Phenyl-5-thiazolylmethanone

Base Information

• Chemical Name: Phenyl-5-thiazolylmethanone
• CAS No.: 91516-29-9
• Molecular Formula: C₁₀H₇NOS
• Molecular Weight: 189.238
• DSSTox Substance ID: DTXSID001309970
• Mol file: 91516-29-9.mol

Synonyms:91516-29-9;phenyl(1,3-thiazol-5-yl)methanone;phenyl-5-thiazolylmethanone;SCHEMBL175110;DTXSID001309970;AKOS019040949

Chemical Property of Phenyl-5-thiazolylmethanone

Chemical Property:

• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 189.02483502
• Heavy Atom Count: 13
• Complexity: 189

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)C2=CN=CS2

Technology Process of Phenyl-5-thiazolylmethanone

There total 4 articles about Phenyl-5-thiazolylmethanone 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: 36.0%

5-bromo-1,3-thiazole (3034-55-7) + benzoic acid (65-85-0,8013-63-6) → (1,3-thiazol-5-yl)(phenyl)methanone (91516-29-9)

Guidance literature:

benzoic acid; With isopropylmagnesium bromide; In tetrahydrofuran; 2-methyltetrahydrofuran; at 10 ℃; Inert atmosphere; Cooling with ice;

5-bromo-1,3-thiazole; In tetrahydrofuran; 2-methyltetrahydrofuran; Inert atmosphere;

With TurboGrignard; In tetrahydrofuran; 2-methyltetrahydrofuran; for 4.5h; Inert atmosphere;

DOI:10.1021/acs.joc.6b00194

Reference yield:

{2-[tert-butyl(dimethyl)silyl]-1,3-thiazol-5-yl}(phenyl)methanone (502627-78-3) → (1,3-thiazol-5-yl)(phenyl)methanone (91516-29-9)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(03)00878-0

Reference yield:

benzonitrile (100-47-0) → (1,3-thiazol-5-yl)(phenyl)methanone (91516-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.5 h / -60 - -20 °C

2: aq. HCl / tetrahydrofuran

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(03)00878-0

upstream raw materials:

thiazole-5-carbonitrile

{2-[tert-butyl(dimethyl)silyl]-1,3-thiazol-5-yl}(phenyl)methanone

benzonitrile

5-bromo-1,3-thiazole

Refernces

• 1、 Frey, Lisa F.,Marcantonio, Karen M.,Chen, Cheng-Yi,Wallace, Debra J.,Murry, Jerry A.,Tan, Lushi,Chen, Weirong,Dolling, Ulf H.,Grabowski, Edward J. J.. "Practical synthesis of a highly functionalized thiazole ketone". . p. 6363 - 6373. Retrieved 2007/10/03.