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504-60-9

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504-60-9 Usage

Chemical Properties

colourless liquid

General Description

A clear colorless liquid with an acrid odor. Flash point of -20°F. Boiling point 5°F. A dangerous fire risk. Vapors are irritating to the eyes and respiratory system. Subject to polymerization if heated or contaminated. If the polymerization takes place inside a container, the container may violently rupture. Insoluble in water. Used to make intermediates and polymers.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

TRANS-1,3-PENTADIENE may react vigorously with strong oxidizing agents. May react exothermically with reducing agents to release hydrogen gas. In the presence of various catalysts (such as acids) or initiators, may undergo exothermic addition polymerization reactions. May undergo autoxidation upon exposure to the air to form explosive peroxides. Violent explosions at low temperatures in ammonia synthesis units have been traced to the addition products of dienes and nitrogen dioxide [Bretherick, 5th Ed., 1995].

Health Hazard

Vapors may cause dizziness or suffocation; contact may irritate skin and eyes.

Check Digit Verification of cas no

The CAS Registry Mumber 504-60-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 4 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 504-60:
(5*5)+(4*0)+(3*4)+(2*6)+(1*0)=49
49 % 10 = 9
So 504-60-9 is a valid CAS Registry Number.
InChI:InChI=1S/C5H8/c1-3-5-4-2/h3-5H,1H2,2H3

504-60-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name TRANS-1,3-PENTADIENE

1.2 Other means of identification

Product number -
Other names 4-methyl-1,3-butadiene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Fuels and fuel additives
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:504-60-9 SDS

504-60-9Synthetic route

3,5-dimethyl-1H-pyrazole
67-51-6

3,5-dimethyl-1H-pyrazole

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
at 800℃; under 0.1 Torr; for 2.77778E-06h; Product distribution; Mechanism; var. temp., deuterium substituted 3,5-dimethylpyrazole;100%
at 456.9℃; under 0.2 - 0.5 Torr; for 2.77778E-05h; Kinetics; Mechanism; Thermodynamic data; Irradiation; various temp., ΔH(excit.);
Conditions
ConditionsYield
With hydrogen bromide; tetrabutyl phosphonium bromide at 200℃; for 0.25h; Menshutkin Reaction; Inert atmosphere;99%
With monoaluminum phosphate at 450℃; under 35 Torr;
With hydrogen bromide
1-penten
109-67-1

1-penten

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With oxygen; Bi-Mo oxide (1/1) at 400℃; Rate constant; Kinetics; also without O2; other temperature;99%
With multi-component bismuth molybdate at 320℃;
2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With borosilicate zeolite B-MWW at 384.84℃; for 48h; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Flow reactor; Green chemistry;86%
With monoaluminum phosphate at 350℃;
With aluminium oxide#titanium oxide at 600℃; under 25 - 40 Torr;
With sodium phosphate at 280℃;
With kaolin at 400℃; under 70 Torr;
1,4-Pentanediol
626-95-9

1,4-Pentanediol

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With Ag/Pr/Zr-Si at 460 - 600℃; Reagent/catalyst; Temperature; Inert atmosphere;76%
With phosphorus at 400℃; Dehydratisierung.;
Multi-step reaction with 2 steps
1: HBr
2: sodium; xylene
View Scheme
With VTi2P5.1O(x) at 350℃; for 3h; Catalytic behavior;
1,3-pentanediol
3174-67-2

1,3-pentanediol

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With H3SiW12O40/SBA In dichloromethane at 300℃; Temperature; Reagent/catalyst;76%
2-methyltetrahydrofuran
96-47-9

2-methyltetrahydrofuran

A

penta-1,3-diene
504-60-9

penta-1,3-diene

B

1,4-Pentadiene
591-93-5

1,4-Pentadiene

Conditions
ConditionsYield
With borosilicate zeolite B-MFI at 384.84℃; for 10h; Catalytic behavior; Kinetics; Reagent/catalyst; Temperature; Flow reactor; Green chemistry;A 76%
B n/a
With 2-(diisopropylphosphonic acid)terephthalate exchanged zirconium terephthalate based metal-organic framework UiO66 at 280℃; under 4.9 Torr; Reagent/catalyst; Temperature;
1,2-pentanediol
5343-92-0

