Product Name

  • Name

    [(2-Chlorophenyl)methylene]malononitrile

  • EINECS 220-278-9
  • CAS No. 2698-41-1
  • Article Data115
  • CAS DataBase
  • Density 1.296 g/cm3
  • Solubility 0.1-0.5 g/100 mL at 16 °C in water
  • Melting Point 68-70 °C(lit.)
  • Formula C10H5ClN2
  • Boiling Point 312.5 °C at 760 mmHg
  • Molecular Weight 188.616
  • Flash Point 148 °C
  • Transport Information UN 3448 6.1/PG 2
  • Appearance white crystalline solid with a peppery smell
  • Safety 26-27-37/39-45-36/37/39
  • Risk Codes 36/37/38-42/43-25
  • Molecular Structure Molecular Structure of 2698-41-1 ([(2-Chlorophenyl)methylene]malononitrile)
  • Hazard Symbols IrritantXi, ToxicT
  • 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;
  • PSA 47.58000
  • LogP 2.77056

Synthetic route

2-chloro-benzaldehyde
89-98-5

2-chloro-benzaldehyde

malononitrile
109-77-3

malononitrile

o-chlorobenzylidene 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%
2-chlorobenzaldehyde dimethyl acetal
70380-66-4

2-chlorobenzaldehyde dimethyl acetal

malononitrile
109-77-3

malononitrile

o-chlorobenzylidene 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%
malononitrile
109-77-3

malononitrile

2-CHLOROBENZYLAMINE
89-97-4

2-CHLOROBENZYLAMINE

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

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

2-chloro-benzaldehyde

acetophenone
98-86-2

acetophenone

malononitrile
109-77-3

malononitrile

A

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

B

3-(2-chlorophenyl)-1-phenylpropenone
3300-67-2

3-(2-chlorophenyl)-1-phenylpropenone

C

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

2-[Butylsulfanyl-(2-chloro-phenyl)-methyl]-malononitrile

A

1-butanethiol
109-79-5

1-butanethiol

B

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

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

ortho-chlorobenzoic acid

o-chlorobenzylidene malononitrile
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
2-Chlorobenzyl alcohol
17849-38-6

2-Chlorobenzyl alcohol

o-chlorobenzylidene malononitrile
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
o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

2,6-diaminopyrimidin-4-ol
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

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%
o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

ethyl 5,5-diphenylpenta-2,3,4-trienoate
1119249-36-3

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

C29H21ClN2O2
1119249-65-8

C29H21ClN2O2

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

4-Chlorophenoxyacetic acid

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

2-(2-(4-chlorophenoxy)-1-(2-chlorophenyl)ethyl)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%
4-hydroxy-6-methyl-2-pyron
675-10-5

4-hydroxy-6-methyl-2-pyron

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

2-amino-4-(2-chlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile

2-amino-4-(2-chlorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

3-(2-chlorophenyl)oxirane-2,2-dicarbonitrile
3513-08-4

3-(2-chlorophenyl)oxirane-2,2-dicarbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

dimedone
126-81-8

dimedone

2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
129354-35-4

2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

1-{[(1R,2S,5R)-5-Methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexylcarbamoyl]-methyl}-pyridinium; chloride

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

3-(2-Chloro-phenyl)-2,2-dicyano-cyclopropanecarboxylic acid [(1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl]-amide

Conditions
ConditionsYield
With triethylamine In acetonitrile at 20℃;96%
tert-butylisonitrile
119072-55-8, 7188-38-7

tert-butylisonitrile

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

methyl 4,4,5,5,5-pentafluoropent-2-ynoate
104721-32-6

methyl 4,4,5,5,5-pentafluoropent-2-ynoate

methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(pentafluoroethyl)cyclopenta-1,4-dienecarboxylate
1431657-47-4

methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(pentafluoroethyl)cyclopenta-1,4-dienecarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 8h;96%
o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

4-((2,4-dihydroxyphenyl)diazenyl)-N-(3-methylisoxazol-5-yl)benzenesulfonamide

4-((2,4-dihydroxyphenyl)diazenyl)-N-(3-methylisoxazol-5-yl)benzenesulfonamide

C26H19ClN6O5S

C26H19ClN6O5S

Conditions
ConditionsYield
With piperidine In ethanol for 1h; Reflux;96%
o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

[1-(2-chlorophenyl)-2,2-dicyanoethyl] phosphonic acid diethyl ester
142012-38-2

[1-(2-chlorophenyl)-2,2-dicyanoethyl] phosphonic acid diethyl ester

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

Br(1-)*C22H36NO2(1+)

Br(1-)*C22H36NO2(1+)

A

C17H17ClN2O2

C17H17ClN2O2

C16H25N

C16H25N

Conditions
ConditionsYield
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

tert-butylisonitrile

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

methyl 4,4,4-trifluoro-2-butynoate
70577-95-6

methyl 4,4,4-trifluoro-2-butynoate

methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(trifluoromethyl)cyclopenta-1,4-dienecarboxylate
1431657-37-2

methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(trifluoromethyl)cyclopenta-1,4-dienecarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 10h;95%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

7‐amino‐5‐(2‐chlorophenyl)‐2,4‐dioxo‐1,3,4,5‐tetrahydro‐2H‐pyrano[2,3‐d]pyrimidine‐6‐carbonitrile
94988-89-3

