3-Methyl-2-butanone

HCID 11251CAS 563-80-4

Grundinformationen

Standard-SMILES
CC(=O)C(C)C
InChIKey
SYBYTAAJFKOIEJ-UHFFFAOYSA-N
Summenformel
C5H10O
Durchschnittliche Molmasse
86,13 g/mol
Monoisotopische Masse
86,07316494

Überblick

3-methylbutan-2-one appears as a colorless liquid with a pleasant odor. Flash point below 70 °F. Less dense than water. May be toxic by inhalation and skin absorption. Used as a solvent.

Namen und Bezeichner

Bevorzugter Name
3-Methyl-2-butanone
IUPAC
3-methylbutan-2-one
Lokaler Name
3-Methylbutanon
Englischer Name
3-Methyl-2-butanone
Summenformel
C5H10O
Molmasse
86.13

Namen und Synonyme

3-METHYL-2-BUTANONE563-80-43-Methylbutan-2-oneMethyl isopropyl ketoneIsopropyl methyl ketone2-Acetylpropane2-Butanone, 3-methyl-MIPKKetone, isopropyl methyl2-Acetyl propaneMethylbutanoneDTXSID0022062
Weitere Namen anzeigen
3-methyl-butan-2-one3-Methylbutanone2-METHYL-3-BUTANONE2-Butanone,3-methyl--2-butanone
V8DP6THY5ONSC-9379DTXCID8020623-methyl butan-2-one2-isopentanoneRefChem:817814209-264-3Methyl butanone-2

Datenbank-Bezeichner

CAS
563-80-4
PubChem CID
11251
DTXSID
DTXSID0022062
ChEMBL
CHEMBL3183920
ChEBI
CHEBI:179699
UNII
V8DP6THY5O
EC Number
209-264-3
Nikkaji
J43.513I

Eigenschaften

Berechnete Struktureigenschaften

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

Experimentelle und physikochemische Eigenschaften

Chemical ClassesFlammable agents - 3rd degree
LipidsFatty Acyls [FA] -> Oxygenated hydrocarbons [FA12]
SolventsSolvents -> Ketones (<C12)
SpringerMaterials PropertiesSchoenflies notation
FragrancesFragrance Ingredient (3-Methyl-2-butanone) -> IFRA transparency List
LogP · 3 Einträge

log Kow = 0.84

0.84

0.84

Physikochemische Eigenschaften

Schmelzpunkt
-92 °C · -92 °C (lit.)
Siedepunkt
94 · 94-95 °C (lit.)
Dichte
0.805 g/mL · 0.805 g/mL at 25 °C (lit.)
Dampfdruck
53.33 hPa · 53.33 hPa (19.9 °C)
Brechungsindex
20 · n20/D 1.388(lit.)
Flammpunkt
6 °C · 6 °C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P271, P280, P303+P361+P353, P304+P340, P317, P319, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: 2-Butanone, 3-methyl-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

2-Butanone, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Butanone, 3-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: 13-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/10392

Isopropyl methyl ketone: Does not have an individual approval but may be used under an appropriate group standard

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.)

DOT LabelFlammable Liquid
Fire Hazards · 3 Einträge

Special Hazards of Combustion Products: Acrid smoke and fumes (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Heating will cause rise in pressure with risk of bursting. Vapour/air mixtures are explosive.

Fire PotentialFlammable when exposed to heat or flame
Health Hazards · 2 Einträge

Irritating to the eyes, nose, throat, upper respiratory tract, and skin. (USCG, 1999)

· Inhalation or contact with material may irritate or burn skin and eyes.

Hazards Summary · 1 Eintrag

A skin, eye, and respiratory tract irritant; Inhalation of high concentrations can cause CNS depression; [ICSC] An irritant; [MSDSonline] Causes narcosis in experimental animals fed high doses by oral gavage; TLV Basis is toxicity to embryo, fetus, and newborn; [ACGIH]

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible)]:

Use foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

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 · 2 Einträge

· 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 · 3 Einträge

Excerpt from NIOSH Pocket Guide for Methyl isopropyl ketone:

General First Aid:

(General first aid procedures)

Safe StorageFireproof. Separated from flammable substances and strong oxidants. Well closed. Store in an area without drain or sewer access.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

Toxikologische Informationen

Body Burden · 1 Eintrag

Methyl isopropyl ketone was detected in exhaled breath samples collected from a prediabetic population of 14 Chicago, Illinois residents(1). During a study of the occurrence of volatile organic compounds in human milk samples from five industrial US cities, methyl isopropyl ketone was detected in one milk sample collected in Jersey City, NJ and one milk sample collected in Pittsburgh, PA(2,3).

Target OrgansEyes, skin, respiratory system
Ecotoxicity Values · 5 Einträge

EC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1110000 ug/L for 24 hr; Effect: behavior, equilibrium

EC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1120000 ug/L for 48 hr; Effect: behavior, equilibrium

LC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1290000 ug/L for 24 hr

LC50; Species: Pimephales promelas (Fathead minnow, age 30 days, length 20 mm, weight 0.128 g); Conditions: freshwater, flow through, 24.1 (22.4-25.5) °C, pH 7.6, hardness 52.0 mg/L CaCO3, alkalinity 35.0 mg/L CaCO3, dissolved oxygen 86.4% (74.5-92.7%); Concentration: 1200000 ug/L for 48 hr

For more Ecotoxicity Values (Complete) data for Methyl isopropyl ketone (6 total), please visit the HSDB record page.

