反应SMILES:CC1CCCCC1=O
HCID11419

2-Methylcyclohexanone

2-methylcyclohexan-1-one

C7H12O112.17 g/molCAS 583-60-8

IDENTITY

结构与身份

标准SMILES
CC1CCCCC1=O
InChIKey
LFSAPCRASZRSKS-UHFFFAOYSA-N
分子式
C7H12O
平均分子量
112.17 g/mol
单同位素质量
112.088815

COMPUTED

结构计算性质

已同步
XLogP
1.5
极性表面积
17.1 Ų
氢键供体
0
氢键受体
1
可旋转键
0
重原子
8
形式电荷
0
复杂度
96

PROPERTIES

实验与物化性质

来源:PubChem
Odor

Acetone-like odor

Odor: characteristic: quality: peppermintlike

Weak, peppermint-like odor.

Density

0.93 (USCG, 1999) - Less dense than water; will float

0.925 at 20 °C/4 °C

0.924-0.926

0.93

0.92 @25 °C

0.93

Color/Form

Water-white to pale yellow liquid

Colorless liquid

Colorless liquid.

Solubility

Insoluble (NIOSH, 2024)

Insol in water; sol in alcohol and ether

insoluble in water; soluble in ether

Miscible at room temperature (in ethanol)

Insoluble

Flash Point

118 °F (USCG, 1999)

118 °F

118 °F

118 °F

Boiling Point

329 °F at 760 mmHg (USCG, 1999)

165.1 °C

162-163 °C

329 °F

165.1 °C @760 [mm Hg]

325 °F

Decomposition

When heated to decomposition it emits acrid smoke and fumes.

Melting Point

-6.8 °F (USCG, 1999)

-14 °C

6.8 °F

-14 °C

7 °F

Vapor Density

3.86 (air = 1)

Odor Threshold

Odor Threshold Low: 0.5 [ppm];Odor threshold from CHEMINFO

Vapor Pressure

1 mmHg (NIOSH, 2024)

2.25 [mmHg]

1 mmHg

1 mmHg

Refractive Index

1.444-1.450

GHS

GHS分类

来源:PubChem
GHS Classification

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids];H332: Harmful if inhaled [Warning Acute toxicity, inhalation]

P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P317, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Warning

HAZARDS

危害信息

来源:PubChem
Regulatory Information

Chemical: Cyclohexanone, 2-methyl-

Regulation (EC) No 1334/2008 (amended)

Status: Active Update: 17-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33492

Cyclohexanone, 2-methyl-: HSNO Approval: HSR001199 Approved with controls

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 Information

Evaluation - Chemicals that are unlikely to require further regulation to manage risks to human health

DOT Label

Flammable Liquid

Fire Hazards

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon monoxide, may be formed when involved in fire. (USCG, 1999)

Fire Potential

MODERATE FIRE RISK.

Health Hazards

May cause irritation of the eyes, nose and throat. Prolonged or repeated contact may cause dermatitis. (USCG, 1999)

Hazards Summary

TLV Basis is liver effects and CNS impairment. TLV-TWA is 20 ppm for Methylcyclohexanone (mixture of the 3 isomers), CAS number 1331-22-2. Causes liver toxicity in feeding study of rats. [ACGIH] A skin, eye, and respiratory tract irritant; [CAMEO]

DOT ID and Guide

2297 128

Reactive Group

Ketones

Reactivity Alerts

Highly Flammable

OSHA Standards

Permissible Exposure Limit: Table Z-1 8-hr Time Weighted Avg: 100 ppm (460 mg/cu m). Skin designation.

Vacated 1989 OSHA PEL TWA 50 ppm (230 mg/cu m); STEL 75 ppm (345 mg/cu m), skin designation, is still enforced in some states.

Reactivity Profile

Contact with strong oxidizers may cause fires and explosions (USCG, 1999).

