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3710-30-3

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3710-30-3 Usage

Chemical Properties

CLEAR COLORLESS TO SLIGHTLY YELLOW LIQUID

Uses

Different sources of media describe the Uses of 3710-30-3 differently. You can refer to the following data:
1. 1,7-Octadiene is used in organic synthesis. It is also used to study and assess the structure and reaction rate in olefin ring-closing metathesis of a series of simple dienes. Further, it is used in a study to investigate micropatterned surfaces prepared by plasma polymerization. It acts as a crosslinker as well as a source of ethylene in cross-enyne metathesis (CEYM)-related reactions.
2. 1,7-Octadiene has been used in a study to assess the structure and reaction rate in olefin ring-closing metathesis of a series of simple dienes. It has also been used in a study to investigate micropatterned surfaces prepared by plasma polymerization.

General Description

1,7-Octadiene can serve as a crosslinker and source of ethylene for a variant of Mori′s conditions in CEYM-related reactions.

Flammability and Explosibility

Highlyflammable

Safety Profile

Mildly toxic by ingestion,inhalation and skin contact. A very dangerous fire hazardwhen exposed to heat or flame; can react vigorously withoxidizing materials. When heated to decomposition itemits acrid smoke and irritating fumes.

Check Digit Verification of cas no

The CAS Registry Mumber 3710-30-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,7,1 and 0 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 3710-30:
(6*3)+(5*7)+(4*1)+(3*0)+(2*3)+(1*0)=63
63 % 10 = 3
So 3710-30-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H14/c1-3-5-7-8-6-4-2/h3-4H,1-2,5-8H2

3710-30-3 Well-known Company Product Price

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  • Alfa Aesar

  • (L07659)  1,7-Octadiene, 97%   

  • 3710-30-3

  • 100ml

  • 611.0CNY

  • Detail
  • Alfa Aesar

  • (L07659)  1,7-Octadiene, 97%   

  • 3710-30-3

  • 500ml

  • 2399.0CNY

  • Detail

3710-30-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name octa-1,7-diene

1.2 Other means of identification

Product number -
Other names 1,7-Octadiene

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:3710-30-3 SDS

3710-30-3Synthetic route

2-(5-hexenyl)thiirane
14122-59-9

2-(5-hexenyl)thiirane

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With hydrogen sulfide; triphenylphosphine; methyltrioxorhenium(VII) In [D3]acetonitrile for 1h; Ambient temperature;100%
With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) In benzene Heating;85%
1-bromo-4-butene
5162-44-7

1-bromo-4-butene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With triethanolamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH3CN)2](PF6)2 In acetonitrile at 23 - 28℃; for 12h; Inert atmosphere; Sealed tube; Irradiation;98%
With diethyl ether; sodium
octa-1,7-dien-3-yl acetate
3491-26-7

octa-1,7-dien-3-yl acetate

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With formic acid; triethylamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine In tetrahydrofuran for 4h; Heating;76%
(E)-1-acetoxy-2,7-octadiene
30460-73-2

(E)-1-acetoxy-2,7-octadiene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With formic acid; triethylamine; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tributylphosphine In tetrahydrofuran for 2h; Heating;67%
With ammonium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;100 % Chromat.
7,8-diazabicyclo<4.2.2>dec-7-ene
32634-64-3

7,8-diazabicyclo<4.2.2>dec-7-ene

A

(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

B

cis-bicyclo<4.2.0>octane
28282-35-1

cis-bicyclo<4.2.0>octane

C

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With 4-tert-Butylcatechol In Petroleum ether at 160 - 170℃; for 69h;A 14%
B 23%
C 30%
In Petroleum ether at 160 - 170℃; for 69h; Mechanism; 4-t-butylpyrocatechol;A 14%
B 23%
C 30%
In Petroleum ether at 170℃;
In Petroleum ether at 170℃; also with deuterio labelled substrate;
cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With lanthanum; iodine In tetrahydrofuran at 67℃; for 2h;26%
With α-picoline; manganese; trifluoroacetic acid; cobalt(II) bromide In acetonitrile at 50℃;
With triethanolamine; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; [Ni(2,2′:6′,2''-terpyridine)(pyridine)(CH3CN)2](PF6)2 for 12h; Irradiation; Inert atmosphere;
C36H50N2NiO(1-)*C12H24KO6(1+)

C36H50N2NiO(1-)*C12H24KO6(1+)

