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

Uses

3-Methyl-3-hepten-5-one is a reagent used to prepare fused nitrogen-heterocycles from β-enamino nitrile and α,β-unsaturated carbonyl compounds.

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

• 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 
• 39121-37-4 5-hydroxy-5-methyl-heptan-3-one 
• 144-62-7 oxalic acid 
• 78-93-3 butanone 
• 925-90-6 ethylmagnesium bromide 
• 2200-54-6 hexa-4,5-dien-3-one 
• 10467-10-4 ethylmagnesium iodide 
• 71-43-2 benzene 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 86119-84-8 phosphoric acid 

Downstream Products

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

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.