SAFETY

安全与防护

来源:PubChem
Fire Fighting

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. CAUTION: For mixtures containing alcohol or polar solvent, alcohol-resistant foam may be more effective.;SMALL FIRE: Dry chemical, CO2, water spray or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam.;LARGE FIRE: Water spray, fog or regular foam. If regular foam is ineffective or unavailable, use alcohol-resistant foam. Avoid aiming straight or solid streams directly onto the product. If it can be done safely, move undamaged containers away from the area around the fire.;FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. For petroleum crude oil, do not spray water directly into a breached tank car. This can lead to a dangerous boil over. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. For massive fire, use unmanned master stream devices or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2024)

First Aid

Excerpt from NIOSH Pocket Guide for o-Methylcyclohexanone:;Eye: IRRIGATE IMMEDIATELY - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: SOAP WASH PROMPTLY - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: RESPIRATORY SUPPORT - If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform artificial respiration. Keep the affected person warm and at rest. Get medical attention as soon as possible.;Swallow: MEDICAL ATTENTION IMMEDIATELY - If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2024)

(General first aid procedures);Eye: Irrigate immediately - If this chemical contacts the eyes, immediately wash (irrigate) the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately.;Skin: Soap wash promptly - If this chemical contacts the skin, promptly wash the contaminated skin with soap and water. If this chemical penetrates the clothing, promptly remove the clothing and wash the skin with soap and water. Get medical attention promptly.;Breathing: Respiratory support;Swallow: Medical attention immediately - If this chemical has been swallowed, get medical attention immediately.

Cleanup Methods

Absorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.

Nonfire Spill Response

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material.;LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2024)

Disposal Methods

Incineration

Spray into the furnace. Incineration will become easier by mixing with a more flammable solvent.

Preventive Measures

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.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Isolation and Evacuation

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:;IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area for at least 50 meters (150 feet) in all directions.;LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet).;FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Respirator Recommendations

NIOSH;Up to 500 ppm:;(APF = 10) Any supplied-air respirator*;Up to 600 ppm:;(APF = 25) Any supplied-air respirator operated in a continuous-flow mode*;(APF = 50) Any self-contained breathing apparatus with a full facepiece;(APF = 50) Any supplied-air respirator with a full facepiece;Emergency or planned entry into unknown concentrations or IDLH conditions:;(APF = 10,000) Any self-contained breathing apparatus that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode;(APF = 10,000) Any supplied-air respirator that has a full facepiece and is operated in a pressure-demand or other positive-pressure mode in combination with an auxiliary self-contained positive-pressure breathing apparatus;Escape:;(APF = 50) Any air-purifying, full-facepiece respirator (gas mask) with a chin-style, front- or back-mounted organic vapor canister;Any appropriate escape-type, self-contained breathing apparatus;Important additional information about respirator selection

Threshold Limit Values (TLV)

20.0 [ppm]

8 hr Time Weighted Avg (TWA): 50 ppm; 15 min Short Term Exposure Limit (STEL): 75 ppm. Skin.

50 ppm [1970]

75 ppm [1970]

Permissible Exposure Limit (PEL)

100.0 [ppm]

100 ppm (460 mg/m³)

TWA 100 ppm (460 mg/m3) [skin] See Appendix G

Protective Action Criteria (PAC)

75 [ppm]

100 [ppm]

600 [ppm]

Recommended Exposure Limit (REL)

50 ppm (230 mg/m³)

75 ppm (345 mg/m³)

TWA 50 ppm (230 mg/m3) ST 75 ppm (345 mg/m3) [skin]

TOXICITY

毒理信息

来源:PubChem
Target Organs

Skin, respiratory system, liver, kidneys, central nervous system

Adverse Effects

Neurotoxin - Acute solvent syndrome;Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

Exposure Routes

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms

In Animals: irritation eyes, mucous membrane; narcosis; dermatitis

Human Toxicity Excerpts

IT HAS LOW TOXICITY FROM ABSORPTION THROUGH SKIN.

