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1-Chlor-2-methylpropen

1-Propene, 1-chloro-2-methyl-

HCID 10555
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
513-37-1
Standard-SMILES
CC(C)=CCl
InChIKey
KWISWUFGPUHDRY-UHFFFAOYSA-N
Summenformel
C4H7Cl
Durchschnittliche Molmasse
90,55 g/mol
Monoisotopische Masse
90,0236279

Überblick

Dimethylvinylchloride can cause cancer according to an independent committee of scientific and health experts.

Namen und Bezeichner

Bevorzugter Name
1-Propene, 1-chloro-2-methyl-
IUPAC
1-chloro-2-methylprop-1-ene
Lokaler Name
1-Chlor-2-methylpropen
Englischer Name
1-Chloro-2-methyl-1-propene
Summenformel
C4H7Cl
Molmasse
90.55

Namen und Synonyme

1-Chloro-2-methylpropene513-37-11-CHLORO-2-METHYL-1-PROPENEIsocrotyl chlorideDimethylvinyl chloridealpha-Chloroisobutylene1-ChloroisobutyleneDimethylvinylchloride1-Propene, 1-chloro-2-methyl-2-Methyl-1-propenyl chloridePropene, 1-chloro-2-methyl-2-Methyl-1-chloropropene
Weitere Namen anzeigen
1-CHLOROISOBUTENEChloromethylpropeneIbufenac Impurity 91-chloro-2-methyl-propen
NCI-C54819DMVCbeta,beta-Dimethylvinyl chlorideJP8N4M44OPRefChem:75363208-158-41-chloro-2-methylprop-1-ene2,2-Dimethylvinyl chloride

Datenbank-Bezeichner

CAS
513-37-1
PubChem CID
10555
DTXSID
DTXSID5020520
ChEMBL
CHEMBL160508
ChEBI
CHEBI:82300

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2,3
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
5
Formalladung
0
Komplexität
41,6

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Other Classes -> Halogenated Aliphatics, Unsaturated

Carcinogens

SpringerMaterials PropertiesSchoenflies notation
Density · 2 Einträge

0.9186 at 68 °F (NTP, 1992) - Less dense than water; will float

0.9186 g/cu cm at 20 °C

Color/Form · 2 Einträge

Clear, colorless to brown liquid at room temperature

Liquid

Solubility · 3 Einträge

1 to 5 mg/mL at 68 °F (NTP, 1992)

Soluble in chloroform

In water, 1000 mg/L at 25 °C

Flash Point · 2 Einträge

30 °F (NTP, 1992)

-1 °C

Boiling Point · 2 Einträge

154 °F at 760 mmHg (NTP, 1992)

68 °C

Decomposition · 2 Einträge

When heated to decomposition /temperature unspecified/ , dimethylvinyl chloride emits highly toxic fumes of hydrochloric acid and other chlorinated compounds.

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P318, P319, P320, P321, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H350: May cause cancer [Danger Carcinogenicity]

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: 1-Propene, 1-chloro-2-methyl-

Hazard Traits - Carcinogenicity

Commission Regulation No 844/2012

1-Propene, 1-chloro-2-methyl-: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - CMR chemicals not registered under REACH: Human health tier II assessment
DOT LabelFlammable Liquid
Fire HazardsThis chemical is flammable. (NTP, 1992)
Health Hazards · 1 Eintrag

SYMPTOMS: Symptoms of exposure to this compound may include local irritation of the eyes, mucous membranes and upper respiratory tract. It may also cause skin irritation. It may cause a burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea and vomiting. Other symptoms include liver and kidney damage and central nervous system effects. It also has anesthetic properties.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 3 Einträge

... The main urinary metabolite of 1-chloro-2-methylpropene was trans-2-amino-6-methyl-4-thia-5- heptene-1,7-dioic acid, indicating oxidation before glutathione conjugation. This metabolite constituted 23% of the total urinary radiolabel, and its corresponding N-acetyl derivative accounted for 9%. The profile of the urinary metabolites was quantitatively and qualitatively similar after one, two and four treatments.

... As in rats, trans-2-amino-6-methyl-4-thia-5-heptene-1,7-dioic acid was the major urinary metabolite /in mice, constituting 35% of the total urinary radiolabel. Its N-acetyl derivative accounted for 12%.

