ChemicalBook Product Catalog Biochemical Engineering Nucleoside drugs Nucleotides and their analogs 6-Chloropurine

6-Chloropurine

6-Chloropurine Chemical Properties
Melting point >300 °C (dec.) (lit.)
Boiling point 254.17°C (rough estimate)
density 1.4649 (rough estimate)
refractive index 1.8430 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility 5 g/L
form crystalline
pka7.47±0.20(Predicted)
color yellow-orange
Water Solubility 5 g/L
Merck 14,2161
BRN 5774
InChIKeyZKBQDFAWXLTYKS-UHFFFAOYSA-N
CAS DataBase Reference87-42-3(CAS DataBase Reference)
NIST Chemistry Reference6-Chloropurine(87-42-3)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-20/21/22
Safety Statements 26-36-36/37/39
WGK Germany 3
RTECS UO7520000
F 10-23
HazardClass IRRITANT
HS Code 29335990
ToxicityLD50 oral in mouse: 720mg/kg
MSDS Information
ProviderLanguage
6-Chloropurine English
ACROS English
SigmaAldrich English
ALFA English
6-Chloropurine Usage And Synthesis
Chemical PropertiesIt is a pale yellow crystal with relatively stable chemical properties that do not cause decomposition at room temperature. Its structure includes nitrogen heterocycles, which give rise to remarkable alkalinity and the formation of volatile acid salts. It is soluble in dimethyl sulfoxide, but has only slight solubility in water.
Uses6-Chloropurine is used in the preparation of 9-alkylpurines through alkylation with various substituted alkyl halides in dimethyl sulfoxide. It is also used to prepare 6-succinoaminopurine.
DefinitionChEBI: 6-Chloro-1H-purine is a member of purines. It is metabolized to form 6-mercaptopurine and has been used as an antineoplastic.
Preparation6-chloropurine is synthesized by reacting hypoxanthine with phosphoryl chloride in the presence of an unreactive base such as dimethyl aniline. It may likewise be formed by heating hypoxanthine under pressure with phosphoryl chloride as well as with a reagent prepared by adding water, preferably about by volume, to dry phosphoryl chloride.
US2832781A
Synthesis Reference(s)Journal of the American Chemical Society, 78, p. 1928, 1956 DOI: 10.1021/ja01590a043
General DescriptionThe acid-catalyzed reaction of 6-chloropurine with 3,4-di-O-acetyl-D-xylal has been investigated.
Purification Methods6-Chloropurine crystallises from water. The UV in water at pH 1 has 264nm (log 3.94). [Beilstein 26 III/IV 1742.]
6-Chloropurine Preparation Products And Raw materials
Preparation ProductsAdenine-->6-benzylaminopurine-->6-CYANOPURINE-->6-BENZYLOXYPURINE-->6-Dimethylaminopurine-->6-ETHYLMERCAPTOPURINE-->6-N-BUTOXYPURINE-->6-Mercaptopurine monohydrate-->6-Chloropurine ribonucleoside-->6-Iodopurine-->6-ETHOXYPURINE-->N-Benzyl-9-(tetrahydro-2H-pyran-2-yl)adenine-->6-CHLORO-7-METHYLPURINE-->N-(4-methylbenzyl)-N-(9H-purin-6-yl)amine
6-CHLOROPURINE-2'-DEOXYRIBOSIDE Allopurinol Adenine 6-Chloropurine 2-Amino-6-chloro-9H-purine-9-riboside,2-Amino-6-chloropurine-9-b-D-riboside Azathioprine Guanine 6-Chloro-7H-purine-2-amine,2-Amino-6-chloro-9H-purine 99%,2-Amino-6-chloro-9H-purine,2-Amino-6-Chloropurine(6-Chloroguanine),2-AMINO-6-CHLOROPURINE 9-METHYL-6-CHLOROPURINE 6-CHLOROPURINE GLUCOSIDE 6-CHLORO-8-METHYL-PURINE 6-CHLORO-9-(TETRAHYDRO-2-PYRANYL)-PURINE Purine 6-Chloropurine ribonucleoside 2,6,8-TRICHLOROPURINE 3,5-DI(ACETYLOXY)-2-[(ACETYLOXY)METHYL]-6-(2,6-DICHLORO-9H-PURIN-9-YL)TETRAHYDRO-2H-PYRAN-4-YL ACETATE 9-Benyl-6-chloro-9H-purine,9-BENZYL-6-CHLORO-9H-PURINE 2-METHYLTHIO-6-CHLOROPURINE
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