METHYLCYCLOHEXANONE IS NOT CONSIDERED A HAZARDOUS MATERIAL IN INDUSTRY; ITS CHIEF POTENTIAL IS /CNS DEPRESSION/ @ HIGH CONCN & IRRITATION @ LOWER LEVELS.

Nervous system disturbances - /CNS depression/

Non-Human Toxicity Excerpts

CONCN OF 450 PPM WERE IRRITATING TO EYES & RESP PASSAGES OF MICE. @ 2500 PPM RABBITS & CATS BECAME VERY SLEEPY, WITH DIFFICULT & IRREGULAR RESP, & UNCERTAIN & STAGGERING GAIT. ... SLIGHT CONJUNCTIVAL CONGESTION IN RABBITS REPEATEDLY EXPOSED @ 514 PPM /WAS FOUND/, BUT NO SYMPTOMS @ 182 PPM. EXPOSURE AT 2890 PPM FOR 4 HR WAS FATAL TO THREE OF SIX RATS.

Probable Routes of Human Exposure

Inhalation, ingestion, skin and eye contact.

...TLV OF 100 PPM SHOULD PROTECT AGAINST NARCOTIC EFFECTS, BUT...IN ORDER TO PREVENT EYE & RESP IRRITATION /ALSO/...TLV OF 50 PPM IS RECOMMENDED.

Toxicity Data

LCLo (rat) = 2,800 ppm/4H

Non-Human Toxicity Values

LD50 Rabbit oral 1-1.25 g/kg

LD50 Rat oral 2.14 ml/kg

REGULATORY

法规信息

来源:PubChem
Regulatory Information

Chemical: Cyclohexanone, 2-methyl-

Regulation (EC) No 1334/2008 (amended)

Status: Active Update: 17-05-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/33492

Cyclohexanone, 2-methyl-: HSNO Approval: HSR001199 Approved with controls

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.)

PHARMACOLOGY

药理信息

来源:PubChem
Metabolism/Metabolites

WHEN A KETONE /METHYLCYCLOHEXANONE/ CAN BE REDUCED TO YIELD 2 PRODUCTS (IE, CIS- & TRANS-ALCOHOL), THE THERMODYNAMICALLY MORE STABLE ALC (ONE HAVING 2 EQUATORIAL SUBSTITUENTS) WAS ALWAYS FOUND TO PREDOMINATE. ...IN VIVO, MORE STABLE ALC REPRESENTED ABOUT 70% OF 2 PRODUCTS.

Cellular Locations

Cytoplasm;Extracellular

USES

用途与制造

来源:PubChem
Uses

Used as a rust remover and a solvent to make lacquers, varnishes, and plastics; [ACGIH]

Painting (Solvents) [Category: Paint];Plastic Composites Manufacturing [Category: Industry]

SOLVENT; LACQUERS

Rust remover

U.S. Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Methods of Manufacturing

OXIDATION (DEHYDROGENATION) OF 2-METHYLCYCLOHEXANOL

...BY HIGH-TEMPERATURE, CATALYTIC HYDROGENATION OF CRESOLS OR BY THE DEHYDROGENATION OF METHYLCYCLOHEXANOL.

Use Classification

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing Information

Cyclohexanone, 2-methyl-: ACTIVE

ALIASES

名称与别名

共 77 条
2-METHYLCYCLOHEXANONE583-60-82-methylcyclohexan-1-oneo-Methylcyclohexanone2-Methyl-1-cyclohexanoneCyclohexanone, 2-methyl-2-Metilcicloesanonealpha-MethylcyclohexanoneMethylanonSexton B2-Methyl-cyclohexanonMETHYL ANONENSC-52456E8224ZFJDTXSID6052245FEMA NO. 3946RefChem:88294DTXCID1030816209-513-6Tetrahydro-o-cresol

REACTIONS

参与反应

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