3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

Base Information

• Chemical Name: 3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile
• CAS No.: 4640-69-1
• Molecular Formula: C11H11 N O3
• Molecular Weight: 205.213
• Hs Code.: 2926909090
• DSSTox Substance ID: DTXSID10427441
• Wikidata: Q72467679
• ChEMBL ID: CHEMBL4903443
• Mol file: 4640-69-1.mol

Synonyms:3-(3,4-dimethoxyphenyl)-3-oxopropanenitrile;4640-69-1;3,4-Dimethoxybenzoylacetonitrile;(3,4-dimethoxybenzoyl)acetonitrile;MFCD02260783;SCHEMBL139147;CHEMBL4903443;DTXSID10427441;JFSNSYKHZRHIGE-UHFFFAOYSA-N;STL290802;AKOS000195188;AA-0868;AB93336;3,4-Dimethoxy-|A-oxobenzenepropanenitrile;3-(3,4-Dimethoxyphenyl)-3-oxopropionitrile;A7229;CS-0206597;FT-0604174;VU0607331-1;C78240;J-510571;F3250-0717;Z317041968

Chemical Property of 3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

Chemical Property:

• Vapor Pressure: 6.71E-06mmHg at 25°C
• Melting Point: 139-141oC
• Boiling Point: 377.5oC at 760 mmHg
• PKA: 8.05±0.12(Predicted)
• Flash Point: 165.1oC
• PSA: 59.32000
• Density: 1.147g/cm3
• LogP: 1.80018
• Storage Temp.: 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 205.07389321
• Heavy Atom Count: 15
• Complexity: 268

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C(=O)CC#N)OC

Technology Process of 3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile

There total 9 articles about 3-(3,4-Dimethoxyphenyl)-3-oxopropanenitrile 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: 100.0%

methyl 3,4-dimethoxybenzoate (2150-38-1) + acetonitrile (75-05-8,26809-02-9) → ω-cyano-3,4-dimethoxyacetophenone (4640-69-1)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

methyl 3,4-dimethoxybenzoate; In tetrahydrofuran; hexane; at -78 - -45 ℃; Further stages.;

DOI:10.1021/jo800428b

Reference yield: 80.0%

N,N-dimethylformamide (DMF) + ethyl veratrate (3943-77-9) → ω-cyano-3,4-dimethoxyacetophenone (4640-69-1)

Guidance literature:

In toluene; acetonitrile;

Reference yield: 76.0%

3,4-dimethoxy-benzaldehyde (120-14-9) + acetonitrile (75-05-8,26809-02-9) → ω-cyano-3,4-dimethoxyacetophenone (4640-69-1)

Guidance literature:

With oxygen; potassium hydroxide; copper dichloride; In N,N-dimethyl acetamide; at 25 ℃; for 24h;

DOI:10.1016/j.ejmech.2018.12.053

upstream raw materials:

potassium cyanide

ethyl veratrate

methyl 3,4-dimethoxybenzoate

3,4-dimethoxybenzoic acid chloride

Downstream raw materials:

(2-amino-6-ethyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-3-yl)-(3,4-dimethoxy-phenyl)-methanone

(Z)-2-cyano-1-(3,4-dimethoxyphenyl)vinyl trifluoromethanesulfonate

ethyl 6-(4-chlorobenzoyl)-2-diethylaminomethyl-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:4,5-c']dipyridine-3-carboxylate

ethyl 8-benzyloxycarbonyl-2-diethylaminomethyl-4-(3,4-dimethoxyphenyl)-5,6,7,8-tetrahydrothieno[2,3-b:5,4-b']dipyridine-3-carboxylate

Refernces

• 1、 Heng, Hao,Wang, Zhijie,Li, Hongmei,Huang, Yatian,Lan, Qingyuan,Guo, Xiaoxing,Zhang, Liang,Zhi, Yanle,Cai, Jiongheng,Qin, Tianren,Xiang, Li,Wang, Shuxian,Chen, Yadong,Lu, Tao,Lu, Shuai. "Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model". . p. 248 - 267. Retrieved 2019/05/21.
• 2、 Jensen, Mikkel T.,Juhl, Martin,Nielsen, Dennis U.,Jacobsen, Mikkel F.,Lindhardt, Anders T.,Skrydstrup, Troels. "Palladium-Catalyzed Carbonylative α-Arylation of tert -Butyl Cyanoacetate with (Hetero)aryl Bromides". . p. 1358 - 1366. Retrieved 2016/03/01.