基本情報
- 標準SMILES
CC1CCCCC1=O- InChIKey
LFSAPCRASZRSKS-UHFFFAOYSA-N- 分子式
- C7H12O
- 平均分子量
- 112.17 g/mol
- 単同位体質量
- 112.088815
名称と識別子
- 優先名称
- 2-Methylcyclohexanone
- IUPAC
- 2-methylcyclohexan-1-one
- 現地名
- 2-メチルシクロヘキサノン
- 英語名
- 2-Methylcyclohexanone
- 分子式
- C7H12O
- 分子量
- 112.17
名称と別名
名称をさらに表示
データベース識別子
- CAS
583-60-8- PubChem CID
- 11419
- DTXSID
DTXSID6052245- ChEMBL
CHEMBL1946183- ChEBI
CHEBI:195390- UNII
- 56E8224ZFJ
- EC Number
- 209-513-6
- Nikkaji
- J3.301D
物性
構造計算による物性
- XLogP
- 1.5
- 極性表面積
- 17.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 8
- 形式電荷
- 0
- 複雑度
- 96
実験および物理化学的性質
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
Melting Point
-6.8 °F (USCG, 1999)
-14 °C
6.8 °F
-14 °C
7 °F
Vapor Pressure
1 mmHg (NIOSH, 2024)
2.25 [mmHg]
1 mmHg
1 mmHg
物理化学的性質
- 融点
- -14 °C · -14 °C
- 沸点
- 162 · 162-163 °C (lit.)
- 比重(密度)
- 0.924 g/mL · 0.924 g/mL at 25 °C (lit.)
- 蒸気圧
- 1 at · 1 at 20 °C (NIOSH, 1997)
- FEMA
- 3946 · 3946 | 2-METHYLCYCLOHEXANONE
- 屈折率
- 20 · n20/D 1.448(lit.)
- 闪点
- 116 °F · 116 °F
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- アルコール、エーテル (Weast, 1986) およびシクロヘキサノンを含む他の多くの極性有機溶媒に可溶。
- 外見
- 液体
- 色
- 無色透明~ごくわずかに黄色
- 臭い (Odor)
- 10 %。ミントペパーミントの清涼感 · ジプロピレングリコール中10.00%。ミントペパーミントの清涼感
- においのタイプ
- ミント系
- 由来生物
- synthetic
- 爆発限界(explosive limit)
- 1.2 % · 1.2%(V)
- 水溶解度
- 水に不溶。メタノール、ジエチルエーテルに可溶。
- 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 データベース
- 583 · 583-60-8(CAS DataBase Reference)
- NISTの化学物質情報
- 2 · Cyclohexanone, 2-methyl-(583-60-8)
- EPAの化学物質情報
- 2 · 2-Methylcyclohexanone (583-60-8)
化学的性質
化学的特性2-Methylcyclohexanone has a weak, peppermint odor and burning sensation
安全と法規制
GHS分類
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
危険有害性情報
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.)
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]
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.
安全と保護具
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.
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]
毒性情報
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.
Non-Human Toxicity Values
LD50 Rabbit oral 1-1.25 g/kg
LD50 Rat oral 2.14 ml/kg
法規制情報
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.)
安全データ
- OEB
- A
- OEL
- TWA: 50 ppm (230 mg/m3), STEL: 75 ppm (345 mg/m3) [skin]
- wgk
- 1
- IDLA
- 600 ppm
- tsca
- TSCA listed
- rtecs
- GW1750000
- ridadr
- UN 2297 3/PG 3
- 毒性
- Acute oral LD50 for rats 2,140 mg/kg, rabbits 1 g/kg (quoted, RTECS, 1985).
- hs_code
- 29142200
- risk_code
- 10-20-20/21/22
- 化審法
- (3)-2411
- 安衛法
- 有機則 第二種有機溶剤等
- 消防法
- 危-4-2-III
- hazard_code
- Xn
- safety_code
- 25-36/37
- hazard_class
- 3
- packing_group
- III
- Hazard Classifications
- Acute Tox. 4 InhalationFlam. Liq. 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 583-60-8(Hazardous Substances Data)
化学と産業
薬理情報
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.
用途と製造
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
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
応用分野
天然物の起源Reported found in cockroaches as attractant pheromone; not reported found in natural foods
使用2-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.
一般的な説明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.
調製方法
2-Methylcyclohexanone is manufactured by the catalytic hydrogenation of o-cresol or by the dehydrogenation of o-methylcyclohexanol. Methylcyclohexanones are used in small amounts as general purpose solvents for cellulose-based finishes and coatings.
製造方法From cyclohexanone by treatment with a base and then with methyl iodide
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