2,6-Dimethyl-2,5-heptadien-4-one supplier

Name
2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE
EINECS 207-986-3
CAS No. 504-20-1
Article Data73
CAS DataBase
Density 0.885
Solubility
Melting Point 23-26 °C(lit.)
Formula C9H14 O
Boiling Point 198-199 °C(lit.)
Molecular Weight 138.21
Flash Point 79 ºC
Transport Information
Appearance
Safety Moderately toxic by subcutaneous route. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO₂, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ISOPHORONE.
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,6-Dimethyl-2,5-heptadien-4-one;Diisobutenyl ketone; Diisopropylidene acetone; Foron; NSC 38718; NSC 403517;Phorone; sym-Diisopropylidene acetone
PSA 17.07000
LogP 2.48790

Synthetic route

: 768-03-6
Phenyl vinyl ketone

A: 504-20-1
phorone

B: 470-99-5
isophorol

Conditions

Conditions	Yield
With aluminium tris(2,6-diphenylphenoxide); n-butyllithium; diisobutylaluminium hydride In toluene at -78 - 25℃; for 0.25h; Yields of byproduct given;	A 99% B n/a

: 52981-86-9
1-benzyl-2,2,6,6-tetramethylpiperidine-4-one

: 504-20-1
phorone

Conditions

Conditions	Yield
With C20H29ClO2P2Pt In water; toluene at 105℃; for 5h; Reagent/catalyst;	90%

: 67-64-1
acetone

A: 141-79-7
4-methyl-pent-3-en-2-one

B: 504-20-1
phorone

C: 123-42-2
4-Hydroxy-4-methyl-2-pentanone

Conditions

Conditions	Yield
With titanium tetrachloride; NCNMe2 In benzene at 25℃;	A 82% B 2% C 8%
With sodium hydroxide In benzene at 40℃; Mechanism; Kinetics; benzyltriethylammonium chloride presence;
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 40℃; reaction order, effect of concentration on the initial rate;
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In benzene at 40℃; Mechanism; effect concentrations, initial rate;
With MgO/ZrO2 mixed oxides at 249.84℃;

...Expand

: 113308-50-2
1,2,2,6,6-pentamethyl-4-piperidone methiodide

: 504-20-1
phorone

Conditions

Conditions	Yield
With potassium hydroxide In water for 1h;	55%

: 2,6-dimethyl-4-(1'-methyl-2'-propenyl)-1,6-heptadien-4-ol

A: 504-20-1
phorone

B: 115819-23-3
(E)-2,5-dimethyl-2,5-heptadien-4-one

C: 5837-45-6
2,6-dimethyl-hepta-1,5-dien-4-one

D: (E)-2,5-dimethyl-1,5-heptadien-4-one

Conditions

Conditions	Yield
With potassium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃;	A 20% B 4% C 47% D 8%

...Expand

: 67-64-1
acetone

A: 504-20-1
phorone

B: 16642-57-2
di-i-propyl peroxide

Conditions

Conditions	Yield
With sodium In tetrahydrofuran Ambient temperature; Reductive dimerization, other metal, using irradiation;	A n/a B 10%

: 81925-78-2
2,6-dimethyl-4-(2'-propenyl)-1,6-heptadien-4-ol

A: 504-20-1
phorone

B: 33698-67-8
6-methyl-hepta-1,5-dien-4-one

C: 5837-45-6
2,6-dimethyl-hepta-1,5-dien-4-one

D: 115818-79-6
(5E)-2-methyl-1,5-heptadien-4-one

Conditions

Conditions	Yield
With potassium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; Yield given;	A n/a B 1% C n/a D 4%

...Expand

: 5857-71-6
6-hydroxy-2,6-dimethyl-hept-2-en-4-one

A: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

B: 504-20-1
phorone

Conditions

Conditions	Yield
beim Erhitzen unter gewoehnlichem Druck;

: 5857-71-6
6-hydroxy-2,6-dimethyl-hept-2-en-4-one

: 504-20-1
phorone

Conditions

Conditions	Yield
With sulfuric acid at 80℃;

: 5682-79-1
3,5-dibromo-2,6-dimethylhepta-2,5-dien-4-one

A: 504-20-1
phorone

B: 71500-18-0
3-methyl-1-[4,4,5,5-tetramethyl-2-(2-methyl-propenyl)-cyclopent-1-enyl]-but-2-en-1-one

