Product Name

  • Name

    6-Mercaptopurine monohydrate

  • EINECS 212-968-3
  • CAS No. 6112-76-1
  • Article Data6
  • CAS DataBase
  • Density
  • Solubility insoluble in water
  • Melting Point 313 °C
  • Formula C5H4N4S.H2O
  • Boiling Point 490.6oC at 760 mmHg
  • Molecular Weight 170.195
  • Flash Point 250.5oC
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 22-36/37/39-45-36/37
  • Risk Codes 22-36/37/38-63-20/21/22
  • Molecular Structure Molecular Structure of 6112-76-1 (6-Mercaptopurine monohydrate)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms 6H-Purine-6-thione,1,7-dihydro-, monohydrate (9CI);Purine-6-thiol, monohydrate (8CI);Mercaptopurine;
  • PSA 98.68000
  • LogP 0.95120

Synthetic route

6-chloro-7H-purine
87-42-3

6-chloro-7H-purine

thiourea
17356-08-0

thiourea

6-mercaptopurine
6112-76-1

6-mercaptopurine

Conditions
ConditionsYield
With formic acid In ethanol at 78 - 80℃; for 1h;83.28%
11-mercaptounadecanoic acid
71310-21-9

11-mercaptounadecanoic acid

6-mercaptopurine
6112-76-1

6-mercaptopurine

C16H24N4O2S2
1228007-63-3

C16H24N4O2S2

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In dimethyl sulfoxide at 20℃; for 1.33333h;60%
(1E,4E)-1-(4-(2-bromoethoxy)phenyl)-5-(4-methylphenyl)pent-1,4-diene-3-one

(1E,4E)-1-(4-(2-bromoethoxy)phenyl)-5-(4-methylphenyl)pent-1,4-diene-3-one

6-mercaptopurine
6112-76-1

6-mercaptopurine

(1E,4E)-1-(4-(2-(9H-purin-6-ylthio)ethoxy)phenyl)-5-(4-methylphenyl)penta-1,4-dien-3-one

(1E,4E)-1-(4-(2-(9H-purin-6-ylthio)ethoxy)phenyl)-5-(4-methylphenyl)penta-1,4-dien-3-one

Conditions
ConditionsYield
Stage #1: 6-mercaptopurine With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h;
Stage #2: (1E,4E)-1-(4-(2-bromoethoxy)phenyl)-5-(4-methylphenyl)pent-1,4-diene-3-one In N,N-dimethyl-formamide at 40℃; for 2.5h;		54.5%
propionic acid
802294-64-0

propionic acid

6-mercaptopurine
6112-76-1

6-mercaptopurine

3-(7H-purin-6-ylthio)acrylic acid

3-(7H-purin-6-ylthio)acrylic acid

Conditions
ConditionsYield
With sodium methylate In methanol for 24h; Reflux;54%
p-(phenylazo)benzyl chloride
96256-46-1

p-(phenylazo)benzyl chloride

6-mercaptopurine
6112-76-1

6-mercaptopurine

(E)-6-((4-(phenyldiazenyl)benzyl)thio)-7H-purine

(E)-6-((4-(phenyldiazenyl)benzyl)thio)-7H-purine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide at 20℃;18%
trimethyltin(IV) hydroxide
56-24-6

trimethyltin(IV) hydroxide

6-mercaptopurine
6112-76-1

6-mercaptopurine

Sn(4+)*3(CH3)(1-)*(C5H3N4S)(1-)=[Sn(CH3)3(C5H3N4S)]

Sn(4+)*3(CH3)(1-)*(C5H3N4S)(1-)=[Sn(CH3)3(C5H3N4S)]

Conditions
ConditionsYield
In acetone Sn compd. and org. compd. refluxed in acetone for 1 h; distn. of solvent, filtration, washing with acetone, drying in vac.; elem. anal.;
dibutyltin chloride
683-18-1

dibutyltin chloride

6-mercaptopurine
6112-76-1

6-mercaptopurine

[Sn(CH2CH2CH2CH3)2(C5H3N4S)2]
96692-57-8

[Sn(CH2CH2CH2CH3)2(C5H3N4S)2]

Conditions
ConditionsYield
With sodium methoxide In methanol org. compd. heated at 150°C for 24 h, deprotonated with equimolar amount of CH3ONa in MeOH, resulting soln. added to soln. of Sn compd. in MeOH, reaction mixture refluxed with stirring for 4 h; evapn., filtration, addn. of soln. to Et2O, filtration, keeping of soln. at -10°C for 1 week, filtraition, washing, drying in vac.; elem. anal.;
6-mercaptopurine
6112-76-1

6-mercaptopurine

C5H4N4O2S
2002-60-0

C5H4N4O2S

Conditions
ConditionsYield
With diperiodatocuprate(III) dihydrate; potassium nitrate; potassium hydroxide at 25℃; for 4h; Kinetics; Concentration; Temperature; Inert atmosphere;
bismuth (III) nitrate pentahydrate

bismuth (III) nitrate pentahydrate

6-mercaptopurine
6112-76-1

6-mercaptopurine

C15H12BiN14O6S3(1+)*NO3(1-)

C15H12BiN14O6S3(1+)*NO3(1-)

Conditions
ConditionsYield
With nitric acid In ethanol at 85℃; for 1h; Reflux;
6-mercaptopurine
6112-76-1

