HuagongsheHuagongshe Chemistry Print Report · For research reference only
5-Methyl-2-hexanone
MIAK · 5-Methylhexan-2-one · METHYL ISOAMYL KETONE · ISOAMYL METHYL KETONE · 5-methyl-hexan-2-one · 5-Methylhexan-2-on · 5-methyl-2-hexanon · 2-Hexanone,5-methyl-
Identifiers & Physical Properties
| CAS No. | 110-12-3 |
|---|---|
| Molecular formula | C7H14O |
| Average molar mass | 114.19 g/mol |
| Monoisotopic mass | 114.10446507 g/mol |
| SMILES | CC(=O)CCC(C)C |
| InChIKey | FFWSICBKRCICMR-UHFFFAOYSA-N |
| PubChem CID | 8034 |
| ChEMBL | CHEMBL45354 |
| ChEBI | CHEBI:88432 |
| EC No. | 203-737-8 |
| DTXSID | DTXSID5021914 |
Chemical & Physical Properties
| XLogP | 1.9 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 3 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 74.5 |
| Chemical classes | Flammable agents - 3rd degreeVolatile Organic Compound (VOC) |
| Lipids | Fatty Acyls [FA] -> Oxygenated hydrocarbons [FA12] |
| Solvents | Solvents -> Ketones (<C12) |
| SpringerMaterials Properties | Boiling point |
| LogP (partition coefficient) | log Kow = 1.881.72 (estimated) |
| Odor | Pleasant, fruity odorpleasant odor |
| Density | 0.81 (NIOSH, 2024) - Less dense than waterwill float0.888 g/cu cm at 20 °C/20 °CRelative density (water = 1): 0.890.89 @ 20°C0.814 g/mL at 25 °C (lit.) |
| Viscosity | 0.77 cP at 20 °C |
| Color/Form | Colorless, clear liquid |
| Solubility | 0.5 % (NIOSH, 2024)In water, 5400 mg/L at 25 °CMiscible with ethanol and ethervery soluble in acetone, benzenesoluble in carbon tetrachlorideMiscible with most org solvents5.4 mg/mL at 25 °CSolubility in water, g/100ml at 20 °C: 0.5 (poor)water: soluble5.4g/L at 25°C5.4 g/L (20 ºC) |
| Flash point | 97 °F (NIOSH, 2024)36 °C96 °F (36 °C) (Closed cup)110 °F (open cup)36 °C c.c.106 °F |
| Boiling point | 291 °F at 760 mmHg (NIOSH, 2024)144 °C144 °C @760 [mm Hg]145 °C (lit.) |
| Melting point | -74 °C |
| Vapor density | 3.94 (vs air) |
| Vapor pressure | 4.5 mm Hg ( 20 °C) |
| Refractive index | n20/D 1.406(lit.) |
| Storage conditions | Store below +30°C. |
| Physical state | Liquid |
| Color | Clear colorless |
| Odor threshold | 0.0021ppm |
| Explosive limits | 1.35-8.2%, 93°F |
| BRN | 506163 |
| Henry's law constant | 6.4×10-2 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Exposure limits | ACGIH:TLV-TWA 20 ppm (93 mg/m3)TLV-STEL 50 ppm (233 mg/m3)OSHA:PEL-TWA 100 ppm (475 mg/m3)NIOSH:REL-TWA 50 ppm |
| InChI | 1S/C7H14O/c1-6(2)4-5-7(3)8/h6H,4-5H2,1-3H3 |
| InChIKey | FFWSICBKRCICMR-UHFFFAOYSA-N |
| SMILES | CC(C)CCC(C)=O |
| LogP (partition coefficient) | 1.88 at 25℃ |
| CAS DataBase Reference | 110-12-3(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 6O4A4A5F28 |
| NIST Chemistry Reference | 2-Hexanone, 5-methyl-(110-12-3) |
| EPA Substance Registry System | Methyl isoamyl ketone (110-12-3) |
| UNSPSC Code | 12352115 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Signal word | Warning |
| GHS hazard statements | H312-H303-H320-H373-H336-H305-H226 |
| GHS precautionary statements | P501-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P312-P331-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P301+P310-P304+P340+P312-P403+P233-P403+P235-P405 |
| Hazard symbols | Xn |
| Risk statements (R) | 10-20 |
| Safety statements (S) | 23-24/25 |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 50 ppm (240 mg/m3) |
| UN transport number | UN 2302 |
| Water hazard class (WGK) | 1 |
| RTECS number | MP3850000 |
| Autoignition temperature | 797 °F |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Acute Tox. 4 InhalationFlam. Liq. 3 |
| Packing group | III |
| Customs code | 29141910 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 110-12-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 3200 mg/kg LD50 dermal Rabbit 8100 mg/kg |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | WarningH226: 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)This chemical does not meet GHS hazard criteria for 0.1% (1 of 771) of reports.H226 (99.9%): Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatory information | Chemical: 2-Hexanone, 5-methyl-2-Hexanone, 5-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Hexanone, 5-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 08-02-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/105382-Hexanone, 5-methyl-: HSNO Approval: HSR001200 Approved with controlsThe 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.) |
| DOT label | Flammable Liquid |
| Fire hazards | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.Flammable. Above 36 °C explosive vapour/air mixtures may be formed. |
| Fire potential | FlammableA flammable liquid when exposed to heat, flame, or oxidizers. |
| Health hazards | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:· Inhalation or contact with material may irritate or burn skin and eyes. |