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

C36H50N2NiO

C36H50N2NiO

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
In tetrahydrofuran-d8 at 22℃; Inert atmosphere; Schlenk technique;A 22%
B 22%
ethene
74-85-1

ethene

cyclohexene
110-83-8

cyclohexene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
In hexane at 16 - 18℃; under 53203.6 Torr; Pressure; Temperature;20.1%
at 25 - 80℃; under 30003 - 150015 Torr; for 24 - 42h; Product distribution / selectivity;
1,7-Octadiyne
871-84-1

1,7-Octadiyne

A

octane
111-65-9

octane

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
palladium anchored polystyrene In neat (no solvent) at 25℃; under 1551.4 Torr; for 36h;A 20%
B 20%
palladium anchored polystyrene In neat (no solvent) at 25℃; under 1551.4 Torr; for 36h;A 20%
B 20%
buta-1,3-diene
106-99-0

buta-1,3-diene

A

1,6-octadiene
3710-41-6

1,6-octadiene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
Stage #1: buta-1,3-diene With TEMPOL; sodium methylate; palladium diacetate In 1-methyl-pyrrolidin-2-one at -5 - 75℃; under 7500.75 Torr; Inert atmosphere;
Stage #2: With formic acid In 1-methyl-pyrrolidin-2-one at 80 - 90℃; under 15001.5 Torr; Product distribution / selectivity; Inert atmosphere;
A 5.5%
B 94.3 %Chromat.
With formic acid; triethylamine; palladium diacetate; triphenylphosphine In DMF (N,N-dimethyl-formamide) at 90℃; under 750.075 Torr; for 1.5h; Product distribution / selectivity;
1,7-Octadiyne
871-84-1

1,7-Octadiyne

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With ammonium sulfate; ammonia; sodium Reagens 4: Aether;
With ethylene dibromide; copper(I) bromide; lithium bromide; zinc In tetrahydrofuran; ethanol Heating;
cyclooctyl acetate
772-60-1

cyclooctyl acetate

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 500℃; Pyrolysis;
4-penten-1-ylmagnesium bromide
34164-50-6

4-penten-1-ylmagnesium bromide

allyl bromide
106-95-6

allyl bromide

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With diethyl ether
4-penten-1-ylmagnesium bromide
34164-50-6

4-penten-1-ylmagnesium bromide

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With diethyl ether
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 550℃;
at 633℃; Thermodynamic data; Rate constant; further temp.; energy of activation;
1,8-octanediyl diacetate
3992-48-1

1,8-octanediyl diacetate

A

oct-7-en-1-yl acetate
5048-35-1

oct-7-en-1-yl acetate

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 500℃;
1,10-decanedioic acid
111-20-6

1,10-decanedioic acid

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With acetic anhydride; bis-triphenylphosphine-palladium(II) chloride at 250℃; under 735.5 Torr; Yield given;
Stage #1: 1,10-decanedioic acid With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium iodide at 20℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: With acetic anhydride at 160℃; for 5h; Inert atmosphere; Schlenk technique; regioselective reaction;
With formate dehydrogenase; 1200 U catalase; OleT in combination with the putidaredoxin electron-transfer system CamAB; P450 monooxygenase OleT; ammonium formate; β-nicotinamide adenine dinucleotide, disodium salt, reduced form In ethanol at 4℃; for 72h; Catalytic behavior; Enzymatic reaction;
Multi-step reaction with 2 steps
1: P450 monooxygenase OleT; OleT in combination with the putidaredoxin electron-transfer system CamAB; formate dehydrogenase; β-nicotinamide adenine dinucleotide, disodium salt, reduced form; 1200 U catalase; ammonium formate / ethanol / Enzymatic reaction
2: P450 monooxygenase OleT; OleT in combination with the putidaredoxin electron-transfer system CamAB; formate dehydrogenase; β-nicotinamide adenine dinucleotide, disodium salt, reduced form; 1200 U catalase; ammonium formate / ethanol / Enzymatic reaction
View Scheme
bicyclo<4.2.0>octane
278-30-8, 28282-35-1, 63296-41-3

bicyclo<4.2.0>octane

A

ethene
74-85-1

ethene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

C

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
In pentane Quantum yield; Irradiation;
(E)-1-phenoxy-2,7-octadiene
15972-89-1

