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

pka

7.47±0.20(Predicted)

color 

yellow-orange

Water Solubility 

5 g/L

Merck 

14,2161

BRN 

5774

InChIKey

ZKBQDFAWXLTYKS-UHFFFAOYSA-N

CAS DataBase Reference

87-42-3(CAS DataBase Reference)

NIST Chemistry Reference

6-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

Toxicity

LD50 oral in mouse: 720mg/kg

MSDS

• Language:English Provider:6-Chloropurine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

6-Chloropurine Usage And Synthesis

Chemical Properties

It 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.

Uses

6-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.

Definition

ChEBI: 6-Chloro-1H-purine is a member of purines. It is metabolized to form 6-mercaptopurine and has been used as an antineoplastic.

Preparation

6-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 Description

The acid-catalyzed reaction of 6-chloropurine with 3,4-di-O-acetyl-D-xylal has been investigated.

Purification Methods

6-Chloropurine crystallises from water. The UV in water at pH 1 has 264nm (log 3.94). [Beilstein 26 III/IV 1742.]

6-Chloropurine(87-42-3)Related Product Information

• Allopurinol
• Purine
• Guanine
• Adenine
• Azathioprine
• 2,6-Dichloropurine
• 6-CHLORO-9-(TETRAHYDRO-2-PYRANYL)-PURINE
• 2-Amino-6-chloro-9H-purine-9-riboside,2-Amino-6-chloropurine-9-b-D-riboside
• 6-Chloropurine ribonucleoside
• 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
• 2,6,8-TRICHLOROPURINE
• 6-CHLOROPURINE-2'-DEOXYRIBOSIDE
• 2,6-Dichloro-7-methylpurine
• CHLOROPURINE, 6-,6-CHLORO-9H-PURINE
• 6-Chloro-2-fluoropurine
• 6-Amino-9-(2-chloro-6-fluorobenzyl)purine
• 8-Chloro-7H-purine
• 2-AMINO-6-CHLOROPURINE, 99+%