Uracil mustard

Base Information

• Chemical Name: Uracil mustard
• CAS No.: 66-75-1
• Molecular Formula: C8H11Cl2N3O2
• Molecular Weight: 252.1
• Hs Code.: 2933599090
• European Community (EC) Number: 200-631-3
• NSC Number: 34462
• UN Number: 2811
• UNII: W7KQ46GJ8U
• DSSTox Substance ID: DTXSID8026270
• Nikkaji Number: J2.362K
• Wikipedia: Uramustine
• Wikidata: Q15211075
• NCI Thesaurus Code: C918
• Metabolomics Workbench ID: 43083
• ChEMBL ID: CHEMBL1488
• Mol file: 66-75-1.mol

Synonyms:5-(Bis(2-chloroethyl)amino)-2,4-(1H,3H)pyrimidinedione;Mustard, Uracil;Uracil Mustard;Uramustine

Chemical Property of Uracil mustard

Chemical Property:

• Appearance/Colour: Creamy white crystals or off-white powder
• Melting Point: 206°C (rough estimate)
• Refractive Index: 1.6100 (estimate)
• PKA: 9.42±0.10(Predicted)
• PSA: 68.96000
• Density: 1.44 g/cm³
• LogP: 0.34720
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 251.0228320
• Heavy Atom Count: 15
• Complexity: 288
• Transport DOT Label: Poison

Purity/Quality:

5-[Bis(2-chloroethyl)amino]pyrimidine-2,4-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)N(CCCl)CCCl
• Description: Uracil mustard appears as creamy/off-white, odourless, crystalline powder. It is used as an anti-cancer medicine. Uracil mustard is a chemotherapy drug that belongs to the class of alkylating agents. It is used for its anti-neoplastic properties. It works by damaging deoxyribonucleic acid (DNA), primarily in cancer cells that preferentially take up the uracil due to their need to make nucleic acids during their rapid cycles of cell division. At high concentrations of the drug, cellular RNA and protein synthesis are also suppressed. The DNA damage leads to apoptosis of the affected cells. Chemically it is a derivative of nitrogen mustard and uracil. Uracil mustard is a non-combustible substance itself; it does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidisers and may ignite combustibles – wood, paper, oil, clothing, etc. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.
• Uses: Antineoplastic.
• Therapeutic Function: Cancer chemotherapy

Technology Process of Uracil mustard

There total 3 articles about Uracil mustard 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:

5-[bis-(2-hydroxy-ethyl)-amino]-1H-pyrimidine-2,4-dione (55476-37-4) → uracil mustard (66-75-1)

Guidance literature:

With 1,2-dimethoxyethane; thionyl chloride; ethanol; water;

DOI:10.1021/ja01556a079

Reference yield:

→ uracil mustard (66-75-1)

Guidance literature:

Reference yield:

→ uramustine (66-75-1)

Guidance literature:

5--uracil, SOCl2, Diaethylenglykol-dimethylaether;

upstream raw materials:

5-[bis-(2-hydroxy-ethyl)-amino]-1H-pyrimidine-2,4-dione

Refernces

• 1、 -. "Anti-Claudin 3 Monoclonal Antibody and Treatment and Diagnosis of Cancer Using the Same". . . Retrieved 2010/05/13.