Ethyl 2-cyano-2-phenylbutanoate

Base Information

• Chemical Name: Ethyl 2-cyano-2-phenylbutanoate
• CAS No.: 718-71-8
• Molecular Formula: C13H15NO2
• Molecular Weight: 217.268
• Hs Code.: 2926909090
• European Community (EC) Number: 700-275-3
• NSC Number: 69121
• DSSTox Substance ID: DTXSID60290526
• Nikkaji Number: J1.459.110I
• Mol file: 718-71-8.mol

Synonyms:ethyl 2-cyano-2-phenylbutanoate;718-71-8;Ethyl-2-phenyl-2-cyanobutylate;Ethylphenylcyano-acetic acid ethyl ester;ETHYL CYANOETHYLPHENYLACETATE;EC 700-275-3;NSC 69121;NSC69121;ethyl ethylphenylcyanoacetate;NCIOpen2_003448;SCHEMBL9214363;Ethyl 2-Phenyl-2-Cyanobutylate;DTXSID60290526;Ethyl 2-cyano-2-phenyl-butanoate;MFCD00068977;NSC-69121;AKOS015890653;ethyl 2-cyano-2-ethyl-2-phenylacetate;DS-18350;2-Cyano-2-phenylbutanoic acid ethyl ester;CS-0152634;FT-0656881;D81906;J-522816;N-(2,4-Dichloro-5-(4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1h-1,2,4-triazol-1-yl)phenyl)-n-(methylsulfonyl)methanesulfonamide

Chemical Property of Ethyl 2-cyano-2-phenylbutanoate

Chemical Property:

• Appearance/Colour: yellowish oil
• Vapor Pressure: 0.000214mmHg at 25°C
• Refractive Index: 1.506
• Boiling Point: 326.6 °C at 760 mmHg
• Flash Point: 153.6 °C
• PSA: 50.09000
• Density: 1.072 g/cm³
• LogP: 2.42108
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, Ether, Ethyl Acetate, Methanol
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 217.110278721
• Heavy Atom Count: 16
• Complexity: 286

Purity/Quality:

99% ^*data from raw suppliers

EthylCyanoethylphenylacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C#N)(C1=CC=CC=C1)C(=O)OCC
• Uses: Ethyl Cyanoethylphenylacetate (cas# 718-71-8) is a compound useful in organic synthesis.

Technology Process of Ethyl 2-cyano-2-phenylbutanoate

There total 16 articles about Ethyl 2-cyano-2-phenylbutanoate 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%

Diphenyliodonium triflate (66003-76-7) + 2-cyano-butyric acid ethyl ester (1619-58-5) → ethyl 2-cyano-2-phenylbutanoate (718-71-8)

Guidance literature:

2-cyano-butyric acid ethyl ester; With potassium tert-butylate; In dichloromethane; at 0 ℃; for 0.0833333h; Schlenk technique; Inert atmosphere;

Diphenyliodonium triflate; In dichloromethane; at 0 ℃; for 0.333333h; Schlenk technique; Inert atmosphere;

DOI:10.1002/adsc.201501013

Reference yield: 80.0%

bromobenzene (108-86-1,52753-63-6) + ethyl iodide (75-03-6) + ethyl 2-cyanoacetate (105-56-6) → ethyl 2-cyano-2-phenylbutanoate (718-71-8)

Guidance literature:

bromobenzene; ethyl 2-cyanoacetate; With 1,1'-bis-(diphenylphosphino)ferrocene; potassium tert-butylate; palladium diacetate; In 1,4-dioxane; at 70 ℃;

ethyl iodide; In 1,4-dioxane; at 70 ℃; for 4h; Further stages.;

DOI:10.1021/jo7024338

Reference yield: 73.0%

ethyl bromide (74-96-4) + ethyl phenylcyanoacetate (4553-07-5) → ethyl 2-cyano-2-phenylbutanoate (718-71-8)

Guidance literature:

N-benzyl-N,N,N-triethylammonium chloride; In N,N-dimethyl-formamide; at 100 - 105 ℃; for 2.5h;

upstream raw materials:

2-phenylbutanenitrile

chloroformic acid ethyl ester

ethyl iodide

ethyl bromide

Downstream raw materials:

2-cyano-2-phenyl-butyric acid benzylamide

6-amino-5-ethyl-5-phenyl-5H-pyrimidine-2,4-dione

2-dimethylaminomethyl-2-phenyl-butan-1-ol

α-Aethyl-α-phenyl-α-aethoxycarbonylthioacetamid

Refernces

• 1、 Yin, Liang,Kanai, Motomu,Shibasaki, Masakatsu. "Cu(I)-catalyzed decarboxylative aldol-type and Mannich-type reactions for asymmetric construction of contiguous trisubstituted and quaternary stereocenters". scheme or table. p. 3497 - 3506. Retrieved 2012/06/15.
• 2、 Wang, Xiang,Guram, Anil,Bunel, Emilio,Cao, Guo-Qiang,Allen, Jennifer R.,Faul, Margaret M.. "Palladium-catalyzed one-pot synthesis of 2-alkyl-2-arylcyanoacetates". . p. 1643 - 1645. Retrieved 2008/09/17.