere;

methanethiosulfonic acid S-methyl ester; In toluene; at 25 ℃; for 1h; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201802123

Reference yield: 82.0%

2-(Methylthio)aniline (2987-53-3) + methyl iodide (74-88-4) → o-(N,N-dimethylamino)phenyl methyl thioether (2388-50-3)

Guidance literature:

With n-butyllithium; In hexane; at -10 ℃; for 12h;

DOI:10.1016/S0022-328X(00)00806-8

upstream raw materials:

methanol

2-(Methylthio)aniline

2-<(2,3-Dihydro-3-methylbenzothiazol-2-yliden)methyl>-2,3-dihydro-3-methylbenzothiazol

dimethyl sulfate

Downstream raw materials:

o-(N,N-dimethylamino)phenyl methyl sulfone

diethyl [2-(N,N-dimethylamino)phenylsulfonyl]methyl phosphonate

(E)-1-[2-(N,N-dimethylamino)phenylsulfonyl]-3-methyl-1-butene

(E)-1-[2-(N,N-dimethylamino)phenylsulfonyl]-1-heptene

Refernces

• 1、 Dunne, John P.,Bockmeyer, Matthias,Tacke, Matthias. "Co-condensation reactions of substituted aromatic compounds with lithium atoms at 77 K". . p. 458 - 466. Retrieved 2003.
• 2、 -. "Preparation method by using amine and imine nitrogen methylation and application thereof". Paragraph 0067; 0068; 0069; 0070; 0071; 0072. . Retrieved 2017/08/10.
• 3、 Fang, Chi,Lu, Chunlei,Liu, Muhua,Zhu, Yiling,Fu, Yao,Lin, Bo-Lin. "Selective formylation and methylation of amines using carbon dioxide and hydrosilane catalyzed by alkali-Metal carbonates". . p. 7876 - 7881. Retrieved 2018/05/23.