Methyl isopropenyl ketone

HCID 13143

Basic information

CAS
54789-11-6
Standard SMILES
C=C(C)C(C)=O
InChIKey
ZGHFDIIVVIFNPS-UHFFFAOYSA-N
Molecular formula
C5H8O
Average molar mass
84.12 g/mol
Monoisotopic mass
84.05751488

Overview

Methyl isopropenyl ketone, stabilized appears as a clear colorless liquid. Flash point of 52 °F. Denser than water and insoluble in water. Hence sinks in water. Vapors heavier than air.

Names & identifiers

Preferred name
Methyl isopropenyl ketone
IUPAC
3-methylbut-3-en-2-one
English name
3-Methyl-3-buten-2-one
Molecular formula
C5H8O
Molecular weight
84.12

Names & synonyms

3-Methyl-3-buten-2-one814-78-83-Methylbut-3-en-2-oneIsopropenyl methyl ketone3-Buten-2-one, 3-methyl-METHYL ISOPROPENYL KETONEMethyl butenone2-Methyl-1-buten-3-oneKetone, methyl isopropenylPropen-2-yl methyl ketone3-Methyl-3-butene-2-one3-Methyl-3-buten-2-on
Show more names
3-Methyl-3-buten-2-one (stabilized with HQ)Stabilizedwithhqmethylbutenone[qr]CH2=C(CH3)C(=O)CH3Methylisopropenylketon3-Methylene-2-butanone
2-Methyl-1-butene-3-one3-Butene-2-one, 3-methylCCRIS 5317HSDB 11643-Methyl-3-buten-2-on [German]EINECS 212-405-1NSC 24150UN1246

Database identifiers

CAS
54789-11-6、814-78-8
PubChem CID
13143
DTXSID
DTXSID9052557
ChEBI
CHEBI:88437
UNII
F64867GQVB
EC Number
212-405-1
Nikkaji
J35.118K

Properties

Computed structural properties

XLogP
0.9
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
1
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesFlammable agents - 3rd degree
PolymersPlastics & Rubber -> Other Monomers
SpringerMaterials PropertiesBoiling point
Odor · 2 items

PLEASANT

PUNGENT

TasteSWEET
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food

Physicochemical properties

Melting point
-54 °C · -54°C
Boiling point
98 °C · 98°C
Density
0 · 0,86 g/cm3
refractive index
1.421 to · 1.4210 to 1.4250
Flash point
9 °C · 9°C
storage temp.
Freezer

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

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

P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P316, P319, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 130 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

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

Hazard information

Regulatory Information · 3 items

Chemical: 3-Buten-2-one, 3-methyl-

3-Buten-2-one, 3-methyl-: 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 · 2 items

Behavior in Fire: May polymerize and explode. (USCG, 1999)

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

Fire PotentialFlammable, dangerous fire risk
Health Hazards · 2 items

Inhalation causes irritation of nose and throat. Liquid may cause severe damage to eyes, resulting possibly in some permanent impairment of vision; vapor produces tears. If not removed promptly from skin, liquid may cause delayed pain and blistering. Ingestion causes irritation of mouth and stomach. (USCG, 1999)

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

Hazards Summary · 1 item

Highly toxic by inhalation, skin absorption, and ingestion; A skin, eye, and respiratory tract irritant; Strong lachrymator; [HSDB] Readily polymerizes; Explosive in air at 1.8-9.0%; [Hawley] Methyl isopropenyl ketone, stabilized (UN1246) has warning of explosive polymerization; [ERG 2016]

Safety & protection

Fire FightingExcerpt from ERG Guide 127 [Flammable Liquids (Water-Miscible); polymerization hazard]:
Accidental Release Measures · 2 items

· 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 · 2 items

INHALATION: remove victim from exposure; give artificial respiration if needed; call physician.

General First Aid:

Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresDry chemical, foam, carbon dioxide. Water may be ineffective. /inhibited/
Storage Conditions · 2 items

...MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS...SHOULD BE STORED IN A COOL, WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, AND SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED...

/Store/...at subzero temp to prevent polymerization.

Toxicology

Adverse EffectsLacrimator (Lachrymator) - A substance that irritates the eyes and induces the flow of tears.
Human Toxicity Excerpts · 3 items

...A DEFINITE SKIN IRRITANT. ...DEVELOPMENT OF BLISTERING & PAIN MAY NOT OCCUR IMMEDIATELY UPON CONTACT. SEVERAL MINUTES MAY ELAPSE BEFORE SUCH MANIFESTATIONS ARISE.

