2-Methylcyclohexanone

HCID 11419CAS 583-60-8

Basic information

Standard SMILES
CC1CCCCC1=O
InChIKey
LFSAPCRASZRSKS-UHFFFAOYSA-N
Molecular formula
C7H12O
Average molar mass
112.17 g/mol
Monoisotopic mass
112.088815

Names & identifiers

Preferred name
2-Methylcyclohexanone
IUPAC
2-methylcyclohexan-1-one
English name
2-Methylcyclohexanone
Molecular formula
C7H12O
Molecular weight
112.17

Names & synonyms

2-METHYLCYCLOHEXANONE583-60-82-methylcyclohexan-1-oneo-Methylcyclohexanone2-Methyl-1-cyclohexanoneCyclohexanone, 2-methyl-2-Metilcicloesanonealpha-MethylcyclohexanoneMethylanonSexton B2-Methyl-cyclohexanonMETHYL ANONE
Show more names
FEMA 3946sextonb[qr]2-Methylcyclohmethylanon[qr]1MethylcyclohexanonKetohexahydrotolueneo-Methylcycloexanone2-Methlcyclohexanone
NSC-52456E8224ZFJDTXSID6052245FEMA NO. 3946RefChem:88294DTXCID1030816209-513-6Tetrahydro-o-cresol

Database identifiers

CAS
583-60-8
PubChem CID
11419
DTXSID
DTXSID6052245
ChEMBL
CHEMBL1946183
ChEBI
CHEBI:195390
UNII
56E8224ZFJ
EC Number
209-513-6
Nikkaji
J3.301D

Properties

Computed structural properties

XLogP
1.5
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
8

Experimental & physicochemical properties

Odor · 3 items

Acetone-like odor

Odor: characteristic: quality: peppermintlike

Weak, peppermint-like odor.

Density · 6 items

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 · 3 items

Water-white to pale yellow liquid

Colorless liquid

Colorless liquid.

Solubility · 5 items

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 · 4 items

118 °F (USCG, 1999)

118 °F

118 °F

118 °F

Boiling Point · 6 items

329 °F at 760 mmHg (USCG, 1999)

165.1 °C

162-163 °C

329 °F

165.1 °C @760 [mm Hg]

325 °F

Physicochemical properties

Melting point
-14 °C · -14 °C
Boiling point
162 · 162-163 °C (lit.)
Density
0.924 g/mL · 0.924 g/mL at 25 °C (lit.)
vapor pressure
1 at · 1 at 20 °C (NIOSH, 1997)
FEMA
3946 · 3946 | 2-METHYLCYCLOHEXANONE
refractive index
20 · n20/D 1.448(lit.)

Safety & regulation

GHS classification

GHS Classification · 6 items

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

Hazard information

Regulatory Information · 5 items

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 InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
DOT LabelFlammable Liquid
Fire HazardsSpecial Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon monoxide, may be formed when involved in fire. (USCG, 1999)
Fire PotentialMODERATE FIRE RISK.
Health HazardsMay cause irritation of the eyes, nose and throat. Prolonged or repeated contact may cause dermatitis. (USCG, 1999)

Safety & protection

Fire Fighting · 1 item

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 · 2 items

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 MethodsAbsorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.
Nonfire Spill Response · 1 item

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 · 2 items

Incineration

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

Preventive Measures · 3 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.

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

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

Toxicology

Target OrgansSkin, respiratory system, liver, kidneys, central nervous system
Adverse EffectsNeurotoxin - 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 Routesinhalation, skin absorption, ingestion, skin and/or eye contact
Signs and SymptomsIn Animals: irritation eyes, mucous membrane; narcosis; dermatitis
Human Toxicity Excerpts · 3 items

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 · 1 item

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.

Regulatory information

Regulatory Information · 5 items

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.)

Safety data

OEB
A
OEL
TWA: 50 ppm (230 mg/m3), STEL: 75 ppm (345 mg/m3) [skin]
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
1
IDLA
600 ppm
tsca
TSCA listed

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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 LocationsCytoplasm;Extracellular

Uses & manufacturing

Uses · 4 items

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 · 2 items

OXIDATION (DEHYDROGENATION) OF 2-METHYLCYCLOHEXANOL

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

Use Classification · 3 items

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

General Manufacturing InformationCyclohexanone, 2-methyl-: ACTIVE
Applications · 6 items

Descriptiono-Methylcyclohexanone is a colorless liquid with a weak peppermint-like odor (also reported to be ace-tone-like). Molecular weight= 112.19; Specific gravity(H2O:1) = 0.93; Boiling point= 162.7℃; Freezing/Meltingpoint= - 13.9℃;Flashpoint = 47.8℃.HazardIdentification (based on NFPA-704 M Rating System):Health 2, Flammability 2, Reactivity 0. Insoluble in water.

OccurrenceReported found in cockroaches as attractant pheromone; not reported found in natural foods

Uses2-Methylcyclohexanone can be used as solvent, lacquers.It has been suggested for use in soap perfumes, industrial fragrances, masking odors, etc. where its power and stability come to use. It may give "lift" to woody soap perfumes and add power to spicy-herbaceous fragrances, but its proper odor is not exactly beautiful.

UsesSolvent; rust remover

Useso-Methyl cyclohexanone is used as a solventfor varnishes, lacquers, and plastics; and asa rust remover.

General DescriptionA water-white to pale yellow liquid with an acetone-like odor. Less dense than water. Vapors heavier than air. Flash point near 135°F. May be toxic by ingestion. Used as a solvent.

Preparation methods

PreparationFrom cyclohexanone by treatment with a base and then with methyl iodide

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]

Related reactions

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Linked notes

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