Product Name

  • Name

    Cystamine dihydrochloride

  • EINECS 200-260-7
  • CAS No. 56-17-7
  • Article Data9
  • CAS DataBase
  • Density 1.172 g/cm3
  • Solubility soluble in water
  • Melting Point 217-220 °C (dec.)(lit.)
  • Formula C4H12N2S2.2HCl
  • Boiling Point 264.8 °C at 760 mmHg
  • Molecular Weight 225.207
  • Flash Point 114 °C
  • Transport Information
  • Appearance white powder
  • Safety 26-36/37/39
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 56-17-7 (Cystamine dihydrochloride)
  • Hazard Symbols HarmfulXn
  • Synonyms Ethanamine,2,2'-dithiobis-, dihydrochloride (9CI);Ethylamine, 2,2'-dithiobis-,dihydrochloride (8CI);2,2'-Dithiobis[ethylamine] dihydrochloride;Bis(2-aminoethyl) disulfide dihydrochloride;Cystamine dichlorohydrate;Cystamine dihydrochloride;Cystamine hydrochloride;WR 352;
  • PSA 102.64000
  • LogP 3.28980

Synthetic route

C23H26N2O3S

C23H26N2O3S

A

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

B

4-phenyl-1-(phenylmethyl)-2,3-azetidinedione

4-phenyl-1-(phenylmethyl)-2,3-azetidinedione

Conditions
ConditionsYield
Stage #1: C23H26N2O3S With hydrogenchloride In ethyl acetate at 60℃; for 4h;
Stage #2: With oxygen In chloroform at 25℃; for 720h; Further stages.;		A n/a
B 99%
2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

Conditions
ConditionsYield
With dimethyl sulfoxide at 90℃; for 6h;98%
With di(benzothiazol-2-yl)disulfide In methanol; chloroform for 2h; Ambient temperature;96.9%
In methanol oxidation;
With dimethyl sulfoxide In water
In dimethyl sulfoxide at 90℃; for 8h;
di(benzothiazol-2-yl)disulfide
120-78-5

di(benzothiazol-2-yl)disulfide

2-mercaptoethylamine hydrochloride
156-57-0

2-mercaptoethylamine hydrochloride

A

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

B

2-(Benzothiazol-2-yldisulfanyl)-ethylamine; hydrochloride

2-(Benzothiazol-2-yldisulfanyl)-ethylamine; hydrochloride

Conditions
ConditionsYield
In ethanol; chloroform Ambient temperature;
...Expand
(3SR,4SR)-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3.4]octan-1-one hydrochloride

(3SR,4SR)-3-phenyl-2-(phenylmethyl)-5-thia-2,8-diazaspiro[3.4]octan-1-one hydrochloride

A

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

B

4-phenyl-1-(phenylmethyl)-2,3-azetidinedione

4-phenyl-1-(phenylmethyl)-2,3-azetidinedione

Conditions
ConditionsYield
In chloroform; dimethyl sulfoxide at 45℃; for 6h;A 23 mg
B 52 mg
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

C23H26N2O7

C23H26N2O7

N,N'-biscystamine
112042-52-1

N,N'-biscystamine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water Ambient temperature;100%
succinic acid anhydride
108-30-5

succinic acid anhydride

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

N,N'-(3,4-dithia-hexanediyl)-bis-succinamic acid
108725-86-6

N,N'-(3,4-dithia-hexanediyl)-bis-succinamic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; pH=10;100%
With sodium hydroxide In water pH=10;100%
Stage #1: succinic acid anhydride; cystamine dihydrochioride With sodium hydroxide In water at 20℃; pH=7 - ~ 10;
Stage #2: With hydrogenchloride In water Product distribution / selectivity;		90%
Stage #1: cystamine dihydrochioride With sodium hydroxide In water pH=10;
Stage #2: succinic acid anhydride In water at 20℃; for 2h; pH=7 - 10;
Stage #3: With hydrogenchloride In water		90%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

(+)-usnic acid
17669-01-1, 56190-51-3, 15853-98-2

(+)-usnic acid

C40H40N2O12S2
1428361-11-8

C40H40N2O12S2

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With pyridine In ethanol at 20℃; for 0.5h; Inert atmosphere;
Stage #2: (+)-usnic acid With pyridine In ethanol for 8h; Reflux;		100%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