...MODERATE TO HIGH DEGREE OF TOXICITY BY SINGLE ORAL EXPOSURE. EYE CONTACT...MAY RESULT IN SEVERE DAMAGE RESULTING...IN...PERMANENT IMPAIRMENT OF VISION... VAPORS ARE ALSO HIGHLY TOXIC AS WELL AS IRRITATING TO THE RESPIRATORY PASSAGES.

METHYL ISOPROPENYL KETONE IS HIGHLY TOXIC BY THE ORAL, PERCUTANEOUS, & RESPIRATORY ROUTES. TOPICAL EXPOSURE TO THE SKIN MAY BE MODERATELY IRRITATING WHILE TOPICAL OR VAPOR EXPOSURE TO THE EYE MAY BE SEVERELY IRRITATING.

Non-Human Toxicity Excerpts · 2 items

When tested by application to rabbit eyes, methyl isopropenyl ketone was found to cause severe irritation & damage. ...moderate irritant to rabbit skin particularly when applied under a wrap. ... Rats survived a 90-min exposure to nominal vapor concn of 524 ppm, but exhibited...irritation of ocular & nasal tissues. At a nominal vapor of 1455 ppm for 30 min.../irritation/ & deaths occurred in minutes. Animals dying during these exposures were cyanotic & died in convulsions.

7-hr exposures of rats, guinea pigs, & rabbits for 20 exposures in 28 days at...30 ppm resulted in...ocular & nasal irritation in all species, death & weight loss in rats, & decreased growth in guinea pigs. In rats, the lungs were severely affected &...changes were found in the kidneys & spleen. Leukocytosis was also observed. Organs of other species were not significantly affected. One hundred 7-hr exposures of 15 ppm...to rats, guinea pigs, & rabbits over 140-day period produced ocular & nasal irritation in all animals. Also, mortality, leukocytosis, & slight renal damage characterized by increased kidney weight & slight tubular damage occurred in the rats.

Probable Routes of Human Exposure · 1 item

Short-term exposures...ranging from 0.291 to 14.5 ppm have been reported. There was a questionable odor but no irritation at 0.291 ppm. At 0.77 ppm, there was an immediate definite odor & the vapors were evident to the eyes after a few min. At 1.45 & 2.91 ppm, eye irritation was apparent. At 14.5 ppm, there was an immediate strong odor with eye irritation...after 2 min. Ocular irritation rapidly increased in severity with time. ... Industrial exposures are likely to be by inhalation, skin & eye contact. Its strong irritating & lacrimatory properties may not prevent toxicity because these effects are often not immediately sensed.

Toxicity DataLCLo (rat) = 125 ppm/4h

Safety data

wgk
WGK 3
tsca
TSCA listed
rtecs
EN0175000
ridadr
UN 1246 (METHYL ISOPROPENYL KETONE, STABILIZED)
hs_code
29141900
risk_code
11-23/24/25-36/37/38-27-25

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Uses & manufacturing

Uses · 3 items

Used to make plastics; [HSDB]

MFR OF PLASTICS

AS MONOMER IN COMMERCIAL COPOLYMERS; SOLVENT

U.S. Exports(1986) No Data
U.S. Imports(1986) No Data
U.S. Production(1986) No Data
Methods of Manufacturing · 2 items

...MADE COMMERCIALLY EITHER BY CATALYTIC HYDRATION OF ISOPROPYL ACETYLENE OR BY CONDENSATION OF ACETYLENE WITH ACETONE TO FORM DIMETHYL ETHYNYL CARBINOL, WHICH IS THEN REACTED WITH ACETIC ACID TO FORM DIMETHYL ACETYL CARBINOL ACETATE. THIS IS THEN PYROLYZED TO METHYL ISOPROPENYL KETONE. IT CAN ALSO BE MADE BY REACTING BUTANONE WITH FORMALDEHYDE IN PRESENCE OF CAUSTIC TO YIELD 2-METHYL-3-KETO-BUTANOL, WHICH IS IN TURN CRACKED TO...2-METHYL-1-BUTENE-3-ONE.

CONDENSATION OF METHYL ETHYL KETONE WITH FORMALDEHYDE IN PRESENCE OF NaOH

General Manufacturing Information · 2 items

3-Buten-2-one, 3-methyl-: ACTIVE

Inhibitor of polymerization: up to 1% hydroquinone. /inhibited/

Applications

UsesPlastics.

General DescriptionA clear colorless liquid. Flash point of 52°F. Denser than water and insoluble in water. Hence sinks in water. Vapors heavier than air.

Additional notes

DefinitionChEBI: 3-Methyl-3-buten-2-one is an olefinic compound. It is functionally related to an acrylic acid.

Related reactions

9 records

Compound notes

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