Ethyl 4-cyanobenzoate

Base Information

• Chemical Name: Ethyl 4-cyanobenzoate
• CAS No.: 7153-22-2
• Molecular Formula: C10H9 N O2
• Molecular Weight: 175.187
• Hs Code.: 2926909090
• European Community (EC) Number: 230-500-6
• NSC Number: 62689
• DSSTox Substance ID: DTXSID10221769
• Nikkaji Number: J227.417E
• Wikidata: Q52773313
• Mol file: 7153-22-2.mol

Synonyms:Ethyl 4-cyanobenzoate;7153-22-2;Benzoic acid, 4-cyano-, ethyl ester;4-Cyano-benzoic acid ethyl ester;4-cyanobenzoic acid ethyl ester;EINECS 230-500-6;MFCD00001824;Benzoic acid, 4-cyano-,ethyl ester;Ethyl4-cyanobenzoate;ethyl p-cyanobenzoate;ethyl-4-cyanobenzoate;p-cyano ethyl benzoate;Ethyl 4-cyanobenzoate, 99%;SCHEMBL1365179;4-Cyanobenzoic acid, ethyl ester;DTXSID10221769;NSC62689;NSC 62689;NSC-62689;STK002554;AKOS005374533;CS-W001928;BENZOIC ACID,4-CYANO,ETHYL ESTER;DS-16734;SY005785;AM20060933;E1167;FT-0626080;EN300-1265958;A837235;W-104519;Q52773313;F8881-1838

Chemical Property of Ethyl 4-cyanobenzoate

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 0.00112mmHg at 25°C
• Melting Point: 52-55 ºC
• Refractive Index: 1.528
• Boiling Point: 300.5 °C at 760 mmHg
• Flash Point: 138.9 °C
• PSA: 50.09000
• Density: 1.14 g/cm³
• LogP: 1.73498
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.5
• 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

Ethyl 4-Cyanobenzoate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Ethyl 4-cyanobenzoate

There total 83 articles about Ethyl 4-cyanobenzoate 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: 95.0%

4-iodobenzoic acid ethyl ester (51934-41-9) → ethyl 4-cyanobenzoate (7153-22-2)

Guidance literature:

4-iodobenzoic acid ethyl ester; With isopropylmagnesium chloride; lithium chloride; In tetrahydrofuran; at -15 ℃; for 0.25h;

With N,N-dimethyl-formamide; In tetrahydrofuran; at 0 ℃; for 2h;

With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2012.12.022

Reference yield: 94.0%

ethanol (64-17-5) + 4-cyanobenzaldehyde (105-07-7) → ethyl 4-cyanobenzoate (7153-22-2)

Guidance literature:

With water; iodine; sodium nitrite; at 20 - 70 ℃; chemoselective reaction;

DOI:10.1055/s-0029-1217121

Reference yield: 92.0%

ethyl trifluoroacetate, (383-63-1) + 1-(4-cyanophenyl)-1-pentanone (30611-20-2) → ethyl 4-cyanobenzoate (7153-22-2) + 1,1,1-trifluoro-2-hexanone (360-34-9)

Guidance literature:

ethyl trifluoroacetate,; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.166667h; Inert atmosphere; Schlenk technique;

1-(4-cyanophenyl)-1-pentanone; In tetrahydrofuran; at 0 ℃; for 5h; Inert atmosphere; Schlenk technique; Reflux;

With hydrogenchloride; In tetrahydrofuran; water; at 0 ℃; for 0.25h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2014.05.017

upstream raw materials:

potassium cyanide

p-aminoethylbenzoate

p-(ethoxycarbonyl)phenyl triflate

ethanolate

Downstream raw materials:

4-[(3,4-dimethoxy-phenylsulfanyl)-carboximidoyl]-benzoic acid ethyl ester

4-methylbenzoic acid ethyl ester

4-cyanobenzohydrazide

ethyl 4-(aminocarbonyl)benzoate

Refernces

• 1、 Chu, Xue-Qiang,Ge, Danhua,Luo, Xin-Long,Xu, Pei,Yu, Zi-Lun. "Vitamin B1-catalyzed aerobic oxidative esterification of aromatic aldehydes with alcohols". supporting information. p. 30937 - 30942. Retrieved 2021/11/19.
• 2、 Tan, Hui,Wang, Shen-An,Yan, Zixi,Liu, Jianzhong,Wei, Jialiang,Song, Song,Jiao, Ning. "N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air". supporting information. p. 2140 - 2144. Retrieved 2020/12/01.