(+)-usnic acid
17669-01-1, 56190-51-3, 15853-98-2

(+)-usnic acid

C40H40N2O12S2

C40H40N2O12S2

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With pyridine In ethanol at 20℃; for 0.5h;
Stage #2: (+)-usnic acid With pyridine In ethanol for 8h; Inert atmosphere; Reflux;		100%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

mitomycin A
4055-39-4

mitomycin A

7-N,7'-N'-bis(2-ethyl)mitomycin C disulfide
93367-29-4

7-N,7'-N'-bis(2-ethyl)mitomycin C disulfide

Conditions
ConditionsYield
With triethylamine In methanol99%
With triethylamine In methanol for 10h; Ambient temperature;99%
With TEA In methanol at 20℃; for 24h;99%
glutaric anhydride,
108-55-4

glutaric anhydride,

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

N,N'-diglutaroylcystamine
109477-57-8

N,N'-diglutaroylcystamine

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; pH=10;99%
With sodium hydroxide In water pH=10;99%
Stage #1: glutaric anhydride,; cystamine dihydrochioride With sodium hydroxide In water at 20℃; pH=7 - ~ 10;
Stage #2: With hydrogenchloride In water		90%
Stage #1: cystamine dihydrochioride With sodium hydroxide In water pH=10;
Stage #2: glutaric anhydride, In water at 20℃; for 2h; pH=7 - 10;
Stage #3: With hydrogenchloride In water		90%
pyrazole-1-methanol
1120-82-7

pyrazole-1-methanol

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

C20H28N10S2

C20H28N10S2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;99%
(3,5-dimethyl-1H-pyrazol-1-yl)methanol
85264-33-1

(3,5-dimethyl-1H-pyrazol-1-yl)methanol

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

C28H44N10S2

C28H44N10S2

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;98%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

Methacryloyl chloride
920-46-7

Methacryloyl chloride

N,N'-(disulfanediylbis(ethane-2,1-diyl))bis(2-methylacryl amide)

N,N'-(disulfanediylbis(ethane-2,1-diyl))bis(2-methylacryl amide)

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With sodium hydroxide In water at 5℃; for 0.5h;
Stage #2: Methacryloyl chloride In water at 5 - 20℃; for 4h;		98%
Stage #1: cystamine dihydrochioride With sodium hydroxide In water for 0.333333h; Cooling with ice;
Stage #2: Methacryloyl chloride In dichloromethane; water at 0℃; for 3h;		47%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

N-methylmitomycin A
18209-14-8

N-methylmitomycin A

7-N,7'-N'-bis(2-ethyl)porfiromycin disulfide

7-N,7'-N'-bis(2-ethyl)porfiromycin disulfide

Conditions
ConditionsYield
With triethylamine In methanol for 10h; Ambient temperature;97%
BOC-glycine
4530-20-5

BOC-glycine

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

N,N'-bis<(tert-butyloxycarbonyl)glycyl>cystamine
97314-11-9

N,N'-bis<(tert-butyloxycarbonyl)glycyl>cystamine

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃;97%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 0℃; for 0.5h;82%
Stage #1: BOC-glycine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 0.333333h;
Stage #2: cystamine dihydrochioride With triethylamine In dichloromethane at 20℃; for 10h; Further stages.;		63%
3-azido-4-fluorobenzoic acid 2,5-dioxopyrrolidin-1-yl ester
934611-70-8

3-azido-4-fluorobenzoic acid 2,5-dioxopyrrolidin-1-yl ester

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

N-(2-aminoethyldisulfide-2'-ethyl)-3-azido-4-fluorobenzamide
934611-73-1

N-(2-aminoethyldisulfide-2'-ethyl)-3-azido-4-fluorobenzamide

Conditions
ConditionsYield
With triethylamine In methanol at 0℃; for 0.666667h;97%
N-(4-fluoro-3-nitrophenyl)acetamide
351-32-6

