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Methylcyclopentan

Methylcyclopentane

HCID 7296
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Grundinformationen

CAS
96-37-7
Standard-SMILES
CC1CCCC1
InChIKey
GDOPTJXRTPNYNR-UHFFFAOYSA-N
Summenformel
C6H12
Durchschnittliche Molmasse
84,16 g/mol
Monoisotopische Masse
84,09390038

Überblick

Methylcyclopentane appears as a colorless liquid. Insoluble in water and less dense than water. Flash point near 20 °F. Very dangerous fire risk. Vapors may be narcotic and irritating. Used to make other chemicals.

Namen und Bezeichner

Bevorzugter Name
Methylcyclopentane
IUPAC
methylcyclopentane
Lokaler Name
Methylcyclopentan
Englischer Name
Methylcyclopentane
Summenformel
C6H12
Molmasse
84.16

Namen und Synonyme

METHYLCYCLOPENTANE96-37-7Cyclopentane, methyl-Methyl cyclopentaneMethylpentamethyleneDTXSID3025590Methyl-cyclopentane5G26CC1ASKNSC-24836DTXCID205590CHEBI:88429cyclopentane, methyl
Weitere Namen anzeigen
MCP1-MethylcyclopentaneMethylcyclopentane,97%MethylcyclopenMethylcyclopentanmethyl-Cyclopetanemethyl-cyclopentanCyclopetane,methyl-
RefChem:6031202-503-2MFCD00001382CCRIS 6058HSDB 876EINECS 202-503-2NSC 24836UN2298

Datenbank-Bezeichner

CAS
96-37-7
PubChem CID
7296
DTXSID
DTXSID3025590
ChEMBL
CHEMBL30940
ChEBI
CHEBI:88429
UNII
5G26CC1ASK
EC Number

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,4
Polarare Oberfläche (TPSA)
0 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
0
Frei drehbare Bindungen
0
Schwere Atome
6
Formalladung
0
Komplexität
33,3

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Aliphatics, Saturated (<C12)
SpringerMaterials PropertiesBoiling point
LogP · 2 Einträge

log Kow = 3.37

3.37

OdorLike gasoline
Density · 3 Einträge

0.749 at 68 °F (USCG, 1999) - Less dense than water; will float

0.7486 @ 20 °C/4 °C

0.750 @ 20°C

Color/FormCOLORLESS LIQUID
Solubility · 3 Einträge

less than 1 mg/mL at 72 °F (NTP, 1992)

Insoluble in water, miscible in ethanol, ether, and acetone.

water solubility = 42 mg/l @ 25 °C

Flash Point · 2 Einträge

-11 °F (NTP, 1992)

Less than 20 °F (less than -7 °C) (Closed Cup)

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 · 5 Einträge

This chemical does not meet GHS hazard criteria for 0.2% (1 of 549) of reports.

Danger

H225 (98.5%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P319, P321, P331, P332+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 549 reports by companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Cyclopentane, methyl-

Cyclopentane, methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclopentane, methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 20-04-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/24573

Methylcyclopentane: 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.)

DOT LabelFlammable Liquid
Fire Hazards · 2 Einträge

Behavior in Fire: Vapor is heavier than air and may travel a considerable distance to a source of ignition and flash back. (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Fire Potential

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesVolatile hydrocarbons are absorbed mainly through the lungs, and may also enter the body after ingestion via aspiration. (A600)
Cellular LocationsMembrane

Verwendung und Herstellung

Uses · 3 Einträge

Used as an extractive solvent, a distillation agent, and in organic synthesis; [Hawley]

ORGANIC SYNTHESIS; EXTRACTIVE SOLVENT; AZEOTROPIC DISTILLATION AGENT

Methylcyclopentane is a component of gasoline.

U.S. Production2023: 100,000,000 - <500,000,000 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesFuel agents
Formulations/PreparationsGrades or Purity: Research: 99.94%; Pure: 99.5%; Technical: 96.5%
Household ProductsInformation on 8 consumer products that contain Methylcyclopentane in the following categories is provided:
General Manufacturing Information · 2 Einträge

Petroleum Refineries

Cyclopentane, methyl-: ACTIVE

Anwendungen

VerwendenMethylcyclopentane can undergo ring opening or ring enlargement to yield various hydrocarbons including branched and unbranched hexanes, cyclohexane and benzene.