Conditions

Conditions	Yield
With hydrogenchloride; amalgamated zinc

: 3682-91-5
2,6-dihydroxy-2,6-dimethyl-heptan-4-one

A: 1197-66-6
2,2,6,6-tetramethyltetrahydropyran-4-one

B: 504-20-1
phorone

Conditions

Conditions	Yield
With sulfuric acid Nebenprod. 2: 6-Hydroxy-2,6-dimethyl-hept-2-en-4-on;

: 3682-91-5
2,6-dihydroxy-2,6-dimethyl-heptan-4-one

: 504-20-1
phorone

: 3682-91-5
2,6-dihydroxy-2,6-dimethyl-heptan-4-one

A: 504-20-1
phorone

B: 5857-71-6
6-hydroxy-2,6-dimethyl-hept-2-en-4-one

Conditions

Conditions	Yield
With sulfuric acid

: 3682-91-5
2,6-dihydroxy-2,6-dimethyl-heptan-4-one

: 144-62-7
oxalic acid

: 504-20-1
phorone

: 3682-91-5
2,6-dihydroxy-2,6-dimethyl-heptan-4-one

: 108-24-7
acetic anhydride

: 504-20-1
phorone

: 75-36-5
acetyl chloride

: 67-64-1
acetone

A: 141-79-7
4-methyl-pent-3-en-2-one

B: 504-20-1
phorone

Conditions

Conditions	Yield
With zinc(II) chloride beim Behandeln des Reaktionsproduktes mit Wasserdampf und Erhitzen des Destillats mit ueberschuessiger alkoh.Kalilauge waehrend einiger Minuten bis nahe zum Sieden;
With zinc(II) chloride beim Bahandeln des Reaktionsproduktes mit Wasserdampf und Erhitzen des Destillats mit ueberschuessiger alkoh. Kalilauge waehrend einiger Minuten bis nahe zum Sieden;
With zinc(II) chloride Behandeln der Reaktionsproduktes mit Wasserdampf und Erhitzen des Destillats mit ueberschuessiger alkoh.Kalilauge waehrend einiger Minuten bis nahe zum Sieden;

...Expand

: 67-63-0
isopropyl alcohol

: 504-20-1
phorone

Conditions

Conditions	Yield
With zinc(II) sulfate at 380 - 400℃;

: 507-19-7
t-butyl bromide

: 67-64-1
acetone

A: 141-79-7
4-methyl-pent-3-en-2-one

B: 504-20-1
phorone

...Expand

: 67-64-1
acetone

: 75-65-0
tert-butyl alcohol

A: 141-79-7
4-methyl-pent-3-en-2-one

B: 504-20-1
phorone

Conditions

Conditions	Yield
With hydrogen bromide

...Expand

: 556-91-2
aluminum tri-tert-butoxide

: 67-64-1
acetone

: 71-43-2
benzene

A: 141-79-7
4-methyl-pent-3-en-2-one

B: 504-20-1
phorone

...Expand

: 67-64-1
acetone

A: 141-79-7
4-methyl-pent-3-en-2-one

B: 504-20-1
phorone

: 67-64-1
acetone

: 504-20-1
phorone

Conditions

Conditions	Yield
With phosphoric acid at 150℃;
With phosphoric acid
With hydrogenchloride; aluminium trichloride

: 67-64-1
acetone

A: 504-20-1
phorone

B: 306-44-5
propanone 1-oxime

Conditions

Conditions	Yield
With nitrosylchloride

: 3350-78-5
3,3-Dimethylacryloyl chloride

: 115-11-7
isobutene

: 504-20-1
phorone

Conditions

Conditions	Yield
With tin(IV) chloride

: 4394-72-3
4-methyl-6-(2-methylprop-1-en-1-yl)-2H-pyran-2-one

: 504-20-1
phorone

Conditions

Conditions	Yield
(i) NaOH, MeOH, (ii) (heating); Multistep reaction;

: 126-84-1
2,2-diethoxypropane

: 504-20-1
phorone

Conditions

Conditions	Yield
(i) PhNHMe, TsOH, (ii) aq. HCl; Multistep reaction;

: 81925-77-1
4-benzyl-2,6-dimethyl-1,6-heptadien-4-ol

A: 504-20-1
phorone

B: 5837-45-6
2,6-dimethyl-hepta-1,5-dien-4-one

Conditions

Conditions	Yield
With potassium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 40℃; Yield given. Yields of byproduct given;