| Hazards summary | A skin and eye irritant[CAMEO] Inhalation of high concentrations may cause kidney injury and unconsciousness[ICSC] Causes liver injury after repeated high-dose inhalation exposures of rats[HSDB] |
| DOT ID and guide | 2302 127 |
| Reactive group | Ketones |
| EC classification | Symbol: XnR: 10-20S: (2)-23-24/25 |
| UN classification | UN Hazard Class: 3UN Pack Group: III |
| Special Reports | European Chemicals BureauIUCLID Dataset, 5-Methyl-hexan-2-one (110-12-3) 15 p. Summarized information provided to the EU by the European chemicals industry as of 2000. Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of November 2, 2007 |
| TSCA requirements | Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 8/4/1995, Reporting date 10/3/1995.Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Methyl isoamyl ketone is included on this list. Effective date 8/4/1995, Sunset date 6/30/1998. |
| Fire fighting | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:Use AFFF, alcohol-resistant foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | Fresh air, rest. Refer for medical attention.First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Refer for medical attention . |
| Accidental release measures | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| First aid | Excerpt from NIOSH Pocket Guide for Methyl isoamyl ketone:General First Aid:(General first aid procedures) |
| Safe storage | Fireproof. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA).10.0 [ppm] |
| Fire fighting procedures | If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. |
| Storage conditions | ... Store in tightly closed containers in a cool, well ventilated area away from sources of oxidizers (such as perchlorates, peroxides, permanganates, chlorates, and nitrates), strong oxidizers (such as chlorine, bromine, and fluorine), reducing agents, and aldehydes. Sources of ignition such as smoking and open flames are prohibited where methyl isoamyl ketone is handled, used or stored. Metal containers involving the transfer of 5 gallons or more of methyl isoamyl ketone should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. |
| Cleanup methods | Evacuate and restrict persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Establish forced ventilation to keep levels below explosive limit. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or similar material and deposit in sealed containers. Keep this chemical out of a confined space ... because of the possibility of an explosion ... It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable.Environmental considerations -- land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents.Environmental considerations -- water spill: Use natural barriers or oil spill control booms to limit spill travel. Remove trapped material with suction hoses.Environmental considerations -- air spill: Apply water spray or mist to knock down vapors. |
| Nonfire spill response | Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]: |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.IncinerationThe following wastewater treatment technologies have been investigated for methyl isoamyl ketone: Activated carbon. |
| Spillage disposal | Personal protection: filter respirator for organic gases and vapours adapted to the airborne concentration of the substance. Ventilation. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Do NOT wash away into sewer. |
| Target organs | Eyes, skin, respiratory system, central nervous system, liver, kidneys |
| Ecotoxicity values | EC50 Pimephales promelas (fathead minnow) 30 days old 159 mg/L/96 hrflow through, 25 °C, pH 7.6, hardness 43.0 mg/L CaCO3, alkalinity 42.5 mg/L CaCO3, dissolved oxygen 6.5 mg/LEffect: Affected fish did not school and lost equilibrium prior to death. /97+% purity/Species: Chlorococcales (Green algae)Conditions: freshwater, staticConcentration: 920 mg/L for 24 hrEffect: physiology, assimilation efficiencyLC50Species: Daphnia magna (Water flea, age < or =24 hr)Conditions: freshwater, static, 20-22 °C, pH 7.6-7.7, hardness 16 dHConcentration: 1700 mg/L for 24 hr |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 5-methyl-2-hexanone is expected to have moderate mobility in soil(SRC). Volatilization of 5-methyl-2-hexanone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-4 atm-cu m/mole(SRC) derived from its vapor pressure, 5.77 mm Hg(4), and water solubility, 5400 mg/L(5). 5-Methyl-2-hexanone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Biodegradation data were not available(SRC, 2007).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.88(2) and a regression-derived equation(3), indicates that 5-methyl-2-hexanone is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 5.77 mm Hg(4), and water solubility, 5400 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 hours and 6.2 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 6(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2007).