2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine

Base Information

• Chemical Name: 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine
• CAS No.: 16097-60-2
• Molecular Formula: C5H3ClF3N3
• Molecular Weight: 197.547
• Hs Code.: 2933599090
• DSSTox Substance ID: DTXSID60517740
• Wikidata: Q82379911
• Mol file: 16097-60-2.mol

Synonyms:16097-60-2;2-amino-4-chloro-6-(trifluoromethyl)pyrimidine;4-chloro-6-(trifluoromethyl)pyrimidin-2-amine;2-AMINO-4-CHLORO-6-TRIFLUOROMETHYL-PYRIMIDINE;2-Pyrimidinamine, 4-chloro-6-(trifluoromethyl)-;MFCD06656426;2-Pyrimidinamine,4-chloro-6-(trifluoromethyl)-;SCHEMBL2396451;DTXSID60517740;AKOS006238097;CS-W018916;SB16109;AC-25692;DS-11147;SY018034;2-amino-4-chloro-6-trifluoromethylpyrimidine;4-chloro-6-trifluoromethylpyrimidine-2-amine;AM20080437;FT-0600091;4-chloro-6-trifluoromethylpyrimidin-2-ylamine;4-chloro-6-(trifluoromethyl)pyrimidine-2-amine;A24638;EN300-317190;J-507841

Chemical Property of 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine

Chemical Property:

• Vapor Pressure: 0.004mmHg at 25°C
• Melting Point: 92-93 °C
• Refractive Index: 1.503
• Boiling Point: 280.733 °C at 760 mmHg
• PKA: 0.29±0.10(Predicted)
• Flash Point: 123.583 °C
• PSA: 51.80000
• Density: 1.598 g/cm³
• LogP: 2.31220
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 196.9967593
• Heavy Atom Count: 12
• Complexity: 163

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Amino-4-chloro-6-trifluoromethyl-pyrimidine ^*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)C(F)(F)F

Technology Process of 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine

There total 8 articles about 2-Amino-4-chloro-6-(trifluoromethyl)pyrimidine 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: 78.0%

2-amino-4-hydroxy-6-(trifluoromethyl)pyrimidine (1513-69-5) → 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine (16097-60-2)

Guidance literature:

With triethylamine; trichlorophosphate; In acetonitrile; for 8h; Reflux;

DOI:10.1016/j.cclet.2013.02.004

Reference yield: 47.0%

2,4-dichloro-6-(trifluoromethyl)-pyrimidine (16097-64-6) → 4-Amino-2-chloro-6-trifluoromethylpyrimidine (85730-36-5) + 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine (16097-60-2)

Guidance literature:

With ammonia; In diethyl ether; -5 to 0 deg C then -15 deg C, overnight;

DOI:10.1002/jhet.5570200145

Reference yield:

4-Chloro-6-trifluoromethylpyrimidin-2-yldichlorophosphate (85730-34-3) → 2-amino-4-chloro-6-(trifluoromethyl)pyrimidine (16097-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / NH₃ / diethyl ether / 1) 5-10 deg C then -15 deg C overnight

2: 83 percent / POCl₃ / diethylaniline / 3 h / Heating

3: 20 percent / NH₃ / diethyl ether / -5 to 0 deg C then -15 deg C, overnight

With ammonia; trichlorophosphate; N,N-diethylaniline; In diethyl ether;

DOI:10.1002/jhet.5570200145

upstream raw materials:

2,4-dichloro-6-(trifluoromethyl)-pyrimidine

2-amino-4-hydroxy-6-(trifluoromethyl)pyrimidine

6-trifluoromethyl-4-hydroxy-2-mercaptopyrimidine

4-Chloro-6-trifluoromethylpyrimidin-2-yldichlorophosphate

Downstream raw materials:

2-Amino-4-methoxy-6-trifluor-methylpyrimidin

C₁₆H₁₇F₃N₆O₂

Refernces

• 1、 Zhao, Yan-Fang,Liu, Zi-Jian,Zhai, Xin,Ge, Dan-Dan,Huang, Qiang,Gong, Ping. "Synthesis and in vitro antitumor activity of novel diaryl urea derivatives". . p. 386 - 388. Retrieved 2013/07/19.
• 2、 -. "PYRIMIDINES REACTING WITH O6-ALKYLGUANINE-DNA ALKYLTRANSFERASE". Page/Page column 23. . Retrieved 2008/06/13.