1,2-pentanediol

A

penta-1,3-diene
504-60-9

penta-1,3-diene

B

pentanal
110-62-3

pentanal

C

2-butyl-4-propyl-1,3-dioxolane

2-butyl-4-propyl-1,3-dioxolane

Conditions
ConditionsYield
With tungsten trioxide on silica; hydrogen In water at 250℃; for 5h; Concentration; Temperature; Inert atmosphere;A 19.9%
B 72%
C 8.6%
4-propenyl-1,3-dioxane
40749-83-5

4-propenyl-1,3-dioxane

ethyl acetate
141-78-6

ethyl acetate

A

6-methyl-3,6-dihydro-2H-pyran
55230-25-6

6-methyl-3,6-dihydro-2H-pyran

B

penta-1,3-diene
504-60-9

penta-1,3-diene

C

1,3,5-hexatriene
2235-12-3

1,3,5-hexatriene

D

2,4-hexadien-1-ol acetate
1516-17-2

2,4-hexadien-1-ol acetate

E

3,5-hexadien-1-ol acetate
75338-23-7

3,5-hexadien-1-ol acetate

Conditions
ConditionsYield
With sulfuric acid at 90℃; for 9h; metal ampul;A 17%
B 3%
C 5%
D 20%
E 50%
methylbutane
78-78-4

methylbutane

A

2-methyl-but-2-ene
513-35-9

2-methyl-but-2-ene

B

penta-1,3-diene
504-60-9

penta-1,3-diene

C

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

cyclopenta-1,3-diene

D

2-Methyl-1-butene
563-46-2

2-Methyl-1-butene

E

3-Methyl-1-butene
563-45-1

3-Methyl-1-butene

F

pentane
109-66-0

pentane

G

isoprene
78-79-5

isoprene

Conditions
ConditionsYield
With platinum-aluminum catalyst at 600℃; Gas phase;A n/a
B n/a
C n/a
D n/a
E n/a
F n/a
G 28.72%
hexa-2,4-dienoic acid
110-44-1

hexa-2,4-dienoic acid

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With 1,10-Phenanthroline; copper hydroxide In 1-methyl-pyrrolidin-2-one at 180℃; for 5h; Inert atmosphere; Green chemistry;14%
piperidine
110-89-4

piperidine

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With phosphoric acid at 380 - 400℃;
Abbau durch erschoepfende Methylierung;
Abbau durch erschoepfende Methylierung; dabei findet Verschiebung einer Doppelbildung statt;
propan-1-ol
71-23-8

propan-1-ol

ethanol
64-17-5

ethanol

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With Lebedew-catalyst
propan-1-ol
71-23-8

propan-1-ol

ethanol
64-17-5

ethanol

A

penta-1,3-diene
504-60-9

penta-1,3-diene

B

buta-1,3-diene
106-99-0

buta-1,3-diene

C

hexa-2,4-diene
592-46-1

hexa-2,4-diene

Conditions
ConditionsYield
ueber Lebedew-Katalysatoren;
phthalic anhydride
85-44-9

phthalic anhydride

1-Penten-3-ol
616-25-1

1-Penten-3-ol

penta-1,3-diene
504-60-9

penta-1,3-diene

3-methyl-1-cyclopentene
1120-62-3

3-methyl-1-cyclopentene

penta-1,3-diene
504-60-9

penta-1,3-diene

n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With aluminum oxide at 390℃;
2-ethoxyprop-1-ene
926-66-9

2-ethoxyprop-1-ene

ethene
74-85-1

ethene

A

penta-1,3-diene
504-60-9

penta-1,3-diene

B

isoprene
78-79-5

isoprene

Conditions
ConditionsYield
at 150 - 160℃; beim Leiten ueber einen Mischkatalysator aus Aluminium und Oxiden des Bors, Wolframs, Urans und Silbers;
at 150 - 160℃; beim Leiten ueber einen Mischkatalysator aus Aluminium und Oxiden des Bors, Wolframs, Urans und Silbers;
1,4-Pentadiene
591-93-5

