6-CP
6-chloro-5H-purine
CAS: 87-42-3
Molecular Formula: C5H3ClN4
6-CP - Names and Identifiers
| Name | 6-chloro-5H-purine |
| Synonyms | 6-CP 6-Chloropurine 6-chloro-1h-purin AKOS BBS-00002143 6-chloro-5H-purine 1H-Purine, 6-chloro- 9H-Purine, 6-chloro- 6-CHLOROPURINE (6ClP) 6-CHLOROPURINE extrapure |
| CAS | 87-42-3 |
| EINECS | 201-745-6 |
| InChI | InChI=1/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-3H |
| InChIKey | ZKBQDFAWXLTYKS-UHFFFAOYSA-N |
6-CP - Physico-chemical Properties
| Molecular Formula | C5H3ClN4 |
| Molar Mass | 154.56 |
| Density | 1.4649 (rough estimate) |
| Melting Point | >300 °C (dec.) (lit.) |
| Boling Point | 254.17°C (rough estimate) |
| Flash Point | 109.1°C |
| Water Solubility | 5 g/L |
| Solubility | 5 g/L |
| Vapor Presure | 0.0242mmHg at 25°C |
| Appearance | White Crystals |
| Color | yellow-orange |
| Merck | 14,2161 |
| BRN | 5774 |
| pKa | 7.47±0.20(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.8430 (estimate) |
| MDL | MFCD00075825 |
| Physical and Chemical Properties | Melting point 300°C water-soluble 5g/L |
| Use | Used as an intermediate in purine products |
| In vivo study | 6-Chloropurine to S-(6-punnyl)glutathione and further metabolism of S-(6-punnyl)glutathione to 6-mercaptopunne may be involved in the mechanism of the 6-Chloropurine-induced antitumor activity. 6-chloropurine and azaserine have been shown to have synergic antitumor properties in a variety of mouse neoplasms when administered simultaneously. |
6-CP - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| WGK Germany | 3 |
| RTECS | UO7520000 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29335990 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 oral in mouse: 720mg/kg |
6-CP - Introduction
Solubility in water: 5g/l. Soluble in ether and dimethylformamide. Decompose at 175~177 ℃ (preheat to 170 ℃ first), and there are also reports that it does not melt at 290 ℃. The maximum absorption wavelength (pH5 · 2) is 265nm(ε 9120),(pH13)274nm(ε 8790).
Last Update：2022-10-16 17:29:28
6-CP - Reference Information
| Introduction | 6-chloropurine is one of the main intermediates in the synthesis of adenine, which is ammoniated at the 6-position to obtain adenine. Adenine, whose chemical name is 6-aminopurine, its derivatives are widely used in the fields of medicine and agricultural chemicals. For example, it is the main raw material for the synthesis of vitamin B4 (adenine phosphate); adefovir dipivoxil (Adefovirdi-pivoxil,9-[2-[bis (tervalanoyloxymethoxy) phosphonomethoxy] ethyl] adenine) developed by Gileadsciences Corporation of the United States, was approved by the FDA in September 2002 and has become a new nucleoside analog drug for the treatment of hepatitis B. After oral administration, it can effectively inhibit the replication of hepatitis B virus DNA chain. |
| preparation method | the dosage ratio of feeding substance is acetylhypoxanthine: phosphorus oxychloride: N,N-dimethylaniline is 1.0: 5.0: 1.0.35.6g acetylhypoxanthine (0.20mol), 152153.0g phosphorus oxychloride (1.00mol) and 24.2gN are added into a 500mL three-mouth flask equipped with thermometer and mechanical stirring, N-dimethylaniline (0.20mol), start stirring, heat to 105 ℃, keep warm for 4 hours, evaporate unreacted phosphorus oxychloride. Cool to 0 ℃, add 100mL of ice water, and adjust the pH value to 8 with 0.1MNaOH solution. After cooling, a large amount of yellow solid is precipitated. Filtration, cold water washing, drying, 6-chloropurine 27.6g, the yield is 90.0% (calculated as acetylhypoxanthine, the same below.), The detected purity is 99.0%. |
| Biological activity | 6-Chloropurine is a chemically synthesized block. Preparation of intermediates of 9-alkylpurines and 6-mercaptopurine. It has anti-tumor activity. |
| in vivo study | 6-Chloropurine to S-(6-punnyl)glutathione and further metabolism of S-(6-punnyl)glutathione to 6-mercaptopunne may be involved in the mechanism of the 6-Chloropurine-induced antitumor activity. 6-Chloropurine and azaserine have been show to have synergic antitumor properties in a variety of house neoplasms when administered simultaneously. |
| chemical properties | light yellow crystals. |
| use | biochemical research. Used as an intermediate for purine products |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
Last Update：2024-04-09 20:49:11
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