Recent metabolism and disposition studies of 1-chloro-2-methylpropene (dimethylvinyl chloride) revealed cysteine and N-acetylcysteine conjugates of 3-chloro-2-methylpropenoic acid as the major metabolites. In the present studies /the authors/ have investigated various steps in the metabolic pathway to determine which step was responsible for the observed trans (E)-stereochemistry of these metabolites. In vitro incubation studies of dimethylvinyl chloride with rat liver microsomes indicated cytochrome P-450-catalyzed aliphatic hydroxylation to be only stereoselective. Both (E)- and (Z)-3-chloro-2-methylpropenols formed in an identical ratio of 2:1 in incubations with microsomes from untreated male and female rats and phenobarbital-treated male rats. No alcohol formation was observed in incubations using microsomes from beta-naphthoflavone-treated male rats. Investigation of the subsequent conjugation reactions of sulfur nucleophiles with haloenoic carbonyl compounds showed that both (E)- and (Z)-3-chloro-2-methylpropenals reacted rapidly with N-acetylcysteine, the E-adduct being the sole product in either case. In contrast, the Michael reaction of the corresponding acids with N-acetylcysteine was very sluggish. Also, whereas the E-acid yielded exclusively the corresponding E-adduct, the Z-isomer afforded both Z- and E-conjugates in the ratio of 3:4. Glutathione S-transferases had poor activity towards conjugation of glutathione with these acids. Formation of only an E-glutathione conjugate could be observed from either the E- or Z-acid in these enzymatic reactions. Direct Michael reaction of glutathione with (E)-3-bromo-2-methylpropenoic acid, used in chemical synthesis of the conjugates, yielded both the E- and Z-adducts in the ratio of 95:5.

Absorption, Distribution and Excretion · 3 Einträge

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
UNII
JP8N4M44OP
EC Number
208-158-4
Nikkaji
J1.572E

When heated to decomposition emits highly toxic fumes of /hydrogen chloride/.

Vapor Pressure · 3 Einträge

172.4 mmHg at 77.9 °F ; 265.3 mmHg at 97 °F (NTP, 1992)

212.0 [mmHg]

158.4 mm Hg at 25 °C

Refractive IndexIndex of refraction: 0.9186 at 20 °C
Physical Description · 2 Einträge

Dimethylvinyl chloride is a clear dark yellow to pale orange liquid. (NTP, 1992)

Colorless, highly volatile liquid; [HSDB] Dark yellow to pale orange liquid; [CAMEO] Very faintly yellow-brown liquid; [MSDSonline]

Other Experimental Properties · 2 Einträge

Colorless to straw-colored, volatile liquid; sharp penetrating odor. Density: 0.925 at 20 °C; BP: 73 °C; Index of refraction: 1.427 at 25 °C /3-Chloro-2-methyl-1-propene/

Flammable and polymerizes easily

Physikochemische Eigenschaften

Schmelzpunkt
-96 °C · -96°C (estimate)
Siedepunkt
68 °C · 68 °C (lit.)
Dichte
0.92 g/mL · 0.92 g/mL at 25 °C (lit.)
Brechungsindex
20 · n20/D 1.424(lit.)
Flammpunkt
30 °F · 30 °F
Löslichkeit
Chloroform (Soluble), Ethyl Acetate (Slightly)
Aggregatzustand
Oil
Farbe
Colourless
Merck
2147 · 2147
BRN
1733843 · 1733843
Henry's Law Constant
5.2 · 5.2×10-4 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Volatile
InChI
1S/C4H7Cl/c1-4(2)3-5/h3H,1-2H3
InChIKey
KWISWUFGPUHDRY-UHFFFAOYSA-N
SMILES
C\C(C)=C\Cl
EPA chemische Informationen
Dimethylvinyl chloride (513-37-1)
Hazards Summary · 1 Eintrag

An eye and respiratory tract irritant; Possesses anesthetic characteristics; Squamous cell carcinomas have been observed in feeding studies with rats; No evidence of mutagenicity in various strains of Salmonella typhimurium; Emergency medical treatment: see Propylene dichloride. [HSDB] A skin, eye, and respiratory tract irritant; May cause liver and kidney injury and CNS effects (anesthesia); [CAMEO] Rapidly excreted by expiration and in urine; Effects in high-dose studies with rats include tissue necrosis in various organs (including small and large intestine, thymus, and spleen) and proliferation of forestomach cells; Observations of mutagenicity in single studies with cultured rodent cells (gene mutation and sister chromatid exchange, but no chromosomal aberrations) and insects (gene and chromosomal mutation); Mutagenic to bacteria; Sufficient evidence for carcinogenicity in laboratory animals; [IARC]

