2,2'-Dithiodianiline

Base Information

• Chemical Name: 2,2'-Dithiodianiline
• CAS No.: 1141-88-4
• Molecular Formula: C12H12N2S2
• Molecular Weight: 248.373
• Hs Code.: 29309090
• European Community (EC) Number: 214-529-1
• NSC Number: 677450,54509,8186
• UNII: Y75Q7B8EAE
• DSSTox Substance ID: DTXSID2061561
• Nikkaji Number: J60.268J
• Wikidata: Q72462845
• ChEMBL ID: CHEMBL122355
• Mol file: 1141-88-4.mol

Synonyms:2,2'-diaminodiphenyldisulfide

Chemical Property of 2,2'-Dithiodianiline

Chemical Property:

• Melting Point: 91-92 °C
• Refractive Index: 1.5700 (estimate)
• Boiling Point: 398.005 °C at 760 mmHg
• PKA: 2.81±0.10(Predicted)
• Flash Point: 194.507 °C
• PSA: 102.64000
• Density: 1.341 g/cm³
• LogP: 4.81280
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Soluble in hot methanol- almost transparent.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 248.04419074
• Heavy Atom Count: 16
• Complexity: 191

Purity/Quality:

98% ^*data from raw suppliers

2,2''-Dithiodianiline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,N,T
• Statements: 41-50/53-25
• Safety Statements: 26-39-61-60-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)N)SSC2=CC=CC=C2N
• Uses: 2,2'-Diaminodiphenyl disulfide, is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It is also used as a primary and secondary intermediate.

Technology Process of 2,2'-Dithiodianiline

There total 104 articles about 2,2'-Dithiodianiline 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: 95.0%

2-(2-aminophenylthio)-4-phenyl-2,3-dihydro-1,5-benzothiazepine (86333-20-2) → 2-Phenylquinoline (612-96-4) + 2-amino-benzenethiol (137-07-5) + 2-Aminophenyl disulfide (1141-88-4)

Guidance literature:

In toluene; for 4h; Heating;

Reference yield: 89.0%

2-bromoaniline (615-36-1) → 2-Aminophenyl disulfide (1141-88-4)

Guidance literature:

With indium(III) oxide; ammonia; water; sulfur; In ethanol; at 60 ℃; Green chemistry;

DOI:10.1080/00397911.2018.1466335

Reference yield: 85.0%

o-chloroaniline (95-51-2) → 2-Aminophenyl disulfide (1141-88-4)

Guidance literature:

With indium(III) oxide; ammonia; water; sulfur; In ethanol; at 60 ℃; Green chemistry;

DOI:10.1080/00397911.2018.1466335

upstream raw materials:

bis(2-nitrophenyl)disulfide

1,3-Benzothiazole

2-amino-benzthiazole

3-benzothiazol-2-yl-acrylic acid

Downstream raw materials:

N,N'-(2,2'-disulfanediyl-diphenyl)-bis-maleamic acid

bis-[2-(furan-2-carbonylamino)-phenyl]-disulfide

2-Methylbenzothiazole

thioacetic acid S-(2-acetylamino-phenyl)ester

Refernces

Synthesis of sulfur heterocycles via domino metal-mediated reactions

10.1080/10426507.2016.1255621

The research focuses on the development of two methodologies for synthesizing sulfur heterocycles (S-heterocycles) and mixed nitrogen-sulfur heterocycles (N,S-heterocycles) through metal-mediated domino reactions. The first methodology involves a cyclocarbopalladation/cross-coupling domino process, utilizing propargyl sulfides or ynethioethers as starting materials and Pd(PPh3)4 as a catalyst, with Stille or Suzuki-Miyaura coupling partners like 2-furyl, 2-thienyl, allyl, and vinyl tributylstannanes, or arylboronic acids. This approach yields benzene-fused five- or six-membered sulfur heterocycles with a stereodefined tetrasubstituted exocyclic double bond. The second methodology is a three-component domino reaction between 2-aminophenyl disulfide, copper cyanide (CuCN), and an electrophile, which accesses N-substituted 2-amino benzothiazoles. The experiments also explore the synthesis of N-substituted 2-imino benzothiazoles using N-protected 2-aminoaryl disulfides as precursors. The analyses used to confirm the structures of the synthesized compounds include X-ray crystallography, with crystallographic data deposited at the Cambridge Crystallographic Data Center.