: 67-64-1
acetone

A: 67-56-1
methanol

B: 141-79-7
4-methyl-pent-3-en-2-one

C: 504-20-1
phorone

D: 123-42-2
4-Hydroxy-4-methyl-2-pentanone

Conditions

Conditions	Yield
at 350.1℃; under 78681.3 Torr; for 0.138889h; Product distribution; var. temp.;

...Expand

: 67-64-1
acetone

A: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

B: 141-79-7
4-methyl-pent-3-en-2-one

C: 504-20-1
phorone

D: 124-38-9
carbon dioxide

E: 201230-82-2
carbon monoxide

F: 115-11-7
isobutene

Conditions

Conditions	Yield
With zeolite HY at 350℃; Product distribution; effect of acidity on the conversion of acetone over AlPO4-5, SAPO-5 phosphates and modifiedY zeolites;

...Expand

: 2,5,5-trimethyl-4-(2'-methyl-2'-propenyl)-1,6-heptadien-4-ol

A: 504-20-1
phorone

B: 5837-45-6
2,6-dimethyl-hepta-1,5-dien-4-one

Conditions

Conditions	Yield
With potassium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 40℃; Yield given. Yields of byproduct given;

: 504-20-1
phorone

: 826-36-8
2,2,6,6-Tetramethyl-4-piperidone

Conditions

Conditions	Yield
With ammonium hydroxide at -80 - 85℃;	98%
With ammonia; water
With ammonia
With ammonium hydroxide; sodium hydroxide 1.) 25 deg C, 3 days, 80 deg C, 60 min; 2.) 0-5 deg C; Yield given. Multistep reaction;
With ammonium hydroxide In water at 55 - 85℃;

: 504-20-1
phorone

: 3,3,3',3'-tetramethyl-5,5'-spirodiisoxazolidine

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium methylate In methanol for 6h; Heating;	95%

: 504-20-1
phorone

: 5518-62-7
1,2-diphosphinoethane

: 1,2-bis(2,2,6,6-tetramethyl-phosphinan-4-on)ethane

Conditions

Conditions	Yield
at 120℃; for 20h;	93%
at 120℃; for 20h;	93%

: 504-20-1
phorone

: 106-95-6
allyl bromide

: (+/-)-2-(3''-butenyl)-1,1-bis[1'-(2'methyl)propenyl]cyclopropane

Conditions

Conditions	Yield
Stage #1: allyl bromide With indium In tetrahydrofuran for 1.5h; Metallation; Stage #2: phorone In tetrahydrofuran Addition; Stage #3: With hydrogenchloride; oxygen; lithium bromide In tetrahydrofuran; diethyl ether Substitution; cyclization; Further stages.;	92%
Yield given. Multistep reaction;

: 504-20-1
phorone

: 108-83-8
diisobutyl ketone

Conditions

Conditions	Yield
With ethanol; lithium; nickel dichloride In tetrahydrofuran at 20℃; for 12h;	91%
With triethylsilane; ethanol; palladium dichloride for 6h; Heating;	90%
With formic acid; (η5-C4Ph4COHOC4Ph4-η5)(μ-H)(CO)4Ru2 at 100℃; for 1.2h;	88%

: 504-20-1
phorone

: 137003-52-2
<15N>-2,2,6,6-tetramethyl-4-piperidone

Conditions

Conditions	Yield
With aq. (15N)ammonia at -80 - 85℃;	91%
With sodium hydroxide; disodium hydrogenphosphate; 15N-ammonium sulfate In benzene at 95℃; for 240h;	86%
With sodium hydroxide In benzene at 90℃; for 240h; double Michael addition;	66%

: 504-20-1
phorone

: 507233-69-4, 594-30-9, 28719-54-2
triphenyl bismuth (2+); dichloride

: 2,6-dimethyl-3-phenylhept-1,5-dien-4-one

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -78 - 20℃; for 2h; Arylation;	89%

: 15362-08-0
dicyano-bis-(1,10-phenanthroline)-iron(II) dihydrate

: 504-20-1
phorone

: 123623-97-2
cis-bis(6-isocyano-2,6-dimethyl-2-hepten-4-one)bis(1,10-phenanthroline)iron(II)-bis(tetrafluoroborate)

Conditions

Conditions	Yield
With Et2O-HBF4 In ethanol dropwise addn. of phorone to a soln. of 54% Et2O-HBF4 and Fe-compd. at room temp., a suspn. develops after 20 min., pptn. on stirring for 20 h; centrifugating, repeated recrystn. (CH2Cl2/ether), washing 3 times with ether and pentane, drying in vac., elem. anal.;	89%