Reactive GroupHalogenated Organic Compounds
Special Reports · 2 Einträge

U.S. Department of Health & Human Services/National Toxicology Program; Twelfth Report on Carcinogens (2011). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. Dimethylvinyl chloride (513-37-1) is listed as reasonably anticipated to be a human carcinogen. First listed in the Sixth Annual Report on Carcinogens (1991).[Available from, as of March 1, 2012: http://ntp.niehs.nih.gov/?objectid=03C9AF75-E1BF-FF40-DBA9EC0928DF8B15]

NTP TR No 316; Route: oral, gavage; Species: rats and mice. NTIS No PB87115184.[NTP; Division of Toxicology Research and Testing; Management Status Report; 07/22/92; p.23]

Reactivity AlertsHighly Flammable
Reactivity ProfileDIMETHYLVINYL CHLORIDE is incompatible with strong oxidizing agents and strong bases. (NTP, 1992)
Air and Water ReactionsHighly flammable. May be sensitive to prolonged exposure to air and light. Slightly soluble in water.
Hazard Classes and Categories · 5 Einträge

Flam. Liq. 2 (100%)

Flammable liquids - Category 2

Carcinogenicity - Category 1B

Acute toxicity (Oral) - Category 3

Carcinogens

Sicherheit und Schutzausrüstung

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 Eintrag

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 calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Storage Conditions · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Cleanup Methods · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

Nonfire Spill Response · 1 Eintrag

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION. Then, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 5 Einträge

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": HEPA (high-efficiency particulate arrestor) filters ... can be disposed of by incineration. For spent charcoal filters, the adsorbed material can be stripped off at high temp & carcinogenic wastes generated by this treatment conducted to & burned in an incinerator. ... LIQUID WASTE: ... Disposal should be carried out by incineration at temp that ... ensure complete combustion. SOLID WASTE: Carcasses of lab animals, cage litter & misc solid wastes ... should be disposed of by incineration at temp high enough to ensure destruction of chem carcinogens or their metabolites. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for 1-CHLORO-2-METHYL-1-PROPENE (6 total), please visit the HSDB record page.

Preventive Measures · 5 Einträge

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.

PRECAUTIONS FOR "CARCINOGENS": Smoking, drinking, eating, storage of food or of food & beverage containers or utensils, & the application of cosmetics should be prohibited in any laboratory. All personnel should remove gloves, if worn, after completion of procedures in which carcinogens have been used. They should ... wash ... hands, preferably using dispensers of liq detergent, & rinse ... thoroughly. Consideration should be given to appropriate methods for cleaning the skin, depending on nature of the contaminant. No standard procedure can be recommended, but the use of organic solvents should be avoided. Safety pipettes should be used for all pipetting. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": In animal laboratory, personnel should remove their outdoor clothes & wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... Clothing should be changed daily but ... discarded immediately if obvious contamination occurs ... /also,/ workers should shower immediately. In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. If gowns are of distinctive color, this is a reminder that they should not be worn outside of lab. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Operations connected with synth & purification ... should be carried out under well-ventilated hood. Analytical procedures ... should be carried out with care & vapors evolved during ... procedures should be removed. ... Expert advice should be obtained before existing fume cupboards are used ... & when new fume cupboards are installed. It is desirable that there be means for decreasing the rate of air extraction, so that carcinogenic powders can be handled without ... powder being blown around the hood. Glove boxes should be kept under negative air pressure. Air changes should be adequate, so that concn of vapors of volatile carcinogens will not occur. /Chemical Carcinogens/

For more Preventive Measures (Complete) data for 1-CHLORO-2-METHYL-1-PROPENE (10 total), please visit the HSDB record page.

Isolation and EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Personal Protective Equipment (PPE) · 2 Einträge

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves.

