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1-Propene, 1,2-dichloro-

HCID 11243
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Basic information

CAS
563-54-2
Standard SMILES
CC(Cl)=CCl
InChIKey
PPKPKFIWDXDAGC-UHFFFAOYSA-N
Molecular formula
C3H4Cl2
Average molar mass
110.97 g/mol
Monoisotopic mass
109.96900549

Overview

1,2-Dichloropropene is a form of dichloropropene (L893).

Names & identifiers

Preferred name
1-Propene, 1,2-dichloro-
IUPAC
1,2-dichloroprop-1-ene
English name
1,2-Dichloropropene
Molecular formula
C3H4Cl2
Molecular weight
110.97

Names & synonyms

563-54-21-Propene, 1,2-dichloro-RefChem:10569981,2-dichloroprop-1-ene1,2-DICHLOROPROPENE1,2-Dichloropropylene1,2-Dichloro-1-propene1,2-dichloro-prop-1-eneSCHEMBL258346SCHEMBL269180SCHEMBL647388DTXSID2060337
Show more names
Dichlor1,2-dichloro-propenallylene dichloride1,2-dichloro-1-propenDichlorpropen-gemisch1,2-DichloropropylenePropene, 1,2-dichloro-1-propene,1,2-dichloro
NS00124449

Database identifiers

CAS
563-54-2
PubChem CID
11243
DTXSID
DTXSID2060337

Properties

Computed structural properties

XLogP
2.1
Topological polar surface area
0 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
0
Rotatable bonds
0
Heavy atoms
5
Formal charge
0
Complexity
46.9

Experimental & physicochemical properties

SolventsSolvents -> Chlorinated Aliphatics
SpringerMaterials PropertiesBoiling point
Density1.1818 @ 20°C
Color/FormLiquid
SolubilityIn water, 2,700 mg/l @ 25 °C.
Boiling Point · 2 items

75 °C

75 °C @760 [mm Hg]

DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/.
Vapor Density3.83 (air= 1)
Vapor Pressure · 3 items

90.8 [mmHg]

90.8 mm Hg @ 20 °C

90.8 [mm Hg] @20 °C

Physical DescriptionLiquid; [HSDB]
Other Experimental Properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Regulatory Information · 3 items

Chemical: 1-Propene, 1,2-dichloro-

Hazard Traits - Environmental tox

Hazard Traits - Environmental tox

Hazards Summary · 1 item

A skin, eye, and respiratory mucosa irritant; Inhalation of high concentrations can cause CNS depression and lacrimation; May cause kidney and liver injury; [HSDB] There is little information available about the isomers other than 1,3-Dichloropropene. [Reference #1] See 1,3-Dichloropropene. See Dichloropropene, all isomers.

Special ReportsDangerous Prop Ind Mater Rep 6 (4): 63-70 (1986). Reviews dichloropropene safety, toxicology and health hazards.
TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1-Propene, 1,2-dichloro- is included on this list.

DOT Emergency Guidelines · 5 items

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. /Dichloropropenes/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Dichloropropenes/

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 2 items

Metabolism of 1,2-D in the rat results in the formation of a mercapturic acid conjugate excreted largely in the urine. Proposed reactive intermediates include 1,2-epoxypropane; this intermediate is suspected of being responsible for mutagenic effects of 1,2-D. Glutathione pathways are seen as a detoxification mechanisms, & liver & kidney toxicity at high concns may be due to saturation of these pathways.

Metabolism of 1,2-D in the rat results in the formation of a mercapturic acid conjugate excreted largely in the urine. Proposed reactive intermediates include 1,2-epoxypropane; this intermediate is suspected of being responsible for mutagenic effects of 1,2-D. Glutathione pathways are seen as a detoxification mechanisms, & liver & kidney toxicity at high concns may be due to saturation of these pathways.

Uses & manufacturing

Uses · 4 items

Used in a mixture as a soil fumigant for control of nematodes affecting roots of plants; [HSDB] 1,3-Dichloropropene is used as a pesticide; 2,3-Dichloropropene is used to make other chemicals; No uses were found for the other isomers (1,1-, 1,2-, and 3,3-); [Reference #1]

Farming (Pesticides) [Category: Industry]

USED IN ... DICHLOROPROPANE-DICHLOROPROPENE MIXTURE AS A SOIL FUMIGANT FOR CONTROL OF NEMATODES AFFECTING ROOTS OF PLANTS

Breathing in contaminated air; drinking contaminated water; eating contaminated food; dermal and eye exposure (L893).

