2,6-Dichloropurine

Base Information

• Chemical Name: 2,6-Dichloropurine
• CAS No.: 5451-40-1
• Molecular Formula: C5H2Cl2N4
• Molecular Weight: 189.004
• Hs Code.: 29349990
• European Community (EC) Number: 226-681-6
• NSC Number: 18395
• DSSTox Substance ID: DTXSID60202922
• Nikkaji Number: J81.036C
• ChEMBL ID: CHEMBL1256006
• Mol file: 5451-40-1.mol

Synonyms:Purine, 2,6-dichloro-;2,6-Dichloro-1H-purine;2,6-Dichloro purine 98%;2,6-Dichloropurine 99%;Purine, 2,6-dichloro- (VAN) (8CI);2,6-dichloro-5H-purine;1H-Purine, 2,6-dichloro-;2,6-dichloro-9H-purine;9H-purine, 2,6-dichloro-;1H-Purine, 2,6-dichloro- (9CI);

Chemical Property of 2,6-Dichloropurine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.07E-06mmHg at 25°C
• Melting Point: 184-186 °C
• Refractive Index: 1.741
• Boiling Point: 405.4 °C at 760 mmHg
• PKA: 5.22±0.20(Predicted)
• Flash Point: 231.3 °C
• PSA: 54.46000
• Density: 1.792 g/cm³
• LogP: 1.65970
• Storage Temp.: 2-8°C
• Solubility.: soluble
• Water Solubility.: soluble
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 187.9656515
• Heavy Atom Count: 11
• Complexity: 155

Purity/Quality:

99% ^*data from raw suppliers

2,6-Dichloropurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 22-24/25-37/39-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1)C(=NC(=N2)Cl)Cl
• Uses: Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1 2,6-Dichloropurine is used in the synthesis of 2,6-diamino-substituted purine derivatives as potential cardiomyogenesis inducing agents. Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.

Technology Process of 2,6-Dichloropurine

There total 25 articles about 2,6-Dichloropurine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

2,6-dihydroxypurine (69-89-6) → 2,6 dichloropurine (5451-40-1)

Guidance literature:

With pyridine; trichlorophosphate; at 180 ℃; for 3h; under 150.015 - 900.09 Torr; Neat (no solvent);

DOI:10.1021/jo2003715

Reference yield: 78.3%

9-acetyl-2-amino-6-chloro-9H-purine (470483-92-2) → 2,6-dichloro-7H-purine (5451-40-1)

Guidance literature:

9-acetyl-2-amino-6-chloro-9H-purine; With chloro-trimethyl-silane; tetraethylammonium chloride; isopentyl nitrite; at 50 - 60 ℃; for 10h;

With sodium hydroxide; In water; pH=4 - 5; Product distribution / selectivity;

Reference yield: 66.1%

2-amino-6-chloropurine (10310-21-1) → 2,6-dichloro-7H-purine (5451-40-1)

Guidance literature:

2-amino-6-chloropurine; With N-benzyl-N,N,N-triethylammonium chloride; dimethylsilicon dichloride; isopentyl nitrite; In n-heptane; at 50 - 60 ℃; for 17h;

With sodium hydroxide; In water; pH=4 - 5; Product distribution / selectivity;

upstream raw materials:

diethoxymethyl acetate

4,5-diamino-2,6-dichloropyrimidine

orthoformic acid triethyl ester

xanthin

Downstream raw materials:

2,6-dipiperidino-7(9)H-purine

2-chloro-6-morpholin-4-yl-7⁽⁹⁾H-purine

2,6-dimorpholino-7(9)H-purine

2-chloro-1,7-dihydro-purine-6-thione

Refernces

• 1、 Zeng, Qi,Huang, Bangzhou,Danielsen, Knut,Shukla, Rajesh,Nagy, Thomas. "Facile and practical synthesis of 2,6-dichloropurine". . p. 962 - 963. Retrieved 2004.
• 2、 -. "SUBSTITUTED BICYCLIC PYRIMIDINE-BASED COMPOUNDS AND COMPOSITIONS AND USES THEREOF". Paragraph 00230; 00231. . Retrieved 2018/08/20.
• 3、 Ruíz-Pérez, Karen M.,Quiroz-García, Beatriz,Hernández-Rodríguez, Marcos. "Prolinamides of Aminouracils, Organocatalyst Modifiable by Complementary Modules". . p. 5763 - 5772. Retrieved 2018/11/10.