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2698-41-1

Basic Information
CAS No.: 2698-41-1
Name: [(2-Chlorophenyl)methylene]malononitrile
Article Data: 115
Molecular Structure:
Molecular Structure of 2698-41-1 ([(2-Chlorophenyl)methylene]malononitrile)
Formula: C10H5ClN2
Molecular Weight: 188.616
Synonyms: Malononitrile,(o-chlorobenzylidene)- (6CI,7CI,8CI);Propanedinitrile,[(2-chlorophenyl)methylene]- (9CI);(o-Chlorobenzal)malononitrile;(o-Chlorobenzylidene)malononitrile;1-Chloro-2-(2,2-dicyanoethenyl)benzene;2-(o-Chlorophenyl)-1,1-dicyanoethylene;2-Chlorobenzalmalononitrile;2-Chlorobenzylidenemalonodinitrile;2-Chlorobenzylidenemalononitrile;2-[(2-Chlorophenyl)methylene]malononitrile;CS;CS (lacrimator);CS(lacrimitor);NSC 542;NSC 637336;o-Chlorobenzylidenemalonic nitrile;b,b-Dicyano-o-chlorostyrene;
EINECS: 220-278-9
Density: 1.296 g/cm3
Melting Point: 68-70 °C(lit.)
Boiling Point: 312.5 °C at 760 mmHg
Flash Point: 148 °C
Solubility: 0.1-0.5 g/100 mL at 16 °C in water
Appearance: white crystalline solid with a peppery smell
Hazard Symbols: IrritantXi, ToxicT
Risk Codes: 36/37/38-42/43-25
Safety: 26-27-37/39-45-36/37/39
Transport Information: UN 3448 6.1/PG 2
PSA: 47.58000
LogP: 2.77056
Synthetic route
89-98-5

2-chloro-benzaldehyde

109-77-3

malononitrile

2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
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%
70380-66-4

2-chlorobenzaldehyde dimethyl acetal

109-77-3

malononitrile

2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
With Ni-Pd nanoparticles supported on poly (styrenesulfonic acid-n-vinylimidazole)/KIT-6 In water at 45℃; for 0.5h; Knoevenagel Condensation;92%
109-77-3

malononitrile

89-97-4

2-CHLOROBENZYLAMINE

2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.75h; Inert atmosphere;78%
89-98-5

2-chloro-benzaldehyde

98-86-2

acetophenone

109-77-3

malononitrile

A

2698-41-1

o-chlorobenzylidene malononitrile

B

3300-67-2

3-(2-chlorophenyl)-1-phenylpropenone

C

77198-47-1

2-amino-4-(2-chlorophenyl)-6-phenylbenzene-1,3-carbodinitrile

Conditions
ConditionsYield
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

A

109-79-5

1-butanethiol

B

2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
at 25℃; Equilibrium constant;
118-91-2

ortho-chlorobenzoic acid

2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
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
17849-38-6

2-Chlorobenzyl alcohol

2698-41-1

o-chlorobenzylidene malononitrile

Conditions
ConditionsYield
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
2698-41-1

o-chlorobenzylidene malononitrile

56-06-4

2,6-diaminopyrimidin-4-ol

2,7-diamino-3,4-dihydro-4-oxo-5-(2-chlorophenyl)pyrido[2,3-d]pyrimidine-6-carbonitrile

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 5h;99%
2698-41-1

o-chlorobenzylidene malononitrile

1119249-36-3

ethyl 5,5-diphenylpenta-2,3,4-trienoate

1119249-65-8

C29H21ClN2O2

Conditions
ConditionsYield
With tributylphosphine In tetrahydrofuran at 60℃; for 1h; Inert atmosphere;99%
122-88-3