PRECAUTIONS FOR "CARCINOGENS": ... Dispensers of liq detergent /should be available./ ... Safety pipettes should be used for all pipetting. ... In animal laboratory, personnel should ... wear protective suits (preferably disposable, one-piece & close-fitting at ankles & wrists), gloves, hair covering & overshoes. ... In chemical laboratory, gloves & gowns should always be worn ... however, gloves should not be assumed to provide full protection. Carefully fitted masks or respirators may be necessary when working with particulates or gases, & disposable plastic aprons might provide addnl protection. ... Gowns ... /should be/ of distinctive color, this is a reminder that they are not to be worn outside the laboratory. /Chemical Carcinogens/

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 61(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-methyl-1-propene is expected to have high mobility in soil(SRC). Volatilization of 1-chloro-2-methyl-1-propene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-2 atm-cu m/mole(SRC), based upon its vapor pressure, 158.4 mm Hg(3), and water solubility, 1,000 mg/L(4). 1-Chloro-2-methyl-1-propene is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). Biodegradation data in soil were not available(SRC, 2012).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 61(SRC), determined from a structure estimation method(2), indicates that 1-chloro-2-methyl-1-propene 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 1.9X10-2 atm-cu m/mole(SRC), from its vapor pressure, 158.4 mm Hg(4), and water solubility, 1,000 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3 hours and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 24(SRC), from an estimated log Kow of 2.58(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2012).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-2-methyl-1-propene, which has a vapor pressure of 158.4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-2-methyl-1-propene 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 7 hours(SRC), calculated from its rate constant of 1.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Chloro-2-methyl-1-propene does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Ongoing Test Status · 1 Eintrag

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=513-37-1]

Medical Surveillance · 1 Eintrag

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

Soil Adsorption/Mobility · 1 Eintrag

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1-chloro-2-methyl-1-propene can be estimated to be 61(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-chloro-2-methyl-1-propene is expected to have high mobility in soil.

TSCA Test Submissions · 1 Eintrag

The mutagenicity of 1-chloro-2-methylpropene was evaluated in Salmonella tester strains TA98, TA100, TA1535, TA1537 and TA1538 (Ames Test) and in Saccharomyces cerevisiae strain D4, both in the presence and absence of added metabolic activation by Aroclor-induced rat liver S9 fraction. Based on preliminary toxicity determinations, 1-chloro-2-methylpropene, diluted in DMSO, was tested at concentrations of 0.01, 0.1, 1, and 5uL/plate using the plate incorporation technique. 1-Chloro-2-methylpropene did not cause a positive response in any tester strain with or without metabolic activation.

Atmospheric ConcentrationsSOURCE DOMINATED: 1-Chloro-2-methyl-1-propene was detected in ambient air at four industrial and chemical waste sites near Curtis Bay, MD at concentrations of 200, 670, 100, and 90 ug/cu m(1).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ A local irritant and /CNS deppressant/ in high concentrations.
Artificial Pollution Sources1-Chloro-2-methyl-1-propene's production and use in organic synthesis and as a research chemical(1) may result in its release to the environment through various waste streams(SRC).
Sediment/Soil ConcentrationsSEDIMENT: A Japanese study has reported trace amounts of 1-chloro-2-methyl-1-propene in sediment samples; detection limit = 0.015 ug/kg(1).
Carcinogen Classification · 6 Einträge

1-Chloro-2-methylpropene

Group 2B: Possibly carcinogenic to humans

Volume 63: (1995) Dry Cleaning, Some Chlorinated Solvents and Other Industrial Chemicals

1995

1995

Dimethylvinyl Chloride (DMVC)

Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 24 was calculated in fish for 1-chloro-2-methyl-1-propene(SRC), using an estimated log Kow of 2.58(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Sicherheitsdaten

wgk
3
ridadr
UN 1993 3/PG 2
hs_code
2903290000
RTECS-Nr.
UC8045000
risk_code
45-11-23/24/25-36/37/38
hazard_code
F,T
safety_code
53-16-27-36/37/39-45
hazard_class
3.1
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
513-37-1(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 1 InhalationAcute Tox. 3 DermalCarc. 1BEye Irrit. 2Flam. Liq. 2Skin Irrit. 2STOT SE 3

(2-(14)C)1-Chloro-2-methylpropene (3.5 mCi/mmol; radiochemical purity, 96%) was administered by gavage to male Fischer 344 rats in single or up to four daily doses of 150 mg/kg bw in corn oil. The compound was extensively absorbed and rapidly excreted: 92% of the single dose was eliminated within 24 hr after treatment. It was rapidly distributed to the tissues; liver and kidney contained higher concentrations of radiolabel than forestomach and glandular stomach, which had similar levels. The tissue concentrations increased monotonically after repeated doses but had declined significantly after four days of recovery following treatment. After a single dose, about 35% of the administered radiolabel was found in urine, 52% was exhaled and 5% was detected in the feces. In the expired air, about 25% of the dose was (14)C-carbon dioxide; 30% was volatile compounds, of which 96% was unchanged compound. ...

