4,6-Dichloro-5-nitropyrimidin-2-amine

Base Information

• Chemical Name: 4,6-Dichloro-5-nitropyrimidin-2-amine
• CAS No.: 134716-82-8
• Molecular Formula: C4H2Cl2N4O2
• Molecular Weight: 208.991
• European Community (EC) Number: 970-753-6
• Nikkaji Number: J2.761.595C
• Mol file: 134716-82-8.mol

Synonyms:4,6-Dichloro-5-nitropyrimidin-2-amine;134716-82-8;SCHEMBL9871854;MFCD17169373;AKOS015995517;SB60178;DB-023336;CS-0309360;E10277;EN300-178383

Chemical Property of 4,6-Dichloro-5-nitropyrimidin-2-amine

Chemical Property:

• Melting Point: 248-250℃
• PSA: 97.62000
• Density: 1.834±0.06 g/cm3 (20℃ 760 Torr)
• LogP: 2.37820
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 207.9554807
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%Min ^*data from raw suppliers

4,6-Dichloro-5-nitropyrimidin-2-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1(=C(N=C(N=C1Cl)N)Cl)[N+](=O)[O-]

Technology Process of 4,6-Dichloro-5-nitropyrimidin-2-amine

There total 2 articles about 4,6-Dichloro-5-nitropyrimidin-2-amine 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: 82.0%

2-acetylamino-6-chloro-5-nitro-4(3H)-pyrimidinone (1195949-92-8) + Vilsmeier reagent (3724-43-4,149409-22-3) → 2-amino-4,5,6-trichloropyrimidine (51501-53-2) + 2-amino-4,6-dichloro-5-nitropyrimidine (134716-82-8)

Guidance literature:

2-acetylamino-6-chloro-5-nitro-4(3H)-pyrimidinone; Vilsmeier reagent; at 100 ℃; for 3.5h; Inert atmosphere;

With water; at 20 ℃;

DOI:10.1016/j.tetlet.2009.08.029

Reference yield: 73.0%

2-Amino-4,6-dichloropyrimidine (56-05-3) → 2-amino-4,6-dichloro-5-nitropyrimidine (134716-82-8)

Guidance literature:

With sulfuric acid; nitric acid; In trifluoroacetic anhydride; at 2 ℃; for 48h; Reagent/catalyst; Temperature;

Reference yield: 42.0%

2-amino-4,6-dichloro-5-nitropyrimidine (134716-82-8) + benzyl alcohol (100-51-6,185532-71-2) → 2-amino-4-benzyloxy-6-chloro-5-nitropyrimidine (1292320-56-9)

Guidance literature:

benzyl alcohol; With sodium hydride; In tetrahydrofuran; for 0.5h; Inert atmosphere;

2-amino-4,6-dichloro-5-nitropyrimidine; In tetrahydrofuran; at 0 - 13 ℃;

DOI:10.1016/j.bmc.2011.01.038

upstream raw materials:

2-acetylamino-6-chloro-5-nitro-4(3H)-pyrimidinone

Vilsmeier reagent

2-Amino-4,6-dichloropyrimidine

Downstream raw materials:

2-amino-4-benzyloxy-6-chloro-5-nitropyrimidine

Refernces

• 1、 Lopez, Sergio,McCabe, Thomas,Stanley McElhinney,McMurry, T. Brian H.,Rozas, Isabel. "Syntheses of 2-amino-4,6-dichloro-5-nitropyrimidine and 2-amino-4,5,6-trichloropyrimidine: an unusual aromatic substitution". supporting information; experimental part. p. 6022 - 6024. Retrieved 2010/03/03.