4-Chloro-6-methylpyrimidine

Base Information

• Chemical Name: 4-Chloro-6-methylpyrimidine
• CAS No.: 3435-25-4
• Molecular Formula: C5H5ClN2
• Molecular Weight: 128.561
• Hs Code.: 2933599090
• European Community (EC) Number: 685-585-6
• DSSTox Substance ID: DTXSID20342439
• Nikkaji Number: J270.678D
• Wikidata: Q72455008
• Mol file: 3435-25-4.mol

Synonyms:4-Chloro-6-methylpyrimidine;3435-25-4;4-Methyl-6-chloropyrimidine;4-Methyl-6-chloro pyrimidine;Pyrimidine, 4-chloro-6-methyl-;4-Chloro-6-methyl-pyrimidine;6-chloro-4-methylpyrimidine;MFCD02322991;4-Chloro-6-methyl-1,3-diazine;6-methyl-4-chloropyrimidin;SCHEMBL367600;F2064-0052;DTXSID20342439;BCP26088;BBL100194;STL252685;AKOS000267495;AC-8954;CS-W002939;PB29204;PS-5600;SB20876;AC-12223;SY021506;A6050;A7881;AM20090531;FT-0600169;FT-0646309;EN300-53137;W-203043;Z787326738;3-Chloro-4-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-y14-chlorophenylether

Chemical Property of 4-Chloro-6-methylpyrimidine

Chemical Property:

• Vapor Pressure: 0.479mmHg at 25°C
• Melting Point: 151-152 °C
• Refractive Index: 1.529
• Boiling Point: 199.6 °C at 760 mmHg
• PKA: 0.83±0.17(Predicted)
• Flash Point: 92.8 °C
• PSA: 25.78000
• Density: 1.234 g/cm³
• LogP: 1.43840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.0141259
• Heavy Atom Count: 8
• Complexity: 76.8

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-6-methylpyrimidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=NC=N1)Cl
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Technology Process of 4-Chloro-6-methylpyrimidine

There total 2 articles about 4-Chloro-6-methylpyrimidine 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:

4-methyl-1H-imidazole (822-36-6) + chloroform (67-66-3,8013-54-5) → 2-chloro-6-methylpyrazine (38557-71-0) + 4-methyl-6-chloropyrimidine (3435-25-4) + 2-chloro-5-methyl-pyrazine (59303-10-5) + 5-chloro-4-methylpyrimidine (54198-82-2)

Guidance literature:

at 550 ℃; Yield given. Yields of byproduct given;

DOI:10.1039/P19800001427

Reference yield:

5-bromo-4-chloro-6-methylpyrimidine (3438-55-9) + phenylboronic acid (98-80-6) → 4-methyl-6-chloropyrimidine (3435-25-4) + 5-bromo-4-methyl-6-phenylpyrimidine (1353577-56-6) + 4-chloro-6-methyl-5-phenylpyrimidine (1353577-55-5) + 4-methyl-5,6-diphenylpyrimidine (1353577-57-7)

Guidance literature:

With potassium phosphate; palladium diacetate; tris-(o-tolyl)phosphine; In ethanol; water; toluene; at 80 ℃; for 16h; regioselective reaction; Inert atmosphere;

DOI:10.1055/s-0030-1260224

Reference yield: 99.0%

4-methyl-6-chloropyrimidine (3435-25-4) + 2-(2-methoxy-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1185019-97-9) → 4-(2-methoxy-4-nitrophenyl)-6-methylpyrimidine (1319068-75-1)

Guidance literature:

With sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In water; acetonitrile; for 3h; Inert atmosphere; Reflux;

upstream raw materials:

4-methyl-1H-imidazole

chloroform

5-bromo-4-chloro-6-methylpyrimidine

phenylboronic acid

Downstream raw materials:

4-thiomethyl-6-methylpyrimidine

4-ethoxy-6-methylpyrimidine

dimethyl-(6-methyl-pyrimidin-4-yl)-amine

6-methylpyrimidine-4(3H)-thione

Refernces

• 1、 Busby, Reginald E.,Khan, Mohammad A.,Khan, Mohammad R.,Parrick, John,Shaw, C. J. Granville,Iqbal, Mohammad. "Reactions of Halogenomethanes in the Vapor Phase. Part 4. The Reactions of Imidazoles with Chloroform at 550 deg C, and a Comparison with their Liquid-phase Reactions with Trichloroacetate Ion or Hexachloroacetone and Base". . p. 1427 - 1430. Retrieved 2007/10/02.