1447-26-3

Basic information

• Product Name: 5-Methyl-4-hepten-3-one
• Synonyms: 5-Methyl-4-hepten-3-one;4-Hepten-3-one,5-Methyl-;5-methylhept-4-en-3-one
• CAS NO: 1447-26-3
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.2
• Mol File: 1447-26-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: -66.9°C (estimate)
• Boiling Point: 166.55°C
• Flash Point: 59.9°C
• Appearance: /
• Density: 0.8591
• Vapor Pressure: 1.78mmHg at 25°C
• Refractive Index: 1.4476
• CAS DataBase Reference: 5-Methyl-4-hepten-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-4-hepten-3-one(1447-26-3)
• EPA Substance Registry System: 5-Methyl-4-hepten-3-one(1447-26-3)

Safety Data

• Hazardous Substances Data: 1447-26-3(Hazardous Substances Data)

Usage

Description

5-Methyl-4-hepten-3-one is an organic compound with the molecular formula C8H14O. It is a colorless to pale yellow liquid with a strong, musty odor. 5-Methyl-4-hepten-3-one is known for its unique chemical properties and is utilized in various applications across different industries.

Uses

Used in Chemical Synthesis:
5-Methyl-4-hepten-3-one is used as a reagent for the preparation of fused nitrogen-heterocycles from β-enamino nitrile and α,β-unsaturated carbonyl compounds. Its unique structure allows it to participate in various chemical reactions, making it a valuable component in the synthesis of complex organic molecules.
Used in Flavor and Fragrance Industry:
In the flavor and fragrance industry, 5-Methyl-4-hepten-3-one is used as a component in the creation of natural and artificial scents. Its strong, musty odor contributes to the development of various fragrances, enhancing the overall sensory experience of products.
Used in Pharmaceutical Industry:
5-Methyl-4-hepten-3-one may also find applications in the pharmaceutical industry, where it can be used as an intermediate in the synthesis of various drugs. Its unique chemical properties make it a potential candidate for the development of new medications.
Used in Research and Development:
Due to its unique chemical structure and properties, 5-Methyl-4-hepten-3-one is often utilized in research and development settings. Scientists and researchers use this compound to study various chemical reactions and to develop new methodologies in organic chemistry.

InChI:InChI=1/C8H14O/c1-4-7(3)6-8(9)5-2/h6H,4-5H2,1-3H3/b7-6+

Synthetic route

4-ethyl-2-hexyn-4-ol (20599-15-9) → (E)-3-ethyl-2-hexen-4-one (80060-60-2) + 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With NH4NO3-exchanged zeolite HSZ-320 In chlorobenzene at 130℃; for 4h; Yield given;	A 80% B n/a
With NH4NO3-exchanged zeolite HSZ-320 In chlorobenzene at 130℃; for 4h; Yields of byproduct given;	A 80% B n/a

ethylmagnesium iodide (10467-10-4) + ethyl (Z)-3-ethoxybut-2-enoate (5331-73-7) → 5-methyl-4-hepten-3-one (1447-26-3)

5-methyl-hepta-1,4-dien-3-one (3018-30-2) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With methanol; palladium on activated charcoal Hydrogenation;

5-hydroxy-5-methyl-heptan-3-one (39121-37-4) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With oxalic acid durch Destillation;
With oxalic acid durch Destillation;

5-methyl-hept-5-en-3-one (1190-34-7) + sodium methylate (124-41-4) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
at 25℃; Gleichgewicht und Geschwindigkeit der Reaktion;

5-methyl-hept-5-en-3-one (1190-34-7) + sodium ethanolate (141-52-6) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
Gleichgewicht der Umlagerung;

ethyl 3-ethoxy-2-butenoate (998-91-4) + ethyl magnesium (1+); iodide → 5-methyl-4-hepten-3-one (1447-26-3)

5-hydroxy-5-methyl-heptan-3-one (39121-37-4) + oxalic acid (144-62-7) → 5-methyl-4-hepten-3-one (1447-26-3)

sodium ethanolate (141-52-6) + butanone (78-93-3) → 5-methyl-hept-5-en-3-one (1190-34-7) + 5-methyl-4-hepten-3-one (1447-26-3)

aluminum tri-tert-butoxide (556-91-2) + butanone (78-93-3) + benzene (71-43-2) → 5-methyl-4-hepten-3-one (1447-26-3)

aluminum tri-tert-butoxide (556-91-2) + butanone (78-93-3) + benzene (71-43-2) → 5-methyl-hept-5-en-3-one (1190-34-7) + 5-methyl-4-hepten-3-one (1447-26-3)

butanone (78-93-3) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With sodium ethanolate
With beryllium(II) chloride; benzene at 130℃;
With aluminum tri-tert-butoxide; benzene

butanone (78-93-3) → 5-methyl-hept-5-en-3-one (1190-34-7) + 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With calcium carbide
With sodium ethanolate
With (Ph3P)3CoCH3 at 23 - 25℃; for 24h;

