Benzylthiouracil

Base Information

• Chemical Name: Benzylthiouracil
• CAS No.: 6336-50-1
• Deprecated CAS: 28176-06-9
• Molecular Formula: C11H10 N2 O S
• Molecular Weight: 218.279
• Hs Code.: 2933599090
• European Community (EC) Number: 228-717-6
• NSC Number: 39511,6508
• UNII: PZ35LUM333
• DSSTox Substance ID: DTXSID30873587
• Nikkaji Number: J206.933D
• Wikipedia: Benzylthiouracil
• Wikidata: Q4890823
• Metabolomics Workbench ID: 154584
• ChEMBL ID: CHEMBL1491306
• Mol file: 6336-50-1.mol

Synonyms:6-benzyl-2-thiouracil;Basdène;benzylthiouracil;Hexaspray

Chemical Property of Benzylthiouracil

Chemical Property:

• Vapor Pressure: 2.76E-08mmHg at 25°C
• Melting Point: 216-219 °C
• Boiling Point: 438.1ºC at 760 mmHg
• PKA: 7.69±0.20(Predicted)
• Flash Point: 218.8ºC
• PSA: 80.74000
• Density: 1.32g/cm3
• LogP: 2.02330
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 218.05138412
• Heavy Atom Count: 15
• Complexity: 306

Purity/Quality:

99% ^*data from raw suppliers

6-Benzyl-2-thiouracil ^*data from reagent suppliers

Safty Information:

• Safety Statements: S22:Do not inhale dust.; S24/25:Avoid contact with skin and eyes.

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2=CC(=O)NC(=S)N2

Technology Process of Benzylthiouracil

There total 10 articles about Benzylthiouracil 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: 86.0%

ethyl 3-oxo-4-phenylbutyrate (718-08-1) + thiourea (17356-08-0) → 6-benzyl-2-thiouracil (6336-50-1)

Guidance literature:

With sodium ethanolate; In ethanol; Reflux;

DOI:10.1016/j.bmc.2010.03.025 DOI:10.1016/j.bmcl.2009.04.051

Reference yield:

methyl 3-oxo-4-phenylbutanoate (37779-49-0) + thiourea (17356-08-0) → 6-benzyl-2-thiouracil (6336-50-1)

Guidance literature:

With sodium; In methanol; for 5h; Heating;

DOI:10.1021/jm00017a010

Reference yield:

ethyl 2-acetyl-3-oxo-4-phenylbutanoate (412019-21-7) → 6-benzyl-2-thiouracil (6336-50-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonia; diethyl ether

2: ethanolic sodium ethylate

With diethyl ether; ammonia; sodium ethanolate;

DOI:10.1021/ja01228a042

upstream raw materials:

ethyl 3-oxo-4-phenylbutyrate

sodium ethanolate

thiourea

methyl 3-oxo-4-phenylbutanoate

Downstream raw materials:

3-(4-benzyl-6-oxo-1,6-dihydro-pyrimidin-2-ylsulfanyl)-propionic acid ethyl ester

6-Benzyl-2-[2-(5-methyl-1H-imidazol-4-ylmethylsulfanyl)-ethylamino]-1H-pyrimidin-4-one; hydrochloride

6-benzyl-1-benzyloxymethyl-5-iodouracil

6-benzyl-5-bromo-1-ethoxymethyluracil

Refernces

• 1、 Zhang, Yu,Sun, Xuefeng,Fan, Ningning,Zhao, Jianxiong,Tu, Jing,Chen, Xiangmei,Liu, Junyi,Wang, Xiaowei. "5-Iodo-2-arylalkylthio-6-aryl pyrimidin-4(3H)-ones as non-nucleoside anti-HBV agents". . p. 1438 - 1443. Retrieved 2015/08/18.
• 2、 Wang, Xiaowei,Zhang, Jianfang,Huang, Yang,Wang, Ruiping,Zhang, Liang,Qiao, Kang,Li, Li,Liu, Chang,Ouyang, Yabo,Xu, Weisi,Zhang, Zhili,Zhang, Liangren,Shao, Yiming,Jiang, Shibo,Ma, Liying,Liu, Junyi. "Design, synthesis, and biological evaluation of 1-[(2-benzyloxyl/alkoxyl) methyl]-5-halo-6-aryluracils as potent HIV-1 non-nucleoside reverse transcriptase inhibitors with an improved drug resistance profile". experimental part. p. 2242 - 2250. Retrieved 2012/05/20.