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2-Methylcyclohexanone

2-Methylcyclohexanone structure

2-Methylcyclohexanone 

structure
  • CAS No:

    583-60-8

  • Formula:

    C7H12O

  • Chemical Name:

    2-Methylcyclohexanone

  • Synonyms:

    Cyclohexanone,2-methyl-;2-Methylcyclohexanone;2-Methyl-1-cyclohexanone;α-Methylcyclohexanone;(±)-2-Methylcyclohexanone;2-Methylcyclohexane-1-one;NSC 524;24965-84-2

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

2-Methylcyclohexanone is an endogenous metabolite.


O-methylcyclohexanone appears as a 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.|Colourless liquid; weak peppermint scent|Colorless liquid with a weak, peppermint-like odor.


O-methylcyclohexanone appears as a 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.

2-Methylcyclohexanone Basic Attributes

112.17

112.17

506751

209-513-6

524

2297

DTXSID6052245

Water-white to pale yellow liquid|Colorless liquid|Colorless liquid.

2914220000

Characteristics

17.1

1.5

Clear colorless to very slightly yellow Liquid

0.925 g/cm3 @ Temp: 20 °C

-14 °C

165.1 °C

116 °F

1.442

Insoluble in water. soluble in methanol and diethyl ether.

Flammables area

1 at 20 °C (NIOSH, 1997)

3.86 (air = 1)

Oral-rat LD50: 2000 mg/kg; Abdominal cavity-mouse LD50: 200 mg/kg

Flammable; spicy and irritating smoke is released from the fire

1.2%(V)

Acetone-like odor

MP: -13.9 °C; BP: 165 °C @ 757 MM HG; DENSITY: 0.9250 @ 20 °C/4 °C; INDEX OF REFRACTION: 1.4483 @ 25 °C/D; SOL IN ALC & ETHER /DL- 2-METHYLCYCLOHEXANONE/|BP: 167-168 °C @ 735 MM HG; DENSITY: 0.9262 @ 18 °C/4 °C; INDEX OF REFRACTION: 1.4440 @ 25 °C/D; SPECIFIC OPTICAL ROTATION: +14.21 @ 25 °C (CHLOROFORM) /D-2-METHYLCYCLOHEXANONE/|BP: 59-60 °C @ 20 MM HG; DENSITY: 0.9230 @ 25 °C/4 °C; INDEX OF REFRACTION: 1.4440 @ 25 °C/D; SPECIFIC OPTICAL ROTATION: -15.22 @ 25 °C (UNDILUTED); SOL IN ALC & ETHER /L-2-METHYLCYCLOHEXANONE/|A mixture of cyclic ketones

Flammable. Slightly soluble in water.

Ketones

Highly Flammable

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

Class II Combustible Liquid: Fl.P. at or above 100°F and below 140°F.

Safety Information

3

UN 2297 3/PG 3

1

10-20-20/21/22

25-36/37

GW1750000

Xn

Treasury is ventilated, low temperature and dry; stored and transported separately from oxidant

Steam and air can be explosive when mixed

P280

H226-H302 + H312 + H332

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

Strong oxidizers

Special Hazards of Combustion Products: Irritating vapors and toxic gases, such as carbon monoxide, may be formed when involved in fire. (USCG, 1999)|Flammable - 2nd degree

|Warning|H226: Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P312, P304+P340, P312, P370+P378, P403+P235, and P501|H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P403+P235, and P501|Aggregated GHS information provided by 350 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P322, P330, P337+P313, P363, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: CAUTION: All 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. LARGE FIRE: Water spray, fog or regular foam. Do not use straight streams. Move containers from fire area if you can do it without risk. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an 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 car or tank truck 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, 2016)

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in 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, 2016)