(E)-3-methyl-pent-3-enoyl chloride (60359-79-7) + ethylzinc iodide (999-75-7) → 5-methyl-4-hepten-3-one (1447-26-3)

ethylmagnesium bromide (925-90-6) + hexa-4,5-dien-3-one (2200-54-6) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
In diethyl ether

butanone (78-93-3) → 5-hydroxy-5-methyl-heptan-3-one (39121-37-4) + 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With (Ph3P)3CoCH3 at 20 - 25℃; for 24h; Yield given. Yields of byproduct given;

β-methyl-β-ethyl-acrylic acid-chloride → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With ethyl zinc iodide

ethylmagnesium iodide (10467-10-4) + β-ethoxycrotonic acid ester → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
With diethyl ether

butanone (78-93-3) + benzene (71-43-2) + BeCl2 → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
at 130℃;

butanone (78-93-3) + magnesium bromide ethylate → 5-methyl-4-hepten-3-one (1447-26-3)

butanone (78-93-3) + benzene (71-43-2) + BeCl2 → 5-methyl-hept-5-en-3-one (1190-34-7) + 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
at 130℃;

butanone (78-93-3) + magnesium bromide ethylate → 5-methyl-hept-5-en-3-one (1190-34-7) + 5-methyl-4-hepten-3-one (1447-26-3)

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + 5-methyl-hept-5-en-3-one (1190-34-7) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
das Gleichgewicht liegt bei 57-58prozent 3-Methyl-hepten-(3)-on-(5);

ethanol (64-17-5) + 5-methyl-hept-5-en-3-one (1190-34-7) + phosphoric acid (86119-84-8, 7664-38-2) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
das Gleichgewicht liegt bei 57-58prozent 3-Methyl-hepten-(3)-on-(5);

ethanol (64-17-5) + 5-methyl-hept-5-en-3-one (1190-34-7) + sulfuric acid (7664-93-9) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
das Gleichgewicht liegt bei 57-58prozent 3-Methyl-hepten-(3)-on-(5);

5-hydroxy-5-methyl-heptan-3-one (39121-37-4) + iodine (7553-56-2) → 5-methyl-4-hepten-3-one (1447-26-3)

diethyl ether (60-29-7) + 3ξ-methyl-pent-3-enoic acid-chloride (98140-06-8) + sodium compound of methylacetoacetic acid ester → 5-methyl-hept-5-en-3-one (1190-34-7) + 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
und beim Kochen mit 10prozentiger alkoholischer Natronlauge;

methanol (67-56-1) + 5-methyl-hepta-1,4-dien-3-one (3018-30-2) + Pd-CaCO3 → 3-oxo-5-methyl-1-heptene (18830-90-5) + 5-methyl-3-heptanone (541-85-5) + 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
Hydrogenation;

5-Hexyn-3-ol (19780-84-8) → 5-methyl-4-hepten-3-one (1447-26-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: CrO3, H2SO4 / acetone 2: diethyl ether View Scheme

chloro-trimethyl-silane (75-77-4) + bis(μ-mercapto)bis(tricarbonyliron) + 5-methyl-4-hepten-3-one (1447-26-3) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → (OC)3Fe(SC(C2H5)(CH3)CH2C(C2H5)(OSi(CH3)3)S)Fe(CO)3

Conditions	Yield
With piperidine In tetrahydrofuran N2-atmosphere; addn. of ketone and piperidine to soln. of Fe-complex, filtration chromy. (silicic acid, CH2Cl2), addn. of Me3SiCl and hexamethyldisilazane, stirring (45 h); solvent removal, filtration chromy. (silicic acid, pentane), recrystn. (pentane); elem. anal., mixture of diastereomers (1:1) not sepd.;	31%

methyl magnesium iodide (917-64-6) + 5-methyl-4-hepten-3-one (1447-26-3) → 3,5-dimethyl-hept-4-en-3-ol

Conditions	Yield
With diethyl ether

diethyl ether (60-29-7) + ethylmagnesium bromide (925-90-6) + 5-methyl-4-hepten-3-one (1447-26-3) → 3-ethyl-5-methyl-hepta-2,4-diene

Conditions	Yield
at -15 - -12℃; und Destillieren des Reaktionsprodukts mit Phthalsaeureanhydrid;

chloroform (67-66-3) + 5-methyl-4-hepten-3-one (1447-26-3) → formic acid (64-18-6) + acetic acid (64-19-7) + propionic acid (802294-64-0) + butanone (78-93-3)