(E)-1-phenoxy-2,7-octadiene

A

1,6-octadiene
3710-41-6

1,6-octadiene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With ammonium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;A 2 % Chromat.
B 98 % Chromat.
3-Phenoxy-1,7-octadien
15972-91-5

3-Phenoxy-1,7-octadien

A

1,6-octadiene
3710-41-6

1,6-octadiene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With ammonium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;A 1 % Chromat.
B 99 % Chromat.
(E)-cyclooctene
931-89-5

(E)-cyclooctene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 633℃; Rate constant; further temperature;
(E)-cyclooctene
931-89-5

(E)-cyclooctene

A

(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 300.1℃; Rate constant; Thermodynamic data; further temperatures; energy of activation; ΔH(exit.); ΔS(exit.);
(E)-cyclooctene
931-89-5

(E)-cyclooctene

A

(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

B

vinylcyclohexane
695-12-5

vinylcyclohexane

C

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 512℃; Rate constant; further temperatures;
octa-1,7-dien-3-yl acetate
3491-26-7

octa-1,7-dien-3-yl acetate

A

1,6-octadiene
3710-41-6

1,6-octadiene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With ammonium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;A 4 % Chromat.
B 96 % Chromat.
(E)-1-acetoxy-2,7-octadiene
30460-73-2

(E)-1-acetoxy-2,7-octadiene

A

1,6-octadiene
3710-41-6

1,6-octadiene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With ammonium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;A 30 % Chromat.
B 70 % Chromat.
With ammonium formate; bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine In 1,4-dioxane at 100℃; for 2h; Product distribution; other catalysts, other ligands;A 21 % Chromat.
B 79 % Chromat.
With ammonium formate; tris(dibenzylideneacetone)dipalladium(0) chloroform complex; triethyl phosphite In 1,4-dioxane for 2h; Product distribution; Heating; var. catalyst,;A 26 % Chromat.
B 74 % Chromat.
(E)-2,7-octadienyl methyl carbonate
92747-31-4

(E)-2,7-octadienyl methyl carbonate

A

1,6-octadiene
3710-41-6

1,6-octadiene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With ammonium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;A 1 % Chromat.
B 99 % Chromat.
7,8-diazabicyclo<4.2.2>dec-7-ene
32634-64-3

7,8-diazabicyclo<4.2.2>dec-7-ene

A

(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

B

cis-bicyclo<4.2.0>octane
28282-35-1

cis-bicyclo<4.2.0>octane

C

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
In cyclohexane at 170℃; Product distribution; Mechanism; var. temps; also direct and sensitised photolysis;A 18 % Chromat.
B 35 % Chromat.
C 47 % Chromat.
(E)-8-chloro-octa-1,6-diene
92747-32-5

(E)-8-chloro-octa-1,6-diene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With sodium formate; tris(dibenzylideneacetone)dipalladium chloroform complex; tributylphosphine In 1,4-dioxane for 2h; Heating;100 % Chromat.
cis-8-thiabicyclo<4.3.0>nonane 8,8-dioxide
66301-61-9

cis-8-thiabicyclo<4.3.0>nonane 8,8-dioxide

A

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

buta-1,3-diene

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

C

benzene
71-43-2

benzene

Conditions
ConditionsYield
at 850℃; under 0.005 Torr; Product distribution; other temperature (925 deg C); flash vacuum pyrolysis of bi- and tricyclic sulfones;A n/a
B 41 % Spectr.
C 2 % Spectr.
(Z)-Cyclooctene
931-88-4, 931-87-3

(Z)-Cyclooctene

A

vinylcyclohexane
695-12-5

vinylcyclohexane

B

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
at 336.9 - 817.9℃; Kinetics; Thermodynamic data; activation energy;
1,7-Octadiene
3710-30-3

1,7-Octadiene

octane
111-65-9

octane

Conditions
ConditionsYield
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30402 Torr; for 24h; Catalytic behavior; Inert atmosphere; Schlenk technique;100%
With [Re(NO)(η(2)-H2)Br2(PiPr3)2]; dimethylamine borane; hydrogen at 90℃; under 7500.75 Torr; for 0.2h; Autoclave;88%
With hydrogen; sodium triethylborohydride In tetrahydrofuran at 23℃; under 30003 Torr; for 48h; Reagent/catalyst; Autoclave;82%
1,7-Octadiene
3710-30-3