Zugehörige Reaktionen

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Reaktionsgleichung von HRID 1774595
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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
202-503-2
Nikkaji
J23.246G
Boiling Point · 3 Einträge

161.2 °F at 760 mmHg (NTP, 1992)

71.8 °C @ 760 MM HG

71.8 °C @760 [mm Hg]

Melting Point · 3 Einträge

-224.3 °F (NTP, 1992)

-142.5 °C

-139.8 °C

Vapor Density · 2 Einträge

2.9 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

2.9 (AIR= 1)

Physikochemische Eigenschaften

Schmelzpunkt
-142.4 °C · -142.4 °C
Siedepunkt
72 °C · 72 °C(lit.)
Dichte
0.749 g/mL · 0.749 g/mL at 25 °C(lit.)
Dampfdruck
232.8 mm · 232.8 mm Hg ( 37.7 °C)
Brechungsindex
20 · n20/D 1.409(lit.)
Flammpunkt
11 °F · −11 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
380 at · In methanol, g/L: 380 at 5 °C, 415 at 10 °C, 500 at 15 °C, 595 at 20 °C, 740 at 25 °C, 1,100 at 30 °C. Miscible at higher temperatures (Kiser et al., 1961).
Aggregatzustand
Adhering Crystals
Farbe
White
Geruch (Odor)
Like gasoline.
Explosionsgrenze
8.35 % · 8.35%
Odor Threshold
1.7 ppm · 1.7ppm
Wasserlöslichkeit
41.8 mg/L · 41.8mg/L(25 ºC)
BRN
1900214 · 1900214
Henry's Law Constant
0.362 atmm3/mol · 0.362 atmm3/mol at 25 °C (Hine and Mookerjee, 1975)
Dielectric constant
2 · 2.0(20℃)
InChI
1S/C6H12/c1-6-4-2-3-5-6/h6H,2-5H2,1H3
InChIKey
GDOPTJXRTPNYNR-UHFFFAOYSA-N
SMILES
CC1CCCC1
LogP
3.37 at · 3.37 at 20℃
CAS Datenbank
96 · 96-37-7(CAS DataBase Reference)
EPA chemische Informationen
Methylcyclopentane (96-37-7)
DANGEROUS, UPON EXPOSURE TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.
Health Hazards · 2 Einträge

Inhalation causes dizziness, nausea, and vomiting; concentrated vapor may cause unconsciousness and collapse. Liquid causes irritation of eyes and mild irritation of skin if allowed to remain. Ingestion causes irritation of stomach. Aspiration causes severe lung irritation, rapidly developing pulmonary edema, and central nervous system excitement followed by depression. (USCG, 1999)

CAUTION: Petroleum crude oil (UN1267) may contain TOXIC hydrogen sulphide gas.

Hazards Summary · 1 Eintrag

A dangerous fire and explosion risk; [Hawley] An eye and mild skin irritant; [HSDB] An eye and mild skin irritant; Inhalation of high concentrations can cause CNS depression; [CAMEO] A mild skin and temporary eye irritant; Inhalation of high concentrations can cause CNS depression; [CHEMINFO] An irritant; Effects in high-dose animal studies include general anesthesia; [MSDSonline]

DOT ID and Guide2298 128
Reactive GroupHydrocarbons, Aliphatic Saturated
TSCA Requirements · 1 Eintrag

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. Methylcyclopentane is included on this list.

Reactivity AlertsHighly Flammable
Reactivity ProfileMETHYLCYCLOPENTANE can react vigorously with oxidizers. (NTP, 1992).
Flammable LimitsLOWER = 1.0%; UPPER = 8.35%

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Accidental Release Measures · 2 Einträge

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 2 Einträge

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.

General First Aid:

Firefighting HazardsFlashback along vapor trail may occur.
Exposure Control and Personal Protection · 2 Einträge

· Wear positive pressure self-contained breathing apparatus (SCBA).

500.0 [ppm]

Fire Fighting Procedures · 2 Einträge

WATER MAY BE INEFFECTIVE.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Keep run-off water out of sewers and water sources.

Storage Conditions · 1 Eintrag

IN GENERAL, MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMP INTO TOXIC COMPONENTS...SHOULD BE STORED IN COOL, WELL VENTILATED PLACE, OUT OF DIRECT RAYS OF SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED & MONITORED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...

Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 1 Eintrag

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.

Preventive Measures · 3 Einträge

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

If material not on fire and not involved in fire: Keep sparks, flames, and other source of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.

Personnel protection: Keep upwind. Avoid breathing vapors.

