2-Chlorobenzylidenemalononitrile

Base Information

• Chemical Name: 2-Chlorobenzylidenemalononitrile
• CAS No.: 2698-41-1
• Molecular Formula: C10H5ClN2
• Molecular Weight: 188.616
• Hs Code.: 2926909090
• European Community (EC) Number: 220-278-9
• ICSC Number: 1065
• NSC Number: 637336,542
• UN Number: 3276,2810
• UNII: D8317IAV7Q
• DSSTox Substance ID: DTXSID9020297
• Nikkaji Number: J14.332D
• Wikipedia: CS_gas
• Wikidata: Q209357
• Pharos Ligand ID: CDJ2377HUYLZ
• ChEMBL ID: CHEMBL1256101
• Mol file: 2698-41-1.mol

Synonyms:2 Chlorobenzylidene Malonitrile;2 Chlorobenzylidenemalonitrile;2-Chlorobenzylidene Malonitrile;2-Chlorobenzylidenemalonitrile;CS Tear Gas;Malonitrile, 2-Chlorobenzylidene;Malonitrile, o-Chlorobenzylidene;Malonitrile, ortho-Chlorobenzylidene;malonotrile, o-Chlorobenzylidene;o Chlorobenzylidene Malonitrile;o Chlorobenzylidene malonotrile;o Chlorobenzylidenemalonitrile;o-Chlorobenzylidene Malonitrile;o-Chlorobenzylidene malonotrile;o-Chlorobenzylidenemalonitrile;ortho Chlorobenzylidene Malonitrile;ortho Chlorobenzylidenemalonitrile;ortho-Chlorobenzylidene Malonitrile;ortho-Chlorobenzylidenemalonitrile;Tear Gas, CS

Chemical Property of 2-Chlorobenzylidenemalononitrile

Chemical Property:

• Appearance/Colour: white crystalline solid with a peppery smell
• Vapor Pressure: 0.000527mmHg at 25°C
• Melting Point: 68-70 °C(lit.)
• Refractive Index: 1.623
• Boiling Point: 312.5 °C at 760 mmHg
• Flash Point: 148 °C
• PSA: 47.58000
• Density: 1.296 g/cm³
• LogP: 2.77056
• Storage Temp.: 2-8°C
• Solubility.: Soluble in acetone, benzene, 1,4-dioxane, ethyl acetate, and methylene chloride (Windholz et al., 1983)
• Water Solubility.: 0.1-0.5 g/100 mL at 16 ºC
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 188.0141259
• Heavy Atom Count: 13
• Complexity: 283

Purity/Quality:

99% ^*data from raw suppliers

2-Chlorobenzalmalononitrile 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T
• Hazard Codes: Xi,T
• Statements: 36/37/38-42/43-25
• Safety Statements: 26-27-37/39-45-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Toxic Gases & Vapors -> Tear Gas Agents
• Canonical SMILES: C1=CC=C(C(=C1)C=C(C#N)C#N)Cl
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying or when dispersed, especially if powdered.
• Effects of Short Term Exposure: Lachrymation. The substance is severely irritating to the eyes, skin and respiratory tract. The substance may cause effects on the lungs.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. Repeated or prolonged contact may cause skin sensitization.
• Description: CS, or o-chlorobenzylidene malononitrile, is the current major riot control agent (RCA) used by U.S. military forces. It was originally synthesized in 1928 by Corson and Stoughton, and the U.S. Army designated the compound ‘CS’ for the authors’ initials. CS replaced CN, chloroacetophenone, in 1959 as the U.S. Army’s premier RCA due to its higher safety ratio over CN. CS is more effective as an RCA, that is to say, more potent and safer than its predecessor CN. CS can be disseminated pyrotechnically, or in the cases of CS1 and CS2, in powder formulations.
• Uses: The defining component of tear gas (CS gas). Riot control agent. Active ingredient in tear gas