: 504-20-1
phorone

: (2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphine

: 2,2,6,6-tetramethyl-1-(2′,4′,6′-triisopropyl-3,6-dimethoxybiphenyl-2-yl)phosphinan-4-one

Conditions

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol at 50℃; Michael Addition;	88%
at 160℃; for 22h; Inert atmosphere;	66%
Heating;

: 504-20-1
phorone

: 73806-71-0
2,3,5,6-tetrabromo-2,6-dimethyl-heptan-4-one

Conditions

Conditions	Yield
With bromine In tetrachloromethane for 0.5h; Ambient temperature;	86%
With carbon disulfide; bromine

: 504-20-1
phorone

: 3-isobutenyl-5,5-dimethyl-2-isoxazoline

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium methylate In methanol for 6h; Heating;	85%

: 504-20-1
phorone

: 108-46-3
recorcinol

: 3127-14-8
4,4,4′,4′-tetramethyl-2,2′-spirobi[chroman]-7,7′-diol

Conditions

Conditions	Yield
With hydrogenchloride In diethyl ether; dichloromethane for 24h; Heating;	85%

: 478658-93-4
1,2-bis(phosphinomethyl)ferrocene

: 504-20-1
phorone

: 1,2-bis-(P-(2,2,6,6,-tetramethylphosphinan-4-one))dimethylferrocene

Conditions

Conditions	Yield
at 120℃; for 20h; Inert atmosphere;	85%

: 473-34-7
N,N-dichloro-p-toluenesulfonamide

: 109-74-0
propyl cyanide

: 504-20-1
phorone

: 1-[2-(1-chloro-propyl)-5,5-dimethyl-3-(toluene-4-sulfonyl)-4,5-dihydro-3H-imidazol-4-yl]-3-methyl-but-2-en-1-one

Conditions

Conditions	Yield
With 4 A molecular sieve at 20℃; for 8h;	81%

...Expand

: 473-34-7
N,N-dichloro-p-toluenesulfonamide

: 504-20-1
phorone

: 75-05-8
acetonitrile

: 1-[2-dichloromethyl-5,5-dimethyl-3-(toluene-4-sulfonyl)-4,5-dihydro-3H-imidazol-4-yl]-3-methyl-but-2-en-1-one

Conditions

Conditions	Yield
With 4 A molecular sieve at 20℃; for 8h;	81%

...Expand

: 504-20-1
phorone

: 75-04-7
ethylamine

: 1392008-77-3
6-ethylamino-2,6-dimethylhept-2-en-4-one

Conditions

Conditions	Yield
In water at 20℃; for 48h;	80%

: 504-20-1
phorone

: 119072-54-7, 2769-71-3
2,6-dimethylphenyl isonitrile

: 2,6-dimethyl-N-(3,3-dimethyl-5-(2-methyl-1-propenyl)-2(3H)-furanylidene)-benzenamine

Conditions

Conditions	Yield
With gallium(III) trichloride In toluene at 100℃; for 12h;	78%

: 504-20-1
phorone

: 1779-49-3
Methyltriphenylphosphonium bromide

: 927-02-6
2,6-dimethyl-4-methylene-2,5-heptadiene

Conditions

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With phenyllithium In diethyl ether; cyclohexane for 0.5h; Stage #2: phorone In diethyl ether; cyclohexane for 0.5h;	77%

: 504-20-1
phorone

: 81454-78-6
3-chloro-2,6-dimethyl-1,5-heptadien-4-one

Conditions

Conditions	Yield
With calcium hypochlorite; Methamphetamin In dichloromethane; water for 3h;	76%
With calcium hypochlorite In water	74%

: 504-20-1
phorone

: 132132-58-2
2,2,6,6-tetramethyltetrahydro-1-selenapyran-4-one

Conditions

Conditions	Yield
With aluminum selenide; sodium acetate In ethanol at 75 - 78℃; for 6h;	74.5%

: 473-34-7
N,N-dichloro-p-toluenesulfonamide

: 504-20-1
phorone

: 107-12-0
propiononitrile

: 1-[2-(1-chloro-ethyl)-5,5-dimethyl-3-(toluene-4-sulfonyl)-4,5-dihydro-3H-imidazol-4-yl]-3-methyl-but-2-en-1-one

Conditions

Conditions	Yield
With 4 A molecular sieve at 20℃; for 8h;	74%

...Expand

: 78-82-0
Isobutyronitrile

: 504-20-1
phorone

: 70-55-3
toluene-4-sulfonamide

: 1-[2-isopropyl-5,5-dimethyl-3-(toluene-4-sulfonyl)-4,5-dihydro-3H-imidazol-4-yl]-3-methyl-but-2-en-1-one

