5-Chloro-6-methyluracil

Base Information

• Chemical Name: 5-Chloro-6-methyluracil
• CAS No.: 16018-87-4
• Molecular Formula: C₅H₅ClN₂O₂
• Molecular Weight: 160.56
• Hs Code.: 2933599090
• European Community (EC) Number: 633-918-0
• NSC Number: 26542
• DSSTox Substance ID: DTXSID70166829
• Wikidata: Q83036097
• Mol file: 16018-87-4.mol

Synonyms:5-chloro-6-methyluracil;16018-87-4;5-Chloro-6-methylpyrimidine-2,4(1H,3H)-dione;5-chloro-6-methyl-1H-pyrimidine-2,4-dione;2,4(1H,3H)-Pyrimidinedione, 5-chloro-6-methyl-;NSC26542;MFCD00466419;5-Chloro-6-methyl-2,4-pyrimidinediol;2,4(1H,3H)-Pyrimidinedione,5-chloro-6-methyl-;NSC 26542;5-chloro-6-methylpyrimidine-2,4-diol;5-chloro-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione;AI3-26569;AMY150;SCHEMBL2888237;SCHEMBL10966104;DTXSID70166829;YFTMPDGCVOWZOZ-UHFFFAOYSA-N;NSC-26542;AKOS001045900;AKOS015916941;SB55519;5-chloro-6-methyl-pyrimidine-2,4-diol;2,4-Pyrimidinediol, 5-chloro-6-methyl-;DS-13145;SY107545;CS-0059294;FT-0600914;A23250;S10270;W-205855;Z56871944

Chemical Property of 5-Chloro-6-methyluracil

Chemical Property:

• Vapor Pressure: 3.29E-07mmHg at 25°C
• Melting Point: 330-332 °C (decomp)
• Refractive Index: 1.565
• Boiling Point: 407.1 °C at 760 mmHg
• PKA: 7.83±0.10(Predicted)
• Flash Point: 200 °C
• PSA: 65.72000
• Density: 1.49 g/cm³
• LogP: 0.02500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 160.0039551
• Heavy Atom Count: 10
• Complexity: 234

Purity/Quality:

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

5-CHLORO-2,4-DIHYDROXY-6-METHYLPYRIMIDINE Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C(C(=O)NC(=O)N1)Cl
• Uses: 5-Chloro-6-methyluracil is used in preparation of herbicide.

Technology Process of 5-Chloro-6-methyluracil

There total 10 articles about 5-Chloro-6-methyluracil 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: 81.0%

6-Methyluracil (626-48-2) → 5-chloro-6-methyluracil (16018-87-4) + 5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil (50610-49-6)

Guidance literature:

With hydrogenchloride; dihydrogen peroxide; In water; at 20 ℃;

DOI:10.1007/s10593-012-1094-z

Reference yield: 75.0%

6-Methyluracil (626-48-2) → 5-chloro-6-methyluracil (16018-87-4)

Guidance literature:

With chlorine; In chloroform; at 20 ℃; for 2h;

DOI:10.1007/s10593-012-1094-z

Reference yield: 65.0%

5-bromo-5-chloro-6-hydroxy-6-methyl-5,6-dihydrouracil (1413433-45-0) → 5-chloro-6-methyluracil (16018-87-4)

Guidance literature:

With acetic anhydride; at 140 ℃; for 5h;

DOI:10.1007/s11172-020-3015-0

upstream raw materials:

5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

5,5-dichloro-6-methoxy-6-methyl-5,6-dihydrouracil

5,5-dichloro-6-hydroxy-6-methyl-5,6-dihydrouracil

6-Methyluracil

Downstream raw materials:

6-Methyl-2,4,5-trichloropyrimidine

4,5-Dichloro-2-N-methylanilino-6-methylpyrimidine

5-Chloro-6-methyl-2,4-bis(N-methylanilino)pyrimidine

2,5-Dichloro-6-methyl-4-N-methylanilinopyrimidine

Refernces

• 1、 Chernikova, I. B.,Yunusov, M. S.. "Halogenation and nitration of 1-carboxymethyl-5-methyluracil. Halophilic reaction involving acetic anhydride". . p. 2159 - 2162. Retrieved 2020/12/07.
• 2、 Kasradze,Ignatyeva,Khusnutdinov,Suponitskii, K. Yu.,Antipin, M. Yu.,Yunusov. "Oxidative halogenation of 6-methyluracil". . p. 1018 - 1027. Retrieved 2013/03/13.