1,4-Pentadiene

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With acetic acid 1-methylbut-3-enyl ester at 550 - 570℃; under 70 - 80 Torr; ueber Glaswolle.;
With borosilicate zeolite B-MWW at 334.84℃; Reagent/catalyst; Flow reactor; Green chemistry;
2-Pentyne
627-21-4

2-Pentyne

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide at 250℃;
1-Pentyne
627-19-0

1-Pentyne

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With aluminium oxide-chromium oxide at 250℃;
1-Pentyne
627-19-0

1-Pentyne

A

penta-1,3-diene
504-60-9

penta-1,3-diene

B

2-Pentyne
627-21-4

2-Pentyne

Conditions
ConditionsYield
With chromium corundum at 250℃;
1,4-dichloropentane
626-92-6

1,4-dichloropentane

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With water; magnesium chloride at 300℃; Kupfer aktivierte Katalysatore;
ethanol
64-17-5

ethanol

2,3-dimethylbutene
590-19-2

2,3-dimethylbutene

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With Lebedew-catalyst; acetone
With trans-Crotonaldehyde; Lebedew-catalyst
3-penten-2-ol
1569-50-2

3-penten-2-ol

penta-1,3-diene
504-60-9

penta-1,3-diene

2-pentanol
584-02-1

2-pentanol

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With sulfuric acid at 100℃; Behandeln des entstandenen Pentens mit Brom in Hexan bei -20grad und Leiten des erhaltenen Dibromids ueber Natronalk bei 500grad.;
pentan-1-ol
71-41-0

pentan-1-ol

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With aluminum oxide; chromium(III) oxide at 600℃; under 130 Torr;
2,3-dichloropentane
600-11-3

2,3-dichloropentane

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With water; magnesium chloride at 300℃; Kupfer aktivierte Katalisator.;
2,3-dibromo-pentane
5398-25-4

2,3-dibromo-pentane

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
With soda lime; carbonic-acid at 600℃;
acetaldol
107-89-1

acetaldol

methylmagnesium bromide
75-16-1

methylmagnesium bromide

penta-1,3-diene
504-60-9

penta-1,3-diene

Conditions
ConditionsYield
man dampft das Reaktionsprodukt mit verd. Schwefelsaeure auf dem Wasserbad ein;
penta-1,3-diene
504-60-9

penta-1,3-diene

di-tert-butyl-diazodicarboxylate
870-50-8

di-tert-butyl-diazodicarboxylate

di-tert-butyl 3-methyl-1,2,3,6-tetrahydropyridazine-1,2-dicarboxylate
1072150-92-5

di-tert-butyl 3-methyl-1,2,3,6-tetrahydropyridazine-1,2-dicarboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; Diels-Alder reaction;100%
penta-1,3-diene
504-60-9

penta-1,3-diene

tert-butyl 2-(4-chlorophenylcarbamoyl)diazenecarboxylate
1425040-20-5

tert-butyl 2-(4-chlorophenylcarbamoyl)diazenecarboxylate

(S)-tert-butyl 2-((4-chlorophenyl)carbamoyl)-6-methyl-2,3-dihydropyridazine-1-(6H)-carboxylate

(S)-tert-butyl 2-((4-chlorophenyl)carbamoyl)-6-methyl-2,3-dihydropyridazine-1-(6H)-carboxylate

