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CAS No.: | 110-12-3 |
---|---|
Name: | 5-Methyl-2-hexanone |
Article Data: | 73 |
Molecular Structure: | |
Formula: | C7H14O |
Molecular Weight: | 114.188 |
Synonyms: | 2-Methyl-5-hexanone;3-Methylbutyl methyl ketone;Isoamyl methyl ketone;Isopentyl methyl ketone;MIAK;Methyl isoamyl ketone;Methyl isopentyl ketone; |
EINECS: | 203-737-8 |
Density: | 0.806 g/cm3 |
Melting Point: | -74 °C |
Boiling Point: | 144 °C at 760 mmHg |
Flash Point: | 41.1 °C |
Solubility: | 5.4 g/L (20 °C) in water |
Appearance: | clear colourless liquid |
Hazard Symbols: | Xn |
Risk Codes: | 10-20 |
Safety: | 23-24/25 |
Transport Information: | UN 2302 3/PG 3 |
PSA: | 17.07000 |
LogP: | 2.01160 |
(E)-4-isopropylbut-3-en-2-one
5-Methyl-2-hexanone
Conditions | Yield |
---|---|
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; |
5-methyl-2-(trimethylsiloxy)-1-hexene
5-Methyl-2-hexanone
Conditions | Yield |
---|---|
With tributyltin fluoride; dichlorobis(tri-O-tolylphosphine)palladium In benzene for 0.5h; Product distribution; Heating; other catalysts; | 96% |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium chlorite In water at 20℃; for 0.0833333h; | 92% |
5-Methyl-2-hexanone
Conditions | Yield |
---|---|
With sulfuric acid In benzene for 4h; Heating; | 90% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 55℃; for 12h; Wacker Oxidation; | 84% |
4-chlorophenyl acetate
(rac,E)-5-methylhex-3-en-2-ol
A
(E)-4-isopropylbut-3-en-2-one
B
5-Methyl-2-hexanone
Conditions | Yield |
---|---|
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% |
methanol
2-iodo-propane
triethyl borane
methyl vinyl ketone
A
n-hexan-2-one
B
5-Methyl-2-hexanone
Conditions | Yield |
---|---|
In hexane; benzene at 25℃; for 0.0833333h; | A 15% B 79% |
Reported in EPA TSCA Inventory.
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
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%.
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%.
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, |