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Substance Name: 2-Chlorobenzalmalononitrile
RN: 2698-41-1
UNII: D8317IAV7Q
InChIKey: JJNZXLAFIPKXIG-UHFFFAOYSA-N

Note

  • A riot control agent which causes temporary irritation of the eyes and the mucosal surface of the respiratory tract. It is a more potent irritant than OMEGA-CHLOROACETOPHENONE, but less incapacitating.

Molecular Formula

  • C10-H5-Cl-N2

Molecular Weight

  • 188.617
 

Classification Codes

Classification Codes

  • Human Data
  • Mutation Data
  • Noxae
  • Reproductive Effect
  • Riot Control Agents, Chemical
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Codes

  • Ceiling (0.05 ppm); skin; Not classifiable as a human carcinogen
  • TWA 0.05 ppm (0.4 mg/m3)
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Names and Synonyms

Name of Substance

  • 2-Chlorobenzalmalononitrile
  • o-Chlorobenzylidenemalonitrile
  • o-Chlorobenzylidenemalononitrile

MeSH Heading

  • o-Chlorobenzylidenemalonitrile

Synonyms

  • ((2-Chloro-phenyl)methylene)propanenitrile
  • (o-Chlorobenzal)malononitrile
  • (o-Chlorobenzylidene)malononitrile
  • 2-09-00-00641 (Beilstein Handbook Reference)
  • 2-Chlorobenzalmalononitrile
  • 2-Chlorobenzylidene malonitrile
  • 2-Chlorobenzylidene malononitrile
  • 2-Chlorobenzylidenemalononitrile
  • 2-Chlorobmn
  • Alonitrile
  • beta,beta-Dicyano-o-chlorostyrene
  • BRN 1866635
  • CCRIS 2377
  • chlorobenzylidenemalononitrile
  • CS
  • CS (lacrimator)
  • EINECS 220-278-9
  • HSDB 4346
  • Malononitrile, (o-chlorobenzylidene)-
  • NCI-C55118
  • NSC 542
  • o-Chlorobenzylidene malonitrile
  • o-Chlorobenzylidene malononitrile
  • o-Chlorobenzylidenemalonic nitrile
  • ortho-Chlorobenzylidene malononitrile
  • Propanedinitrile, ((2-chlorophenyl)methylene)
  • TL 238
  • UNII-D8317IAV7Q
  • USAF KF-11

Systematic Names

  • ((2-Chlorophenyl)methylene)malononitrile
  • Malononitrile, o-chlorobenzylidene-
  • o-Chlorobenzalmalononitrile
  • Propanedinitrile, ((2-chlorophenyl)methylene)-
  • Propanedinitrile, 2-((2-chlorophenyl)methylene)-

Superlist Names

  • o-Chlorobenzalmalononitrile
  • o-Chlorobenzylidene malononitrile
  • Propanedinitrile, ((2-chlorophenyl)methylene)-

Registry Numbers

CAS Registry Number

  • 2698-41-1

FDA UNII

  • D8317IAV7Q

System Generated Number

  • 0002698411

Structure Descriptors

InChI

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

InChIKey

JJNZXLAFIPKXIG-UHFFFAOYSA-N

Smiles

c1(\C=C(\C#N)C#N)c(cccc1)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LCLo inhalation 2600mg/m3/23M (2600mg/m3) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Federation Proceedings, Federation of American Societies for Experimental Biology. Vol. 30(1), Pg. 86, 1971.
guinea pig LCLo inhalation 2326mg/m3/10M (2326mg/m3) BLOOD: HEMORRHAGE

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
guinea pig LD50 intraperitoneal 73mg/kg (73mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: COMA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
guinea pig LD50 oral 212mg/kg (212mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: COMA

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
human TCLo inhalation 1500ug/m3/90M (1.5mg/m3) SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: COUGH
Archives of Environmental Health. Vol. 6, Pg. 366, 1963.
mouse LCLo inhalation 2753mg/m3/20M (2753mg/m3) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BLOOD: HEMORRHAGE

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
mouse LD subcutaneous > 800mg/kg (800mg/kg)   Toxicology and Applied Pharmacology. Vol. 4, Pg. 656, 1962.
mouse LD50 intraperitoneal 32320ug/kg (32.32mg/kg) IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASE IN HUMORAL IMMUNE RESPONSE Toxicology Letters. Vol. 8, Pg. 73, 1981.
mouse LD50 intravenous 47700ug/kg (47.7mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Toxicology and Applied Pharmacology. Vol. 25, Pg. 111, 1973.
mouse LD50 oral 282mg/kg (282mg/kg)   National Technical Information Service. Vol. AD837-111,
rabbit LCLo inhalation 1802mg/m3/10M (1802mg/m3) BLOOD: HEMORRHAGE

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rabbit LD50 intraperitoneal 32065ug/kg (32.065mg/kg) BLOOD: OTHER CHANGES Toxicologist. Vol. 3, Pg. 64, 1983.
rabbit LD50 intravenous 8mg/kg (8mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 4, Pg. 656, 1962.
rabbit LD50 oral 143mg/kg (143mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat LCLo inhalation 1806mg/m3/45M (1806mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA

BLOOD: HEMORRHAGE
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat LD50 intraperitoneal 48mg/kg (48mg/kg)   Toxicology and Applied Pharmacology. Vol. 24, Pg. 45, 1973.
rat LD50 intravenous 28mg/kg (28mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
Archives of Toxicology. Vol. 40, Pg. 75, 1978.
rat LD50 oral 178mg/kg (178mg/kg) GASTROINTESTINAL: GASTRITIS Archives of Environmental Health. Vol. 24, Pg. 449, 1972.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 95.5 deg C   EXP
Boiling Point 312.5 deg C   EXP
log P (octanol-water) 2.760 (none)   EST
Water Solubility 51.9 mg/L 25 EST
Vapor Pressure 3.40E-05 mm Hg 20 EXP
Henry's Law Constant 1.02E-08 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.51E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.