2698-41-1

Usage

Uses

Used in Riot Control:
[(2-Chlorophenyl)methylene]malononitrile is used as a riot control agent for its effectiveness in controlling and dispersing crowds during civil unrest or protests. Its potency and safety make it a preferred choice over its predecessor, CN.
Used in Military Operations:
In the military, [(2-Chlorophenyl)methylene]malononitrile is used as an active ingredient in tear gas for non-lethal crowd control and area denial during operations. Its combustion properties allow for dissemination through pyrotechnical means, while CS1 and CS2 can be used in powder formulations.
Used in Law Enforcement:
Law enforcement agencies also utilize [(2-Chlorophenyl)methylene]malononitrile as a component of tear gas for controlling and subduing suspects during high-risk situations, such as hostage rescues or apprehending dangerous criminals.
Used in Chemical Research:
As a chemical compound, [(2-Chlorophenyl)methylene]malononitrile may also be used in research and development for understanding its properties and potential applications in various fields, including chemistry, materials science, and pharmaceuticals.

Air & Water Reactions

The finely powdered nitrile is a significant dust explosion hazard. Slightly soluble in water.

Reactivity Profile

[(2-Chlorophenyl)methylene]malononitrile may react with strong oxidizers.

Hazard

Toxic by inhalation and skin contact. Strong irritant to eyes and mucous membranes.

Health Hazard

o-Chlorobenzylidene malononitrile (CS) aerosol is a potent lacrimator and upper respiratory irritant. Characteristic effects of CS exposure are instantaneous conjunctivitis, blepharospasm, burning, and pain.1 Prolonged exposure to high concentrations in enclosed spaces may cause pulmonary edema and severe bronchospasm.

Fire Hazard

Flash point data for [(2-Chlorophenyl)methylene]malononitrile are not available, but [(2-Chlorophenyl)methylene]malononitrile is probably combustible.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. Moderately toxic by inhalation. Human systemic effects by inhalation: conjunctiva irritation, cough, and unspecified respiratory system effects. A human skin and eye irritant. Human exposure data suggest relatively low systemic toxicity, but intense irritation of eyes, skin, and mucous membranes. Mutation data reported. A tear gas used for riot control. When heated to decomposition it emits very toxic fumes of Cl-, NOx, and CN-. See also NITRILES.

Potential Exposure

CS tear gas is used as a riot control agent and is also used as an agent in CS1, CS2, and CSX riot control, and tear gases.

Carcinogenicity

o-Chlorobenzylidene malononitrile did not cause a mutagenic response when tested in a variety of assays that examined point mutations, germinal gene mutations, chromosomal breaks, and mitotic chromosome misdistribution. 5 Although limited, a study of the repeated inhalation toxicity of CS in mice, rats, and guinea pigs did not find a relationship between tumors in a particular site and total dose of CS.6 F344N rats exposed at 0.075, 0.25, or 0.75mg/ m3 and B6C3F1 mice exposed at 0.75 or 1.5mg/m3 6 hours/day, 5 days/week for 2 years had no compound-related incidences of neoplasm. 7 Nonneoplastic lesions occurred primarily in the nasal passages and included hyperplasia and squamous metaplasia of the respiratory epithelium.

Environmental fate

Chemical/Physical. Hydrolyzes in water forming 2-chlorobenzaldehyde and malononitrile (quoted, Verschueren, 1983).

Shipping

UN2810 Toxic liquids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required. Military driver shall be given full and complete information regarding shipment and conditions in case of emergency. AR 50-6 deals specifically with the shipment of chemical agents. Shipments of agent will be escorted in accordance with AR 740-32.

