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
malononitrile
o-chlorobenzylidene malononitrile
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% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.75h; Inert atmosphere; | 78% |
2-chloro-benzaldehyde
acetophenone
malononitrile
A
o-chlorobenzylidene malononitrile
B
3-(2-chlorophenyl)-1-phenylpropenone
C
2-amino-4-(2-chlorophenyl)-6-phenylbenzene-1,3-carbodinitrile
Conditions | Yield |
---|---|
With potassium carbonate at 60℃; for 0.133333h; neat (no solvent); | A n/a B n/a C 67% |
Conditions | Yield |
---|---|
at 25℃; Equilibrium constant; |
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
o-chlorobenzylidene malononitrile
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 |
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride In water at 90℃; for 5h; | 99% |
o-chlorobenzylidene malononitrile
ethyl 5,5-diphenylpenta-2,3,4-trienoate
C29H21ClN2O2
Conditions | Yield |
---|---|
With tributylphosphine In tetrahydrofuran at 60℃; for 1h; Inert atmosphere; | 99% |
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% |
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; |
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
dimedone
2-amino-4-(2-chlorophenyl)-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
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
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at 20℃; | 96% |
tert-butylisonitrile
o-chlorobenzylidene malononitrile
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
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 8h; | 96% |
o-chlorobenzylidene malononitrile
Conditions | Yield |
---|---|
With piperidine In ethanol for 1h; Reflux; | 96% |
o-chlorobenzylidene malononitrile
phosphonic acid diethyl ester
[1-(2-chlorophenyl)-2,2-dicyanoethyl] phosphonic acid diethyl ester
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% |
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
o-chlorobenzylidene malononitrile
methyl 4,4,4-trifluoro-2-butynoate
methyl 4-(tert-butylamino)-2-(2-chlorophenyl)-3,3-dicyano-5-(trifluoromethyl)cyclopenta-1,4-dienecarboxylate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 10h; | 95% |
BARBITURIC ACID
o-chlorobenzylidene malononitrile
7‐amino‐5‐(2‐chlorophenyl)‐2,4‐dioxo‐1,3,4,5‐tetrahydro‐2H‐pyrano[2,3‐d]pyrimidine‐6‐carbonitrile
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
2-[1-(4-methylphenyl)ethylidene]malononitrile
2-amino-4-(4-methylphenyl)-6-(2-chlorophenyl)-cyclohexa-2,4-diene-1,1,3-tricarbonitrile
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
edaravone
2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile
Conditions | Yield |
---|---|
In methanol | 94% |
O-methylresorcine
o-chlorobenzylidene malononitrile
2-amino-4-(2-chlorophenyl)-7-methoxy-4H-chromene-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol; water at 20℃; for 2h; | 94% |
With piperidine In ethanol at 60℃; | 93% |
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
ethyl acetoacetate
ethyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate
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
3-methyl-2-pyrazoline-5-one
2-[(2-Chloro-phenyl)-(3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)-methyl]-malononitrile
Conditions | Yield |
---|---|
In methanol for 0.2h; | 93% |
o-chlorobenzylidene malononitrile
(2-oxo-2-phenylethyl)triphenylarsonium bromide
cis-1-benzoyl-2-(2-chlorophenyl)-3,3-dicyanocyclopropane
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
3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone
Conditions | Yield |
---|---|
N-benzyl-N,N,N-triethylammonium chloride In water for 8h; Heating; | 93% |
o-chlorobenzylidene malononitrile
5-tert-butoxycarbonylamino-1-aminopentane
(5-isothiocyanato-pentyl)-carbamic acid tert-butyl ester
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
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
Conditions | Yield |
---|---|
at 160℃; | 93% |
5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
o-chlorobenzylidene malononitrile
2-amino-4-(2-chlorophenyl)-4,8-dihydro-6-(hydroxymethyl)-8-oxopyrano[3,2-b]pyran-3-carbonitrile
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
recorcinol
2-amino-7-hydroxy-4-(2'-chlorophenyl)-4H-chromene-3-carbonitrile
Conditions | Yield |
---|---|
With triethylamine In ethanol; water at 20℃; for 2h; | 92% |
With morpholine In acetone for 0.0833333h; Heating; | 74% |
o-chlorobenzylidene malononitrile
1,2,3,4-tetrahydro-1-naphthylidene malononitrile
Conditions | Yield |
---|---|
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In water at 50℃; for 10h; | 92% |
ethyl 2,3-butadienoate
o-chlorobenzylidene malononitrile
(S)-ethyl 5-(2-chlorophenyl)-4,4-dicyanocyclopent-1-enecarboxylate
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
o-chlorobenzylidene malononitrile
methyl 4,4,4-trifluoro-2-butynoate
methyl 2-(2-chlorophenyl)-3,3-dicyano-4-(cyclohexylamino)-5-(trifluoromethyl)cyclopenta-1,4-diene carboxylate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 6h; | 92% |
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):
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.
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 |
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.
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: Xi,T
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
OSHA PEL: CL 0.05 ppm (skin)
ACGIH TLV: CL 0.05 ppm (skin); Not Classifiable as a Human Carcinogen
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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