6-Chlorouracil

Base Information

• Chemical Name: 6-Chlorouracil
• CAS No.: 4270-27-3
• Molecular Formula: C4H3ClN2O2
• Molecular Weight: 146.533
• Hs Code.: 29335990
• European Community (EC) Number: 224-258-0
• NSC Number: 210419,43265
• DSSTox Substance ID: DTXSID70195396
• Nikkaji Number: J205.677A
• Wikidata: Q72460617
• Mol file: 4270-27-3.mol

Synonyms:6-chlorouracil

Chemical Property of 6-Chlorouracil

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.48E-05mmHg at 25°C
• Melting Point: 290-295 °C
• Refractive Index: 1.635
• Boiling Point: 300 °C
• PKA: 6.24±0.10(Predicted)
• Flash Point: 182°C
• PSA: 65.72000
• Density: 1.61 g/cm³
• LogP: -0.28340
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Soluble in Ammonium Hydroxide
• Water Solubility.: 4.885g/L(25 oC)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 145.9883050
• Heavy Atom Count: 9
• Complexity: 199

Purity/Quality:

98% ^*data from raw suppliers

6-Chlorouracil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC(=O)NC1=O)Cl
• Uses: 6-Chlorouracil acts as an inhibitor of yeast alcohol dehydrogenase (ADH-H). 6-Chlorouracil is a potential inhibitor of DNA repair glycosylases. Chlorouracil (4-Chlorouracil; 6-Chlorouracil) is a halogenated uracil that is useful in studies of the effects of halogenation on nucleic acid base-pair stability and alkali metal ion affinity. Reaction of 6-chlorouracil with 4-(dimethylamino)pyridine, 4-methylpyridine, and pyridin-4-yl-morpholine yielded pyridinium-substituted uracils as chlorides which were converted into pyridinium uracilates by deprotonation. These heterocyclic mesomeric betaines are cross-conjugated and thus possess separate cationic (pyridinium) and anionic (uracilate) moieties. Calculations and X-ray single crystal analyses may be used to characterize these systems and to compare the salts with the betaines.

Technology Process of 6-Chlorouracil

There total 7 articles about 6-Chlorouracil 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: 98.0%

2,4,6-trichloropyrimidine (3764-01-0) → 6-chlorouracil (4270-27-3)

Guidance literature:

With sodium hydroxide; In water; for 3.5h; Reflux;

DOI:10.1002/ejoc.200800504

Reference yield: 92.0%

6-chloro-2,4-dihydroxypyrimidine (4270-27-3) → 6-chlorouracil (4270-27-3)

Guidance literature:

With sodium hydroxide; Reflux; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.7b03854

Reference yield: 82.0%

2,4,6-trichloropyrimidine (3764-01-0) → 6-chloro-2,4-dihydroxypyrimidine (4270-27-3)

Guidance literature:

With sodium hydroxide; In water; for 1h; Reflux;

DOI:10.1515/HC.2008.14.6.443

upstream raw materials:

6-chloro-2,4-dimethoxypyrimidine

2,4,6-trichloropyrimidine

6-hydroxyuracil

Downstream raw materials:

6-(methylamino)pyrimidine-2,4(1H,3H)-dione

1-<(Benzyloxy)methyl>-6-chlorouracil

1,1'-trimethylenebis<3-benzene>

6-<(2-aminophenyl)thio>uracil

Refernces

• 1、 Murthy Bandaru, Siva Sankar,Bhilare, Shatrughn,Chrysochos, Nicolas,Gayakhe, Vijay,Trentin, Ivan,Schulzke, Carola,Kapdi, Anant R.. "Pd/PTABS: Catalyst for Room Temperature Amination of Heteroarenes". supporting information. p. 473 - 476. Retrieved 2018/01/28.
• 2、 Dickens, Michael P.,Roxburgh, Patricia,Hock, Andreas,Mezna, Mokdad,Kellam, Barrie,Vousden, Karen H.,Fischer, Peter M.. "5-Deazaflavin derivatives as inhibitors of p53 ubiquitination by HDM2". . p. 6868 - 6877. Retrieved 2013/11/06.