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4,4'-Dithiodianiline
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Name

4,4'-Dithiodianiline

 EINECS 211-961-2
CAS No. 722-27-0 Density 1.34 g/cm3
PSA 102.64000 LogP 4.81280
Solubility N/A Melting Point 77-78 °C(lit.)
Formula C12H12N2S2 Boiling Point 447 °C at 760 mmHg
Molecular Weight 248.373 Flash Point 224.2 °C
Transport Information N/A Appearance yellow powder
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 722-27-0 (4,4'-Dithiodianiline) Hazard Symbols IrritantXi
Synonyms

Aniline,4,4'-dithiodi- (6CI,7CI,8CI);Aniline, p,p'-dithiobis- (3CI);4,4'-Diaminodiphenyl disulfide;4,4'-Diaminophenyl disulfide;4-Aminophenyl disulfide;Bis(4-aminophenyl) disulfide;Bis(p-aniline)disulfide;Dithiobis[4-aminobenzene];NSC 62984;NSC 677451;VTI8;p,p'-Diaminodiphenyl disulfide;p,p'-Dithiobisaniline;p-Aminophenyldisulfide;

Article Data 105

4,4'-Dithiodianiline Synthetic route

1193-02-8

4-aminotiophenol

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With dihydrogen peroxide; sodium iodide In water; ethyl acetate at 20℃; for 24h;99%
With cobalt(II)phthalocyanine-tetra-sodium sulfonate In water at 60℃; for 6h; Schlenk technique;96%
With oxygen In water at 55℃; under 6750.68 Torr; for 7h;96%
57-67-0

1-amino-4-({[amino(imino)methyl]amino}sulfonyl)benzene

A

722-27-0

bis(4-aminophenyl)disulfide

B

63-74-1

sulfanilamide

C

62-53-3

aniline

D

121-57-3

4-aminobenzene sulfonic acid

Conditions
ConditionsYield
In methanol for 76h; Product distribution; Mechanism; Irradiation; λ=254 nm;A n/a
B 4.4%
C 95.1%
D 2.7%
540-37-4

p-aminoiodobenzene

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
Stage #1: p-aminoiodobenzene With potassium 5-methyl-1,3,4-oxadiazole-2-thiolate In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #2: With copper(l) chloride In N,N-dimethyl-formamide at 130℃; for 7h;		94%
With dmap; nickel(II) chloride hexahydrate; potassium thioacyanate; N,N-dimethyl-formamide at 140℃; for 20h;92%
With copper(l) iodide; water; oxygen; sodium hydrogencarbonate; thiourea at 115 - 120℃; for 16h; Green chemistry;81%
2987-46-4

4-thiocyanatoaniline

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With ammonium hydroxide In 1,4-dioxane at 100℃; sealed ampoule;93.5%
With hydrogenchloride beim Behandeln des Reaktionsprodukts mit Eisen(III)-chlorid oder mit wss.Wasserstoffperoxid;
106-40-1

4-bromo-aniline

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With dmap; nickel(II) chloride hexahydrate; potassium thioacyanate; N,N-dimethyl-formamide at 140℃; for 22h;92%
With copper(l) iodide; hexachloroethane; sodium carbonate; thiourea In water at 120℃; for 18h;85%
With copper(l) iodide; water; oxygen; sodium hydrogencarbonate; thiourea at 115 - 120℃; for 18h; Green chemistry;82%
100-32-3

di(p-nitrophenyl) disulfide

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With iron; ammonium chloride In methanol at 80℃; for 6h;90.6%
With bis(acetylacetonate)nickel(II) In 1,4-dioxane at 80℃;88%
With ethanol; nickel Hydrogenation;
100-00-5

4-chlorobenzonitrile

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With sodium sulfide; water; dihydrogen peroxide
With sodium sulfide; water
With sodium disulfide; water
With sodium sulfide; water
With sodium sulfide; water
142-04-1

aniline hydrochloride

62-53-3

aniline

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With sulfur
62-53-3

aniline

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With hydrogenchloride; sulfur at 150℃; laesst weitere 6-Stdn.gelinde Kochen;
With sulfur
With hydrogenchloride; sulfur
103-84-4

Acetanilid

722-27-0

bis(4-aminophenyl)disulfide

Conditions
ConditionsYield
With disulfur dichloride at 100℃; entstehen 4.4'-Bis-acetamino-diphenyldisulfid (a) und 4.4'-Bis-acetamino-diphenyltrisulfid (b);aus der Loesung des Produktes in Eisessig krystallisiert das (b);das (a) zerlegt man durch Erhitzen mit verd.Schwefelsaeure;

4,4'-Dithiodianiline Consensus Reports

Reported in EPA TSCA Inventory.

4,4'-Dithiodianiline Specification

The 4-Aminophenyl disulfide is an organic compound with the formula C12H12N2S2. The IUPAC name of this chemical is 4-[(4-aminophenyl)disulfanyl]aniline. With the CAS registry number 722-27-0, it is also named as Benzenamine, 4,4'-dithiobis-. The product's category is Amines. Besides, it is a yellow powder, which should be stored in a closed cool and dry place. It is used for curing agent of polyurethane rubber.

Physical properties about 4-Aminophenyl disulfide are: (1)ACD/LogP: 1.65; (2)ACD/LogD (pH 5.5): 1.63; (3)ACD/LogD (pH 7.4): 1.65; (4)ACD/BCF (pH 5.5): 10.09; (5)ACD/BCF (pH 7.4): 10.49; (6)ACD/KOC (pH 5.5): 180.12; (7)ACD/KOC (pH 7.4): 187.14; (8)#H bond acceptors: 2; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 57.08 Å2; (12)Index of Refraction: 1.74; (13)Molar Refractivity: 74.72 cm3; (14)Molar Volume: 185.1 cm3; (15)Polarizability: 29.62×10-24cm3; (16)Surface Tension: 71.3 dyne/cm; (17)Density: 1.34 g/cm3; (18)Flash Point: 224.2 °C; (19)Enthalpy of Vaporization: 70.53 kJ/mol; (20)Boiling Point: 447 °C at 760 mmHg; (21)Vapour Pressure: 3.47E-08 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: S(Sc1ccc(cc1)N)c2ccc(N)cc2
(2)InChI: InChI=1/C12H12N2S2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H,13-14H2
(3)InChIKey: MERLDGDYUMSLAY-UHFFFAOYAI
(4)Std. InChI: InChI=1S/C12H12N2S2/c13-9-1-5-11(6-2-9)15-16-12-7-3-10(14)4-8-12/h1-8H,13-14H2
(5)Std. InChIKey: MERLDGDYUMSLAY-UHFFFAOYSA-N

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