Isolation and Evacuation · 2 Einträge

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:

Immediate precautionary measure

Threshold Limit Values (TLV) · 2 Einträge

500.0 [ppm]

1000.0 [ppm]

Toxikologische Informationen

Body Burden · 1 Eintrag

Methylcyclopentane was detected in the expired air from 4 out of 8 subjects(all male: 2 smokers and 2 non-smokers) at levels of 0.98 and 0.027 ug/hour for the non-smokers and 11.0 and 0.31 ug/hour for the smokers(1). Methylcyclopentane was detected in the expired air from a control, prediabetic, and diabetic population of 62 non-smokers(2). Methylcyclopentane has been identified in 4 out of 12 human breath samples from subjects in New Jersey (nine people) and in North Carolina (3 people)(3).

TreatmentTreatment is mainly symptomatic and supportive. Gastric lavage, emesis, and the administration of activated charcoal should be avoided, as vomiting increases the risk of aspiration. (A600)
Health EffectsPetroleum distillates are aspiration hazards and may cause pulmonary damage, central nervous system depression, and cardiac effects such as cardiac arrhythmias. They may also affect the blood, immune system, liver, and kidney. (A600, L1297)
Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 1600(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that methylcyclopentane should have low mobility in soil(SRC). Volatilization of methylcyclopentane may be important from moist soil surfaces(SRC) given an experimental Henry's Law constant of 0.369 atm-cu m/mole(4), and from dry soil surfaces(SRC) based on an experimental vapor pressure of 138 mm Hg(5). Insufficient data are available to determine the rate or importance of biodegradation of methylcyclopentane in soil(SRC).

AQUATIC FATE: An estimated Koc value of 1600(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that methylcyclopentane should adsorb to suspended solids and sediment(SRC) in the water(2,SRC). Methylcyclopentane would volatilize from water surfaces(2,SRC) based on an experimental Henry's Law constant of 0.369 atm-cu m/mole(3). Estimated half-lives for a model river and model lake are 2.7 hours and 3.6 days, respectively(2,SRC). An estimated BCF value of 210(2,SRC), from an experimental log Kow(1), suggests that methylcyclopentane will bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(4). Insufficient data are available to determine the rate or importance of biodegradation of methylcyclopentane in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methylcyclopentane, which has an experimental vapor pressure of 138 mm Hg at 25 °C(2) will exist primarily in the vapor phase in the ambient atmosphere. Vapor-phase methylcyclopentane 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 about 2.3 days(3,SRC). Particulate-phase methylcyclopentane may be physically removed from the air by wet deposition(SRC).

Food Survey ValuesMethylcyclopentane has been identified as a volatile component of baked potatoes(1) and beef(2).
Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesOral (L400) ; inhalation (L400) ; dermal (L400)
Milk ConcentrationsMethylcyclopentane was qualitatively found in samples of mother's milk collected from Bayonne, NJ (1 sample), Jersey City, NJ (1 sample), Pittsburgh, PA (2 samples), and Baton Rouge, LA (2 samples)(1).
Toxicity SummaryPetroleum distillates are central nervous system depressants and cause pulmonary damage. (A600)
Signs and Symptoms · 1 Eintrag

Petroleum distillate poisoning may cause nausea, vomiting, cough, pulmonary irritation progressing to pulmonary edema, bloody sputum, and bronchial pneumonia. At high amounts, central nervous system depression may also occur, with symptoms such as weakness, dizziness, slow and shallow respiration, unconsciousness, and convulsions. Petroleum distillates are also irritating to the skin. (A594)

Effluent Concentrations · 3 Einträge

OTHER EFFLUENTS: Methylcyclopentane was detected during the incineration of plastics(1). Methylcyclopentane was detected in 10 out of 63 industrial effluents (9 samples were less than 10 ug/l and 1 sample was in the range of 10-100 ug/l)(2).

Methylcyclopentane represents 0.8% (by weight) of the hydrocarbons (non-methane organic gases) in engine exhaust, 1.1% for headspace gasoline vapors, and 2.5% for whole gasoline(1). Levels of methylcyclopentane from jet engine exhaust from flight condition simulation experiments using two engine types (YJ93-GE-3 and J85-GE-SB) ranged from 0.06-6.9 ppm C depending on where in the exhaust stream the measurement was taken(2). Average methylcyclopentane concns taken from 8 trips in a car (6 trips in a new car and 2 trips in older cars) and in a commuter train were 5.0 and 0.8 ug/cu m, respectively(3). Exhaust samples from 67 different automobiles with no emission control devices were found to contain an average of 1% wt/wt methylcyclopentane(4). The concn of methylcyclopentane in gasoline vapors from refueling cars at service stations ranged between 0.006 and 0.88 ppm(5). The average percentages of methylcyclopentane in three gasoline vapors are: Amoco Oil (bulk terminal exposure), 1.1 wt%; Amoco Oil (marine loading exposure), 1.5 wt%; and Shell Oil, 1.3 vol%(6). A study conducted in Atlanta (1990) found the average concn of methylcyclopentane in roadway, whole gas (average of six octanes), whole gas (87 octane), whole gas (89 octane), whole gas (92/93 octane), headspace gas (at 24 °C and average of six octanes), headspace gas (at 32 °C and average of six octanes), airport, and aircraft emissions were: 0.783, 1.10, 1.31, 1.04, 0.6, 0.81, 0.86, 0.6, and 0.344 ppbC%, respectively(7).