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-methyl-2-hexanone, which has a vapor pressure of 5.77 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 5-methyl-2-hexanone is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 37 hours(SRC), calculated from its rate constant of 1.0X10-11 cu cm/molecule-sec at 25 °C(3). 5-Methyl-2-hexanone contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| Food survey values | 5-Methyl-2-hexanone was detected not quantified as a volatile component of roasted filberts(1), fried bacon(2), cooked beef(3) and cooked pork(3). |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Exposure routes | The substance can be absorbed into the body by inhalation of its vapour.inhalation, ingestion, skin and/or eye contact |
| Signs and Symptoms | Cough. Headache. Dizziness. Drowsiness. Laboured breathing. Sore throat.Dry skin. Redness.Nausea. See Inhalation.irritation eyes, skin, mucous membraneheadache, narcosis, comadermatitisIn Animals: liver, kidney damage |
| Effluent Concentrations | 5-Methyl-2-hexanone has been identified, not quantified in wastewater effluent concentrates collected from an advanced wastewater treatment facility in Lake Tahoe, CA(1). 5-Methyl-2-hexanone was identified in the emissions of semiconductor manufacturing plants in Hsin-chu, Taiwan over the period from October 2000 to September 2001(2). |
| Soil Adsorption/Mobility | The Koc of 5-methyl-2-hexanone is estimated as 250(SRC), using a log Kow of 1.88(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 5-methyl-2-hexanone is expected to have moderate mobility in soil. |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Repeated skin exposure may result in contact dermatitis of both the allergic and nonallergic types. |
| Artificial Pollution Sources | 5-Methyl-2-hexanone's production and use as a solvent for high-solids coatings(1), nitrocellulose, cellulose acetate, acrylics and vinyl copolymers(2) will result in its release to the environment through various waste streams(SRC). |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| FIFRA requirements | Methyl isoamyl ketone is exempted from the requirement of a tolerance when used as a solvent, cosolvent in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops only. |
| Occupational exposure band (OEB) | A |
| Occupational exposure limit (OEL) | TWA: 50 ppm (240 mg/m3) |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| RTECS number | MP3850000 |
| UN transport number | UN 2302 |
| Customs code | 29141910 |
| Toxicity | LD50 orally in Rabbit: 3200 mg/kg LD50 dermal Rabbit 8100 mg/kg |
| Risk statements (R) | 10-20 |
| Signal word | Warning |
| GHS pictogram | GHS02,GHS07,GHS08 |
| Hazard symbols | Xn |
| Safety statements (S) | 23-24/25 |
| Hazard class | 3Acute Tox. 4 InhalationFlam. Liq. 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | III |
| GHS hazard statements | H312-H303-H320-H373-H336-H305-H226 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| Autoignition temperature | 797 °F |
| GHS precautionary statements | P501-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P370+P378-P312-P331-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P301+P310-P304+P340+P312-P403+P233-P403+P235-P405 |
| Hazardous substances data | 110-12-3(Hazardous Substances Data) |
Applications & Uses
Description
MIAK is a colorless liquid with a pleasant,fruity odor. Molecular weight = 114.21; Specific gravity(H2O:1) 5 0.81; Boiling point = 144℃; Freezing/Meltingpoint 5 2 74℃; Vapor pressure 5 5 mmHg at 20℃; Flashpoint 5 36.1℃ (cc); Autoignition temperature 5 191℃.Explosive limits: LEL 5 1.0% at 93.3℃; UEL 5 8.2% at93.3℃. Hazard Identification (based on NFPA-704 MRating System): Health 1, Flammability 2, Reactivity 0.Slightly soluble in water; solubility 5 0.5%.
Uses
5-Methyl-2-hexanone is used as a solvent for the production of high-solids coatings, because it possesses a high solubility for alkyd resins, acrylic resins, cellulose esters, cellulose nitrate, and vinylic copolymers. 5-Methyl-2-hexanone may be used to synthesize N,N′-bis(1,4-dimethylpentyl)-p-phenylenediamine (BMPPD) via reductive alkylation of p-nitroaniline in the presence of copper-based catalysts.
General Description
5-methylhexan-2-one appears as a colorless liquid with a pleasant fruity odor. Less dense than water. Vapors heavier than air. Used as a solvent and for making other chemicals.
Preparation & Synthesis
Preparation
5-Methyl-2-hexanone is produced by condensation of acetone with isobutyraldehyde. This reaction may be carried out in one or two steps, in the liquid or in the gas phase.