4,4'-Thiodianiline

Base Information

• Chemical Name: 4,4'-Thiodianiline
• CAS No.: 139-65-1
• Molecular Formula: C12H12N2S
• Molecular Weight: 216.307
• Hs Code.: 29309090
• European Community (EC) Number: 205-370-9
• NSC Number: 6191
• UNII: 6GGU990BQF
• DSSTox Substance ID: DTXSID9021344
• Nikkaji Number: J5.645F
• Wikipedia: 4,4%27-Thiodianiline,4'-Thiodianiline
• Wikidata: Q10859491
• NCI Thesaurus Code: C44322
• ChEMBL ID: CHEMBL348856
• Mol file: 139-65-1.mol

Synonyms:4,4'-thiodianiline

Chemical Property of 4,4'-Thiodianiline

Chemical Property:

• Appearance/Colour: brown to brown-violet powder or needles
• Melting Point: 105-107 °C(lit.)
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 464.8 °C at 760 mmHg
• PKA: 4.55±0.10(Predicted)
• Flash Point: 234.9 °C
• PSA: 77.34000
• Density: 1.26 g/cm³
• LogP: 4.16460
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 216.07211956
• Heavy Atom Count: 15
• Complexity: 162

Purity/Quality:

4,4''-Thiodianiline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, N
• Hazard Codes: T,N
• Statements: 45-22-51/53
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC(=CC=C1N)SC2=CC=C(C=C2)N
• Uses: 4,4′-Thiodianiline was used almost exclusively as a chemical intermediate in the production of three dyes: C.I. mordant yellow 16, milling red G, and milling red FR. However, only mordant yellow 16 had any commercial significance in the United States (IARC 1982, HSDB 2009); it was used to dye wool and for printing on wool, silk, and cotton (SDC 1971). Mordant yellow 16 has been used as an indicator in the U.S. government’s nerve gas detector program (SOCMA 2002). However, no uses of either 4,4′-thiodianiline or mordant yellow 16 since the early 1990s have been reported. 4,4''-Thiodianiline is a carcinogenic aromatic amine used in the textile industry. It can also be used to modify electrodes in solar cells. Dyes and metabolites, Environmental Testing. 4,4′-Diaminodiphenyl sulfide may be employed for the fabrication of quantum wires and quantum dots by chemical vapor deposition. It may be used for the preparation of the following:polypyromellitimidessulfur-containing copolyimidespolyamides

Technology Process of 4,4'-Thiodianiline

There total 48 articles about 4,4'-Thiodianiline 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: 87.0%

4-chlorobenzonitrile (100-00-5) + 4-aminotiophenol (1193-02-8) → 4,4'-thiobisaniline (139-65-1)

Guidance literature:

With potassium hydroxide; In poly(ethylene glycol)-600; at 100 ℃; for 2h;

DOI:10.1021/ol100816g

Reference yield: 86.0%

4-bromo-aniline (106-40-1) → 4,4'-thiobisaniline (139-65-1)

Guidance literature:

With dmap; nickel(II) chloride hexahydrate; potassium thioacyanate; at 140 ℃; for 24h;

DOI:10.1016/j.jorganchem.2016.08.026

Reference yield: 79.0%

aniline (62-53-3) + 4-aminotiophenol (1193-02-8) → 4,4'-thiobisaniline (139-65-1)

Guidance literature:

With 5-ethyl-1,3,7,8-tetramethylalloxazinium triflate; iodine; oxygen; In acetonitrile; at 60 ℃; for 24h; Schlenk technique; Green chemistry;

DOI:10.1016/j.tetlet.2020.152141

upstream raw materials:

bis(4-aminophenyl)disulfide

4-thiocyanatoaniline

4-amino-4'-nitrodiphenyl sulfide

diphenyl sulfide

Downstream raw materials:

2-[(4-{4-[bis(2-hydroxyethyl)amino]phenylthio}phenyl)(2-hydroxyethyl)amino]ethan-1-ol

bis-(4-furfurylidenamino-phenyl)-sulfide

bis-[4-(2-carboxy-benzoylamino)-phenyl]-sulfide

diphenyl sulfide

Refernces

• 1、 -. "Diamine compound containing sulfoxide-based bridge chain as well as synthesis method and application of diamine compound containing sulfoxide-based bridge chain". . . Retrieved 2020/10/21.
• 2、 Jiang, Xinpeng,Shen, Zhifeng,Zheng, Cong,Fang, Liyun,Chen, Keda,Yu, Chuanming. "Flavin/I2 catalyzed aerobic oxidative C–H sulfenylation of anilines". supporting information. . Retrieved 2020/07/24.