N-(1-isopropylallyloxycarbonyl)aniline
A
4-methyl-1,3-pentadiene
B
4-methyl-3-(phenylamino)pent-1-ene
C
aniline
Conditions | Yield |
---|---|
PdLn In 1,4-dioxane at 100℃; for 0.25h; | A n/a B 2 % Chromat. C 98% |
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In dimethyl sulfoxide at 25℃; | 72% |
(E)-but-2-en-1-yl phenylcarbamate
A
4-methyl-1,3-pentadiene
B
(E)-N-(2-butenyl)aniline
C
aniline
Conditions | Yield |
---|---|
PdLn In 1,4-dioxane at 100℃; for 6h; | A n/a B 70% C 30% |
3,3-dimethyl acrylaldehyde
Methyltriphenylphosphonium bromide
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With n-butyllithium In diethyl ether; pentane for 12h; Ambient temperature; | 57% |
With n-butyllithium In diethyl ether; toluene at 20℃; Inert atmosphere; | 14% |
1,3,3-trimethylcyclopropene
A
4-methyl-1,3-pentadiene
B
4-methylpent-2-yne
C
2-methyl-2,3-pentadiene
D
trans-2-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
In pentane at 23℃; Irradiation; Further byproducts given; | A 37% B 14% C 31% D 11% |
1,3,3-trimethylcyclopropene
A
4-methyl-1,3-pentadiene
B
4-methylpent-2-yne
C
2-methyl-2,3-pentadiene
D
2,3-dimethyl-buta-1,3-diene
Conditions | Yield |
---|---|
In pentane at 23℃; Irradiation; Further byproducts given; | A 37% B 14% C 31% D 7% |
1,3,3-trimethylcyclopropene
A
4-methyl-1,3-pentadiene
B
4-methylpent-2-yne
C
2-methyl-2,3-pentadiene
D
trans-2-methyl-1,3-pentadiene
E
2,3-dimethyl-buta-1,3-diene
Conditions | Yield |
---|---|
In pentane at 23℃; Product distribution; Irradiation; | A 37% B 14% C 31% D 11% E 7% |
A
4-methyl-1,3-pentadiene
B
1,3-Dimethyl-1,3-butadien
C
1,3-dimethylcyclobutene
Conditions | Yield |
---|---|
With tert.-butyl lithium | A 19% B 32% C 37% |
2-methyl-2,4-pentanediol
A
4-methyl-1,3-pentadiene
B
trans-2-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With hydrogen bromide In water Dehydration; | A 7% B n/a |
2,4,4,6-tetramethyl-1,3-dioxane
A
4-methyl-1,3-pentadiene
B
1,3-Dimethyl-1,3-butadien
Conditions | Yield |
---|---|
With phosphate-catalyst; water at 325℃; |
2-methyl-2,4-pentanediol
aniline hydrobromide
A
4-methyl pent-3-en-2-ol
B
4-methyl-1,3-pentadiene
2-methyl-2,4-pentanediol
aniline hydrobromide
A
4-methyl-1,3-pentadiene
B
4-methyl-4-penten-2-ol
C
(E)-2-methyl-1,3-heptadiene
Conditions | Yield |
---|---|
With iodine | |
With hydrogen bromide | |
With aniline hydrobromide | |
With aluminium trichloride at 160℃; |
Conditions | Yield |
---|---|
Abspaltung von Wasser; | |
With dimethyl sulfoxide | |
Multi-step reaction with 2 steps 1: aluminium phosphate / 300 - 310 °C 2: zirconium (IV)-oxide /pumice stone / 300 - 310 °C View Scheme | |
Multi-step reaction with 2 steps 1: chromium (III)-oxide-aluminium oxide / 200 °C 2: chromium (III)-oxide-aluminium oxide / 250 °C View Scheme |
2-methylpent-4-en-2-ol
A
4-methyl-1,3-pentadiene
B
1,3-Dimethyl-1,3-butadien
Conditions | Yield |
---|---|
With chromium corundum at 250℃; |
4-methyl-pent-3-en-2-one
aluminum tri-sec-butoxide
A
4-methyl pent-3-en-2-ol
B
4-methyl-1,3-pentadiene
C
1,3-Dimethyl-1,3-butadien
2-methyl-1,4-pentadiene
A
4-methyl-1,3-pentadiene
B
1,3-Dimethyl-1,3-butadien
Conditions | Yield |
---|---|
