ChemicalBook >> CAS DataBase List >>2,6-Dichloropurine

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;2,6-Dichloropurine>Cefepime Intermediate;2,6-Dichloropurine.97%
CBNumber:
CB1720642
Molecular Formula:
C5H2Cl2N4
Molecular Weight:
189
MDL Number:
MFCD09749894
MOL File:
5451-40-1.mol
MSDS File:
SDS
Last updated:2024-12-10 09:15:32

2,6-Dichloropurine 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
pka 5.22±0.20(Predicted)
form Crystalline Powder
color White to yellow
Water Solubility soluble
BRN 9354
InChIKey RMFWVOLULURGJI-UHFFFAOYSA-N
CAS DataBase Reference 5451-40-1(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301
Precautionary statements  P264-P270-P301+P310-P405-P501
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
NFPA 704
1
3 0

2,6-Dichloropurine price More Price(39)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D73103 2,6-Dichloropurine 97% 5451-40-1 1g $17.48 2024-03-01 Buy
Sigma-Aldrich D73103 2,6-Dichloropurine 97% 5451-40-1 5g $83.2 2024-03-01 Buy
TCI Chemical D2470 2,6-Dichloropurine >97.0%(HPLC)(T) 5451-40-1 1g $24 2024-03-01 Buy
TCI Chemical D2470 2,6-Dichloropurine >97.0%(HPLC)(T) 5451-40-1 5g $60 2024-03-01 Buy
Alfa Aesar B21289 2,6-Dichloropurine, 97% 5451-40-1 1g $76.65 2024-03-01 Buy
Product number Packaging Price Buy
D73103 1g $17.48 Buy
D73103 5g $83.2 Buy
D2470 1g $24 Buy
D2470 5g $60 Buy
B21289 1g $76.65 Buy

2,6-Dichloropurine Chemical Properties,Uses,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

2,6-Dichloropurine is used in the synthesis of 2,6-diamino-substituted purine derivatives as potential cardiomyogenesis inducing agents.

Uses

Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1

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:
preparation of 2,6-dichloropurine

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.

10310-21-1
5451-40-1
Synthesis of 2,6-Dichloropurine from 6-Chloroguanine
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View Lastest Price from 2,6-Dichloropurine manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2,6-Dichloropurine pictures 2024-12-23 2,6-Dichloropurine
5451-40-1
US $100.00-75.00 / kg 1kg 99% 5000 HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
2,6-Dichloropurine pictures 2024-12-23 2,6-Dichloropurine
5451-40-1
US $79.00-38.00 / kg 1kg 99% 20ton Hebei Zhuanglai Chemical Trading Co Ltd
2,6-Dichloropurine pictures 2024-12-13 2,6-Dichloropurine
5451-40-1
US $0.00 / Kg/Bag 1KG 98%min 100KG WUHAN FORTUNA CHEMICAL CO., LTD
  • 2,6-Dichloropurine pictures
  • 2,6-Dichloropurine
    5451-40-1
  • US $100.00-75.00 / kg
  • 99%
  • HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
  • 2,6-Dichloropurine pictures
  • 2,6-Dichloropurine
    5451-40-1
  • US $79.00-38.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co Ltd
2,6-DICHLOROPURINE 2,6-Dichloropurine.97% 1H-Purine, 2,6-dichloro- Dichloropurine Cefepime Intermediate 9H-Purine, 2,6-dichloro- 6-Dichloropurine NSC 18395 2,6-Dichloropurine> 2,6-Dichloropurine USP/EP/BP 2,6-DICHLORO-9H-PURINE 2,6-dichloro-1H-purine 2,6-dichloro-7H-purine 5451-40-1 2001-2-5 5451-41-0 C5H2ClN4 HETERO CHLORIDE Building Blocks Halogenated Heterocycles Heterocyclic Building Blocks Purines 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