N-(4-fluoro-3-nitrophenyl)acetamide

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

di-2-[(4-acetylamino-2-nitrophenyl)arnino]ethyl disuifide

di-2-[(4-acetylamino-2-nitrophenyl)arnino]ethyl disuifide

Conditions
ConditionsYield
With sodium hydrogencarbonate In dimethyl sulfoxide at 45 - 80℃; for 7h;97%
With sodium hydrogencarbonate In dimethyl sulfoxide at 45 - 80℃; for 7h;97%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

di-tert-butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate
67385-10-8

di-tert-butyl(disulfanediylbis(ethane-2,1-diyl))dicarbamate

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 3h; Ambient temperature;96%
With triethylamine In 1,4-dioxane; water96%
With triethylamine In dichloromethane at 20℃; for 15h;96%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

mitomycin J
74985-82-3

mitomycin J

7-N,7'-N'-bis(2-thioethyl)dimitomycin E

7-N,7'-N'-bis(2-thioethyl)dimitomycin E

Conditions
ConditionsYield
With triethylamine In methanol for 10h; Ambient temperature;96%
5-(dimethylamino)naphth-1-ylsulfonyl chloride
605-65-2

5-(dimethylamino)naphth-1-ylsulfonyl chloride

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

N,N’-(disulfanediylbis(ethane-2,1-diyl))bis(5-(dimethylamino)naphthalene-1-sulfonamide)
881013-37-2

N,N’-(disulfanediylbis(ethane-2,1-diyl))bis(5-(dimethylamino)naphthalene-1-sulfonamide)

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With dmap; triethylamine In dichloromethane for 0.5h; Inert atmosphere;
Stage #2: 5-(dimethylamino)naphth-1-ylsulfonyl chloride In dichloromethane for 16h; Inert atmosphere;		96%
With sodium hydroxide; sodium hydrogencarbonate In water; acetone at 20℃; for 2h; pH=7.5;84%
With dmap; triethylamine In dichloromethane at 20℃;80%
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

Fmoc-cystamine
896465-25-1

Fmoc-cystamine

Conditions
ConditionsYield
With sodium carbonate In water; acetone at 20℃; for 2.5h;96%
nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

bis(cystamine)nickel(II) chloride

bis(cystamine)nickel(II) chloride

Conditions
ConditionsYield
With KOH In ethanol byproducts: KCl; addn. of KOH (0.01 mol) soln. (deaerated) to suspn. of cystamine, stirring, ice cooling, filtration, addn. of filtrate (dropwise, under N2 atm.) to NiCl2 (5 mmol) soln. (stirring), filtration; washing (EtOH, Et2O); elem.anal.;95%
2-pyrrole aldehyde
1003-29-8

2-pyrrole aldehyde

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

bis(2-(pyrrol-2-ylmethylenamino)ethyl)disulfide
132029-04-0

bis(2-(pyrrol-2-ylmethylenamino)ethyl)disulfide

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With sodium hydrogencarbonate In ethanol; water at 20℃; for 1h;
Stage #2: 2-pyrrole aldehyde In ethanol; water		95%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

Stearoyl chloride
112-76-5

Stearoyl chloride

{2-[(2-aminoethyl)disulfanyl]ethyl}octadecanamide
1256376-02-9

{2-[(2-aminoethyl)disulfanyl]ethyl}octadecanamide

Conditions
ConditionsYield
Stage #1: cystamine dihydrochioride With pyridine In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: Stearoyl chloride In N,N-dimethyl-formamide at 5 - 20℃; for 11h;		95%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

benzoyl chloride
98-88-4

benzoyl chloride

N,N'-(2,2'-disulfanediylbis(ethane-2,1-diyl))dibenzamide
5205-42-5

N,N'-(2,2'-disulfanediylbis(ethane-2,1-diyl))dibenzamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 20h; Inert atmosphere;95%
With triethylamine In dichloromethane at 0 - 20℃;721 mg
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

C34H28N2S2
1539267-22-5

C34H28N2S2

Conditions
ConditionsYield
With triethylamine In ethanol for 1h; Reflux;95%
L-(-)-(tert-butyloxycarbonyl)-2,2-bimethylthiazolidine-4-carboxylic acid
19907-83-6

L-(-)-(tert-butyloxycarbonyl)-2,2-bimethylthiazolidine-4-carboxylic acid

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

L-(-)-(tert-butyloxycarbonyl)-2,2-bimethylthiazolidine-4-carboxylic acid

L-(-)-(tert-butyloxycarbonyl)-2,2-bimethylthiazolidine-4-carboxylic acid

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water94.4%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