Conditions

Conditions	Yield
With N-chloro-succinimide; molecular sieve In acetonitrile at 50℃; for 60h;	74%

...Expand

: 504-20-1
phorone

: 52187-72-1
N,N-dichloro-2-nitrobenzenesulfonamide

: 75-05-8
acetonitrile

: 1-(2-dichloromethyl-3-(2-nitrobenzenesulfonyl)-5,5-dimethyl-4,5-dihydro-3H-imidazol-4-yl)-3-methyl-but-2-en-1-one

Conditions

Conditions	Yield
With N-chloro-succinimide at 50℃; for 60h;	74%

...Expand

: 504-20-1
phorone

: 542-92-7
cyclopenta-1,3-diene

: 6,6-Bis(2-methyl-1-propenyl)fulvene

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 60℃; for 2h;	73%

: 504-20-1
phorone

: 638-21-1
phenylphosphane

: 13887-05-3
1-phenyl-2,2,6,6-tetramethyl-4-phosphorinanone

Conditions

Conditions	Yield
at 120℃; for 6h;	72.5%
at 120℃; for 21h;	58%
at 150℃; for 15h; Inert atmosphere;	47%
(i) NaOMe, EtOH, (ii) AcOH; Multistep reaction;
at 115 - 130℃;

: 504-20-1
phorone

: 36768-62-4
4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE

Conditions

Conditions	Yield
With ammonia; acetic acid In methanol	71%
With acetic acid In methanol	64%
With ammonia; acetic acid In methanol	54%
With ammonia; acetic acid In methanol	41.5%
With acetic acid In methanol	38%

: 504-20-1
phorone

: 70-55-3
toluene-4-sulfonamide

: 75-05-8
acetonitrile

: 1-[2-dichloromethyl-5,5-dimethyl-3-(toluene-4-sulfonyl)-4,5-dihydro-3H-imidazol-4-yl]-3-methyl-but-2-en-1-one

Conditions

Conditions	Yield
With N-chloro-succinimide; molecular sieve at 50℃; for 48h;	70%

...Expand

2,6-Dimethyl-2,5-heptadien-4-one Chemical Properties

Phorone is a yellow crystalline substance with a geranium odor. It is a self-condensation product of acetone. It has some synonyms like 2,5-Heptadien-4-one,2,6-dimethyl-;2,6-dimethyl-5-heptadien-4-one;2,6-dimethyl-hepta-2,5-dien-4-one;5-Heptadien-4-one,2,6-dimethyl-2;Diisobutenyl ketone;diisobutenylketone;diisopropylidineacetone;Foron,and so on.

Molecular Formula: C₉H₁₄O
Molecular Weight: 138.21
EINECS: 207-986-3
Melting point: 23-26 °C(lit.)
Boiling point: 198-199 °C(lit.)
Density: 0.885 g/mL at 25 °C(lit.)
Vapor density: 4.8 (vs air)
Vapor pressure: 0.38 mm Hg ( 20 °C)
Refractive index: n20/D 1.497(lit.)
Flash point: 175 °F
Merck: 7333

2,6-Dimethyl-2,5-heptadien-4-one Production

Phorone is a self-condensation product of acetone and it can also be obtained from certain camphor compounds.

2,6-Dimethyl-2,5-heptadien-4-one Toxicity Data With Reference

scu-rbt LDLo:700 mg/kg

AEXPBL Archiv fuer Experimentelle Pathologie und Pharmakologie. 56 (1906),346.

RTECS: MI5500000

2,6-Dimethyl-2,5-heptadien-4-one Consensus Reports

Reported in EPA TSCA Inventory.

2,6-Dimethyl-2,5-heptadien-4-one Safety Profile

Moderately toxic by subcutaneous route. Combustible when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO₂, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

WGK Germany: 3

Product Name

2,6-DIMETHYL-2,5-HEPTADIEN-4-ONE

Synthetic route

2,6-Dimethyl-2,5-heptadien-4-one Chemical Properties

2,6-Dimethyl-2,5-heptadien-4-one Production

2,6-Dimethyl-2,5-heptadien-4-one Toxicity Data With Reference

2,6-Dimethyl-2,5-heptadien-4-one Consensus Reports

2,6-Dimethyl-2,5-heptadien-4-one Safety Profile

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