Toxicity evaluation

Tests conducted at Eglin Air Force Base near Ft. Walton Beach, Florida, concluded that CS in soil has a ‘conservative’ half-life of 3.9 days. Degradation of CS increases with soil and air moisture, and with light exposure as it undergoes a slow hydrolysis process. Olajos (2004) concluded that CS degrades to o-chlorobenzaldehyde and malononitrile, the former of which is ultimately converted to catechol under aerobic conditions. Nitriles such as the malononitrile degradation product of CS have a short half-life in soil and can be converted readily to organic acids. Anaerobically, microalgae have been reported to transform CS breakdown products into benzoate. The U.S. Army Edgewood Research Development and Engineering Center (USAERDEC) reports a solubility of 200 mg l-1. CS concentrations attenuate in the atmosphere through three processes: reaction with hydroxyl radicals, hydrolysis reactions with atmospheric humidity, and deposition of particulate CS. It should be noted that vapor pressure increases with temperature, as should be expected. At 20°C, CS vapor pressure is 3.5×10-5 mmHg, and at 60°C, it is 5–7 mmHg.

Incompatibilities

Contact with strong oxidizers may cause fire and explosion. May be explosive if dust mixes with air.

InChI:InChI=1/C10H5ClN2/c11-10-4-2-1-3-9(10)5-8(6-12)7-13/h1-5H

Synthetic route

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

Conditions	Yield
With poly(4-vinylpyridine) supported on MCM-48 at 25℃; for 0.133333h; Knoevenagel condensation; neat (no solvent);	100%
Stage #1: malononitrile; piperidine In water at 20 - 30℃; Stage #2: 2-chloro-benzaldehyde In water at 50℃; Product distribution / selectivity; Knoevenagel Condensation;	99.5%
In N,N-dimethyl-formamide for 1h; Knoevenagel Condensation;	99.9%

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

Conditions	Yield
With Ni-Pd nanoparticles supported on poly (styrenesulfonic acid-n-vinylimidazole)/KIT-6 In water at 45℃; for 0.5h; Knoevenagel Condensation;	92%

malononitrile (109-77-3) + 2-CHLOROBENZYLAMINE (89-97-4) → o-chlorobenzylidene malononitrile (2698-41-1)

Conditions	Yield
With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.75h; Inert atmosphere;	78%

2-chloro-benzaldehyde (89-98-5) + acetophenone (98-86-2) + malononitrile (109-77-3) → o-chlorobenzylidene malononitrile (2698-41-1) + 3-(2-chlorophenyl)-1-phenylpropenone (3300-67-2) + 2-amino-4-(2-chlorophenyl)-6-phenylbenzene-1,3-carbodinitrile (77198-47-1)

Conditions	Yield
With potassium carbonate at 60℃; for 0.133333h; neat (no solvent);	A n/a B n/a C 67%

2-[Butylsulfanyl-(2-chloro-phenyl)-methyl]-malononitrile → 1-butanethiol (109-79-5) + o-chlorobenzylidene malononitrile (2698-41-1)

Conditions	Yield
at 25℃; Equilibrium constant;

ortho-chlorobenzoic acid (118-91-2) → o-chlorobenzylidene malononitrile (2698-41-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / diethyl ether / 1 h / 20 °C 2: dinitrogen tetraoxide / 18 h / 20 °C 3: methanol / 3 h View Scheme

2-Chlorobenzyl alcohol (17849-38-6) → o-chlorobenzylidene malononitrile (2698-41-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: dinitrogen tetraoxide / 18 h / 20 °C 2: methanol / 3 h View Scheme
Multi-step reaction with 2 steps 1: copper(I) bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate / water / 8 h / 20 °C / Green chemistry 2: dimethyl 3-methyl-9-oxo-7-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)-2,4-di(pyridin-2-yl)-3,7-diazabicyclo-[3.3.1]nonane-1,5-dicarboxylate / water / 2 h / 40 °C View Scheme
Multi-step reaction with 2 steps 1: Co2+ immobilized on highly ordered mesoporous graphitic carbon nitride; air / acetonitrile / 12 h / 20 °C / Irradiation; Green chemistry 2: Co2+ immobilized on highly ordered mesoporous graphitic carbon nitride / acetonitrile / 6 h / 80 °C / Green chemistry View Scheme
Multi-step reaction with 2 steps 1: [bis(acetoxy)iodo]benzene / acetonitrile / 4 h / 20 °C 2: (2,2,6,6-tetramethylpiperidin-1-yl)oxyl containing Pd-organic cages within amino-functionalized mesoporous carbon / acetonitrile / 0.17 h / 60 °C View Scheme

o-chlorobenzylidene malononitrile (2698-41-1) + 2,6-diaminopyrimidin-4-ol (56-06-4) → 2,7-diamino-3,4-dihydro-4-oxo-5-(2-chlorophenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 5h;	99%

o-chlorobenzylidene malononitrile (2698-41-1) + ethyl 5,5-diphenylpenta-2,3,4-trienoate (1119249-36-3) → C29H21ClN2O2 (1119249-65-8)