4-Chlorophenoxyacetic acid

2698-41-1

o-chlorobenzylidene malononitrile

2-(2-(4-chlorophenoxy)-1-(2-chlorophenyl)ethyl)malononitrile

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

IUPAC Name: 2-[(2-Chlorophenyl)methylidene]propanedinitrile
Molecular Formula: C10H5ClN2
Molecular Weight: 188.61 g/mol
EINECS: 220-278-9
Density: 1.296 g/cm3
Flash Point: 148 °C
Melting point: 95 °C
Index of Refraction: 1.623
Surface Tension: 56.4 dyne/cm
Enthalpy of Vaporization: 55.35 kJ/mol
Boiling Point: 310-315 °C at 760 mmHg
Vapour Pressure: 0.000527 mmHg at 25 °C
Water Solubility:  0.1-0.5 g/100 mL at 16 °C 
Appearance: White crystalline solid or light beige powder
Following is the structure of O-Chlorobenzylidene malononitrile (CAS NO.2698-41-1):
      

Uses

 O-Chlorobenzylidene malononitrile (CAS NO.2698-41-1) malononitrile can be used as riot control agent. It is used primarily as an incapacitating agent, both by military & law enforcement personnel. It can be disseminated in burning grenades & weapon-fired projectiles, as an aerosol from the finely divided solid chemical, or from a solution of the chemical dissolved in methylene chloride or acetone.

Toxicity Data With Reference

1.    

skn-hmn 10 mg/1H MLD

    BJDEAZ    British Journal of Dermatology. 90 (1974),657.
2.    

eye-man 5 mg/m3/20S SEV

    MMEDA9    Military Medicine. 134 (1969),219.
3.    

eye-man 624 ng

    APTOA6    Acta Pharmacologica et Toxicologica. 35 (1974),412.
4.    

skn-rat 12%/6H open MLD

    ARTODN    Archives of Toxicology. 40 (1978),75.
5.    

skn-rbt 12%/6H open MLD

    ARTODN    Archives of Toxicology. 40 (1978),75.
6.    

eye-rbt 5 mg

    TXAPA9    Toxicology and Applied Pharmacology. 4 (1962),656.
7.    

eye-rbt 1 mg MLD

    TXAPA9    Toxicology and Applied Pharmacology. 17 (1970),295.
8.    

eye-rbt 1150 ng

    APTOA6    Acta Pharmacologica et Toxicologica. 35 (1974),412.
9.    

skn-gpg 12%/6H open MLD

    ARTODN    Archives of Toxicology. 40 (1978),75.
10.    

eye-gpg 429 ng

    APTOA6    Acta Pharmacologica et Toxicologica. 35 (1974),412.
11.    

mmo-sat 100 µg/plate

    ARTO

Consensus Reports

 O-Chlorobenzylidene malononitrile (CAS NO.2698-41-1) was reported in EPA TSCA Inventory. Cyanide and its compounds are on the Community Right-To-Know List.

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.
Hazard Codes:  IrritantXi,ToxicT
Risk Statements: 36/37/38-42/43-25 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42/43:May cause sensitization by inhalation and skin contact. 
R25 :Toxic if swallowed.
Safety Statements: 26-27-37/39-45-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S27:Take off immediately all contaminated clothing. 
S37/39:Wear suitable gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 3448 6.1/PG 2
RTECS:  OO3675000
WGK Germany: 3
HazardClass: 6.1(a)
PackingGroup: I 

Standards and Recommendations

OSHA PEL: CL 0.05 ppm (skin)
ACGIH TLV: CL 0.05 ppm (skin); Not Classifiable as a Human Carcinogen

Specification

 O-Chlorobenzylidene malononitrile , with a CAS name of 2698-41-1, it has some synonyms like 2-[(2-chlorophenyl)methylene]malononitrile or ((2-Chlorophenyl)methylene)propanedinitrile.
 O-Chlorobenzylidene malononitrile (CAS NO.2698-41-1) is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should immediately flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water.Then, get medical aid. Or in the eyes: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously get medical aid. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. Immediately While, it's inhaled: Immediately leave the contaminated area; take deep breaths of fresh air.Then, get medical aid. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used. Then you have the ingesting of the product :  If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical. Get medical aid immediately. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. Do not induce vomiting. Transport the victim immediately to a hospital.