6-mercaptopurine

C47H83N5O5S2

C47H83N5O5S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dimethyl sulfoxide / 1.33 h / 20 °C
2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane; N,N-dimethyl-formamide / 20 h / 20 °C
View Scheme
6-mercaptopurine
6112-76-1

6-mercaptopurine

C51H91N5O5S2

C51H91N5O5S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dimethyl sulfoxide / 1.33 h / 20 °C
2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane; N,N-dimethyl-formamide / 20 h / 20 °C
View Scheme
6-mercaptopurine
6112-76-1

6-mercaptopurine

C51H91N5O5S2

C51H91N5O5S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dimethyl sulfoxide / 1.33 h / 20 °C
2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane; N,N-dimethyl-formamide / 20 h / 20 °C
View Scheme
6-mercaptopurine
6112-76-1

6-mercaptopurine

C55H99N5O5S2

C55H99N5O5S2

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dimethyl sulfoxide / 1.33 h / 20 °C
2: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine / dichloromethane; N,N-dimethyl-formamide / 20 h / 20 °C
View Scheme
pentasodium 5-phosphoribosyl-α-1-pyrophosphate

pentasodium 5-phosphoribosyl-α-1-pyrophosphate

6-mercaptopurine
6112-76-1

6-mercaptopurine

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid
53-83-8

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-sulfanyl-9H-purin-9-yl)oxolan-2-yl]methoxy}phosphonic acid

Conditions
ConditionsYield
With potassium dihydrogenphosphate; recombinant Thermus thermophilus HB27 hypoxanthine phosphoribosyltransferase; magnesium chloride In aq. buffer at 60℃; for 24h; pH=8; Reagent/catalyst; Enzymatic reaction;

6-Mercaptopurine monohydrate Chemical Properties

Detail of 6-Mercaptopurine monohydrate (CAS NO.6112-76-1):
Molecular Structure:

IUPAC Name: 3,7-dihydropurine-6-thione hydrate
CAS Number: 6112-76-1
Molecular Formula: C5H4N4S.H2O
Molecular Weight: 170.21
EINECS: 212-968-3
Melting Point: 313 °C
Solubility: negligible
Storage temp: Store at 0-5 °C
Water Solubility: INSOLUBLE
BRN: 4012091
Synonyms of 6-Mercaptopurine monohydrate (CAS NO.6112-76-1): 1,7-Dihydro-6h-purin-6-thion,monohydrat ; 1,7-Dihydro-6h-purine-6-thionemonohydrate ; 1,7-Dihydro-6h-purine-6-thionmonohydrate ; 6h-Purin-6-thion,monohydrat ; 6-Merkaptopurin,monohydrat ; Purin-6-thiol,monohydrat
Product Categories: Pyridines, Pyrimidines, Purines and Pteredines; Purine; Heterocyclic Compounds; Antitumors for Research and Experimental Use; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids; Bases & Related Reagents; Heterocycles; Nucleotides; Sulfur & Selenium Compounds

6-Mercaptopurine monohydrate Uses

 6-Mercaptopurine monohydrate (CAS NO.6112-76-1) can be used as an immunosuppressive drug used to treat leukemia. It is also used for pediatric non-Hodgkin lymphoma, polycythemia vera, and psoriatic arthritis

6-Mercaptopurine monohydrate Toxicity Data With Reference

1.    

dlt-mus-ipr 500 mg/kg/40D-I

     DCTODJ    Drug and Chemical Toxicology. 6 (1983),83.
2.    

orl-mus LD50:1250 mg/kg

     MUREAV    Mutation Research. 223 (1989),349.
3.    

ipr-mus LD50:224 mg/kg

     MUREAV    Mutation Research. 223 (1989),349.

6-Mercaptopurine monohydrate Safety Profile

An experimental teratogen. A poison by intraperitoneal route. Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of SOx and NOx. See also MERCAPTANS.
Safety Information of 6-Mercaptopurine monohydrate (CAS NO.6112-76-1):
Hazard Codes:XnHarmful,XiIrritant
Risk Statements:22-36/37/38-63-20/21/22 
R22:Harmful if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R63:Possible risk of harm to the unborn child. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements:22-36/37/39-45-36/37 
S22:Do not breathe dust. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37:Wear suitable protective clothing and gloves.
WGK Germany:3
 RTECS:UP0400000
HS Code:29335995

6-Mercaptopurine monohydrate Specification

Stability and Reactivity of 6-Mercaptopurine monohydrate (CAS NO.6112-76-1):
Chemical Stability: Stable under normal temperatures and pressures. 
Conditions to Avoid: Incompatible materials, strong oxidants. 
Incompatibilities with Other Materials Strong oxidizing agents, strong acids, strong bases. 
Hazardous Decomposition Products Irritating and toxic fumes and gases. 
Hazardous Polymerization Has not been reported. 
Handling and Storage of 6-Mercaptopurine monohydrate (CAS NO.6112-76-1):
Handling: Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. 
Storage: Store in a cool, dry place. Keep container closed when not in use. 
First Aid Measures of 6-Mercaptopurine monohydrate (CAS NO.6112-76-1):
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. 
Skin: Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. 
Ingestion: Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. 
Inhalation: Remove from exposure and move to fresh air immediately. 

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