Ethyl benzylidenecyanoacetate

Base Information

• Chemical Name: Ethyl benzylidenecyanoacetate
• CAS No.: 2169-69-9
• Deprecated CAS: 756509-63-4
• Molecular Formula: C12H11 N O2
• Molecular Weight: 201.225
• European Community (EC) Number: 217-972-9,634-979-6
• Nikkaji Number: J134.545A,J80.417G
• ChEMBL ID: CHEMBL4091929
• Mol file: 2169-69-9.mol

Synonyms:2169-69-9;alpha-Cyanocinnamic acid ethyl ester;Ethyl benzylidenecyanoacetate;2025-40-3;Ethyl 2-Cyano-3-phenylacrylate;ethyl (E)-2-cyano-3-phenylprop-2-enoate;(E)-Ethyl 2-cyano-3-phenylacrylate;(E)-2-Cyano-3-phenyl-acrylic acid ethyl ester;Ethyl trans-alpha-cyanocinnamate;ethyl (2E)-2-cyano-3-phenylprop-2-enoate;Cinnamic acid, alpha-cyano-, ethyl ester;2-Propenoic acid, 2-cyano-3-phenyl-, ethyl ester;(E)-Ethyl 2-Cyano-3-phenyl-2-propenoate;Ethyl .alpha.-cyanocinnamate;Ethyl (E)-2-cyano-3-phenylacrylate;2-Cyano-3-phenylacrylic Acid Ethyl Ester;NSC 8904;EINECS 217-972-9;Ethyl alpha-cyano-beta-phenylcinnamate;AI3-10525;Ethyl alpha-cyanocinnamate;ethyl trans-a-cyanocinnamate;benzylidene ethyl cyanoacetate;SCHEMBL278655;CHEMBL4091929;Ethyl trans- alpha -cyanocinnamate;HMS1661F17;trans-Ethyl .alpha.-cyanocinnamate;(E)-Ethyl2-cyano-3-phenylacrylate;AMY25107;BBL002782;CCG-54264;MFCD00009137;STK390983;AKOS003238530;ethyl (2E)-2-cyano-3-phenylacrylate;Ethyl trans-alpha-cyanocinnamate, 99%;GS-6011;Ethyl(2E)-2-cyano-3-phenyl-2-propenoate;ethyl (E)-2-cyano-3-phenyl-prop-2-enoate;CS-0120772;Ethyl (2E)-2-cyano-3-phenyl-2-propenoate #;H11338;J-014239;SR-01000643371-1

Chemical Property of Ethyl benzylidenecyanoacetate

Chemical Property:

• Melting Point: 51-53 °C(lit.)
• Refractive Index: 1.5560 (estimate)
• Boiling Point: 188 °C15 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 50.09000
• Density: 1.1574 (rough estimate)
• LogP: 2.15668
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 201.078978594
• Heavy Atom Count: 15
• Complexity: 292

Purity/Quality:

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

Ethyl trans-α-cyanocinnamate 99% ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(=CC1=CC=CC=C1)C#N
• Isomeric SMILES: CCOC(=O)/C(=C/C1=CC=CC=C1)/C#N
• Uses: Ethyl trans-α-cyanocinnamate may be used in chemical synthesis studies.

Technology Process of Ethyl benzylidenecyanoacetate

There total 31 articles about Ethyl benzylidenecyanoacetate 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%

benzaldehyde dimethyl acetal (1125-88-8) + ethyl 2-cyanoacetate (105-56-6) → ethyl (E)-2-cyano-3-phenyl-2-propenoate (2169-69-9)

Guidance literature:

With NH₂-modied HSZs(0.2); In water; at 80 ℃; for 24h; Reagent/catalyst; Green chemistry;

DOI:10.1039/c4ra11865k

Reference yield: 100.0%

benzaldehyde (100-52-7) + ethyl 2-cyanoacetate (105-56-6) → ethyl (E)-2-cyano-3-phenyl-2-propenoate (2169-69-9)

Guidance literature:

With tetramethyl ammoniumhydroxide; at 60 ℃; for 0.5h;

DOI:10.1039/a900384c

Reference yield: 93.0%

2-phenyl-1,3-dioxolane (936-51-6) + ethyl 2-cyanoacetate (105-56-6) → ethyl (E)-2-cyano-3-phenyl-2-propenoate (2169-69-9)

Guidance literature:

With polymeric benzene sulfonic acid and polymeric 4-dimethylaminopyridine encapsualted in Cr-MIL-101; In water; dimethyl sulfoxide; at 70 ℃; for 12h;

DOI:10.1002/chem.201801416

upstream raw materials:

benzaldehyde

ethyl 2-cyanoacetate

α-nitro-stilbene

ethyl bromocyanoacetate

Downstream raw materials:

3t-phenyl-2-cyano-acrylic acid-ureide

3-Cyano-6-[(E)-cyanoimino]-2,4-diphenyl-piperidine-3-carboxylic acid methyl ester

3-Cyano-6-[(E)-cyanoimino]-2-phenyl-4-p-tolyl-piperidine-3-carboxylic acid methyl ester

4-(4-Chloro-phenyl)-3-cyano-6-[(E)-cyanoimino]-2-phenyl-piperidine-3-carboxylic acid methyl ester

Refernces

• 1、 Oka, Yuya,Kuroda, Yoshiyuki,Matsuno, Takamichi,Kamata, Keigo,Wada, Hiroaki,Shimojima, Atsushi,Kuroda, Kazuyuki. "Preparation of Mesoporous Basic Oxides through Assembly of Monodispersed Mg–Al Layered Double Hydroxide Nanoparticles". . p. 9362 - 9368. Retrieved 2017.
• 2、 Zhang, Fang,Jiang, Huangyong,Li, Xiaoyan,Wu, Xiaotao,Li, Hexing. "Amine-functionalized go as an active and reusable acid-base bifunctional catalyst for one-pot cascade reactions". . p. 394 - 401. Retrieved 2014.
• 3、 Minato, Takuo,Suzuki, Kosuke,Kamata, Keigo,Mizuno, Noritaka. "Synthesis of α-Dawson-type silicotungstate [α-Si 2W18O62]8- and protonation and deprotonation inside the aperture through intramolecular hydrogen bonds". . p. 5946 - 5952. Retrieved 2014.
• 4、 Zhang, Guangcai,Zhang, Tong,Zhang, Xiongfu,Yeung, King Lun. "Continuous flow ZIF-8/NaA composite membrane microreactor for efficient Knoevenagel condensation". . p. 93 - 96. Retrieved 2015.
• 5、 Waghmare, Smita R.. "Ammonium chloride catalyzed Knoevenagel condensation in PEG-400 as ecofriendly solvent". . p. 849 - 855. Retrieved 2021/09/28.
• 6、 Meyer, Maximilian,Peri?, Milica,Sch?mberg, Fritz,Vilotijevi?, Ivan. "trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines". supporting information. . Retrieved 2021/10/04.