Formulations/Preparations · 2 items

Telone II contains approximately 89% cis- and trans-1,3-dichloropropene, 2.5% 1,2-dichloropropene, 1.5% of a trichloropropene isomer, and 1.0% epichlorhydrin. /Telone/

DICHLOR

General Manufacturing InformationProduction ... of DD mixture has been discontinued by the Dow Chemical Co.

Upstream & downstream products

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Related reactions

2 records
New reaction record
HRID 979539 reaction equation
HRID 979539As reactantuspto-grants-1987_05
HRID 1761787 reaction equation
HRID 1761787As reactantuspto-grants-1989_05

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
· 2 items

BP: 77 °C; density: 1.1818 @ 20 °C/4 °C; index of refraction: 1.4471 @ 20 °C/D; insoluble in water; very soluble in ethanol, carbon tetrachloride, and methanol. /trans-1,2-Dichloropropene/

BP: 93 °C; index of refraction: 1.4549 @ 20deg C/D; insoluble in water; soluble in acetone, benzene, and chloroform. /cis-1,2-Dichloropropene/

Physicochemical properties

Boiling point
88.32 °C · 88.32°C (rough estimate)
Density
1.1748 · 1.1748 (estimate)
refractive index
1.448 · 1.4480
Henry's Law Constant
2 · 2.0×10-3 mol/(m3Pa) at 25℃, HSDB (2015)
CAS DataBase Reference
563 · 563-54-2
EWG's Food Scores
1 · 1
FDA UNII
5 LKV1J95 · ET5LKV1J95
EPA Substance Registry System
1 · 1,2-Dichloropropene (563-54-2)
Hazardous Substances Data
563 · 563-54-2(Hazardous Substances Data)

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Dichloropropenes/

/GUIDE 129: FLAMMABLE LIQUIDS (POLAR/WATER-MISCIBLE/NOXIOUS)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Dichloropropenes/

For more DOT Emergency Guidelines (Complete) data for 1,2-DICHLOROPROPENE (8 total), please visit the HSDB record page.

Toxic Combustion ProductsWhen heated to decomposition it emits toxic fumes of /hydrogen chloride/.
Shipment Methods and Regulations · 3 items

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 2 items

UN 2047; Dichloropropenes

IMO 3.3; Dichloropropenes

Skin, Eye, and Respiratory Irritations · 1 item

IRRITATION OF EYES & UPPER RESP MUCOSA APPEARS PROMPTLY AFTER EXPOSURE TO CONCN VAPORS. LACRIMATION IS PROMINENT. ... SEVERE SKIN IRRITATION WITH MARKED INFLAMMATORY RESPONSE OF EPIDERMIS & UNDERLYING TISSUES /FROM DERMAL EXPOSURES/. /DICHLOROPROPENES/

Safety & protection

Disposal Methods · 4 items

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

The following wastewater treatment technology has been investigated for 1,2-dichloropropylene: Concentration process: Stripping.

The following wastewater treatment technology has been investigated for 1,2-dichloropropylene: Concentration process: Solvent extraction.

The following wastewater treatment technology has been investigated for 1,2-dichloropropylene: Concentration process: Activated carbon.

Preventive Measures · 2 items

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

Protective Action Criteria (PAC) · 3 items

10 [mg/m3]

66 [mg/m3]

400 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

Chemical Protective Clothing Material Vendor Ratings: "Fair" or "poor" ratings were given by less than three vendors. "Good" and "fair" ratings, with "fair" predominating, were given by several vendors for butyl, natural rubber, neoprene and nitrile materials used in occupational exposure to dichloropropenes.

Toxicology

Body BurdenDichloropropene was detected in one of 8 samples of mother's milk from 4 urban areas in the US but the isomer was not specified(1) /Dichloropropene/.
Treatment · 1 item

Following oral exposure, administer charcoal as a slurry. Monitor liver and kidney function; elevations may not be seen for several days. Following eye exposure, irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If irritation, pain, swelling, lacrimation, or photophobia persist, the patient should be seen in a health care facility. Following dermal exposure, remove contaminated clothing and wash exposed area thoroughly with soap and water. Following inhalation, move patient to fresh air, even though initial symptoms and signs are mild; keep the victim quiet, in a semi-reclining position. Minimum physical activity limits the likehood of pulmonary edema. If victim is not breathing, clear the airway of secretions and resuscitate with positive pressure oxygen apparatus. If this is not available, use chest compression to sustain respiration. (T36, A568)

Health Effects · 1 item

Ingestion of 1,2-D can lead to developed gastrointestinal distress, adult respiratory distress syndrome, hematological and hepatorenal functional impairment, acute gastrointestinal distress with pulmonary congestion and edema, central nervous depression, perhaps even in the absence of impaired oxygen uptake. Moreover, this can lead to death. Coma may occur rapidly after inhalation. Severe skin irritation with marked inflammatory response of epidermis can underlying tissues can follow dermal exposure. By any route, possible late injuries to liver, kidneys and heart (T48).

