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メチルシクロペンタン

Methylcyclopentane

HCID 7296
ノート反応
基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
部分構造検索類似構造を探す

基本情報

CAS
96-37-7
標準SMILES
CC1CCCC1
InChIKey
GDOPTJXRTPNYNR-UHFFFAOYSA-N
分子式
C6H12
平均分子量
84.16 g/mol
単同位体質量
84.09390038

概要

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.

名称と識別子

優先名称
Methylcyclopentane
IUPAC
methylcyclopentane
現地名
メチルシクロペンタン
英語名
Methylcyclopentane
分子式
C6H12
分子量
84.16

名称と別名

METHYLCYCLOPENTANE96-37-7Cyclopentane, methyl-Methyl cyclopentaneMethylpentamethyleneDTXSID3025590Methyl-cyclopentane5G26CC1ASKNSC-24836DTXCID205590CHEBI:88429cyclopentane, methyl
名称をさらに表示
メチルシクロペンタン1-メチルシクロペンタン3-メチルシクロペンタンメチルシクロペンタン, 96%MCP1-MethylcyclopentaneMethylcyclopentane,97%MethylcyclopenMethylcyclopentanmethyl-Cyclopetanemethyl-cyclopentanCyclopetane,methyl-
RefChem:6031202-503-2MFCD00001382CCRIS 6058HSDB 876EINECS 202-503-2NSC 24836UN2298

データベース識別子

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

物性

構造計算による物性

XLogP
3.4
極性表面積
0 Ų
水素結合供与体数
0
水素結合受容体数
0
回転可能結合数
0
重原子数
6
形式電荷
0
複雑度
33.3

実験および物理化学的性質

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

log Kow = 3.37

3.37

OdorLike gasoline
Density · 3 件

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 件

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 件

-11 °F (NTP, 1992)

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

Boiling Point · 3 件

161.2 °F at 760 mmHg (NTP, 1992)

71.8 °C @ 760 MM HG

71.8 °C @760 [mm Hg]

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

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.

危険有害性情報

Regulatory Information · 5 件

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 件

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 PotentialDANGEROUS, UPON EXPOSURE TO HEAT OR FLAME; CAN REACT VIGOROUSLY WITH OXIDIZING MATERIALS.
Health Hazards

化学と産業

薬理情報

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

用途と製造

Uses · 3 件

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 件

Petroleum Refineries

Cyclopentane, methyl-: ACTIVE

応用分野 · 3 件

用途溶剤、クリーナー添加剤。

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

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.

関連反応

2 件
反応記録を作成
HRID 1774595 の反応式
HRID 1774595反応物としてuspto-grants-2016_02
HRID 1906992 の反応式
HRID 1906992反応物としてuspto-grants-1987_03

化合物ノート

読み込み中…

このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
EC Number
202-503-2
Nikkaji
J23.246G
Melting Point · 3 件

-224.3 °F (NTP, 1992)

-142.5 °C

-139.8 °C

Vapor Density · 2 件

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

2.9 (AIR= 1)

物理化学的性質

融点
-142.4 °C · -142.4 °C
沸点
72 °C · 72 °C(lit.)
比重(密度)
0.749 g/mL · 0.749 g/mL at 25 °C(lit.)
蒸気圧
232.8 mm · 232.8 mm Hg ( 37.7 °C)
屈折率
20 · n20/D 1.409(lit.)
闪点
11 °F · −11 °F
貯蔵温度
30 °C · Store below +30°C.
溶解性
5 °C · メタノール中の溶解度 g/L: 5 °C で 380、10 °C で 415、15 °C で 500、20 °C で 595、25 °C で 740、30 °C で 1,100。高温で混和する (Kiser et al., 1961)。
外見
結晶の付着
色
白い
臭い (Odor)
ガソリンのように。
爆発限界(explosive limit)
8.35 % · 8.35%
臭気閾値(Odor Threshold)
1.7 ppm · 1.7ppm
水溶解度
41.8 mg/L · 41.8mg/L(25℃)
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 データベース
96 · 96-37-7(CAS DataBase Reference)
EPAの化学物質情報
Methylcyclopentane (96-37-7)
化学的性質 · 1 件

化学的特性Methylcyclopentane is a colorless, flammable liquid with a sweet gasoline-like odor. An odor threshold concentration of 1.7 ppmv was reported by Nagata and Takeuchi (1990). Soluble in ether, miscible with alcohol and benzene, insoluble in water.

· 2 件

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 件

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 件

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%

安全と保護具

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

· 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 件

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 件

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

500.0 [ppm]

Fire Fighting Procedures · 2 件

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 件

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 件

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 件

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 件

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

Immediate precautionary measure

Threshold Limit Values (TLV) · 2 件

500.0 [ppm]

1000.0 [ppm]

毒性情報

Body Burden · 1 件

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 件

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 件

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 件

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 件

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).

法規制情報

TSCA Requirements · 1 件

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.

安全データ

wgk
3
tsca
TSCA listed
rtecs
GY4640000
ridadr
UN 2298
hs_code
2902 19 00
risk_code
11-22-36/37/38-65
化審法
(3)-4669
消防法
危-4-1-II
hazard_code
F,Xn
safety_code
16-26-33-36-62
hazard_class
3
packing_group
II
自然発火温度
624 °F
Hazard Classifications
Asp. Tox. 1Flam. Liq. 2
ストレージクラス
3 - Flammable liquids
有毒物質データの
96-37-7(Hazardous Substances Data)
一般的な説明
調製方法 · 3 件

製造方法Methylcyclopentane 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.

合成方法ベンゼンの水素化の副反応により生成する

純化方法Purification procedures include passage through columns of silica gel (prepared by heating in nitrogen to 350o prior to use) and activated basic alumina, distillation from sodium-potassium alloy, and azeotropic distillation with MeOH, followed by washing out the methanol with water, drying and distilling. It can be stored with CaH2 or sodium. [Vogel J Chem Soc 1331 1938, Beilstein 5 III 55, 5 IV 84.]

上流・下流製品情報

上流原料

Industrial hexane

下流製品

2-メチルヘキサン4-エチルオクタンテトラデカフルオロヘキサン1-メチル-1-シクロペンテンビシクロヘキシル1-ヘキセンシクロペンタンヘキサン
補足説明 · 1 件

定義ChEBI: 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.