Conditions
ConditionsYield
With C50H56O4P(1-)*Ag(1+)*H2O In dichloromethane at -40℃; for 4h; Diels-Alder Cycloaddition; Darkness;99%
penta-1,3-diene
504-60-9

penta-1,3-diene

4-chloropent-2-ene
1458-99-7

4-chloropent-2-ene

Conditions
ConditionsYield
With hydrogenchloride at -10 - -5℃;98%
With hydrogenchloride at -5 - 0℃;98%
With hydrogenchloride; N,N-dimethyl-formamide at -10 - -5℃;98%
penta-1,3-diene
504-60-9

penta-1,3-diene

bromomethanesulfonyl bromide
54730-18-6

bromomethanesulfonyl bromide

4-bromo-2-pentenyl bromomethyl sulfone
102683-77-2

4-bromo-2-pentenyl bromomethyl sulfone

Conditions
ConditionsYield
In dichloromethane at 0℃;98%
D-Galactose
10257-28-0

D-Galactose

penta-1,3-diene
504-60-9

penta-1,3-diene

3-acetyl-2-methyl-5-(α,β-D-threofuranosyl)furan
81148-33-6, 112677-77-7, 125589-85-7, 125589-86-8

3-acetyl-2-methyl-5-(α,β-D-threofuranosyl)furan

Conditions
ConditionsYield
With zinc(II) chloride In ethanol; water for 48h; Heating;95%
penta-1,3-diene
504-60-9

penta-1,3-diene

2-phenyl-2,3-((4-methoxyphenyl)imino)-2,3-dihydro-1,4-naphthoquinone
79060-54-1

2-phenyl-2,3-((4-methoxyphenyl)imino)-2,3-dihydro-1,4-naphthoquinone

3,4-benzo-9-(4-methoxyphenyl)-1-phenyl-8-(1-propenyl)-9-azabicyclo<4.2.1>nonene-2,5-dione
87373-43-1

3,4-benzo-9-(4-methoxyphenyl)-1-phenyl-8-(1-propenyl)-9-azabicyclo<4.2.1>nonene-2,5-dione

Conditions
ConditionsYield
In benzene for 80h; Irradiation;95%
penta-1,3-diene
504-60-9

penta-1,3-diene

(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)boronic acid
1130728-52-7

(3-methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)boronic acid

(1RS,4aSR,9aRS)-1,4,4a,9a-tetrahydro-1,4a-dimethylanthracene-9,10-dione

(1RS,4aSR,9aRS)-1,4,4a,9a-tetrahydro-1,4a-dimethylanthracene-9,10-dione

Conditions
ConditionsYield
In dichloromethane at 25℃; for 2h; Diels-Alder reaction;95%
bis(1,5-cyclooctadiene)nickel (0)
1295-35-8

bis(1,5-cyclooctadiene)nickel (0)

penta-1,3-diene
504-60-9

penta-1,3-diene

1,2-bis(di-tert-butyl)phosphinoethane
4141-59-7

1,2-bis(di-tert-butyl)phosphinoethane

[(dtbpe)Ni( piperylene)]

[(dtbpe)Ni( piperylene)]

Conditions
ConditionsYield
In tetrahydrofuran-d8 at 100℃; for 24h; Inert atmosphere;95%
penta-1,3-diene
504-60-9

penta-1,3-diene

phenylsilane
694-53-1

phenylsilane

C11H16Si

C11H16Si

Conditions
ConditionsYield
With C16H18Cl2CoN2O; sodium triethylborohydride In tetrahydrofuran at -30 - 25℃; for 12h; Inert atmosphere; enantioselective reaction;95%
dimethylenecyclourethane
497-25-6

dimethylenecyclourethane

penta-1,3-diene
504-60-9

penta-1,3-diene

(E)-3-(pent-3-en-2-yl)oxazolidin-2-one

(E)-3-(pent-3-en-2-yl)oxazolidin-2-one

Conditions
ConditionsYield
With bismuth(lll) trifluoromethanesulfonate; tetrakis(actonitrile)copper(I) hexafluorophosphate; 1,2-bis-(diphenylphosphino)ethane In 1,4-dioxane at 50℃; for 18h;94%
penta-1,3-diene
504-60-9

penta-1,3-diene

N,N'-di-tert-butyldiaziridinone
19656-74-7

N,N'-di-tert-butyldiaziridinone

1,3-di-tert-butyl-4-methyl-5-vinyl-imidazolidin-2-one

1,3-di-tert-butyl-4-methyl-5-vinyl-imidazolidin-2-one

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0) In benzene-d6 at 65℃; Inert atmosphere;94%
penta-1,3-diene
504-60-9

penta-1,3-diene

2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid
1130728-55-0

2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid

(4aSR,5RS,8aSR)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione
55756-89-3, 97521-93-2, 117661-49-1, 117661-66-2

