Methyl 4-(cyanoacetyl)benzoate

Base Information

• Chemical Name: Methyl 4-(cyanoacetyl)benzoate
• CAS No.: 69316-08-1
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Hs Code.: 29269095
• European Community (EC) Number: 628-939-7
• DSSTox Substance ID: DTXSID00352910
• Nikkaji Number: J308.937A
• Wikidata: Q72489555
• Mol file: 69316-08-1.mol

Synonyms:Methyl 4-(cyanoacetyl)benzoate;69316-08-1;methyl 4-(2-cyanoacetyl)benzoate;MFCD00015378;methyl 4-cyanoacetylbenzoate;Methyl 4-cyanoacettylbenzoate;SCHEMBL753410;methyl-4-(cyanoacetyl)benzoate;DTXSID00352910;AM1145;AKOS015890036;Methyl 4-(cyanoacetyl)benzoate, 98%;CS-W008257;s11985;BP-12960;SY110302;FT-0628582;Benzoic acid, 4-(2-cyanoacetyl)-, methyl ester;A836427

Chemical Property of Methyl 4-(cyanoacetyl)benzoate

Chemical Property:

• Appearance/Colour: beige flaky crystals
• Vapor Pressure: 1.56E-06mmHg at 25°C
• Melting Point: 171-173 °C
• Refractive Index: 1.535
• Boiling Point: 397.7 °C at 760 mmHg
• PKA: 7.01±0.10(Predicted)
• Flash Point: 174 °C
• PSA: 67.16000
• Density: 1.204 g/cm³
• LogP: 1.56958
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 294

Purity/Quality:

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

Methyl 4-(cyanoacetyl)benzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)C(=O)CC#N
• Uses: Methyl 4-(cyanoacetyl)benzoate may be used in chemical synthesis.

Technology Process of Methyl 4-(cyanoacetyl)benzoate

There total 10 articles about Methyl 4-(cyanoacetyl)benzoate 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%

2-trimethylsilylacetonitrile (18293-53-3) + carbon monoxide (201230-82-2) + methyl 4-iodobenzoate (619-44-3) → methyl-4-(2-cyanoacetyl)benzoate (69316-08-1)

Guidance literature:

With zinc(II) fluoride; (2-methylallyl)palladium-chloride dimer; copper(ll) bromide; In N,N-dimethyl-formamide; at 80 ℃; for 12h; under 7600.51 Torr;

DOI:10.1021/ol300035u

Reference yield: 80.0%

4-Methoxycarbonylbenzoyl chloride (7377-26-6) + cyanoacetic acid (372-09-8) → methyl-4-(2-cyanoacetyl)benzoate (69316-08-1)

Guidance literature:

cyanoacetic acid; With [2,2]bipyridinyl; n-butyllithium; magnesium sulfate; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

4-Methoxycarbonylbenzoyl chloride; In tetrahydrofuran; methanol; hexane; at -78 - 20 ℃; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; hexane; water;

DOI:10.1016/j.tetlet.2011.03.009

Reference yield: 72.0%

potassium cyanide + methyl 4-(2-bromoacetyl)benzoate (56893-25-5) → methyl-4-(2-cyanoacetyl)benzoate (69316-08-1)

Guidance literature:

In ethanol; water; at 0 - 20 ℃; for 1h;

DOI:10.1021/jm2015167

upstream raw materials:

1,4-benzenedicarboxylic acid dimethyl ester

acetonitrile

methyl ethyl benzene-1,4-dicarboxylate

4-Methoxycarbonylbenzoyl chloride

Downstream raw materials:

4-(2-cyanoacetyl)benzoic acid

3-(4-Methoxycarbonyl-phenyl)-2-oximino-3-oxo-propionitril

4-[5-amino-1-(2,2-diethoxy-ethyl)-1H-pyrazol-3-yl]-benzoic acid methyl ester

LUF₅₄₉₂

Refernces

• 1、 Shen, Hang,Li, Jiaqiang,Liu, Qing,Pan, Jing,Huang, Ruofeng,Xiong, Yan. "Umpolung Strategy for Synthesis of β-Ketonitriles through Hypervalent Iodine-Promoted Cyanation of Silyl Enol Ethers". . p. 7212 - 7218. Retrieved 2015/07/28.
• 2、 Hou, Zengye,Nakanishi, Isao,Kinoshita, Takayoshi,Takei, Yoshinori,Yasue, Misato,Misu, Ryosuke,Suzuki, Yamato,Nakamura, Shinya,Kure, Tatsuhide,Ohno, Hiroaki,Murata, Katsumi,Kitaura, Kazuo,Hirasawa, Akira,Tsujimoto, Gozoh,Oishi, Shinya,Fujii, Nobutaka. "Structure-based design of novel potent protein kinase CK2 (CK2) inhibitors with phenyl-azole scaffolds". supporting information; experimental part. p. 2899 - 2903. Retrieved 2012/06/01.