Conditions	Yield
With tributylphosphine In tetrahydrofuran at 60℃; for 1h; Inert atmosphere;	99%

4-Chlorophenoxyacetic acid (122-88-3) + o-chlorobenzylidene malononitrile (2698-41-1) → 2-(2-(4-chlorophenoxy)-1-(2-chlorophenyl)ethyl)malononitrile

Conditions	Yield
With iron(III) sulfate; bis[(2-pyridyl)methyl]amine In 1,2-dichloro-ethane at 20℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;	99%

4-hydroxy-6-methyl-2-pyron (675-10-5) + o-chlorobenzylidene malononitrile (2698-41-1) → 2-amino-4-(2-chlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 6h;	98%
With morpholine In ethanol for 0.0833333h; Heating;

o-chlorobenzylidene malononitrile (2698-41-1) → 3-(2-chlorophenyl)oxirane-2,2-dicarbonitrile (3513-08-4)

Conditions	Yield
With calcium hypochlorite In tetrachloromethane at 20℃;	97%
With [bis(acetoxy)iodo]benzene; water In acetonitrile at 20℃; for 0.833333h; Sonication;	69%
With oxone; iodobenzene; trifluoroacetic acid In chloroform at 20℃; for 1.33333h; Sonication;	65%

o-chlorobenzylidene malononitrile (2698-41-1) + dimedone (126-81-8) → 2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile (129354-35-4)

Conditions	Yield
With urea/choline chloride eutectic salt In water at 20℃; Michael Addition; Green chemistry;	96%
With aspartic Acid In ethanol; water at 20℃; for 1.5h;	94%
With N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 0.0833333h;	93%

o-chlorobenzylidene malononitrile (2698-41-1) + 1-{[(1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexylcarbamoyl]-methyl}-pyridinium; chloride → 3-(2-Chloro-phenyl)-2,2-dicyano-cyclopropanecarboxylic acid [(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl]-amide

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	96%

tert-butylisonitrile (119072-55-8, 7188-38-7) + o-chlorobenzylidene malononitrile (2698-41-1) + methyl 4,4,5,5,5-pentafluoropent-2-ynoate (104721-32-6) → methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(pentafluoroethyl)cyclopenta-1,4-dienecarboxylate (1431657-47-4)

Conditions	Yield
In dichloromethane at 20℃; for 8h;	96%

o-chlorobenzylidene malononitrile (2698-41-1) + 4-((2,4-dihydroxyphenyl)diazenyl)-N-(3-methylisoxazol-5-yl)benzenesulfonamide → C26H19ClN6O5S

Conditions	Yield
With piperidine In ethanol for 1h; Reflux;	96%

o-chlorobenzylidene malononitrile (2698-41-1) + phosphonic acid diethyl ester (762-04-9) → [1-(2-chlorophenyl)-2,2-dicyanoethyl] phosphonic acid diethyl ester (142012-38-2)

Conditions	Yield
With mercapto-functionalized silica-coated nano γ-Fe2O3-pyridine In neat (no solvent) at 70℃; for 1.5h; Michael Addition; Green chemistry;	95%
With 3-aminopropylated silica gel at 50℃; for 0.25h; phospha-Michael addition; Neat (no solvent);	91%
With iron-doped single walled carbon nanotubes In neat (no solvent) at 50℃; for 3h; Green chemistry; chemoselective reaction;	90%
at 100℃; for 8h;	72%

o-chlorobenzylidene malononitrile (2698-41-1) + Br(1-)*C22H36NO2(1+) → C17H17ClN2O2 + C16H25N