(4aSR,5RS,8aSR)-2,5,8a-trimethyl-4a,5,8,8a-tetrahydronaphthalene-1,4-dione

Conditions
ConditionsYield
In dichloromethane at 25℃; for 1h; Diels-Alder reaction;93%
penta-1,3-diene
504-60-9

penta-1,3-diene

pinacol vinylboronate
75927-49-0

pinacol vinylboronate

(1E,4Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-methylhexa-1,4-diene

(1E,4Z)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-methylhexa-1,4-diene

Conditions
ConditionsYield
With (η6-naphthalene)(η4-1,5-cyclooctadiene)ruthenium(0) In benzene at 30℃; for 1h; Inert atmosphere; Schlenk technique;93%
penta-1,3-diene
504-60-9

penta-1,3-diene

trans-1,2-cyclohexandiol
1460-57-7

trans-1,2-cyclohexandiol

(4aRS,5RS,8aSR)-5-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-4a,8a-diol

(4aRS,5RS,8aSR)-5-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalene-4a,8a-diol

Conditions
ConditionsYield
With dodecacarbonyl-triangulo-triruthenium; 2,2'-bis(diphenylphosphino)biphenyl In toluene at 130℃; for 48h; Inert atmosphere; diastereoselective reaction;91%
penta-1,3-diene
504-60-9

penta-1,3-diene

C31H54O

C31H54O

C36H62O

C36H62O

Conditions
ConditionsYield
With bis(trifluoromethane)sulfonimide lithium In methyl cyclohexane at 20℃; Diels-Alder Cycloaddition; Electrochemical reaction;91%
penta-1,3-diene
504-60-9

penta-1,3-diene

acrylonitrile
107-13-1

acrylonitrile

2-methyl-1,2,5,6-tetrahydrobenzonitrile
4736-16-7

2-methyl-1,2,5,6-tetrahydrobenzonitrile

Conditions
ConditionsYield
With hydroquinone at 140℃; for 12h;90%
penta-1,3-diene
504-60-9

penta-1,3-diene

1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one
461677-71-4

1-benzyl-3-diazo-1,3-dihydro-2H-indol-2-one

1'-(phenylmethyl)-2-[1-prop-1-en-1-yl]spiro[cyclopropane-1,3'-indol]-2'(1'H)-one
864949-91-7

1'-(phenylmethyl)-2-[1-prop-1-en-1-yl]spiro[cyclopropane-1,3'-indol]-2'(1'H)-one

Conditions
ConditionsYield
With dirhodium tetraacetate In benzene for 4h; Heating;90%
penta-1,3-diene
504-60-9

penta-1,3-diene

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine
35024-12-5

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine

2-(1-propenyl)-4-oxo-6,6-dimethyl-2,3,4,5,6,7-hexahydrobenzofuran
92898-20-9

2-(1-propenyl)-4-oxo-6,6-dimethyl-2,3,4,5,6,7-hexahydrobenzofuran

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1h; Cycloaddition; Irradiation;89%
penta-1,3-diene
504-60-9

penta-1,3-diene

methyl 2-(diethoxyphosphoryl)imino-3,3,3-trifluoropropionate
503312-47-8

methyl 2-(diethoxyphosphoryl)imino-3,3,3-trifluoropropionate

methyl 1-diethoxyphosphoryl-6-methyl-2-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylate

methyl 1-diethoxyphosphoryl-6-methyl-2-trifluoromethyl-1,2,3,6-tetrahydropyridine-2-carboxylate

