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2-Methyl-cyclohexanon

2-Methylcyclohexanone

HCID 11419
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Grundinformationen

CAS
583-60-8
Standard-SMILES
CC1CCCCC1=O
InChIKey
LFSAPCRASZRSKS-UHFFFAOYSA-N
Summenformel
C7H12O
Durchschnittliche Molmasse
112,17 g/mol
Monoisotopische Masse
112,088815

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
2-Methylcyclohexanone
IUPAC
2-methylcyclohexan-1-one
Lokaler Name
2-Methyl-cyclohexanon
Englischer Name
2-Methylcyclohexanone
Summenformel
C7H12O
Molmasse
112.17

Namen und Synonyme

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

Datenbank-Bezeichner

CAS
583-60-8
PubChem CID
11419
DTXSID
DTXSID6052245
ChEMBL
CHEMBL1946183
ChEBI
CHEBI:195390

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,5
Polarare Oberfläche (TPSA)
17,1 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
0
Schwere Atome
8
Formalladung
0
Komplexität
96,6

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 2nd degree
SolventsSolvents -> Ketones (<C12)
Odor · 3 Einträge

Acetone-like odor

Odor: characteristic: quality: peppermintlike

Weak, peppermint-like odor.

Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density · 6 Einträge

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

Flavoring AgentsEU Flavoring substances
Color/Form · 3 Einträge

Water-white to pale yellow liquid

Colorless liquid

Colorless liquid.

Solubility · 5 Einträge

Insoluble (NIOSH, 2024)

Insol in water; sol in alcohol and ether

insoluble in water; soluble in ether

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 · 6 Einträge

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

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

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P317, P302+P352, P303+P361+P353, P304+P340, P317, P321, P330, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 5 Einträge

Chemical: Cyclohexanone, 2-methyl-

Regulation (EC) No 1334/2008 (amended)

REACH registered substance: 2-methylcyclohexanone (EC: 209-513-6)

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)

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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

Verwendung und Herstellung

Uses · 4 Einträge

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

Painting (Solvents) [Category: Paint]

SOLVENT; LACQUERS

Rust remover

U.S. Production(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS
Methods of Manufacturing · 2 Einträge

OXIDATION (DEHYDROGENATION) OF 2-METHYLCYCLOHEXANOL

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

Use Classification · 3 Einträge

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
Anwendungen · 2 Einträge

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

Verwenden2-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.

Zugehörige Reaktionen

50
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Reaktionsgleichung von HRID 65616
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Reaktionsgleichung von HRID 153540
HRID 153540als EduktTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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UNII
56E8224ZFJ
EC Number
209-513-6
Nikkaji
J3.301D

Miscible at room temperature (in ethanol)

Insoluble

Flash Point · 4 Einträge

118 °F (USCG, 1999)

118 °F

118 °F

118 °F

Boiling Point · 6 Einträge

329 °F at 760 mmHg (USCG, 1999)

165.1 °C

162-163 °C

329 °F

165.1 °C @760 [mm Hg]

325 °F

DecompositionWhen heated to decomposition it emits acrid smoke and fumes.
Melting Point · 5 Einträge

-6.8 °F (USCG, 1999)

-14 °C

6.8 °F

-14 °C

7 °F

Physikochemische Eigenschaften

Schmelzpunkt
-14 °C · -14 °C
Siedepunkt
162 · 162-163 °C (lit.)
Dichte
0.924 g/mL · 0.924 g/mL at 25 °C (lit.)
Dampfdruck
1 at · 1 at 20 °C (NIOSH, 1997)
FEMA
3946 · 3946 | 2-METHYLCYCLOHEXANONE
Brechungsindex
20 · n20/D 1.448(lit.)
Flammpunkt
116 °F · 116 °F
storage temp.
2 · Sealed in dry,2-8°C
Löslichkeit
Soluble in alcohol, ether (Weast, 1986), and many other polar organic solvents including cyclohexanone.
Aggregatzustand
Liquid
Farbe
Clear colorless to very slightly yellow
Geruch (Odor)
10 % · at 10.00 % in dipropylene glycol. minty peppermint cooling
Geruchsart
minty
Biologische Quelle
synthetic
Explosionsgrenze
1.2 % · 1.2%(V)
Wasserlöslichkeit
Insoluble in water. Soluble in methanol and diethyl ether.
JECFA Number
1102 · 1102
BRN
506751 · 506751
Dielectric constant
14 · 14.0(20℃)
InChI
1S/C7H12O/c1-6-4-2-3-5-7(6)8/h6H,2-5H2,1H3
InChIKey
LFSAPCRASZRSKS-UHFFFAOYSA-N
SMILES
CC1CCCCC1=O
LogP
1.54 at · 1.54 at 25℃
CAS Datenbank
583 · 583-60-8(CAS DataBase Reference)
NIST chemische Informationen
2 · Cyclohexanone, 2-methyl-(583-60-8)
EPA chemische Informationen
2 · 2-Methylcyclohexanone (583-60-8)
Hazards Summary · 1 Eintrag

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 Guide2297 128
Reactive GroupKetones
Reactivity AlertsHighly Flammable
OSHA Standards · 2 Einträge

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

Sicherheit und Schutzausrüstung

Fire FightingExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
First Aid · 2 Einträge

Excerpt from NIOSH Pocket Guide for o-Methylcyclohexanone:

(General first aid procedures)

Cleanup MethodsAbsorb on paper. Evaporate on a glass or iron dish in hood. Burn the paper.
Nonfire Spill ResponseExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Disposal Methods · 2 Einträge

Incineration

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

Preventive Measures · 3 Einträge

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 EvacuationExcerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]:
Respirator RecommendationsNIOSH
Threshold Limit Values (TLV) · 4 Einträge

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) · 3 Einträge

100.0 [ppm]

100 ppm (460 mg/m³)

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

Protective Action Criteria (PAC) · 3 Einträge

75 [ppm]

100 [ppm]

600 [ppm]

Recommended Exposure Limit (REL) · 3 Einträge

50 ppm (230 mg/m³)

75 ppm (345 mg/m³)

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

Toxikologische Informationen

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

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 Eintrag

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 · 2 Einträge

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 DataLCLo (rat) = 2,800 ppm/4H
Non-Human Toxicity Values · 2 Einträge

LD50 Rabbit oral 1-1.25 g/kg

LD50 Rat oral 2.14 ml/kg

Sicherheitsdaten

OEB
A
OEL
TWA: 50 ppm (230 mg/m3), STEL: 75 ppm (345 mg/m3) [skin]
wgk
1
IDLA
600 ppm
tsca
TSCA listed
ridadr
UN 2297 3/PG 3
hs_code
29142200
RTECS-Nr.
GW1750000
risk_code
10-20-20/21/22
Toxizität
Acute oral LD50 for rats 2,140 mg/kg, rabbits 1 g/kg (quoted, RTECS, 1985).
hazard_code
Xn
safety_code
25-36/37
hazard_class
3
packing_group
III
Speicherklasse
3 - Flammable liquids
Giftige Stoffe Daten
583-60-8(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 4 InhalationFlam. Liq. 3

Darstellung

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

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

2,2-Dimethylcyclohexanonecis-2-Methylcyclohexanoltrans-2-Methylcyclohexanol3-Methylcyclohexan-1,2-dion1-MethylcyclohexanolCyclohexanol, 2-methyl-1-(4-methylphenyl)-