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 57(SRC), determined from a water solubility of 2,700 mg/l(2) and a regression-derived equation(3), indicates that 1,2-dichloropropene is expected to have high mobility in soil(SRC). Volatilization of 1,2-dichloropropene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant estimated as 4.9X10-3 atm-cu m/mole(SRC) derived from a vapor pressure of 90.8 mm Hg(4), and its water solubility(2). The potential for volatilization of 1,2-dichloropropene from dry soil surfaces may exist(SRC) based upon its vapor pressure(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 57(SRC), determined from a water solubility of 2,700(2) and a regression-derived equation(3), indicates that 1,2-dichloropropene is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.9X10-3 atm-cu m/mole(SRC), derived from its vapor pressure, 90.8 mm Hg(4), and water solubility(2). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hrs and 4 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 7(SRC), from its water solubility(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,2-dichloropropene, which has a vapor pressure of 90.8 mm Hg at 20 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,2-dichloropropene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 days(SRC), calculated from its rate constant of 3.9X10-12 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesInhalation (L893) ; oral (L893) ; dermal (L893) ; eye contact (L893).
Milk ConcentrationsDichloropropene was detected in one of 8 samples of mother's milk from 4 urban areas in the US but the isomer was not specified(1) /Dichloropropene/.
Toxicity Summary · 1 item

Metabolism of 1,2-D in the rat results in the formation of a mercapturic acid conjugate excreted largely in the urine. Proposed reactive intermediates include 1,2-epoxypropane; this intermediate is suspected of being responsible for mutagenic effects of 1,2-D. Glutathione pathways are seen as a detoxification mechanisms, & liver & kidney toxicity at high concns may be due to saturation of these pathways (A568).

Signs and Symptoms · 1 item

Symptoms occuring after inhalation include gasping, refusal to breathe, coughing, substernal pain; lacrimation and headache are prominant. After inhalation exposures, malaise, headache, chest and abdominal discomfort and irritability can persist during weeks or years. Moreover, Irritation of eyes and upper respiratory mucosa appears promptly after exposure to concentrated vapors. Ingestion can cause cough, sore throat, headache, dizziness, nausea, vomiting, unconsciousness, and laboured breathing (T48, L893).

Soil Adsorption/Mobility · 1 item

The Koc of 1,2-dichloropropene is estimated as 57(SRC), using a water solubility of 2,700 mg/l(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,2-dichloropropene is expected to have high mobility in soil.

Atmospheric ConcentrationsRURAL: Grand Canyon, AZ (7 samples) not detected, detection limit not given(1). SOURCE AREAS: US (16 samples) 7.3 parts per trillion median, 570 parts per trillion maximum for all dichloropropene isomers(1).
Human Toxicity Excerpts · 3 items

Symptomatology: 1A) Inhalation, high vapor concn: gasping, refusal to breathe, coughing, substernal pain, & extreme respiratory distress at vapor concn over 1500 ppm. Irritation of eyes & upper respiratory mucosa appears promptly after exposure to concentrated vapors. Lacrimation & headache are prominent. Coma may occur rapidly. B) Inhalation, low vapor concn: central nervous depression & moderate irritation of respiratory system. Headache is frequent. 2) Dermal: severe skin irritation with marked inflammatory response of epidermis & underlying tissues. 3) Oral: acute gastrointestinal distress with pulmonary congestion & edema. Central nervous depression, perhaps even in the absence of impaired oxygen uptake. 4) By any route, possible late injuries to liver, kidneys & heart. 5) After inhalation exposures, malaise, headache, chest & abdominal discomfort & irritability have been reported to persist for several weeks & perhaps for several years.

Intense irritation of eyes, skin, & resp mucosa. /Dichloropropene/

Exposures to 1,2-D results in injury to the liver & kidneys.

Regulatory information

TSCA Requirements · 1 item

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1-Propene, 1,2-dichloro- is included on this list.

Safety data

Hazardous Substances Data
563-54-2(Hazardous Substances Data)
DIALLATEAllyl chloride2,3-Dichloropropene