Conditions
ConditionsYield
In dichloromethane at 20℃; for 150h; aza Diels-Alder reaction;89%
penta-1,3-diene
504-60-9

penta-1,3-diene

Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

Dimethyl-((Z)-pent-2-enyl)-phenyl-silane

Dimethyl-((Z)-pent-2-enyl)-phenyl-silane

Conditions
ConditionsYield
With diisobutylaluminium hydride; triethylphosphine; bis(acetylacetonate)nickel(II) In toluene at 80℃; for 24h;89%
penta-1,3-diene
504-60-9

penta-1,3-diene

methyl 3,3,3-trifluoropyruvate
13089-11-7

methyl 3,3,3-trifluoropyruvate

6-trifluoromethyl-6-methoxycarbonyl-2-methyl-5,6-dihydro-2H-pyran
134224-64-9

6-trifluoromethyl-6-methoxycarbonyl-2-methyl-5,6-dihydro-2H-pyran

Conditions
ConditionsYield
In hexane at 20℃; for 24h;88%
penta-1,3-diene
504-60-9

penta-1,3-diene

-1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene
139118-84-6

-1-(2-phenylpropylsulfinyl)-2-nitrocyclopentene

(3aS,4S,7aR)-4-Methyl-3a-nitro-7a-((R)-(S)-2-phenyl-propane-1-sulfinyl)-2,3,3a,4,7,7a-hexahydro-1H-indene

(3aS,4S,7aR)-4-Methyl-3a-nitro-7a-((R)-(S)-2-phenyl-propane-1-sulfinyl)-2,3,3a,4,7,7a-hexahydro-1H-indene

Conditions
ConditionsYield
With hydroquinone In dichloromethane under 6000480 Torr; for 120h; Ambient temperature;88%
penta-1,3-diene
504-60-9

penta-1,3-diene

acetic acid
64-19-7

acetic acid

Acetic acid (E)-4-bromo-1-methyl-but-2-enyl ester

Acetic acid (E)-4-bromo-1-methyl-but-2-enyl ester

Conditions
ConditionsYield
With N-Bromosuccinimide Ambient temperature;88%
penta-1,3-diene
504-60-9

penta-1,3-diene

2-(cyclohex-2-en-1-yl)-6-methylaniline
84487-52-5

2-(cyclohex-2-en-1-yl)-6-methylaniline

6-methyl-4-(1-methyl-2-buten-1-yl)-2-(2-cyclohexen-1-yl)aniline

6-methyl-4-(1-methyl-2-buten-1-yl)-2-(2-cyclohexen-1-yl)aniline

Conditions
ConditionsYield
With aluminium trichloride In benzene at 135℃; for 3h;88%
2,3-Dimethyl-2-butene
563-79-1

2,3-Dimethyl-2-butene

penta-1,3-diene
504-60-9

penta-1,3-diene

polymer; monomer(s): 1,3-pentadiene; 2,3-dimethyl-2-butene

polymer; monomer(s): 1,3-pentadiene; 2,3-dimethyl-2-butene

Conditions
ConditionsYield
With aluminium trichloride In pentane at 20℃; for 2h;87%
penta-1,3-diene
504-60-9

penta-1,3-diene

6-methyl-2-(1-cyclohexen-1-yl)aniline
418760-99-3

6-methyl-2-(1-cyclohexen-1-yl)aniline

6-methyl-4-(1-methyl-2-buten-1-yl)-2-(1-cyclohexen-1-yl)aniline

6-methyl-4-(1-methyl-2-buten-1-yl)-2-(1-cyclohexen-1-yl)aniline

Conditions
ConditionsYield
With aluminium trichloride In benzene at 135℃; for 3h;87%

504-60-9Relevant articles and documents

Production of renewable 1,3-pentadiene over LaPO4 via dehydration of 2,3-pentanediol derived from 2,3-pentanedione

Bai, Chenxi,Cui, Long,Dai, Quanquan,Feng, Ruilin,Liu, Shijun,Qi, Yanlong

, (2022/02/07)