With chromium corundum at 250℃; | |
With pumice stone; zirconium(IV) oxide at 300℃; | |
With pumice stone; zirconium(IV) oxide at 300 - 310℃; |
2,5-dibromo-2-methylpentane
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With potassium hydroxide |
2,5-dibromo-2-methylpentane
A
4-methyl-1,3-pentadiene
B
5-ethoxy-2-methyl-pent-2-ene
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
Destillation ueber mit H2SO4 gatraenkten Bimsstein; | |
With hydrogen bromide | |
With acetic anhydride at 100℃; | |
With hydrogen bromide Destillation; | |
With aniline hydrobromide |
2-methyl-pent-3-en-2-ol
aniline hydrobromide
A
4-methyl-1,3-pentadiene
B
1,3-Dimethyl-1,3-butadien
Conditions | Yield |
---|---|
Wasserabspaltung; |
2-methyl-pent-3-en-2-ol
A
4-methyl-1,3-pentadiene
B
1,3-Dimethyl-1,3-butadien
Conditions | Yield |
---|---|
With hydrogen bromide |
Conditions | Yield |
---|---|
With 2-ethoxy-ethanol; potassium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide | |
With 2-ethoxy-ethanol; potassium hydroxide | |
With potassium hydroxide |
4-chloro-4-methyl-1-pentetne
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With alcoholic alkali |
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With silver(l) oxide nachfolgende Destillation der erhaltenen Ammoniumbase; |
Conditions | Yield |
---|---|
bei der trocknen Destillation; |
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
bei der Destillation; |
Conditions | Yield |
---|---|
bei der Destillation; |
Conditions | Yield |
---|---|
at 130 - 140℃; |
Conditions | Yield |
---|---|
In benzene educts in stoich. amt.; | 100% |
Conditions | Yield |
---|---|
in stoihometric amt.; | 100% |
in stoihometric amt.; | 100% |
4-methyl-1,3-pentadiene
C18H23F3O5S
1-(((1R,6S)-1,6-dimethyl-2-(4-methylpent-3-enyl)cyclohex-2-enyl)methyl)-2-methoxybenzene
Conditions | Yield |
---|---|
Stage #1: 4-methyl-1,3-pentadiene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 0 - 23℃; for 2.5h; Suzuki coupling; Inert atmosphere; Stage #2: C18H23F3O5S With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; triphenyl-arsane In tetrahydrofuran; water; N,N-dimethyl-formamide at 55℃; Suzuki coupling; Inert atmosphere; | 99% |
4-methyl-1,3-pentadiene
C17H21F3O4S
1-(((1R,6S)-1,6-dimethyl-2-(4-methylpent-3-enyl)cyclohex-2-enyl)methyl)-2-methoxybenzene
Conditions | Yield |
---|---|
Stage #1: 4-methyl-1,3-pentadiene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 0 - 23℃; for 2.5h; Suzuki coupling; Inert atmosphere; Stage #2: C17H21F3O4S With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; triphenyl-arsane In tetrahydrofuran; water; N,N-dimethyl-formamide at 55℃; Suzuki coupling; Inert atmosphere; | 98% |
dichloro bis(acetonitrile) palladium(II)
4-methyl-1,3-pentadiene
di-μ-chlorobis[(1,2,3-η)-4-hydroxy-4-methyl-2-penten-1-yl]dipalladium
Conditions | Yield |
---|---|
With water; potassium hydrogencarbonate In acetone to slurry of PdCl2(MeCN)2 (1.25 mmol) and KHCO3 (1.25 mmol) in acetone at 20°C added soln. of CH2CHCHCMe2 (1.00 mmol) and H2O (20.0 mmol) in acetone, stirred for 26 h at 20°C; filtered through Celite, ppt. washed with EtOAc, combined soln. concd. at water-aspirator pressure, flash chromd. (column, silica gel 60 (0.040-0.063 mm, Merck), EtOAc); | 95% |