(2-(14)C)1-Chloro-2-methylpropene (3.5 mCi/mmol; radiochemical purity, 96%) was administered by gavage to male B6C3F1 mice as a single dose of 150 mg/kg bw in corn oil. The compound was extensively absorbed and rapidly excreted; urine contained about 46% of the dose after 24 hr, 25% was expired as carbon dioxide and 5% as the unchanged compound, whereas 9% of the dose was found in the feces. The highest levels of radiolabel in tissues were detected in kidney, liver, forestomach and thymus 24 hr after administration. ...

A recent 2 yr carcinogenicity study found that gavage admin of 3-chloro-2-methylpropene containing 5% 1-chloro-2-methylpropene (dimethylvinyl chloride), caused forestomach neoplasms in rats and mice. Similar chronic studies revealed that dimethylvinyl chloride caused forestomach neoplasms in both rats and mice; neoplasms of the nasal and oral cavities were observed in rats but not in mice. In the current studies, /the metabolic basis/ of these differences /has been investigated/. Daily doses of 150 mg/kg of 2-(14)C-dimethylvinyl chloride or 2-(14)C-3-chloro-2-methylpropene were admin to rats for 1, 2, or 4 consecutive days. One daily dose of 150 mg/kg of dimethylvinyl chloride was admin to mice. Both /cmpds/ were rapidly metabolized; however, 3-chloro-2-methylpropene was cleared at a slightly lower rate. Rats exhaled approx 25 and 10% of the dimethylvinyl chloride and 3-chloro-2-methylpropene as C02, respectively. Mice exhaled 25% of the dimethylvinyl chloride as C02. Rats expired 30% of the administered dimethylvinyl chloride unchanged in the 24 hr after dosing compared to only 7% of the administered 3-chloro-2-methylpropene. Mice expired 5% of the administered dimethylvinyl chloride in the same time period. This observation may explain the occurrence of tumors in the nasal and oral cavities of rats treated with dimethylvinyl chloride but not in rats treated with 3-chloro-2-methylpropene or in mice treated with dimethylvinyl chloride in 2 yr carcinogenicity studies. The 24 hr urinary excretion in rats was 35% of the administered dimethylvinyl chloride compared to 58% of 3-chloro-methylpropene. Mice excreted 47% of the administered dimethylvinyl chloride in 24 hr in the urine. An unusual urinary metabolite of dimethylvinyl chloride, 2-amino-6-methyl-4-thia-5-heptene-1,7-dioic acid, was identified.

Verwendung und Herstellung

Uses · 3 Einträge

Used in organic synthesis and as a research chemical; [Merck Index] Not commercially produced in the US; [HSDB] Impurity in the manufacture of 3-chloro-2-methylpropene; No known commercial use; [IARC]

In organic synthesis; research chemical.

CHEMICAL INTERMEDIATE FOR ORG ISOBUTYLENE COMPDS (USED IN LABS)

Impurities1-Chloro-2-methylpropene is available commercially at a purity of at least 98%. 3-Chloro-2-methylpropene has been reported as an impurity.
U.S. Production · 2 Einträge

(1972) NOT PRODUCED COMMERCIALLY IN US

(1975) NOT PRODUCED COMMERCIALLY IN US

Methods of Manufacturing · 2 Einträge

Prepared from isobutyraldehyde; ... by isomerization of 3-chloro-2-methylpropene with 80% H2SO4.

1-Chloro-2-methylpropene is a by-product of the production of 3-chloro-2-methylpropene

Anwendungen

VerwendenDimethylvinyl chloride is not used commercially, but is used for research purposes. It has been used in organic syntheses and as a chemical intermediate for the production of isobutylene compounds for laboratory use (IARC 1995, HSDB 2009).

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

PentachlorphosphoranEthandiolIsobutyraldehyd

Nachgelagerte Produkte

β,β-Dimethylstyrol2,5-Dimethylhexa-2,4-dien

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