Skin: Wear appropriate personal protective clothing to prevent skin contact. Eyes: Wear appropriate eye protection to prevent eye contact. Wash skin: The worker should immediately wash the skin when it becomes contaminated. Remove: Work clothing that becomes wet or significantly contaminated should be removed and replaced. Change: No recommendation is made specifying the need for the worker to change clothing after the work shift. (NIOSH, 2016)|Wear appropriate personal protective clothing to prevent skin contact.|Wear appropriate eye protection to prevent eye contact.|Recommendations for respirator selection. Max concn for use: 500 ppm. Respirator Class(es): Any supplied-air respirator. May require eye protection.|Recommendations for respirator selection. Max concn for use: 600 ppm. Respirator Class(es): Any supplied-air respirator operated in a continuous flow mode. May require eye protection. Any self-contained breathing apparatus with a full facepiece. Any supplied-air respirator with a full facepiece.|For more Personal Protective Equipment (PPE) (Complete) data for 2-METHYLCYCLOHEXANONE (7 total), please visit the HSDB record page.|(See protection codes)

MODERATE FIRE RISK.

Combustible

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

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.

/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. Substances may be transported hot. /Methylcyclohexanone/|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Health: Inhalation or contact with material may irritate or burn skin and eyes. Fire may produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution. /Methylcyclohexanone/|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering. /Methylcyclohexanone/|/GUIDE 128: FLAMMABLE LIQUIDS (NON-POLAR/WATER-IMMISCIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection. /Methylcyclohexanone/|For more DOT Emergency Guidelines (Complete) data for 2-METHYLCYCLOHEXANONE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Mild irritation - eye, nose, throat, skin|Irritation to eyes and respiratory tract.

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.

Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 50 ppm (230 mg/cu m), skin.|Recommended Exposure Limit: 15 Min Short-Term Exposure Limit: 75 ppm (345 mg/cu m), skin.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.| 0 - Materials that in themselves are normally stable, even under fire conditions.

Toxicity

moderately toxic

LD50 Rabbit oral 1-1.25 g/kg|LD50 Rat oral 2.14 ml/kg

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.

Drug Information

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.

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

Eye: If this chemical contacts the eyes, immediately wash the eyes with large amounts of water, occasionally lifting the lower and upper lids. Get medical attention immediately. Contact lenses should not be worn when working with this chemical. Skin: 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: If a person breathes large amounts of this chemical, move the exposed person to fresh air at once. If breathing has stopped, perform mouth-to-mouth resuscitation. Keep the affected person warm and at rest. Get medical attention as soon as possible. Swallow: If this chemical has been swallowed, get medical attention immediately. (NIOSH, 2016)|(See procedures)

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/

2-methylcyclohexanone

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

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

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

2-Methylcyclohexanone Use and Manufacturing

Methods of Manufacturing

OXIDATION (DEHYDROGENATION) OF 2-METHYLCYCLOHEXANOL|...BY HIGH-TEMPERATURE, CATALYTIC HYDROGENATION OF CRESOLS OR BY THE DEHYDROGENATION OF METHYLCYCLOHEXANOL.

Uses

o-Methyl cyclohexanone is used as a solventfor varnishes, lacquers, and plastics; and asa rust remover. 2-Methylcyclohexanone can be used as solvent, lacquers.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS

Cyclohexanone, 2-methyl-: ACTIVE

NIOSH Method: 2521. Analyte: 2-Methylcyclohexanone. Matrix: Air. Procedure: Gas chromatography, flame ionization detector. For 2-methylcyclohexanone this method has an estimated detection limit of 0.09 mg/sample. The precision/RSD is 0.041 @ 0.7 to 2.9 mg/sample and the recovery is not determined. Applicability: The working range is 100 to 800 mg/cu m (20 to 170 ppm) for a 5 liter air sample. Interferences: None reported.

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Fire Hazards -> Flammable - 2nd degree

Flavoring Agents

Computed Properties

Molecular Weight:112.17
XLogP3:1.5
Hydrogen Bond Acceptor Count:1
Exact Mass:112.088815002
Monoisotopic Mass:112.088815002
Topological Polar Surface Area:17.1
Heavy Atom Count:8
Complexity:96.6
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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