N,N'-<(ethanodithio)ethano>bis-
23516-74-7

N,N'-<(ethanodithio)ethano>bis-

Conditions
ConditionsYield
With sodium hydroxide In dichloromethane; water at 20℃; for 12h;94%
With sodium hydroxide In diethyl ether; water 1.) 1 h, 0 deg C; 2.) 2 h, r.t.;90%
With sodium hydroxide In dichloromethane; water at 20℃; for 12h;90%
dabsyl chloride
56512-49-3

dabsyl chloride

cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

(E)-4-((4-(dimethylamino)phenyl)diazenyl)-N-(2-mercaptoethyl)benzenesulfonamide

(E)-4-((4-(dimethylamino)phenyl)diazenyl)-N-(2-mercaptoethyl)benzenesulfonamide

Conditions
ConditionsYield
Stage #1: dabsyl chloride; cystamine dihydrochioride With triethylamine In acetonitrile at 0℃; for 2h;
Stage #2: With diothiothreitol In acetonitrile for 2h;		94%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

1,2-bis(2-azidoethyl)disulfane
352305-38-5

1,2-bis(2-azidoethyl)disulfane

Conditions
ConditionsYield
With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate In methanol at 20℃; for 12h;94%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

mitomycin B
4055-40-7

mitomycin B

7-N,7'-N'-bis(2-thioethyl)dimitomycin D

7-N,7'-N'-bis(2-thioethyl)dimitomycin D

Conditions
ConditionsYield
With triethylamine In methanol for 10h; Ambient temperature;93%
cystamine dihydrochioride
56-17-7

cystamine dihydrochioride

Ethyl oxalyl chloride
4755-77-5

Ethyl oxalyl chloride

N,N'-bis(ethoxyoxalyl)cystamine
1256735-90-6

N,N'-bis(ethoxyoxalyl)cystamine

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 0℃; for 1h; Schotten-Baumann reaction;93%

Cystamine dihydrochloride Chemical Properties

IUPAC Name: 2-(2-Aminoethyldisulfanyl)ethanamine dihydrochloride 
Molecular Formula: C4H14Cl2N2S2
Molecular Weight: 225.22g/mol
EINECS: 200-260-7
Density: 1.172g/cm3
Melting Point: 217-220 °C
Boiling Point: 264.8°C at 760mmHg
Flash Point: 114°C
Solubility: soluble
Chemical Properties: white powder
Freely Rotating Bonds: 7 
Polar Surface Area: 57.08 Å2 
Polarizability: 10-24cm3 
Enthalpy of Vaporization: 50.27 kJ/mol 
Vapour Pressure: 0.00949 mmHg at 25°C
Stability: stable,incompatible with strong oxidizing agents
The chemical synonyms of Cystamine dihydrochloride (56-17-7) are Bis-(2-aminoethyl)disulfide dihydrochloride ; 2,2'-Dithiodi(ethylammonium) dichloride ; 2,2'-Diaminodiethyl disulfide dihydrochloride ; 2,2'-Dithiobis(ethylamine) dihydrochloride ; Decarboxycystine dihydrochloride .Product categories of Cystamine dihydrochloride (56-17-7) are Pharmaceutical Intermediates .The molecular structure of Cystamine dihydrochloride (56-17-7) is .

Cystamine dihydrochloride Uses

It can be used in the synthesis of heparin antagonist body and fructose bisphosphatase .

Cystamine dihydrochloride Toxicity Data With Reference

1.    

scu-rat LDLo:200 mg/kg

     AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 185 (1937),461.
2.    

ipr-mus LD50:405 mg/kg

     ARZNAD    Arzneimittel-Forschung. Drug Research. 21 (1971),284.
3.    

scu-cat LDLo:200 mg/kg

     AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 185 (1937),461.
4.    

scu-gpg LDLo:300 mg/kg

     AEPPAE    Naunyn-Schmiedebergs Archiv fuer Experimentelle Pathologie und Pharmakologie. 185 (1937),461.

Cystamine dihydrochloride Consensus Reports

Reported in EPA TSCA Inventory.

Cystamine dihydrochloride Safety Profile

A poison by subcutaneous and intraperitoneal routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of HCl, SOx, and NOx. See also SULFIDES.
Hazard Codes:  Xn
Xn:  Harmful
Risk Statements:  22-36/37/38
22:  Harmful if swallowed
36/37/38:  Irritating to eyes, respiratory system and skin
Safety Statements:  37/39-26-36/37/39
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
37/39:  Wear suitable gloves and eye/face protection
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 

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