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436372

Sigma-Aldrich

4,4′-Diaminodiphenyl sulfide

98%

Synonym(s):

4,4′-Thiodianiline

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About This Item

Linear Formula:
S(C6H4NH2)2
CAS Number:
139-65-1
Molecular Weight:
216.30
Beilstein/REAXYS Number:
1875513
EC Number:
205-370-9
MDL number:
MFCD00025342
UNSPSC Code:
12352100
PubChem Substance ID:
24867296
NACRES:
NA.22

assay

98%

form

solid

mp

105-107 °C (lit.)

SMILES string

Nc1ccc(Sc2ccc(N)cc2)cc1

InChI

1S/C12H12N2S/c13-9-1-5-11(6-2-9)15-12-7-3-10(14)4-8-12/h1-8H,13-14H2

InChI key

ICNFHJVPAJKPHW-UHFFFAOYSA-N

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General description

4,4′-Diaminodiphenyl sulfide is a diaminodiphenyl analog. On oral administration to rats, it induces haematological and pathological changes indicative of erythrocyte destruction. It has been reported to generate hydrogen peroxide in erythrocytes in vitro. Enzymatic oxidation of 4,4′-diaminodiphenyl sulfide to their sulfoxide derivatives in guinea pig liver homogenates has been reported.

Application

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:
  • polypyromellitimides
  • sulfur-containing copolyimides
  • polyamides

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2 - Carc. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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R Munday et al.
Journal of applied toxicology : JAT, 5(6), 414-417 (1985-12-01)
Diphenyl disulphide, 4,4'-diaminodiphenyl disulphide, 2,2'-diaminodiphenyl disulphide, 4,4'-dimethyldiphenyl disulphide and 4,4'-dinitrodiphenyl disulphide, when administered orally to rats, induced haematological and pathological changes indicative of erythrocyte destruction in vivo. No evidence of haemolysis was detected, however, in animals receiving diphenyl disulphide-2,2'-dicarboxylic acid
The enzymatic formation of sulfoxides: the oxidation of chlorpromazine and 4,4'-diaminodiphenyl sulfide by guinea pig liver microsomes.
J R GILLETTE et al.
The Journal of pharmacology and experimental therapeutics, 130, 262-267 (1960-11-01)
R Munday
Journal of applied toxicology : JAT, 5(6), 409-413 (1985-12-01)
Diphenyl disulphide has been shown to generate hydrogen peroxide in erythrocytes in vitro. It also induces oxidative damage (reversible and irreversible haemoglobin oxidation, depletion of non-protein and protein-bound thiols) in these cells. Such changes were also recorded in erythrocytes exposed
Synthesis and characterization of novel, soluble sulfur-containing copolyimides with high refractive indices.
Dusselberg D, et al.
J. Mater. Sci., 46(14), 4872-4879 (2011)
Polycondensation of pyridine-2,6-dicarboxylic acid with some di-and tetraamino compounds.
Banihashemi A and Eghbali M.
Journal of Polymer Science, 14(11), 2659-2664 (1976)
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