3-(4-Methoxyphenyl)-3-oxopropanenitrile

Base Information

• Chemical Name: 3-(4-Methoxyphenyl)-3-oxopropanenitrile
• CAS No.: 3672-47-7
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.187
• Hs Code.: 29269095
• European Community (EC) Number: 678-864-9
• NSC Number: 31895
• DSSTox Substance ID: DTXSID70283505
• Nikkaji Number: J1.275.200H
• Wikidata: Q72489207
• Mol file: 3672-47-7.mol

Synonyms:3-(4-methoxyphenyl)-3-oxopropanenitrile;4-Methoxybenzoylacetonitrile;3672-47-7;MFCD00067889;4-Methoxybenzoyl acetonitrile;NSC31895;4'-METHOXYBENZOYLACETONITRILE;Maybridge1_004582;p-methoxybenzoylacetonitrile;3-OXO-3-(4-METHOXYPHENYL)PROPIONITRILE;Oprea1_697326;SCHEMBL135620;HMS554I06;IKEPUFCALLUUBC-UHFFFAOYSA-;AMY2012;DTXSID70283505;AM945;4-Methoxybenzoylacetonitrile, 97%;AB1487;NSC-31895;STL432201;AKOS000206306;AA-0854;CS-W017454;3-(4-methoxyphenyl)-3-oxo-propionitrile;FT-0604215;J-510724;Z55928932;InChI=1/C10H9NO2/c1-13-9-4-2-8(3-5-9)10(12)6-7-11/h2-5H,6H2,1H3

Chemical Property of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 1.69E-05mmHg at 25°C
• Melting Point: 129-132 °C
• Refractive Index: 1.525
• Boiling Point: 364.4 °C at 760 mmHg
• PKA: 8.27±0.10(Predicted)
• Flash Point: 159.3 °C
• PSA: 50.09000
• Density: 1.131 g/cm³
• LogP: 1.79158
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 175.063328530
• Heavy Atom Count: 13
• Complexity: 220

Purity/Quality:

99% ^*data from raw suppliers

4-Methoxybenzoylacetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,T
• Hazard Codes: Xn,T
• Statements: 20/21/22-36/37/38-25
• Safety Statements: 36/37-60-45-26-20

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of 3-(4-Methoxyphenyl)-3-oxopropanenitrile

There total 66 articles about 3-(4-Methoxyphenyl)-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: 83.0%

4,N-dimethoxy-N-methylbenzamide (52898-49-4) + acetonitrile (75-05-8,26809-02-9) → 3-oxo-3-(4'-methoxyphenyl)propanenitrile (3672-47-7)

Guidance literature:

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

4,N-dimethoxy-N-methylbenzamide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1.5h; Inert atmosphere;

DOI:10.1039/c4ob02398f

Reference yield: 82.7%

methyl 4-methoxybenzoate (121-98-2) + acetonitrile (75-05-8,26809-02-9) → 3-oxo-3-(4'-methoxyphenyl)propanenitrile (3672-47-7)

Guidance literature:

methyl 4-methoxybenzoate; acetonitrile; With sodium methylate; In dimethyl sulfoxide; at 110 ℃; for 2h;

With water; In dimethyl sulfoxide; acetonitrile; at 15 ℃;

With hydrogenchloride; In water; dimethyl sulfoxide; acetonitrile; at 20 ℃; pH=7.9;

Reference yield: 81.0%

4-chlorophenyl acetate (876-27-7) + 3-hydroxy-3-(p-methoxyphenyl)-propanenitrile (144119-13-1,51241-27-1) → 3-oxo-3-(4'-methoxyphenyl)propanenitrile (3672-47-7) + (S)-2-cyano-1-(p-methoxyphenyl)ethyl acetate

Guidance literature:

With Novozym-435 (Candida antarctica Lipase B); [bis(2,3,4,5-tetraphenylcyclopentadienol)(CO)2Ru]2; In toluene; at 100 ℃; for 36h; Enzymatic reaction;

DOI:10.1002/1615-4169(200108)343:6/7<726::aid-adsc726>3.3.co;2-5

upstream raw materials:

5-(4-methoxyphenyl)-1,2-oxazole

3-amino-3-(4-methoxyphenyl)acrylonitrile

Methyl 2-Cyano-3-(4-methoxyphenyl)-3-oxopropanoate

methyl 4-methoxybenzoate

Downstream raw materials:

(2Z,4E)-2-(4-Methoxy-benzoyl)-5-phenyl-penta-2,4-dienenitrile

3-amino-1-(p-methoxyphenyl)-1-propanol

(4R,6S)-6-hydroxy-2-(4-methoxyphenyl)-4-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

4-cyano-5-(4-methoxyphenyl)-2-methyl-2-(2-thienyl)-2,3-dihydrofuran-3-carboxamide

Refernces

• 1、 James, Michelle L.,Fulton, Roger R.,Henderson, David J.,Eberl, Stefan,Meikle, Steven R.,Thomson, Sally,Allan, Robin D.,Dolle, Frederic,Fulham, Michael J.,Kassiou, Michael. "Synthesis and in vivo evaluation of a novel peripheral benzodiazepine receptor PET radioligand". . p. 6188 - 6194. Retrieved 2005.
• 2、 Zhai, Min'an,Liu, Shiyuan,Gao, Meiqi,Wang, Long,Sun, Jun,Du, Jianan,Guan, Qi,Bao, Kai,Zuo, Daiying,Wu, Yingliang,Zhang, Weige. "3,5-Diaryl-1H-pyrazolo[3,4-b]pyridines as potent tubulin polymerization inhibitors: Rational design, synthesis and biological evaluation". . p. 426 - 435. Retrieved 2019.
• 3、 Farahat, Aya A.,Samir, Eman M.,Zaki, Mayssoune Y.,Serya, Rabah A. T.,Abdel-Aziz, Hatem A.. "Synthesis and in vitro antiproliferative activity of certain novel pyrazolo[3,4-b]pyridines with potential p38α MAPK-inhibitory activity". . . Retrieved 2021/11/23.