Conditions	Yield
Stage #1: Br(1-)*C22H36NO2(1+) With triethylamine In dichloromethane Stage #2: o-chlorobenzylidene malononitrile In dichloromethane at 20℃; optical yield given as %ee; enantioselective reaction;	A 92% B 95%

tert-butylisonitrile (119072-55-8, 7188-38-7) + o-chlorobenzylidene malononitrile (2698-41-1) + methyl 4,4,4-trifluoro-2-butynoate (70577-95-6) → methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(trifluoromethyl)cyclopenta-1,4-dienecarboxylate (1431657-37-2)

Conditions	Yield
In dichloromethane at 20℃; for 10h;	95%

BARBITURIC ACID (67-52-7) + o-chlorobenzylidene malononitrile (2698-41-1) → 7‐amino‐5‐(2‐chlorophenyl)‐2,4‐dioxo‐1,3,4,5‐tetrahydro‐2H‐pyrano[2,3‐d]pyrimidine‐6‐carbonitrile (94988-89-3)

Conditions	Yield
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 90℃; for 3h;	94%
With water for 0.0666667h; microwave irradiation;	89%
In 1,4-dioxane; water Heating;	79%
With dimethyl amine In ethanol at 20℃; for 0.3h;

o-chlorobenzylidene malononitrile (2698-41-1) + 2-[1-(4-methylphenyl)ethylidene]malononitrile (3111-61-3) → 2-amino-4-(4-methylphenyl)-6-(2-chlorophenyl)-cyclohexa-2,4-diene-1,1,3-tricarbonitrile (77198-31-3)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 50℃; for 12h;	94%
With triethylamine In ethanol for 0.25h; Ambient temperature;	93%

o-chlorobenzylidene malononitrile (2698-41-1) + edaravone (89-25-8) → 2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile (82805-66-1)

Conditions	Yield
In methanol	94%

O-methylresorcine (150-19-6) + o-chlorobenzylidene malononitrile (2698-41-1) → 2-amino-4-(2-chlorophenyl)-7-methoxy-4H-chromene-3-carbonitrile (1649471-86-2)

Conditions	Yield
With triethylamine In ethanol; water at 20℃; for 2h;	94%
With piperidine In ethanol at 60℃;	93%

1H-indene-1,3(2H)-dione (606-23-5) + o-chlorobenzylidene malononitrile (2698-41-1) → 3-(2-chlorophenyl)-1′,3′-dioxo-1′,3′-dihydrospiro[cyclopropane-1,2′-indene]-2,2-dicarbonitrile

Conditions	Yield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; sodium acetate In ethanol at 20℃; for 0.0333333h; Reagent/catalyst;	94%
With dmap; iodine In acetonitrile at 40℃; for 4h;	67%

o-chlorobenzylidene malononitrile (2698-41-1) + ethyl acetoacetate (141-97-9) → ethyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate (72568-49-1)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In water at 100℃; for 8h;	93%
With piperidine In ethanol for 3h; Heating;	80%
With dimethyl amine In ethanol at 20℃; for 0.15h;

o-chlorobenzylidene malononitrile (2698-41-1) + 3-methyl-2-pyrazoline-5-one (108-26-9) → 2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile (89607-55-6)

Conditions	Yield
In methanol for 0.2h;	93%

o-chlorobenzylidene malononitrile (2698-41-1) + (2-oxo-2-phenylethyl)triphenylarsonium bromide (42350-78-7) → cis-1-benzoyl-2-(2-chlorophenyl)-3,3-dicyanocyclopropane (94360-55-1)

Conditions	Yield
With potassium fluoride In 1,2-dimethoxyethane at 20℃; for 4h;	93%
With potassium carbonate In water at 20℃; for 4h;	76%

o-chlorobenzylidene malononitrile (2698-41-1) + 3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone (36646-78-3) → 2-amino-4-(2-chlorophenyl)-7,7-dimethyl-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

Conditions	Yield
N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Heating;	93%

o-chlorobenzylidene malononitrile (2698-41-1) + 5-tert-butoxycarbonylamino-1-aminopentane (51644-96-3) → (5-isothiocyanato-pentyl)-carbamic acid tert-butyl ester (347890-46-4)