4-methyl-1,3-pentadiene
C17H21F3O4S
(1S,9aR)-8-methoxy-1,9a-dimethyl-2,3,9,9a-tetrahydro-1H-fluorene
Conditions | Yield |
---|---|
Stage #1: 4-methyl-1,3-pentadiene With 9-borabicyclo[3.3.1]nonane dimer In tetrahydrofuran at 0 - 23℃; for 2.5h; Suzuki coupling; Inert atmosphere; Stage #2: C17H21F3O4S With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In tetrahydrofuran; 1,4-dioxane at 85℃; Suzuki coupling; Inert atmosphere; | 91% |
4-methyl-1,3-pentadiene
N,N’-di-tert-butylthiadiaziridine-1,1-dioxide
C14H28N2O2S
Conditions | Yield |
---|---|
With tributylphosphine; copper(l) chloride In chloroform at 20℃; for 24h; sealed vial; Inert atmosphere; regioselective reaction; | 89% |
4-methyl-1,3-pentadiene
L-menthyl diazoacetate
Conditions | Yield |
---|---|
With trans-RuIICl2-(2,6-di-<<(S)-4-isopropyl>oxazol-2-yl>pyridine)-(CH2=CH2) In dichloromethane | 86% |
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -78℃; for 0.0833333h; Nazarov cyclization; stereoselective reaction; | 85% |
Conditions | Yield |
---|---|
With Hexamethyldisiloxane; mono(trimethylphosphine)(diallyl ether)palladium(0) In benzene-d6 at 30℃; for 2h; | 85% |
Conditions | Yield |
---|---|
With nafion In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; | 84% |
4-methyl-1,3-pentadiene
1,3-Dimethyl-1,3-butadien
1-Methyl-2-acetyl-1,3-dithiolanium fluorosulfonate
2-Acetyl-3,6-dihydro-3,5-dimethyl-2-methylthio-2H-thiopyran
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In dichloromethane for 60h; Ambient temperature; | 82% |
7-acetoxy-8-iodoflavone
4-methyl-1,3-pentadiene
Conditions | Yield |
---|---|
Stage #1: 7-acetoxy-8-iodoflavone With silver carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane for 0.0833333h; Stage #2: 4-methyl-1,3-pentadiene In 1,4-dioxane; water at 100℃; for 24h; | 82% |
With silver carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane; water at 100℃; for 24h; | 82% |
2-(di-tert-butylphosphino)-1,1'-biphenylgold(I) chloride
4-methyl-1,3-pentadiene
([P(t-Bu)2-o-biphenyl]Au[η2-4-methyl-1,3-pentadiene])SbF6
Conditions | Yield |
---|---|
In dichloromethane (N2); dissolving a mixt. of Au complex, Ag salt and diene in CH2Cl2, stirring in the dark at room temp. for 6 h; filtration through Celite, eluting with CH2Cl2, concn., addn. of hexanes, cooling to 4°C overnight; elem. anal.; | 82% |
Conditions | Yield |
---|---|
With nafion In 1,2-dichloro-ethane at 110℃; for 24h; Reagent/catalyst; Solvent; Temperature; Sealed tube; | 82% |
Conditions | Yield |
---|---|
With nafion In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; | 81% |
Conditions | Yield |
---|---|
With tetrabutylammonium tetrafluoroborate In N,N-dimethyl-formamide electroreductive coupling; | 80% |
4-methyl-1,3-pentadiene
ethyl (E)-2-diazo-6-phenyl-1-hexa-3,5-dienoate
ethyl 4,4-dimethyl-3-((E)-2-phenylethenyl)cyclohepta-1,5-diene-1-carboxylate
Conditions | Yield |
---|---|
rhodium(II) hexanoate In dichloromethane a) 10 deg C, 30 min, b) reflux, 10 min; | 80% |
4-methyl-1,3-pentadiene
benzaldehyde
2-ethyl-3-methyl-1-phenyl-3-buten-1-one
