Benzylidenemalononitrile

Base Information

• Chemical Name: Benzylidenemalononitrile
• CAS No.: 2700-22-3
• Molecular Formula: C10H6N2
• Molecular Weight: 154.171
• Hs Code.: 29269095
• European Community (EC) Number: 220-283-6
• NSC Number: 490
• UNII: 2HQB24UJ25
• DSSTox Substance ID: DTXSID10181490
• Nikkaji Number: J41.614B
• Wikidata: Q83052120
• Mol file: 2700-22-3.mol

Synonyms:Benzylidenemalononitrile;2-Benzylidenemalononitrile;2700-22-3;Benzalmalononitrile;Benzylidenemalonodinitrile;alpha-Cyanocinnamonitrile;Benzylidene malononitrile;MALONONITRILE, BENZYLIDENE-;2-benzylidenepropanedinitrile;Benzal-malonitril;beta,beta-Dicyanostyrene;2,2-Dicyano-1-phenylethylene;2-Phenyl-1,1-dicyanoethylene;Propanedinitrile, (phenylmethylene)-;2-(phenylmethylidene)propanedinitrile;beta,beta-Styrenedicarbonitrile;NSC 490;2-Benzylidene-malononitrile;Benzal-malonitril [German];AI3-19689;EINECS 220-283-6;F 2370;TL 237;.alpha.-Cyanocinnamonitrile;.beta.,.beta.-Dicyanostyrene;2HQB24UJ25;NSC-490;Propanedinitrile, 2-(phenylmethylene)-;benzylidenepropanedinitrile;Benzalmalonitrile;2-(phenylmethylene)Propanedinitrile;benzylidenemalonitrile;I+/--Cyanocinnamonitrile;WLN: NCYCN&1R;Malonodinitrile, benzylidene;UNII-2HQB24UJ25;2-Benzylidenemalononitrile #;SCHEMBL60843;(Phenylmethylene)malononitrile;1,1-Dicyano-2-phenylethene;2-Phenyl-1,1-dicyanoethene;2-benzylidene-propanedinitrile;2-Cyano-3-phenylacrylonitrile;Benzylidenemalononitrile, 98%;1,1-Dicyano-2-phenylethylene;NSC490;(Phenylmethylene)propanedinitrile;WAVNYPVYNSIHNC-UHFFFAOYSA-;DTXSID10181490;HMS1787C07;.beta.,.beta.-Styrenedicarbonitrile;MCK102227;MFCD00001855;STL139251;AKOS001012099;AS-58817;LS-88854;A5283;B0947;CS-0186558;FT-0622851;D88718;J-016644;Z44299997;F6782-3634

Chemical Property of Benzylidenemalononitrile

Chemical Property:

• Appearance/Colour: slightly yellow needle-like crystalline powder
• Vapor Pressure: 0.00159mmHg at 25°C
• Melting Point: 83-85 °C(lit.)
• Refractive Index: 1.612
• Boiling Point: 294.8 °C at 760 mmHg
• Flash Point: 138 °C
• PSA: 47.58000
• Density: 1.154 g/cm³
• LogP: 2.11716
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Methanol
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 154.053098200
• Heavy Atom Count: 12
• Complexity: 247

Purity/Quality:

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

2-Benzylidenemalononitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=C(C#N)C#N
• Uses: Benzylidenemalononitrile was used in fluorescence-based assay for determination of soluble methane monooxygenase activity in solution.

Technology Process of Benzylidenemalononitrile

There total 73 articles about Benzylidenemalononitrile 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) + malononitrile (109-77-3) → Benzylidenemalononitrile (2700-22-3)

Guidance literature:

With FeO_x, Al₂O_{3 and} ZrO₂ dispersed pyrogallic acid (PG)-assisted layer-by-layer coated hierarchically porous silica; In water; toluene; at 80 ℃; for 3h; Reagent/catalyst;

DOI:10.1039/c6ra12088a

Reference yield: 99.0%

malononitrile (109-77-3) + benzyl alcohol (100-51-6,185532-71-2) → Benzylidenemalononitrile (2700-22-3)

Guidance literature:

With oxygen; In toluene; at 100 ℃; for 13h; under 760.051 Torr; Reagent/catalyst; Solvent; Temperature;