7‐amino‐5‐(2‐chlorophenyl)‐2,4‐dioxo‐1,3,4,5‐tetrahydro‐2H‐pyrano[2,3‐d]pyrimidine‐6‐carbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

2-[1-(4-methylphenyl)ethylidene]malononitrile
3111-61-3

2-[1-(4-methylphenyl)ethylidene]malononitrile

2-amino-4-(4-methylphenyl)-6-(2-chlorophenyl)-cyclohexa-2,4-diene-1,1,3-tricarbonitrile
77198-31-3

2-amino-4-(4-methylphenyl)-6-(2-chlorophenyl)-cyclohexa-2,4-diene-1,1,3-tricarbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

edaravone
89-25-8

edaravone

2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile
82805-66-1

2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile

Conditions
ConditionsYield
In methanol94%
O-methylresorcine
150-19-6

O-methylresorcine

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

2-amino-4-(2-chlorophenyl)-7-methoxy-4H-chromene-3-carbonitrile
1649471-86-2

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

Conditions
ConditionsYield
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

1H-indene-1,3(2H)-dione

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

3-(2-chlorophenyl)-1′,3′-dioxo-1′,3′-dihydrospiro[cyclopropane-1,2′-indene]-2,2-dicarbonitrile

3-(2-chlorophenyl)-1′,3′-dioxo-1′,3′-dihydrospiro[cyclopropane-1,2′-indene]-2,2-dicarbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

ethyl acetoacetate
141-97-9

ethyl acetoacetate

ethyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate
72568-49-1

ethyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

3-methyl-2-pyrazoline-5-one
108-26-9

3-methyl-2-pyrazoline-5-one

2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile
89607-55-6

2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile

Conditions
ConditionsYield
In methanol for 0.2h;93%
o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

(2-oxo-2-phenylethyl)triphenylarsonium bromide
42350-78-7

(2-oxo-2-phenylethyl)triphenylarsonium bromide

cis-1-benzoyl-2-(2-chlorophenyl)-3,3-dicyanocyclopropane
94360-55-1

cis-1-benzoyl-2-(2-chlorophenyl)-3,3-dicyanocyclopropane

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone
36646-78-3

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

2-amino-4-(2-chlorophenyl)-7,7-dimethyl-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

2-amino-4-(2-chlorophenyl)-7,7-dimethyl-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

Conditions
ConditionsYield
N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Heating;93%
o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

5-tert-butoxycarbonylamino-1-aminopentane
51644-96-3

5-tert-butoxycarbonylamino-1-aminopentane

(5-isothiocyanato-pentyl)-carbamic acid tert-butyl ester
347890-46-4

(5-isothiocyanato-pentyl)-carbamic acid tert-butyl ester

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
166883-88-1

9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one

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

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

Conditions
ConditionsYield
at 160℃;93%
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
501-30-4

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

2-amino-4-(2-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxopyrano[3,2-b]pyran-3-carbonitrile
665000-76-0

2-amino-4-(2-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxopyrano[3,2-b]pyran-3-carbonitrile

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

recorcinol
108-46-3

recorcinol

2-amino-7-hydroxy-4-(2'-chlorophenyl)-4H-chromene-3-carbonitrile
111861-29-1

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

Conditions
ConditionsYield
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

o-chlorobenzylidene malononitrile

1,2,3,4-tetrahydro-1-naphthylidene malononitrile
2510-03-4

1,2,3,4-tetrahydro-1-naphthylidene malononitrile

3-amino-1-(2-chlorophenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

3-amino-1-(2-chlorophenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

Conditions
ConditionsYield
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In water at 50℃; for 10h;92%
ethyl 2,3-butadienoate
14369-81-4

ethyl 2,3-butadienoate

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

(S)-ethyl 5-(2-chlorophenyl)-4,4-dicyanocyclopent-1-enecarboxylate
1239019-72-7

(S)-ethyl 5-(2-chlorophenyl)-4,4-dicyanocyclopent-1-enecarboxylate

Conditions
ConditionsYield
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

Cyclohexyl isocyanide

o-chlorobenzylidene malononitrile
2698-41-1

o-chlorobenzylidene malononitrile

methyl 4,4,4-trifluoro-2-butynoate
70577-95-6

methyl 4,4,4-trifluoro-2-butynoate

methyl 2-(2-chlorophenyl)-3,3-dicyano-4-(cyclohexylamino)-5-(trifluoromethyl)cyclopenta-1,4-diene carboxylate
1431657-43-0

methyl 2-(2-chlorophenyl)-3,3-dicyano-4-(cyclohexylamino)-5-(trifluoromethyl)cyclopenta-1,4-diene carboxylate

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

[(2-Chlorophenyl)methylene]malononitrile Chemical Properties

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):
      

[(2-Chlorophenyl)methylene]malononitrile 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.

[(2-Chlorophenyl)methylene]malononitrile 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

[(2-Chlorophenyl)methylene]malononitrile 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.

[(2-Chlorophenyl)methylene]malononitrile 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 

[(2-Chlorophenyl)methylene]malononitrile Standards and Recommendations

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

[(2-Chlorophenyl)methylene]malononitrile 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.

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