Technology Process of 2-Chlorobenzylidenemalononitrile

There total 9 articles about 2-Chlorobenzylidenemalononitrile 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%

2-chloro-benzaldehyde (89-98-5) + malononitrile (109-77-3) → o-chlorobenzylidene malononitrile (2698-41-1)

Guidance literature:

With poly(4-vinylpyridine) supported on MCM-48; at 25 ℃; for 0.133333h; neat (no solvent);

DOI:10.1016/j.catcom.2011.04.004

Reference yield: 99.0%

→ o-chlorobenzylidene malononitrile (2698-41-1)

Guidance literature:

With C₆₀H₅₂N₄O₈S₄*2Zn⁽²⁺⁾*2C₈H₄O₄^(2-)*8C₃H₇NO*2CH₄O; In methanol; at 60 ℃; for 1h; Catalytic behavior;

Reference yield: 92.0%

2-chlorobenzaldehyde dimethyl acetal (70380-66-4) + malononitrile (109-77-3) → o-chlorobenzylidene malononitrile (2698-41-1)

Guidance literature:

With Ni-Pd nanoparticles supported on poly (styrenesulfonic acid-n-vinylimidazole)/KIT-6; In water; at 45 ℃; for 0.5h;

DOI:10.1002/aoc.4800

upstream raw materials:

2-chloro-benzaldehyde

malononitrile

acetophenone

ortho-chlorobenzoic acid

Downstream raw materials:

2-[1-(2-Chloro-phenyl)-3-oxo-3-thiophen-2-yl-propyl]-malononitrile

2,7-Diamino-4-(2-chloro-phenyl)-4H-chromene-3-carbonitrile

2-Amino-4-(2-chloro-phenyl)-5-hydroxy-4H-chromene-3-carbonitrile

2-amino-7-hydroxy-4-(2'-chlorophenyl)-4H-chromene-3-carbonitrile

Refernces

• 1、 Bahrami, Kiumars,Khodaei, Mohammad M.,Babajani, Nasrin,Naali, Fardin. "Knoevenagel condensation in aqueous micellar media using EDAHS as a new Bronsted acidic ionic liquid". . p. 1675 - 1680. Retrieved 2014.
• 2、 Ma, Li,Wu, Hua,Yang, Jin,Liu, Ying-Ying,Ma, Jian-Fang. "Syntheses, crystal structures and knoevenagel condensation reactions of three coordination polymers assembled with Lewis basic ligand". . p. 6 - 10. Retrieved 2018.
• 3、 Yao, Cheng,Zhou, Shaolin,Kang, Xiaojing,Zhao, Yang,Yan, Rui,Zhang, Yan,Wen, Lili. "A Cationic Zinc-Organic Framework with Lewis Acidic and Basic Bifunctional Sites as an Efficient Solvent-Free Catalyst: CO2 Fixation and Knoevenagel Condensation Reaction". . p. 11157 - 11164. Retrieved 2018.
• 4、 Davoodnia, Abolghasem. "An efficient method for knoevenagel condensation catalyzed by tetrabutylammonium hexatungstate [TBA]2[W6O19] as novel and reusable heterogeneous catalyst". . p. 1022 - 1026. Retrieved 2012.
• 5、 Zhang, Ming,Zhang, Ai-Qin,Chen, Huan-Huan,Chen, Jun,Chen, Hai-Yan. "Fast method for synthesis of ylidenemalononitriles". . p. 3441 - 3445. Retrieved 2006.
• 6、 Ren, Zhongjiao,Cao, Weigud,Tong, Weiqi. "The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile by grinding in the absence of solvents and catalysts". . p. 3475 - 3479. Retrieved 2002.
• 7、 Rahmatizadeh-Pashaki, Zahra,Daneshvar, Nader,Shirini, Farhad. "Introduction of bis-imidazolium dihydrogen phosphate as a new green acidic ionic liquid catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives". . p. 2135 - 2149. Retrieved 2021/02/01.