2,6-Dichloropurine CAS 5451-40-1
Introduction：Basic information about 2,6-Dichloropurine CAS 5451-40-1, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2,6-Dichloropurine Basic information
| Product Name: | 2,6-Dichloropurine |
| Synonyms: | 2,6-DICHLORO-9H-PURINE;2,6-DICHLOROPURINE;2,6-Dichloropurine.97%;2,6-dichloro-1H-purine;1H-Purine, 2,6-dichloro-;Dichloropurine;Cefepime Intermediate;2,6-dichloro-7H-purine |
| CAS: | 5451-40-1 |
| MF: | C5H2Cl2N4 |
| MW: | 189 |
| EINECS: | 226-681-6 |
| Product Categories: | Building Blocks;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Intermediates & Fine Chemicals;Pharmaceuticals;Nucleotides;Fused Ring Systems;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;PurinesHeterocyclic Building Blocks;Biochemistry;Nucleobases and their analogs;Nucleosides, Nucleotides & Related Reagents;Nucleic acids;Bases & Related Reagents;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Purine;Nucleotides and Nucleosides;Purines;FINE Chemical & INTERMEDIATES;Starting Raw Materials & Intermediates;Heterocycles;5451-40-1 |
| Mol File: | 5451-40-1.mol |
2,6-Dichloropurine Chemical Properties
| Melting point | 185-195 °C (dec.) (lit.) |
| Boiling point | 310.62°C (rough estimate) |
| density | 1.7265 (rough estimate) |
| refractive index | 1.6300 (estimate) |
| storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
| solubility | soluble |
| form | Crystalline Powder |
| pka | 5.22±0.20(Predicted) |
| color | White to yellow |
| Water Solubility | soluble |
| BRN | 9354 |
| InChI | InChI=1S/C5H2Cl2N4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11) |
| InChIKey | RMFWVOLULURGJI-UHFFFAOYSA-N |
| SMILES | N1C2C(=NC(Cl)=NC=2Cl)NC=1 |
| CAS DataBase Reference | 5451-40-1(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn,Xi |
| Risk Statements | 36/37/38-22 |
| Safety Statements | 22-24/25-37/39-26-36 |
| RIDADR | UN2811 |
| WGK Germany | 3 |
| HazardClass | IRRITANT |
| HS Code | 29349990 |
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
| Hazard Classifications | Acute Tox. 3 Oral |
| Description | 2,6-Dichloropurine is an important pharmaceutical intermediate. It is widely used in the preparation of purine nucleosides and purine nucleotides[1]. |
| Chemical Properties | white to light yellow crystal powder |
| Uses | Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1 |
| Uses | 2,6-Dichloropurine is used in the synthesis of 2,6-diamino-substituted purine derivatives as potential cardiomyogenesis inducing agents. |
| Synthesis Reference(s) | Journal of the American Chemical Society, 80, p. 404, 1958 DOI: 10.1021/ja01535a040 |
| Synthesis | 2,6-Dichloropurine is prepared in two main ways: (1) By chlorination of the purine ring structure, e.g., chlorination of xanthine (2,6-dihydroxypurine) with pyrophosphoryl chloride at high temperatures in sealed tubes in the presence of a phase-transfer catalyst or with phosphorus oxychloride under reflux, and chlorination of 6-chloropurine, hypoxanthine, or their N-oxides with phosphorus oxychloride, and chlorination with chlorine gas at low temperatures. Chlorination of 2,6-dithiopurine. (2) The purine ring is constructed using barbituric acid derivatives or 2,4-dichloro-5,6-diaminopyridine as starting materials. However, both methods are not very suitable for industrial production. The industrial preparation of 2,6-dichloropurine involves the direct chlorination of xanthine with phosphorus trichloride and a weakly nucleophilic organic base (e.g., amidine, guanidine base, or proton sponge)[1]. The reaction process is shown below: |
| Purification Methods | It can be recrystallised from 150 parts of boiling H2O and dried at 100o to constant weight. It is soluble in EtOAc. The HgCl2 salt separates from EtOH solution. UV: max 275nm ( 8.9K) at pH 1; and 280nm ( 8.5K) at pH 11 [Elion & Hitchings J Am Chem Soc 78 3508 1956, Schaeffer & Thomas J Am Chem Soc 80 3738 1958, Beaman & Robins J Appl Chem (London) 12 432 1962, Montgomery J Am Chem Soc 78 1928 1956]. [Beilstein 26 III/IV 1747.] |
| References | [1] QI ZENG. Facile and Practical Synthesis of 2,6-Dichloropurine[J]. Organic Process Research & Development, 2004, 8 6: 962-963. DOI:10.1021/op049878r. |
2,6-Dichloropurine Preparation Products And Raw materials
| Raw materials | HYPOXANTHINE-1-OXIDE-->ADENINE N(1)-OXIDE MONOHYDRATE, 98-->1,5-Dihydropyrrolo[3,2-a]pyrimidine-2,4-dion-->Isoamyl nitrite-->Xanthine-->6-Chloroguanine-->Guanine |
| Preparation Products | 2,6-Dichloro-7-methylpurine-->Cladribine-->7H-Purine, 2,6-dichloro-7-(1-methylethyl)--->2,6-dichloro-9-(1-methylethyl)-9H-purine-->9H-Purine, 2,6-dichloro-9-propyl- |
