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5-Methyl-2-hexanone

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Name

5-Methyl-2-hexanone

EINECS 203-737-8
CAS No. 110-12-3 Density 0.806 g/cm3
PSA 17.07000 LogP 2.01160
Solubility 5.4 g/L (20 °C) in water Melting Point -74 °C
Formula C7H14O Boiling Point 144 °C at 760 mmHg
Molecular Weight 114.188 Flash Point 41.1 °C
Transport Information UN 2302 3/PG 3 Appearance clear colourless liquid
Safety 23-24/25 Risk Codes 10-20
Molecular Structure Molecular Structure of 110-12-3 (5-Methyl-2-hexanone) Hazard Symbols HarmfulXn
Synonyms

2-Methyl-5-hexanone;3-Methylbutyl methyl ketone;Isoamyl methyl ketone;Isopentyl methyl ketone;MIAK;Methyl isoamyl ketone;Methyl isopentyl ketone;

Article Data 73

5-Methyl-2-hexanone Synthetic route

1669-43-8, 5166-53-0, 1821-29-0

(E)-4-isopropylbut-3-en-2-one

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With water; zinc; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 90℃; for 20h;99%
With dicobalt octacarbonyl; water In 1,2-dimethoxyethane for 2h; Heating;91 % Chromat.
With 1,3-bis-(diphenylphosphino)propane; caesium carbonate; isopropyl alcohol; bis(1,5-cyclooctadiene)diiridium(I) dichloride In toluene at 80℃; for 4h;
73503-97-6

5-methyl-2-(trimethylsiloxy)-1-hexene

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With tributyltin fluoride; dichlorobis(tri-O-tolylphosphine)palladium In benzene for 0.5h; Product distribution; Heating; other catalysts;96%
627-59-8

5-methylhexan-2-ol

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With pyridine; tert-butylhypochlorite In dichloromethane for 1h;93%
With Oxone; sodium chloride In water; ethyl acetate at 20℃; for 4h;80%
With potassium permanganate; sulfuric acid
624-44-2

5-methyl-hexan-2-one oxime

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With hydrogenchloride; sodium chlorite In water at 20℃; for 0.0833333h;92%

(5-methyl-2-hexen-2-yl)pentamethyl phosphoric triamide

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With sulfuric acid In benzene for 4h; Heating;90%
3524-73-0

5-methyl-1-hexene

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetonitrile at 55℃; for 12h; Wacker Oxidation;84%
876-27-7

4-chlorophenyl acetate

146513-95-3, 146560-03-4, 93399-99-6

(rac,E)-5-methylhex-3-en-2-ol

A

1669-43-8, 5166-53-0, 1821-29-0

(E)-4-isopropylbut-3-en-2-one

B

110-12-3

5-Methyl-2-hexanone

C

(R,E)-5-methylhex-3-en-2-yl acetate

Conditions
ConditionsYield
With RuCl3H(p-cymene)2; immobilized lipase from Pseudomonas cepacia; triethylamine In dichloromethane at 20 - 25℃; for 48h; Acetylation; oxidation; reduction; Enzymatic reaction;A n/a
B n/a
C 83%
67-56-1

methanol

75-30-9

2-iodo-propane

97-94-9

triethyl borane

78-94-4

methyl vinyl ketone

A

591-78-6

n-hexan-2-one

B

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
In hexane; benzene at 25℃; for 0.0833333h;A 15%
B 79%
67-56-1

methanol

75-30-9

2-iodo-propane

78-94-4

methyl vinyl ketone

A

591-78-6

n-hexan-2-one

B

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With triethyl borane In hexane; benzene at 25℃; for 0.0833333h;A 15%
B 79%
With triethyl borane In hexane; benzeneA 15%
B 79%
67-56-1

methanol

97-94-9

triethyl borane

78-94-4

methyl vinyl ketone

A

591-78-6

n-hexan-2-one

B

110-12-3

5-Methyl-2-hexanone

Conditions
ConditionsYield
With 2-iodo-propane In hexane; benzeneA 15%
B 79%

5-Methyl-2-hexanone Consensus Reports

Reported in EPA TSCA Inventory.