1,7-Octadiene

cyclohexene
110-83-8

cyclohexene

Conditions
ConditionsYield
With diazomethyl-trimethyl-silane; ruthenium Schiff-base In toluene at 70℃; for 1h; ring-closing metathesis;100%
With diazomethyl-trimethyl-silane; ruthenium In toluene at 85℃; for 17h; Product distribution; Further Variations:; Catalysts;100%
[2-((2,6-iPr2-Ph-imino)methyl)phenol][p-cymene][=CHPh]Ru2Cl3 In various solvent(s) at 70℃; for 4h; Product distribution; Further Variations:; Catalysts; Temperatures;100%
5-Bromoisoindoline-1,3-dione
6941-75-9

5-Bromoisoindoline-1,3-dione

1,7-Octadiene
3710-30-3

1,7-Octadiene

C24H20N2O4
1620872-13-0

C24H20N2O4

Conditions
ConditionsYield
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 150℃; for 24h; Heck Reaction;100%
With palladium diacetate; triethylamine; triphenylphosphine In N,N-dimethyl-formamide at 150℃; for 24h; Heck Reaction;100%
1-ethynyl-4-fluorobenzene
766-98-3

1-ethynyl-4-fluorobenzene

1,7-Octadiene
3710-30-3

1,7-Octadiene

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-(4-fluorophenyl)-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-(4-fluorophenyl)-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;99%
4-ethynyl-1,2-difluorobenzene
143874-13-9

4-ethynyl-1,2-difluorobenzene

1,7-Octadiene
3710-30-3

1,7-Octadiene

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-(3,4-difluorophenyl)-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-(3,4-difluorophenyl)-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;99%
1-ethynyl-2-methoxybenzene
767-91-9

1-ethynyl-2-methoxybenzene

1,7-Octadiene
3710-30-3

1,7-Octadiene

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-(2-methoxyphenyl)-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-(2-methoxyphenyl)-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;99%
4-trifluoromethylphenylacetylene
705-31-7

4-trifluoromethylphenylacetylene

1,7-Octadiene
3710-30-3

1,7-Octadiene

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-(4-trifluoromethylphenyl)-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-(4-trifluoromethylphenyl)-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;99%
1,7-Octadiene
3710-30-3

1,7-Octadiene

phenylacetylene
536-74-3

phenylacetylene

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

2-phenyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione
6337-31-1

2-phenyl-1,4,4a,9a-tetrahydroanthracene-9,10-dione

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;99%
1,7-Octadiene
3710-30-3

1,7-Octadiene

4-methoxyphenylacetylen
768-60-5

4-methoxyphenylacetylen

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-(4-methoxyphenyl)-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-(4-methoxyphenyl)-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;99%
1,1,1,3,3-pentamethyl-1,3-disiloxane
1438-82-0

1,1,1,3,3-pentamethyl-1,3-disiloxane

1,7-Octadiene
3710-30-3

1,7-Octadiene

1,8-bis(1,1,3,3,3-pentamethyl-disiloxanyl)octane

1,8-bis(1,1,3,3,3-pentamethyl-disiloxanyl)octane

Conditions
ConditionsYield
With cobalt pivalate; 1-adamantyl isocyanide at 80℃; for 24h; Inert atmosphere;99%
With cobalt pivalate; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene at 80℃; for 24h; Inert atmosphere;60%
2,4-bis[2,6-bis(2,4,6-trimethylphenyl)phenyl]-1,3-diphospha-2,4-diazacyclobutane
1338063-88-9

2,4-bis[2,6-bis(2,4,6-trimethylphenyl)phenyl]-1,3-diphospha-2,4-diazacyclobutane

1,7-Octadiene
3710-30-3

1,7-Octadiene

C56H64N2P2

C56H64N2P2

Conditions
ConditionsYield
In benzene at 20℃; for 1h; Inert atmosphere;99%
ethyl 2,2-difluoro-2-iodoacetate
7648-30-8

ethyl 2,2-difluoro-2-iodoacetate

1,7-Octadiene
3710-30-3

1,7-Octadiene

diethyl 2,2,11,11-tetrafluoro-4,9-diiodododecanedioate

diethyl 2,2,11,11-tetrafluoro-4,9-diiodododecanedioate

Conditions
ConditionsYield
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere;99%
tetrafluoroboric acid diethyl ether
67969-82-8

tetrafluoroboric acid diethyl ether

(η5-C5H5)(Me)(NO)(PPh3)rhenium(II)

(η5-C5H5)(Me)(NO)(PPh3)rhenium(II)

