2-Amino-6-chloropurine

Base Information

• Chemical Name: 2-Amino-6-chloropurine
• CAS No.: 10310-21-1
• Molecular Formula: C5H4ClN5
• Molecular Weight: 169.573
• Hs Code.: DERIVATION
• European Community (EC) Number: 233-686-7
• NSC Number: 29570
• UNII: 83V03P835E
• DSSTox Substance ID: DTXSID9074432
• Nikkaji Number: J236.697E
• Wikidata: Q27139921
• Pharos Ligand ID: URVXHJKJH7CW
• Metabolomics Workbench ID: 65954
• ChEMBL ID: CHEMBL226396
• Mol file: 10310-21-1.mol

Synonyms:2-amino-6-chloropurine

Chemical Property of 2-Amino-6-chloropurine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.75E-15mmHg at 25°C
• Melting Point: 300 °C
• Refractive Index: 1.826
• Boiling Point: 623.9 °C at 760 mmHg
• PKA: 6.65±0.20(Predicted)
• Flash Point: 331.1 °C
• PSA: 80.48000
• Density: 1.77 g/cm³
• LogP: 1.16970
• Storage Temp.: Keep Cold
• Solubility.: Solubility in 1mol/L NaOH; very faint turbidity.
• Water Solubility.: 1.7 g/L (20 ºC)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 169.0155228
• Heavy Atom Count: 11
• Complexity: 154

Purity/Quality:

99% ^*data from raw suppliers

2-Amino-6-chloropurine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N1)C(=NC(=N2)N)Cl
• 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. 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).
• Uses: 2-Amino-6-chloropurine may be used:in the enzymatic synthesis of 2′-deoxyguanosinein the synthesis of 9-alkyl purinesin the synthesis of (R)- and (S)-N-(2-phosphonomethoxypropyl) derivatives of purine and pyrimidine bases 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.

Technology Process of 2-Amino-6-chloropurine

There total 23 articles about 2-Amino-6-chloropurine 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: 96.2%

N2-acetylguanine (19962-37-9) → 2-Amino-6-chloropurin (10310-21-1)

Guidance literature:

N²-acetylguanine; With N-methylcyclohexylamine; thionyl chloride; 1,1,1,3,3,3-hexachloro-propan-2-one; at 85 ℃; for 24h;

With sodium hydroxide; In water; at 25 ℃; for 6h; Reagent/catalyst;

Reference yield: 96.2%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C4H4ClN5O → 2-Amino-6-chloropurin (10310-21-1)

Guidance literature:

formaldehyd; C₄H₄ClN₅O; With sodium pyrosulfate; In water; at 70 - 115 ℃; for 3h;

With toluene-4-sulfonic acid; In toluene; at 105 - 110 ℃; for 18h;

Reference yield: 94.0%

Guanine (8039-79-0) → 2-amino-6-chloropurine (10310-21-1)

Guidance literature:

With thionyl chloride; dihydrogen peroxide; at 40 ℃; for 3h; Temperature;

upstream raw materials:

thioguanin

2,9-diacetylguanine

2-amino-1,9-dihydro-6H-purin-6-one

formic acid

Downstream raw materials:

thioguanin

C₃₁H₂₄ClN₅O₇

C₃₁H₂₄ClN₅O₇

1-(2-Amino-6-chloro-purin-9-yl)-3-azido-propan-2-ol

Refernces

• 1、 Lidak et al.. "-". . . Retrieved 1970.
• 2、 -. "Preparation method of purine nucleotide intermediate". Paragraph 0028-0032; 0037-0041; 0046-0050. . Retrieved 2021/06/21.
• 3、 -. "Preparation methods for 2-amino-6-chloroguanine and intermediates of 2-amino-6-chloroguanine". Paragraph 0055; 0067; 0070-0071; 0075; 0078-0079. . Retrieved 2021/08/25.