DOI:10.1002/ejic.201500808

Reference yield: 99.0%

benzylidene phenylamine (538-51-2) + malononitrile (109-77-3) → Benzylidenemalononitrile (2700-22-3)

Guidance literature:

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1S,2R)-1-(piperidin-1-yl)-2,3-dihydro-1H-inden-2-yl)thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; at 20 ℃; for 0.333333h; Molecular sieve;

DOI:10.1002/chem.201103136

upstream raw materials:

2-cyano-3-phenylacrylamide

2-benzylidenepropanediamide

sodium ethanolate

benzaldehyde

Downstream raw materials:

2-phenyl-ethane-1,1,2-tricarbonitrile

2-benzhydrylmalononitrile

chloro-(α-chloro-benzyl)-malononitrile

3,3,5,5-Tetracyano-2,4,6-triphenylpiperidine

Refernces

• 1、 Miao, Zongcheng,Luan, Yi,Qi, Chao,Ramella, Daniele. "The synthesis of a bifunctional copper metal organic framework and its application in the aerobic oxidation/Knoevenagel condensation sequential reaction". . p. 13917 - 13924. Retrieved 2016.
• 2、 Dang, Qiang,Huang, Hanlin,Li, Liuyi,Lyu, Xiaolin,Zhong, Shenghong,Yu, Yan,Xu, Dongsheng. "Yolk-Shell-Structured Covalent Organic Frameworks with Encapsulated Metal-Organic Frameworks for Synergistic Catalysis". . p. 5690 - 5699. Retrieved 2021.
• 3、 Guo, Changyan,Zhang, Yonghong,Zhang, Li,Zhang, Yi,Wang, Jide. "2-Methylimidazole-assisted synthesis of a two-dimensional MOF-5 catalyst with enhanced catalytic activity for the Knoevenagel condensation reaction". . p. 5327 - 5331. Retrieved 2018.
• 4、 Beheshti, Saeideh,Morsali, Ali. "Post-synthetic cation exchange in anionic metal-organic frameworks; A novel strategy for increasing the catalytic activity in solvent-free condensation reactions". . p. 41825 - 41830. Retrieved 2014.
• 5、 Agarwal, Rashmi A.,Mukherjee, Soumya. "Two-dimensional flexible Ni(II)-based porous coordination polymer showing single-crystal to single-crystal transformation, selective gas adsorption and catalytic properties". . p. 228 - 237. Retrieved 2016.
• 6、 Huo, Hang,Jiang, Yanqiu,Zhao, Tingting,Wang, Junlei,Li, Defeng,Xu, Xianzhu,Lin, Kaifeng. "Periodic Mesoporous Organosilicas as Efficient Nanoreactors in Cascade Reactions Preparing Cyclopropanic Derivatives". . p. 1496 - 1505. Retrieved 2019.
• 7、 Qi, Yue,Luan, Yi,Peng, Xiong,Yang, Ming,Hou, Junying,Wang, Ge. "Design and Synthesis of an Au@MIL-53(NH2) Catalyst for a One-Pot Aerobic Oxidation/Knoevenagel Condensation Reaction". . p. 5099 - 5105. Retrieved 2015.
• 8、 Zhang, Yue,Wang, Yuxiang,Liu, Lin,Wei, Na,Gao, Ming-Liang,Zhao, Dan,Han, Zheng-Bo. "Robust Bifunctional Lanthanide Cluster Based Metal-Organic Frameworks (MOFs) for Tandem Deacetalization-Knoevenagel Reaction". . p. 2193 - 2198. Retrieved 2018.
• 9、 Arion, Vladimir B.,Breza, Martin,Darvasiová, Denisa,Dobrov, Anatolie,Fesenko, Anastasia,Martins, Luísa M. D. R. S.,Pombeiro, Armando J. L.,Rapta, Peter,Shutalev, Anatoly,Stepanenko, Iryna,Yankov, Alexander. "Nickel(II), Copper(II) and Palladium(II) Complexes with Bis-Semicarbazide Hexaazamacrocycles: Redox-Noninnocent Behavior and Catalytic Activity in Oxidation and C-C Coupling Reactions". . . Retrieved 2020.
• 10、 Wang, Jiajia,Han, Yuqing,Xu, Haitao,Xu, Zhen-Liang. "Microporous assembly and shape control of a new Zn metal–organic framework: Morphology-dependent catalytic performance". . . Retrieved 2018.