1,3-Pentadiene plays an extremely important role in the production of polymers and fine chemicals. Herein, the LaPO4 catalyst exhibits excellent catalytic performance for the dehydration production of 1,3-pentadiene with 2,3-pentanediol, a C5 diol platform compound that can be easily obtained by hydrogenation of bio-based 2,3-pentanedione. The relationships of catalyst structure-acid/base properties-catalytic performance was established, and an acid-base synergy effect was disclosed for the on-purpose synthesis of 1,3-pentadiene. Thus, a balance between acid and base sites was required, and an optimized LaPO4 with acid/base ratio of 2.63 afforded a yield of 1,3-pentadiene as high as 61.5% at atmospheric pressure. Notably, the Br?nsted acid sites with weak or medium in LaPO4 catalyst can inhibit the occurrence of pinacol rearrangement, resulting in higher 1,3-pentadiene production. In addition, the investigation on reaction pathways demonstrated that the E2 mechanism was dominant in this dehydration reaction, accompanied by the assistance of E1 and E1cb.

Synthesis method of pentanediol, and synthesis method for preparing biomass-based pentadiene through conversion of levulinic acid and derivatives of levulinic acid

-

Paragraph 0157; 0161-0165; 0170; 0174-0177; 0178; 0182-0185, (2021/04/07)

The invention provides a synthesis method of pentanediol, and the method comprises the following steps: carrying out conversion reaction on a mixed solution obtained by mixing levulinic acid and/or levulinic acid derivatives, a catalyst and an organic solvent in a hydrogen-containing atmosphere to obtain the pentanediol. According to the method, a large amount of cheap and easily available bio-based chemical levulinic acid or derivatives thereof can be utilized, pentanediol is obtained through catalytic conversion, and m-pentadiene is further obtained. The raw materials are derived from renewable resources, the m-pentadiene is prepared through hydrogenation and dehydration, and particularly, a green and sustainable process route for synthesizing the m-pentadiene is finally obtained through a dehydration reaction route and construction of a dehydration catalyst. The invention provides a method for green and sustainable synthesis of linear pentadiene based on bio-based chemical conversion, and the method has the advantages of simple operation, short flow, no need of harsh experimental conditions, easy preparation of raw materials and catalysts, and large-scale synthesis prospect.

Dehydra-decyclization of 2-methyltetrahydrofuran to pentadienes on boron-containing zeolites

Dauenhauer, Paul J.,Kumar, Gaurav,Liu, Dongxia,Ren, Limin,Tsapatsis, Michael,Xu, Dandan

supporting information, p. 4147 - 4160 (2020/07/14)

1,3-Pentadiene (piperylene) is an important monomer in the manufacturing of adhesives, plastics, and resins. It can be derived from biomass by the tandem ring-opening and dehydration (dehydra-decyclization) of 2-methyltetrahydrofuran (2-MTHF), but competing reaction pathways and the formation of another isomer (1,4-pentadiene) have limited piperylene yields to MFI > BEA at a given temperature (523 K), indicating the non-identical nature of active sites in these weak solid acids. The diene distribution remained far from equilibrium and was tuned towards the desirable conjugated diene (1,3-pentadiene) by facile isomerization of 1,4-pentadiene. This tuning capability was facilitated by high bed residence times, as well as the smaller micropore sizes among the zeolite frameworks considered. The suppression of competing pathways, and promotion of 1,4-pentadiene isomerization events lead to a hitherto unreported ~86percent 1,3-pentadiene yield and an overall ~89percent combined linear C5 dienes' yield at near quantitative (~98percent) 2-MTHF conversion on the borosilicate B-MWW, without a significant reduction in diene selectivities for at least 80 hours time-on-stream under low space velocity (0.85 g reactant per g cat. per h) and high temperature (658 K) conditions. Finally, starting with iso-conversion levels (ca. 21-26percent) and using total turnover numbers (TONs) accrued over the entire catalyst lifetime as the stability criterion, borosilicates were demonstrated to be significantly more stable than aluminosilicates under reaction conditions (~3-6× higher TONs).

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