6-Chloroguanine CAS 10310-21-1
Introduction：Basic information about 6-Chloroguanine CAS 10310-21-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
6-Chloroguanine Basic informationDescription
| Product Name: | 6-Chloroguanine |
| Synonyms: | Clofarabine Impurity 3;AURORA KA-689;2-amino-6-chloro-purin;2-AMINO-6-CHLOROPURINE;6-CHLORO-2-AMINOPURINE;6-CHLORO-9H-PURIN-2-YLAMINE;6-CHLOROGUANINE;6-Chloro-7H-purin-2-ylamine |
| CAS: | 10310-21-1 |
| MF: | C5H4ClN5 |
| MW: | 169.57 |
| EINECS: | 233-686-7 |
| Product Categories: | Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Nucleotides;Fused Ring Systems;Amines;Purine;Nucleotides and Nucleosides;Purines;FINE Chemical & INTERMEDIATES;Starting Raw Materials & Intermediates;Miscellaneous Biochemicals;Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Aromatics;Heterocycles |
| Mol File: | 10310-21-1.mol |
6-Chloroguanine Chemical Properties
| Melting point | >300 °C (lit.) |
| Boiling point | 279.76°C (rough estimate) |
| density | 1.4937 (rough estimate) |
| refractive index | 1.6110 (estimate) |
| storage temp. | 2-8°C |
| solubility | Solubility in 1mol/L NaOH |
| pka | 6.65±0.20(Predicted) |
| form | Powder |
| color | White to yellow |
| Water Solubility | 1.7 g/L (20 ºC) |
| BRN | 9626 |
| InChI | InChI=1S/C5H4ClN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11) |
| InChIKey | RYYIULNRIVUMTQ-UHFFFAOYSA-N |
| SMILES | N1C2C(=NC(N)=NC=2Cl)NC=1 |
| CAS DataBase Reference | 10310-21-1(CAS DataBase Reference) |
| EPA Substance Registry System | 6-Chloro-2-aminopurine (10310-21-1) |
Safety Information
| Hazard Codes | Xi,Xn |
| Risk Statements | 20/21/22-36/37/38 |
| Safety Statements | 22-24/25-36-26 |
| WGK Germany | 3 |
| RTECS | UO7502000 |
| F | 10 |
| Hazard Note | Irritant/Keep Cold |
| HazardClass | IRRITANT, KEEP COLD |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Description | 6-Chloroguanine, also be known as 2-Amino-6-chloropurine may be used in the enzymatic synthesis of 2′-deoxyguanosine, 9-alkyl purines (R)and (S)-N(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. It is also useful during the synthesis of guanine. |
| Description | 2-Amino-6-chloropurine is a precursor in the synthesis of nucleoside analogs with antiviral activity against Epstein-Barr virus (EBV) and human herpes virus 6 (HHV-6). |
| Chemical Properties | white to light yellow crystal powder |
| Uses | 2-Amino-6-chloropurine finds its uses in the enzymatic synthesis of 2?-deoxyguanosine, 9-alkyl purines and (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases. |
| Uses | 2-Amino-6-chloropurine may be used:
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| Definition | ChEBI: 6-chloroguanine is an organochlorine compound that is 7H-purin-2-amine substituted by a chloro group at position 6. It is a member of 2-aminopurines and an organochlorine compound. |
| General Description | 2-Amino-6-chloropurine is a 6-substituted purine. Tautomeric purine forms of 2-amino-6-chloropurine were investigated by vibrational spectroscopy and quantum chemical method. |
| Synthesis | Preparation of 2-amino-6-chloropurine: Diacetyl guanine (8.0g, 0.034 moles), triethyimethylammonium chloride (15.45g, 0.102 moles), and triethylamine (4.74 mis, 0.034 moles) were heated together with stirring in acetonitrile (70mls) to 50°C. Phosphorus oxychioride (6.34 mis, 0.068 moles) was then added and stirring continued for 4 hours. The reaction mixture was cooled and then added to aqueous sodium hydroxide solution (20g in 300mls water). The reaction mixture was heated to 80°C for 2 hours and then the volume made up to 300 mis with water. The mixture was cooled to 25°C and the pH adjuster to 7 using 10% hydrochloric acid. The resulting slurry was stirred for fifteen minutes and the product filtered off and washed with water 30 mis and then dried at 80°C under vacuum to give a cream/off white coloured product, 2-amino-6-chioropurine 4.69 g (74.6% yield). |
| References | [1] Heterocycles, 2008, vol. 75, # 11, p. 2803 - 2808 [2] Patent: US5389637, 1995, A [3] Patent: US4736029, 1988, A [4] Patent: EP203685, 1991, B1 [5] Patent: US4736029, 1988, A |
6-Chloroguanine Preparation Products And Raw materials
| Raw materials | Guanine-->2,4,5-Triamino-6-chloropyrimidine-->Formamide, N-(6-chloro-9H-purin-2-yl)--->N,N-Dimethylformamide-->Ammonium hydroxide-->Water-->trichlorophosphate |
| Preparation Products | 6-Thioguanine-->6-O-Benzylguanine-->Ganciclovir-->Famciclovir-->2-Amino-6-iodopurine-->Penciclovir-->2-Amino-6-chloropurine Riboside-->2-(t-Butyldiphenylsilanyloxy)Ethanol-->2-Aminopurine-->2-Amino-6-chloro-9H-purine-9-acetic acid benzyl ester-->tert-butyl 2-amino-6-chloro-9H-purine-9-carboxylate-->6-(pyrrolidin-1-yl)-9H-purin-2-aMine-->BIIB-021 |