1,7-Octadiene
3710-30-3

1,7-Octadiene

{((C5H5)Re(NO)(P(C6H5)3))2(CH2CH(CH2)4HCCH2)}(2+)*2BF4(1-)={((C5H5)Re(NO)(P(C6H5)3))2(CH2CH(CH2)4HCCH2)}(BF4)2

{((C5H5)Re(NO)(P(C6H5)3))2(CH2CH(CH2)4HCCH2)}(2+)*2BF4(1-)={((C5H5)Re(NO)(P(C6H5)3))2(CH2CH(CH2)4HCCH2)}(BF4)2

Conditions
ConditionsYield
In chlorobenzene under N2, addn. of HBF4*OEt2 to cooled soln. of Re-compd. at -45°C, then addn. of diene to the intermediate with stirring, stirring 15 h at 100°C; soln. filtered into hexane, filtration, washing (pentane), drying, mixt. of isomers;98%
1,7-Octadiene
3710-30-3

1,7-Octadiene

phenylacetylene
536-74-3

phenylacetylene

2-phenyl-1,3-butadiene
2288-18-8

2-phenyl-1,3-butadiene

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; Sealed tube; Inert atmosphere;98%
1,7-Octadiene
3710-30-3

1,7-Octadiene

phenylacetylene
536-74-3

phenylacetylene

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-phenyl-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-phenyl-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 20h; Diels-Alder reaction; Sealed tube; Inert atmosphere;98%
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

1,7-Octadiene
3710-30-3

1,7-Octadiene

1,1,1,2,2,3,3,4,4,13,13,14,14,15,15,16,16,16-octadecafluoro-6,11-diiodohexadecane
13105-46-9

1,1,1,2,2,3,3,4,4,13,13,14,14,15,15,16,16,16-octadecafluoro-6,11-diiodohexadecane

Conditions
ConditionsYield
With Sodium thiosulfate pentahydrate; 2,2'-azobis-(2,4-dimethylvaleronitrile) at 85℃; for 3h;97.5%
(E)-1-phenyl-N-(1-phenylethylidene)methanamine
14428-98-9, 98325-59-8, 98359-08-1

(E)-1-phenyl-N-(1-phenylethylidene)methanamine

1,7-Octadiene
3710-30-3

1,7-Octadiene

1-(2-octyl-phenyl)-ethanone

1-(2-octyl-phenyl)-ethanone

Conditions
ConditionsYield
Stage #1: (E)-1-phenyl-N-(1-phenylethylidene)methanamine; 1,7-Octadiene With molecular sieve; tris(triphenylphosphine)rhodium(I) chloride In toluene at 150℃; for 2h;
Stage #2: With water Acid hydrolysis;
Stage #3: With hydrogen; palladium on activated charcoal
97%
triphenylmethylacetonitrile oxide
13412-55-0

triphenylmethylacetonitrile oxide

1,7-Octadiene
3710-30-3

1,7-Octadiene

5-(5-hexenyl)-3-(triphenylmethyl)-2-isoxazoline
123622-56-0

5-(5-hexenyl)-3-(triphenylmethyl)-2-isoxazoline

Conditions
ConditionsYield
In benzene for 48h; Heating;96%
1,7-Octadiene
3710-30-3

1,7-Octadiene

1,2,7,8-diepoxyoctane
2426-07-5

1,2,7,8-diepoxyoctane

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃;95%
With 3-chloro-benzenecarboperoxoic acid at 10 - 23℃; for 16h;95.2%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24h;94%
(NH4)2WO4

(NH4)2WO4

1,7-Octadiene
3710-30-3

1,7-Octadiene

Adipic acid
124-04-9

Adipic acid

Conditions
ConditionsYield
With manganese dioxide; dihydrogen peroxide In 1,4-dioxane; acetic acid95%
With manganese dioxide; dihydrogen peroxide In 1,4-dioxane51%
1,7-Octadiene
3710-30-3

1,7-Octadiene

3,5-bis(trifluoromethyl)phenylacetylene
88444-81-9

3,5-bis(trifluoromethyl)phenylacetylene

diethyl Fumarate
623-91-6

diethyl Fumarate

(trans)-diethyl 4-[3,5-bis(trifluoromethyl)phenyl]-4-cyclohexene-1,2-dicarboxylate

(trans)-diethyl 4-[3,5-bis(trifluoromethyl)phenyl]-4-cyclohexene-1,2-dicarboxylate

