2,6-Dichloropurine
- Product Name
- 2,6-Dichloropurine
- CAS No.
- 5451-40-1
- Chemical Name
- 2,6-Dichloropurine
- Synonyms
- 2,6-DICHLORO-9H-PURINE;2,6-dichloro-7H-purine;2,6-dichloro-1H-purine;NSC 18395;Dichloropurine;6-Dichloropurine;2,6-DICHLOROPURINE;Cefepime Intermediate;2,6-Dichloropurine>2,6-Dichloropurine.97%
- CBNumber
- CB1720642
- Molecular Formula
- C5H2Cl2N4
- Formula Weight
- 189
- MOL File
- 5451-40-1.mol
2,6-Dichloropurine Property
- 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
- InChIKey
- RMFWVOLULURGJI-UHFFFAOYSA-N
- CAS DataBase Reference
- 5451-40-1(CAS DataBase Reference)
Safety
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H301Toxic if swalloed
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- D73103
- Product name
- 2,6-Dichloropurine
- Purity
- 97%
- Packaging
- 1g
- Price
- $17.48
- Updated
- 2024/03/01
- Product number
- D73103
- Product name
- 2,6-Dichloropurine
- Purity
- 97%
- Packaging
- 5g
- Price
- $83.2
- Updated
- 2024/03/01
- Product number
- D2470
- Product name
- 2,6-Dichloropurine
- Purity
- >97.0%(HPLC)(T)
- Packaging
- 1g
- Price
- $24
- Updated
- 2024/03/01
- Product number
- D2470
- Product name
- 2,6-Dichloropurine
- Purity
- >97.0%(HPLC)(T)
- Packaging
- 5g
- Price
- $60
- Updated
- 2024/03/01
- Product number
- B21289
- Product name
- 2,6-Dichloropurine, 97%
- Packaging
- 1g
- Price
- $76.65
- Updated
- 2024/03/01
2,6-Dichloropurine Chemical Properties,Usage,Production
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
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View Lastest Price from 2,6-Dichloropurine manufacturers
- Product
- 2,6-Dichloropurine 5451-40-1
- Price
- US $100.00-75.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 5000
- Release date
- 2024-08-15
- Product
- 2,6-Dichloropurine 5451-40-1
- Price
- US $79.00-38.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-11-19
- Product
- 2,6-Dichloropurine 5451-40-1
- Price
- US $0.00/Kg/Bag
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 100KG
- Release date
- 2021-06-01