Conditions	Yield
Beim Ozonisieren und folgenden Zersetzen mit wss.H2O2;

5-methyl-hept-5-en-3-one (1190-34-7) + sodium diethylmalonate (996-82-7) + 5-methyl-4-hepten-3-one (1447-26-3) → ethanol (64-17-5) + 2-ethyl-2,5-dimethyl-4,6-dioxo-cyclohexanecarboxylic acid ethyl ester

ethylmagnesium bromide (925-90-6) + 5-methyl-4-hepten-3-one (1447-26-3) → 3-ethyl-5-methyl-hepta-2,4-diene

Conditions	Yield
at -15 - -12℃; Behandeln des Reaktionsprodukts mit Phthalsaeureanhydrid;

5-methyl-4-hepten-3-one (1447-26-3) + phosphonic acid diethyl ester (762-04-9) → 5-(diethoxyphosphinoyl)-5-methylheptan-3-one (75761-30-7)

Conditions	Yield
With sodium ethanolate

→ 5-methyl-3-heptanol

5-methyl-4-hepten-3-one (1447-26-3) → 5-methyl-hept-4-en-3-one semicarbazone (1116-48-9)

5-methyl-4-hepten-3-one (1447-26-3) → 5-methyl-3-heptanone (541-85-5)

Conditions	Yield
With platinum Hydrogenation;

potassium thioacyanate (333-20-0) + 5-methyl-4-hepten-3-one (1447-26-3) → 5-isothiocyanato-5-methyl-heptan-3-one (50677-57-1)

Conditions	Yield
With sulfuric acid

tris(dimethylamino)stibine (7289-92-1) + 5-methyl-4-hepten-3-one (1447-26-3) → [(E)-1-Eth-(Z)-ylidene-3-methyl-pent-2-enyl]-dimethyl-amine (56617-85-7)

5-methyl-4-hepten-3-one (1447-26-3) → 4,5-epoxy-5-methyl-3-heptanone (344325-11-7)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol for 18h;

Upstream product

• 10467-10-4 ethylmagnesium iodide 
• 5331-73-7 ethyl (Z)-3-ethoxybut-2-enoate 
• 3018-30-2 5-methyl-hepta-1,4-dien-3-one 
• 39121-37-4 5-hydroxy-5-methyl-heptan-3-one 
• 1190-34-7 5-methyl-hept-5-en-3-one 
• 124-41-4 sodium methylate 
• 141-52-6 sodium ethanolate 
• 998-91-4 ethyl 3-ethoxy-2-butenoate 
• 144-62-7 oxalic acid 
• 78-93-3 butanone 
• 556-91-2 aluminum tri-tert-butoxide 
• 71-43-2 benzene 
• 60359-79-7 (E)-3-methyl-pent-3-enoyl chloride 
• 999-75-7 ethylzinc iodide 

Downstream Products

• 64-18-6 formic acid 
• 64-19-7 acetic acid 
• 802294-64-0 propionic acid 
• 78-93-3 butanone 
• 64-17-5 ethanol 
• 18720-65-5 5-methyl-3-heptanol 
• 541-85-5 5-methyl-3-heptanone 
• 344325-11-7 4,5-epoxy-5-methyl-3-heptanone 
• 74097-61-3 3,t-5-diethyl-r-4-hydroxy-5-methyl-1-p-tosyl-2-pyrazoline 
• 2050-82-0 3,5,5-trimethyl-hept-3-ene 
• 101935-28-8 3,5-dimethyl-hepta-2,4-diene 

Relevant articles and documents

Reactions on aluminum oxides. 2. Rearrangements of butan-2-one on aluminum oxide

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Catalysis by cobalt compounds of aldol and retroaldol reactions

Aldol condensation of acetone, butanone, and 2-pentanone, and retroaldol reaction of neat diacetone alcohol and 3-methyl-3-hydroxyheptan-5-one are catalyzed by (Ph3P)3CoCH3 and (Ph3P)3CoSi(CH3)3.The condensations are reversible and the retroaldol reaction is favoured.Several hindered or cyclic ketones, such as higher homologues, 3-pentanone, methyl isopropyl ketone or cyclohexanone do not condense.By comparison, aliphatic aldehydes react fast and irreversibly to yield products comprised of three aldehyde units. (Ph3P)3CoCH3 also catalyzes protium/deuterium scramblingbetween ketones and acetone-d6.This exchange takes place preferably at the C3 carbon whereas condensation takes place at the C1 carbon.The reactions take place at 20 deg C or below, and of the several organometallic compounds tested only the two mentioned above were found to be active.