Methylcyclopentane was detected in the Craebeckx Tunnel (Antwerp, Belgium) in 1991 at concns that were similar for congested (0.049 g/kg carbon and total yearly emissions: 188 tons/year) and non-congested traffic (0.039 g/kg carbon and total yearly emissions: 150 tons/year)(1). A study conducted in Chicago found the average concn of methylcyclopentane in regular fuel (87 octane), mid-grade (89 octane), premium (93 octane), hot soak, cold start, roadway, and petroleum refinery emissions to be 0.98, 0.84, 0.34, 1.17, 1.65, 1.22, and 0.83 wt%, respectively(2). In Southern California, the methylcyclopentane profile for various emissions for vehicle exhaust was 0.92, 1.77, 0.77, 0.00, 0.83, and 0.86 wt% for a 46 car study, 13 samples from the Caldecott Tunnel, cold start, stabilized, hot start, and from an older fleet, respectively(3). Gasoline emission profiles for methylcyclopentane are as follows: 0.69, 1.14, 0.20, 2.44, 2.19, 1.08, and 1.49 wt% for diurnal evaporative emissions (older fleet), hot soak evaporative emissions (older fleet), running loss (older fleet), summer liquid gas, winter liquid gas, summer gas headspace, and winter gas headspace, respectively(3). In oil field emissions (Tulsa, OK), methylcyclopentane was detected at average concn of 164.6 ppbC and approximately 85 ppbC for two different samples(4). A study conducted along US Highway 70 near Raleigh, NC detected methylcyclopentane in automobile emissions at average percents of 1.17, 1.09, 1.13, 1.22, 1.03, and 1.00 %ppbC at five different sites(5). Samples of air taken from the Tingstad Tunnel in Goteborg, Sweden, on five different days, contained methylcyclopentane at 1.6, 1.6, 1.8, 2.0, and 1.9% of non-methane volatile hydrocarbons(6). Methylcyclopentane composition in the vapor of different types of petrol is 2.2 (conventional "cracked" Statoil 95), 2.6 (conventional "reformate" Shell 95), 0.2 (reformulated "alkylate" Aspen 2T), and 0.04% (reformulated "alkylate" OK Special)(7).

Soil Adsorption/Mobility · 1 Eintrag

The Koc of methylcyclopentane is estimated as approximately 1600(SRC), using an experimental log Kow of 3.37(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that methylcyclopentane should have low mobility in soil(SRC).

Regulatorische Informationen

TSCA Requirements · 1 Eintrag

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. Methylcyclopentane is included on this list.

Sicherheitsdaten

wgk
3
tsca
TSCA listed
ridadr
UN 2298
hs_code
2902 19 00
RTECS-Nr.
GY4640000
risk_code
11-22-36/37/38-65
hazard_code
F,Xn
safety_code
16-26-33-36-62
hazard_class
3
packing_group
II
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
96-37-7(Hazardous Substances Data)
Hazard Classifications
Asp. Tox. 1Flam. Liq. 2
Selbstentzündungstemperatur
624 °F
Darstellung · 1 Eintrag

synthetischeMethylcyclopentane mainly exists in industrial hexane, accounting for about 5%. However, because its boiling point is close to that of n-hexane (68.74°C), it is difficult to completely separate it by general rectification methods. Therefore, methylcyclopentane with a purity of more than 99% can be obtained by azeotropic distillation with methanol.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Industrial hexane

Nachgelagerte Produkte

2-Methylhexan4-ETHYLOCTANETetradecafluorhexan1-MethylcyclopentenBicyclohexylHex-1-enCyclopentann-Hexan
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Methylcyclopentane is a cycloalkane that is cyclopentane substituted by a single methyl group. It has a role as a human metabolite and a plant metabolite. It is a cycloalkane and a volatile organic compound. It derives from a hydride of a cyclopentane.