5-Methyl-2-hexanone Standards and Recommendations

OSHA PEL: TWA 50 ppm
ACGIH TLV: TWA 50 ppm
NIOSH REL: Ketones (Methyl Isoamyl Ketone) TWA 230 mg/m3
DOT Classification:  3; Label: Flammable Liquid

5-Methyl-2-hexanone Specification

The IUPAC name of Methyl isoamyl ketone is 5-methylhexan-2-one. With the CAS registry number 110-12-3 and EINECS 203-737-8, it is also named as 2-Hexanone, 5-methyl-. The classification codes are Agricultural Chemical; Skin / Eye Irritant; TSCA Flag T [Subject to the Section 4 test rule under TSCA]; Unspecified / Unclassified pesticide. It is clear colourless liquid with a pleasant fruity odor. When heated to decomposition it emits acrid smoke and irritating fumes. So the storage environment should be well-ventilated, low-temperature and dry. Keep Methyl isoamyl ketone separate from oxidant.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.78; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.78; (4)ACD/LogD (pH 7.4): 1.78; (5)ACD/BCF (pH 5.5): 13.36; (6)ACD/BCF (pH 7.4): 13.36; (7)ACD/KOC (pH 5.5): 222.62; (8)ACD/KOC (pH 7.4): 222.62; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 17.07 Å2; (13)Index of Refraction: 1.401; (14)Molar Refractivity: 34.46 cm3; (15)Molar Volume: 141.5 cm3; (16)Polarizability: 13.66×10-24 cm3; (17)Surface Tension: 23.9 dyne/cm; (18)Density: 0.806 g/cm3; (19)Flash Point: 41.1 °C; (20)Enthalpy of Vaporization: 38.11 kJ/mol; (21)Boiling Point: 144 °C at 760 mmHg; (22)Vapour Pressure: 5.2 mmHg at 25°C.

Preparation of Methyl isoamyl ketone: It can be obtained by 5-methyl-2-(trimethylsiloxy)-1-hexene. This reaction needs reagent tributyltin fluoride, catalytic agent PdCl2(P(o-MeC6H4)3)2 and solvent benzene by heating. The reaction time is 30 min. The yield is 96%.

Methyl isoamyl ketone can be obtained by 5-methyl-2-(trimethylsiloxy)-1-hexene

Uses of Methyl isoamyl ketone: It is used in organic synthesis. For example: it can react with 4-methoxy-benzaldehyde to get 1-(4-methoxy-phenyl)-6-methyl-hept-1-en-3-one. This reaction needs catalytic agent Ba(OH)2 C-200 and solvent ethanol by heating. The reaction time is 1 hours. The yield is 89%.

Methyl isoamyl ketone can react with 4-methoxy-benzaldehyde to get 1-(4-methoxy-phenyl)-6-methyl-hept-1-en-3-one

When you are using this chemical, please be cautious about it as the following:
It is not only flammable, but also harmful by inhalation. So people should not breathe vapour and avoid contact with skin and eyes.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C(C)CCC(C)C
2. InChI:InChI=1/C7H14O/c1-6(2)4-5-7(3)8/h6H,4-5H2,1-3H3
3. InChIKey:FFWSICBKRCICMR-UHFFFAOYAQ

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD skin > 20mL/kg (20mL/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0535379,
mouse LD50 intraperitoneal 800mg/kg (800mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0535379,
mouse LD50 oral 2542mg/kg (2542mg/kg)   Toxicology Letters. Vol. 30, Pg. 13, 1986.
rabbit LD50 skin 10mL/kg (10mL/kg)   Union Carbide Data Sheet. Vol. 8/7/1963,
rat LC50 inhalation 3813ppm/6H (3813ppm) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0535379,
rat LD50 oral 3200mg/kg (3200mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0535379,
rat LDLo intraperitoneal 400mg/kg (400mg/kg) CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
National Technical Information Service. Vol. OTS0535379,

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