3-Oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile

Base Information

• Chemical Name: 3-Oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile
• CAS No.: 50606-35-4
• Molecular Formula: C12H13 N O4
• Molecular Weight: 235.24
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID00594277
• Wikidata: Q82489073
• Mol file: 50606-35-4.mol

Synonyms:3,4,5-Trimethoxybenzoylacetonitrile;50606-35-4;3-oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile;MFCD02260785;SCHEMBL6440815;DTXSID00594277;GFEMIDXDJDTTKQ-UHFFFAOYSA-N;STL434893;AKOS000174214;A7505;2-OXO-2-(3,4,5-TRIMETHOXYPHENYL)ETHYL CYANIDE

Chemical Property of 3-Oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile

Chemical Property:

• Vapor Pressure: 1.62E-06mmHg at 25°C
• Boiling Point: 397.1oC at 760 mmHg
• Flash Point: 173.7oC
• PSA: 68.55000
• Density: 1.159g/cm3
• LogP: 1.80878
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 235.08445790
• Heavy Atom Count: 17
• Complexity: 295

Purity/Quality:

99% ^*data from raw suppliers

3,4,5-trimethoxybenzoylacetonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C(=O)CC#N

Technology Process of 3-Oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile

There total 5 articles about 3-Oxo-3-(3,4,5-trimethoxyphenyl)propanenitrile 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: 83.0%

ethyl 3,4,5-trimethoxybenzoate (6178-44-5) + acetonitrile (75-05-8,26809-02-9) → 3-(3',4',5'-trimethoxyphenyl)-3-oxopropanenitrile (50606-35-4)

Guidance literature:

With sodium hydride;

DOI:10.1016/j.bmcl.2006.08.065

Reference yield: 79.0%

N-methoxy-N-methyl-3,4,5-trimethoxybenzamide (118779-14-9) + acetonitrile (75-05-8,26809-02-9) → 3-(3',4',5'-trimethoxyphenyl)-3-oxopropanenitrile (50606-35-4)

Guidance literature:

acetonitrile; With methyllithium; lithium bromide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h; Inert atmosphere;

N-methoxy-N-methyl-3,4,5-trimethoxybenzamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c4ob02398f

Reference yield: 77.2%

3,4,5-trimethoxybenzoic acid methyl ester (1916-07-0) + acetonitrile (75-05-8,26809-02-9) → 3-(3',4',5'-trimethoxyphenyl)-3-oxopropanenitrile (50606-35-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 80 ℃; for 5h;

DOI:10.1016/j.ejmech.2018.05.010

upstream raw materials:

3,4,5-trimethoxybenzoic acid methyl ester

acetonitrile

ethyl 3,4,5-trimethoxybenzoate

Eudesmic acid

Downstream raw materials:

2-(2,2-diethoxy-ethyl)-5-(3,4,5-trimethoxy-phenyl)-2H-pyrazol-3-ylamine

Refernces

• 1、 Huang, Liancheng,Liu, Meng,Man, Shuai,Ma, Deyi,Feng, Dongjie,Sun, Zhongqiao,Guan, Qi,Zuo, Daiying,Wu, Yingliang,Zhang, Weige,Bao, Kai. "Design, synthesis and bio-evaluation of novel 2-aryl-4-(3,4,5-trimethoxy-benzoyl)-5-substituted-1,2,3-triazoles as the tubulin polymerization inhibitors". . . Retrieved 2020.
• 2、 Lai, Qinhuai,Wang, Yuxi,Wang, Ruixue,Lai, Weirong,Tang, Liangze,Tao, Yiran,Liu, Yu,Zhang, Ruirui,Huang, Luyi,Xiang, Haotian,Zeng, Shaoxue,Gou, Lantu,Chen, Hao,Yao, Yuqin,Yang, Jinliang. "Design, synthesis and biological evaluation of a novel tubulin inhibitor 7a3 targeting the colchicine binding site". . p. 162 - 179. Retrieved 2018/07/13.