4-(Methylthio)aniline

Base Information

• Chemical Name: 4-(Methylthio)aniline
• CAS No.: 104-96-1
• Molecular Formula: C7H9NS
• Molecular Weight: 139.221
• Hs Code.: 29309090
• European Community (EC) Number: 203-256-3
• NSC Number: 75842
• DSSTox Substance ID: DTXSID7059309
• Nikkaji Number: J28.395I
• Wikidata: Q27454756
• Mol file: 104-96-1.mol

Synonyms:thioanisidine

Chemical Property of 4-(Methylthio)aniline

Chemical Property:

• Appearance/Colour: clear orange to brown-red liquid
• Vapor Pressure: 0.00578mmHg at 25°C
• Melting Point: 156 - 158oC
• Refractive Index: n20/D 1.639(lit.)
• Boiling Point: 273.3 °C at 760 mmHg
• PKA: 4.35(at 25℃)
• Flash Point: 119.1 °C
• PSA: 51.32000
• Density: 1.12 g/cm³
• LogP: 2.57190
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Sensitive.: Stench
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 139.04557046
• Heavy Atom Count: 9
• Complexity: 77

Purity/Quality:

98% ^*data from raw suppliers

4-(Methylthio)aniline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CSC1=CC=C(C=C1)N

Technology Process of 4-(Methylthio)aniline

There total 52 articles about 4-(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: 99.5%

1-methylthio-4-nitro-benzene (701-57-5) → 4-methylsulfanylaniline (104-96-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In toluene; at 180 ℃; for 18.3333h; under 22502.3 Torr; Temperature; Kinetics; Catalytic behavior; Autoclave;

DOI:10.1016/j.apcata.2015.02.043

Reference yield: 96.0%

(4-bromophenyl)thioanisole (104-95-0) → 4-methylsulfanylaniline (104-96-1)

Guidance literature:

With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane; In toluene; at 100 ℃; for 2h; Glovebox; Sealed tube;

DOI:10.1021/acs.organomet.8b00567

Reference yield: 95.0%

α-methyl-4-(methylthio)benzenemethanol (32293-73-5) → 4-methylsulfanylaniline (104-96-1)

Guidance literature:

With sodium azide; trifluoroacetic acid; In hexane; at 40 ℃; for 4h; Sealed tube;

DOI:10.1038/s41557-018-0156-y

upstream raw materials:

1-methylthio-4-nitro-benzene

4'-(methylthio)acetanilide

N,N'-bis-(4-methylsulfanyl-phenyl)-hydrazine

diethylamine

Downstream raw materials:

p-(methylthio)-N,N-bis(2-hydroxyethyl)aniline

N-(4-methylsulfanyl-phenyl)-maleamic acid

4'-(methylthio)acetanilide

6,6-dimethyl-1-(4-methylsulfanyl-phenyl)-1,6-dihydro-[1,3,5]triazine-2,4-diamine

Refernces

• 1、 Moody, Christopher J.,Pitts, Michael R.. "Indium as a reducing agent: Reduction of aromatic nitro groups". . p. 1028 - 1028. Retrieved 1998.
• 2、 Zhu, Kailong,Shaver, Michael P.,Thomas, Stephen P.. "Chemoselective nitro reduction and hydroamination using a single iron catalyst". . p. 3031 - 3035. Retrieved 2016.
• 3、 Wei, Zhongzhe,Mao, Shanjun,Sun, Fanfei,Wang, Jing,Mei, Bingbao,Chen, Yiqing,Li, Haoran,Wang, Yong. "The synergic effects at the molecular level in CoS2 for selective hydrogenation of nitroarenes". . p. 671 - 679. Retrieved 2018.
• 4、 Wei, Zhongzhe,Wang, Jing,Mao, Shanjun,Su, Diefeng,Jin, Haiyan,Wang, Yihe,Xu, Fan,Li, Haoran,Wang, Yong. "In Situ-Generated Co0-Co3O4/N-Doped Carbon Nanotubes Hybrids as Efficient and Chemoselective Catalysts for Hydrogenation of Nitroarenes". . p. 4783 - 4789. Retrieved 2015.
• 5、 Xiong, Renjie,Zhao, Wenqiang,Wang, Zhiqiang,Zhang, Minghui. "A sulfur-tolerant phosphorus doped Pd/C catalyst for hydrogenation of 4-nitrothioanisole". . . Retrieved 2021.
• 6、 Du, Jialei,Chen, Jie,Xia, Hehuan,Zhao, Yiwei,Wang, Fang,Liu, Hong,Zhou, Weijia,Wang, Bin. "Commercially Available CuO Catalyzed Hydrogenation of Nitroarenes Using Ammonia Borane as a Hydrogen Source". . p. 2426 - 2430. Retrieved 2020.
• 7、 Goyal, Vishakha,Sarki, Naina,Natte, Kishore,Ray, Anjan. "Pd/C-catalyzed transfer hydrogenation of aromatic nitro compounds using methanol as a hydrogen source". . . Retrieved 2021.
• 8、 Lopes, Rita,Pereira, Mariette M.,Royo, Beatriz. "Selective Reduction of Nitroarenes with Silanes Catalyzed by Nickel N-Heterocyclic Carbene Complexes". . p. 3073 - 3077. Retrieved 2017.
• 9、 Kumar, J.S.Dileep,Ho, ManKit M.,Toyokuni, Tatsushi. "Simple and chemoselective reduction of aromatic nitro compounds to aromatic amines: Reduction with hydriodic acid revisited". . p. 5601 - 5603. Retrieved 2001.
• 10、 Sorribes, Iván,Wienh?fer, Gerrit,Vicent, Cristian,Junge, Kathrin,Llusar, Rosa,Beller, Matthias. "Chemoselective transfer hydrogenation to nitroarenes mediated by cubane-type Mo3S4 cluster catalysts". . p. 7794 - 7798. Retrieved 2012.