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 38(SRC), determined from a log Kow of 0.84(2) and a regression-derived equation(3), indicates that methyl isopropyl ketone is expected to have very high mobility in soil(SRC). Volatilization of methyl isopropyl ketone from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.13X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 52.2 mm Hg at 25 °C(4), and water solubility, 5.237X10+4 mg/L(5). Methyl isopropyl ketone is expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(4). Methyl isopropyl ketone reached 99% of its theoretical BOD using an activated sludge inoculum in the Japanese MITI test(6) suggesting that biodegradation is an important environmental fate process for this substance in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 38(SRC), determined from a log Kow of 0.84(2) a regression-derived equation(3), indicates that methyl isopropyl ketone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 1.13X10-4 atm-cu m/mole(SRC), derived from its vapor pressure, 52.2 mm Hg at 25 °C(5), and water solubility, 5.237X10+4 mg/L at 30 °C(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 5.8 hours and 5.9 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 1.4(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Methyl isopropyl ketone reached 99% of its theoretical BOD using an activated sludge inoculum in the Japanese MITI test(9) suggesting that biodegradation is an important environmental fate process for this substance in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), methyl isopropyl ketone, which has a vapor pressure of 52.2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase methyl isopropyl ketone 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 5.6 days(SRC), calculated from its rate constant of 2.87X10-12 cu cm/molecule-sec at 25 °C(3). Methyl isopropyl ketone's UV absorption spectrum shows maximum absorption near 280 nm with a shoulder extending above 290 nm(4); therefore, this substance may be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values · 1 Eintrag

Methyl isopropyl ketone has been detected in the meat volatiles of chicken and beef(1). Reported mean concentrations of methyl isopropyl ketone measured in the headspace volatiles of wines from six regions of the Napa Valley, California ranged from 0.001 to 0.225 mg/L(2).

Adverse EffectsNeurotoxin - Acute solvent syndrome

Sicherheitsdaten

OEB
A
OEL
TWA: 200 ppm (705 mg/m3)
wgk
1
tsca
TSCA listed
ridadr
UN 2397
hs_code
29141990

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

Ketones are not readily metabolized in the body. With most of the lower ketones as much as 50% of the dose may be eliminated unchanged from the body, mainly in the exhaled air and to a small extent in the urine. The major metabolic pathway of ketones is reduction to the corresponding secondary alcohols, which are usually eliminated as glucuronic acids. In rats, 38-54% of a dose of 1000 mg/kg bw methyl isopropyl ketone was eliminated unchanged in about 25-35 hours, mainly in the expired air. Administration of this ketone to rabbits increased the glucuronic acid output. It has been suggested that MIPK is a normal constituent of human urine.

Absorption, Distribution and ExcretionWhen a dose of 1000 mg/kg methyl isopropyl ketone was administered to rats, 38-54% was eliminated unchanged in 25-35 hours, predominantly in the expired air.

Verwendung und Herstellung

Uses · 5 Einträge

A pyrolysis product from hot gas welding of PVC plastic; [ACGIH]

Burning Synthetic Polymers [Category: Burn]

3-Methyl-2-butanone is employed predominantly as an intermediate for the production of pharmaceuticals, herbicides, and dye precursors. It is also used in the synthesis of rubber auxiliaries and for the selective extraction of rare earth elements.

Solvent for nitrocellulose lacquers.

Solvent

U.S. Production · 4 Einträge

2023: 1,000,000 - <5,000,000 lb

2-Butanone, 3-methyl- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7756]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Butanone, 3-methyl-. Aggregated National Production Volume: 1 to < 10 million lbs.

Industry UsesIntermediate
Methods of Manufacturing · 5 Einträge

Condensation of 2-butanone, formaldehyde, and hydrogen in a single step over palladium, or in two steps by condensation on a strongly acidic cation exchanger, isolation of the 2-methyl-1-buten-3-one, followed by hydrogenation.

By reaction of isobutyraldehyde with acetaldehyde in the gas phase over manganese oxide-aluminum oxide at 450 °C. Isobutyric acid and acetic acid may be used in place of isobutyraldehyde and acetaldehyde.

By addition of water to isoprene at ca. 200 °C in the presence of phosphoric acid on silica.

By oxidation of 2-methyl-2-butene with oxygen or hydroperoxides in the presence of molybdenum naphthenate at 150 °C.

Synthetic, also by fermentation.

Use ClassificationFragrance Ingredients
General Manufacturing Information · 3 Einträge

All Other Basic Organic Chemical Manufacturing

2-Butanone, 3-methyl-: ACTIVE

Synthetic, also by fermentation.

Anwendungen

Verwenden3-Methyl-2-butanone is used for synthesis of heterocyclic compounds and important intermediate of medicine. It is used as an industrial solvent.

Darstellung

synthetische3-Methyl-2-butanone is produced by oxidation of Methyl-iso-propylcarbinol (2-Methyl-3-butanol).

Anbieter50 Anbieter

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