Conditions	Yield
Stage #1: o-chlorobenzylidene malononitrile; 5-tert-butoxycarbonylamino-1-aminopentane In tetrahydrofuran at 20℃; for 14h; Stage #2: With CYANAMID; triethylamine at 4℃; for 3h;	93%

o-chlorobenzylidene malononitrile (2698-41-1) + 9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one (166883-88-1) → 2-amino-4-(2-chlorophenyl)-1-(3-chloro-4-fluorophenyl)-7,7-dimethyl-1,4,5,6,7,8-hexahydro-5-oxo-quinoline-3-carbonitrile (1032467-71-2)

Conditions	Yield
at 160℃;	93%

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4) + o-chlorobenzylidene malononitrile (2698-41-1) → 2-amino-4-(2-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxopyrano[3,2-b]pyran-3-carbonitrile (665000-76-0)

Conditions	Yield
In water at 100℃; Michael Addition; Microwave irradiation; Sealed tube; Green chemistry;	93%
With triethylamine In ethanol at 80℃; for 0.0833333h;

o-chlorobenzylidene malononitrile (2698-41-1) + recorcinol (108-46-3) → 2-amino-7-hydroxy-4-(2'-chlorophenyl)-4H-chromene-3-carbonitrile (111861-29-1)

Conditions	Yield
With triethylamine In ethanol; water at 20℃; for 2h;	92%
With morpholine In acetone for 0.0833333h; Heating;	74%

o-chlorobenzylidene malononitrile (2698-41-1) + 1,2,3,4-tetrahydro-1-naphthylidene malononitrile (2510-03-4) → 3-amino-1-(2-chlorophenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In water at 50℃; for 10h;	92%

ethyl 2,3-butadienoate (14369-81-4) + o-chlorobenzylidene malononitrile (2698-41-1) → (S)-ethyl 5-(2-chlorophenyl)-4,4-dicyanocyclopent-1-enecarboxylate (1239019-72-7)

Conditions	Yield
With N-((2S,3S)-1-(diphenylphosphino)-3-methylpentan-2-yl)-3,5-bis(trifluoromethyl)benzamide In toluene at 20℃; for 1h; optical yield given as %ee; enantioselective reaction;	92%

Cyclohexyl isocyanide (931-53-3) + o-chlorobenzylidene malononitrile (2698-41-1) + methyl 4,4,4-trifluoro-2-butynoate (70577-95-6) → methyl 2-(2-chlorophenyl)-3,3-dicyano-4-(cyclohexylamino)-5-(trifluoromethyl)cyclopenta-1,4-diene carboxylate (1431657-43-0)

Conditions	Yield
In dichloromethane at 20℃; for 6h;	92%

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 109-77-3 malononitrile 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 17849-38-6 2-Chlorobenzyl alcohol 
• 70380-66-4 2-chlorobenzaldehyde dimethyl acetal 
• 118-91-2 ortho-chlorobenzoic acid 
• 98-86-2 acetophenone 

Downstream Products

• 134305-36-5 3-amino-4-cyano-5-(m-chlorophenyl)benzocoumarin 
• 72568-49-1 ethyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate 
• 144464-55-1 4-Amino-2-(2-chloro-phenyl)-2H-thiochromene-3-carbonitrile 
• 82805-66-1 2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile 
• 111861-42-8 2,7-Diamino-4-(2-chloro-phenyl)-4H-chromene-3-carbonitrile 
• 111861-47-3 3-amino-1-(2-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile 
• 127118-60-9 2,6-diamino-4-(2-chlorophenyl)-4H-thiopyran-3,5-dicarbonitrile 
• 164026-54-4 2-Amino-4-(2-chloro-phenyl)-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 181058-45-7 5-(4-Chloro-phenyl)-2-[1-(2-chloro-phenyl)-meth-(Z)-ylidene]-7-methyl-3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 187398-62-5 7-amino-2,4-dioxo-5-(2-chlorophenyl)-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine-6-carbonitrile 
• 220986-34-5 2-amino-4-(2-chlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile 

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