Conditions
ConditionsYield
With [2-(i-PrO)-C6H4]C(H)=RuCH[(Mes)NCH2CH2N(Mes)]Cl2 In toluene at 90℃; for 30h; Diels-Alder reaction; Sealed tube; Inert atmosphere;95%
C17H13Cl3O2

C17H13Cl3O2

1,7-Octadiene
3710-30-3

1,7-Octadiene

C19H17Cl3O2

C19H17Cl3O2

Conditions
ConditionsYield
With C29H31F3I2N2RuS In benzene-d6 at 80℃; for 1h;95%
phenylsilane
694-53-1

phenylsilane

1,7-Octadiene
3710-30-3

1,7-Octadiene

1,8-bis(phenylsilyl)octane

1,8-bis(phenylsilyl)octane

Conditions
ConditionsYield
[Y(C5Me4CH2SiMe2NCMe3)(THF)] In hexane at 20℃; for 48h;94%
With ((HBPIMes,H)FeBr2); sodium triethylborohydride at 20℃; for 24h; Inert atmosphere; Schlenk technique;14%
1,7-Octadiene
3710-30-3

1,7-Octadiene

(E,E)-2,6-octadiene
18152-31-3

(E,E)-2,6-octadiene

Conditions
ConditionsYield
With C24H42N2PRu(1+)*F6P(1-) In [(2)H6]acetone at 20℃; for 0.166667h; stereoselective reaction;94%
carbon monoxide
201230-82-2

carbon monoxide

1,7-Octadiene
3710-30-3

1,7-Octadiene

2,7-dimethyl-octanedioic acid
1188-08-5

2,7-dimethyl-octanedioic acid

Conditions
ConditionsYield
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride In tetrahydrofuran under 760 Torr; for 18h; Ambient temperature;93%
1,1,1-triphenyl-3,3-dimethyldisiloxane
100891-32-5

1,1,1-triphenyl-3,3-dimethyldisiloxane

1,7-Octadiene
3710-30-3

1,7-Octadiene

C48H58O2Si4

C48H58O2Si4

Conditions
ConditionsYield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex at 70 - 90℃; for 24h;93%
With dihydrogen hexachloroplatinate; platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 70 - 90℃; for 24.1667h;93%
perfluoroisopropyl iodide
677-69-0

perfluoroisopropyl iodide

1,7-Octadiene
3710-30-3

1,7-Octadiene

9,10,10,10-Tetrafluoro-7-iodo-9-trifluoromethyldec-1-ene
143766-68-1

9,10,10,10-Tetrafluoro-7-iodo-9-trifluoromethyldec-1-ene

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; iron In ethanol at 55℃; for 10h; other per(poly)fluoroalkyl iodides and bromides;92%
With bis(cyclopentadienyl)titanium dichloride; iron In ethanol at 55℃; for 10h;92%
2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

1,7-Octadiene
3710-30-3

1,7-Octadiene

Conditions
ConditionsYield
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane for 20h;92%

3710-30-3Relevant articles and documents

-

Gardner,Wright

, p. 163 (1972)

-

-

Tsuji,J.,Yamakawa,T.

, p. 613 - 616 (1979)

-

-

Takamuku et al.

, p. 2562 (1971)

-

Photoredox-Assisted Reductive Cross-Coupling: Mechanistic Insight into Catalytic Aryl-Alkyl Cross-Couplings

Paul, Avishek,Smith, Mark D.,Vannucci, Aaron K.

, p. 1996 - 2003 (2017/02/26)

Here, we describe a photoredox-assisted catalytic system for the direct reductive coupling of two carbon electrophiles. Recent advances have shown that nickel catalysts are active toward the coupling of sp3-carbon electrophiles and that well-controlled, light-driven coupling systems are possible. Our system, composed of a nickel catalyst, an iridium photosensitizer, and an amine electron donor, is capable of coupling halocarbons with high yields. Spectroscopic studies support a mechanism where under visible light irradiation the Ir photosensitizer in conjunction with triethanolamine are capable of reducing a nickel catalyst and activating the catalyst toward cross-coupling of carbon electrophiles. The synthetic methodology developed here operates at low 1 mol % catalyst and photosensitizer loadings. The catalytic system also operates without reaction additives such as inorganic salts or bases. A general and effective sp2-sp3 cross-coupling scheme has been achieved that exhibits tolerance to a wide array of functional groups.

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