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Basic Information
CAS No.: 814-78-8
Name: Methyl isopropenyl ketone
Article Data: 108
Molecular Structure:
Molecular Structure of 814-78-8 (Methyl isopropenyl ketone)
Formula: C5H8O
Molecular Weight: 84.1179
Synonyms: 2-Methyl-1-buten-3-one;3-Methyl-3-buten-2-one;3-Methylene-2-butanone;Isopropenyl methyl ketone;Methyl isopropenyl ketone;NSC 24150;Propen-2-yl methyl ketone;
EINECS: 212-405-1
Density: 0.816 g/cm3
Melting Point: -54 °C
Boiling Point: 98 °C at 760 mmHg
Flash Point: 11 °C
Solubility: insoluble in water
Appearance: clear colorless liquid
Hazard Symbols: Xi
Risk Codes: 11-23/24/25-36/37/38
Safety: 16-29-33-36/37/39
PSA: 17.07000
LogP: 1.15150
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid

Specification

The IUPAC name of Methyl isopropenyl ketone is 3-methylbut-3-en-2-one. With the CAS registry number 814-78-8, it is also named as 2-Methyl-1-buten-3-one. Besides, it is clear colorless liquid, which should be stored in sealed container in cool and dry place. In addition, it is denser than water and insoluble in water.

The other characteristics of this product can be summarized as: (1)EINECS: 212-405-1; (2)ACD/LogP: 0.59; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 0.59; (5)ACD/LogD (pH 7.4): 0.59; (6)ACD/BCF (pH 5.5): 1.66; (7)ACD/BCF (pH 7.4): 1.66; (8)ACD/KOC (pH 5.5): 49.99; (9)ACD/KOC (pH 7.4): 49.99; (10)H bond acceptors: 1; (11)H bond donors: 0; (12)Freely Rotating Bonds: 1; (13)Index of Refraction: 1.396; (14)Molar Refractivity: 24.81 cm3; (15)Molar Volume: 103 cm3; (16)Surface Tension: 21.2 dyne/cm; (17)Density: 0.816 g/cm3; (18)Flash Point: 11 °C; (19)Melting Point: -54 °C; (20)Enthalpy of Vaporization: 33.74 kJ/mol; (21)Boiling Point: 98 °C at 760 mmHg; (22)Vapour Pressure: 40.7 mmHg at 25 °C.

Preparation of Methyl isopropenyl ketone: this chemical can be prepared by 4-Hydroxy-3-methyl-butan-2-one.



This reaction needs P2O5, H3PO4, Cu and Hydroquinone at temperature of 130 °C. The yield is 69 %.

Uses of Methyl isopropenyl ketone: this chemical is used as solvent and monomer of some polymers. Additionally, it can react with Cyclopenta-1,3-diene to get 1-(2-Methyl-norborn-5-en-2-yl)-ethanone.



This reaction needs ATPH and CH2Cl2 at temperature of -78-0 °C. The yield is 87 %.

When you are using this chemical, please be cautious about it as the following: it is highly flammable and toxic by inhalation, in contact with skin and if swallowed. Please keep away from sources of ignition. And do  not empty into drains. Moreover, it is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing, gloves and eye/face protection. And please take precautionary measures against static discharges. 

People can use the following data to convert to the molecule structure.
(1)SMILES:O=C(\C(=C)C)C
(2)InChI:InChI=1/C5H8O/c1-4(2)5(3)6/h1H2,2-3H3
(3)InChIKey:ZGHFDIIVVIFNPS-UHFFFAOYAC
(4)Std. InChI:InChI=1S/C5H8O/c1-4(2)5(3)6/h1H2,2-3H3
(5)Std. InChIKey:ZGHFDIIVVIFNPS-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LCLo inhalation 250ppm/4H (250ppm)   National Technical Information Service. Vol. OTS0556100,
mouse LD50 intraperitoneal 490mg/kg (490mg/kg)   Personal Communication from H. Zollner, Institut fur Biochemie, Der Universitat, Gras, Oct. 23, 1975Vol. 23OCT1975,
rabbit LD50 skin 230uL/kg (0.23mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LCLo inhalation 125ppm/4H (125ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LD50 oral 180mg/kg (180mg/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.