Conditions | Yield |
---|---|
With carbonylchlorohydridotris(triphenylphosphine)ruthenium (II) In toluene at 90℃; for 24h; Inert atmosphere; | 80% |
4-methyl-1,3-pentadiene
7-acetoxy-4,8-dimethyl-6-iodocoumarin
Conditions | Yield |
---|---|
With silver carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane; water at 100℃; for 24h; | 79% |
4-methyl-1,3-pentadiene
7-acetoxy-8-iodo-4-methylcoumarin
Conditions | Yield |
---|---|
With silver carbonate; 1,2-bis-(diphenylphosphino)ethane; bis(dibenzylideneacetone)-palladium(0) In 1,4-dioxane; water at 100℃; for 24h; | 78% |
4-methyl-1,3-pentadiene
1,3-cylohexanedione
2,2-dimethyl-2,3,4,6,7,8-hexahydro-5H-chromen-5-one
Conditions | Yield |
---|---|
With nafion In 1,2-dichloro-ethane at 110℃; for 24h; Sealed tube; | 74% |
4-methyl-1,3-pentadiene
Trichloroacetyl chloride
2,2-Dichloro-3-(2-methylpropenyl)-cyclobutanone
Conditions | Yield |
---|---|
With zinc; trichlorophosphate In diethyl ether for 12h; Ambient temperature; | 71% |
4-methyl-1,3-pentadiene
2-oxopent-3-enenitrile
4-Methyl-6-(2-methyl-propenyl)-5,6-dihydro-4H-pyran-2-carbonitrile
Conditions | Yield |
---|---|
With aluminium trichloride In benzene Ambient temperature; | 70% |
4-methyl-1,3-pentadiene
phenylselenyl benzenesulfonate
4-Methyl-2-(phenylsulfonyl)-1,3-pentadiene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid In dichloromethane Ambient temperature; 1) 17 h, 2) 15 min; | 68% |
4-methyl-1,3-pentadiene
N,N-dibenzylformamide
1-(N,N-dibenzylamino)-2-ethenyl-3,3-dimethylcyclopropane
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; methylmagnesium chloride; cyclohexylmagnesium bromide In tetrahydrofuran; diethyl ether at 20℃; for 10h; | 64% |
Conditions | Yield |
---|---|
With triphenyl phosphite; copper(l) chloride In benzene-d6 at 20℃; for 6h; | 62% |
IUPAC Name: 4-Methylpenta-1,3-diene
Synonyms: 4-Methylpenta-1,3-diene ; 1,3-Pentadiene, 4-methyl- ; 3-Methyl-1,4-pentadiene ; 4-Methyl-1,3-pentadiene ; Penta-1,3-diene, 4-methyl-
The Molecular Formula of 4-Methylpenta-1,3-diene (CAS NO.926-56-7):C6H10
The Molecular Weight of 4-Methylpenta-1,3-diene (CAS NO.926-56-7):82.1436g/mol
The Molecular Structure of 4-Methylpenta-1,3-diene (CAS NO.926-56-7):
Index of Refraction: 1.421
Molar Refractivity: 29.47 cm3
Molar Volume: 116 cm3
Surface Tension: 19.2 dyne/cm
Density: 0.707 g/ cm3
Flash Point: -18°C
Enthalpy of Vaporization: 30.44 kJ/mol
Boiling Point: 76.5 °C at 760 mmHg
Vapour Pressure: 111 mmHg at 25°C
4-Methylpenta-1,3-diene ,whose cas register No. is 926-56-7, can be used as reducing agent.
A very dangerous fire hazard when exposed to heat or flame. When heated to decomposition it emits acrid smoke and irritating fumes. See also 2-METHYL-1,3-PENTADIENE.
Hazard Codes: F,Xn
Risk Statements: 11-65
R11:Highly flammable.
R65:Harmful: may cause lung damage if swallowed.
Safety Statements: 16-36-62
S16:Keep away from sources of ignition.
S36:Wear suitable protective clothing.
S62:If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label.
RIDADR: UN 2461 3/PG 2
WGK Germany: 3
HazardClass: 3.1
PackingGroup: II
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