111-66-0

Basic information

• Product Name: 1 -Octene
• Synonyms: 1-n-Octene;Dialen 8;Caprylene;Gulftene 8;Linealene 8;α-Octylene;NSC 8457;n-1-Octene;n-octene-1;α-Octene
• CAS NO: 111-66-0
• Molecular Formula: C₈H₁₆
• Molecular Weight: 112.21
• EINECS: 203-893-7
• Mol File: 111-66-0.mol

Chemical Properties

• Melting Point: -102℃
• Boiling Point: 120.946 °C at 760 mmHg
• Flash Point: 21.111 °C
• Appearance: colourless liquid
• Density: 0.721 g/cm³
• Vapor Pressure: 17.9mmHg at 25°C
• Refractive Index: 1.413
• CAS DataBase Reference: 1 -Octene(CAS DataBase Reference)
• NIST Chemistry Reference: 1 -Octene(111-66-0)
• EPA Substance Registry System: 1 -Octene(111-66-0)

Safety Data

• Hazard Codes: F:Highly flammable
• Statements: R11:Highly flammable.; R65:Harmful: may cause lung damage if swallowed.
• Safety Statements: S16:Keep away from sources of ignition - No smoking.; S33:Take precautionary measures against static discharges.
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 111-66-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Production:
1-Octene is used as a raw material for the production of various chemicals, such as plastics, synthetic lubricants, and surfactants. Its versatility as a chemical feedstock makes it a valuable component in the synthesis of these products.
Used in Organic Synthesis:
1-Octene is used as a solvent in organic synthesis, facilitating various chemical reactions and processes. Its reactivity as an alkene allows it to participate in a wide range of reactions, making it a useful compound in the field of organic chemistry.
Used in Polymer Production:
1-Octene is used as a precursor for the production of octene-based polymers. Its ability to form long chains through polymerization reactions contributes to the development of new materials with specific properties and applications.
Used in Plastics Industry:
1-Octene is used as a co-monomer in the production of linear low-density polyethylene (LLDPE) and high-density polyethylene (HDPE). Its incorporation into these plastics helps to modify their properties, such as flexibility and strength, for various applications.
Used in Industrial Processes:
1-Octene is considered a valuable building block for various industrial processes due to its high reactivity and versatility as a chemical feedstock. Its use in these processes contributes to the development of new products and technologies across different industries.

InChI:InChI=1/C8H16/c1-3-5-7-8-6-4-2/h3H,1,4-8H2,2H3

Synthetic route

n-octyne (629-05-0) → oct-1-ene (111-66-0)

Conditions	Yield
With zirconocene dichloride; tert-butylmagnesium chloride; water Product distribution; multistep reaction; other hydrozirconation agents; other substrates;	100%
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 2.5h;	95%
With 2,6-bis[1-(2,6-diisopropylphenylimino)ethyl]pyridine cobalt(II) dichloride; diethoxymethylane; sodium triethylborohydride In neat (no solvent) at -78 - 40℃; for 1h;	95%

(S)-2-octyl chloroformate (191331-78-9) → trans-2-Octene (13389-42-9) + oct-1-ene (111-66-0) + (R)-2-chlorooctane (18651-57-5)

Conditions	Yield
With hexabutylguanidinium chloride In neat (no solvent) for 10h;	A n/a B n/a C 100%

octanol (111-87-5) → oct-1-ene (111-66-0)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 0℃; for 3h;	97%
With aluminum oxide at 350℃;
With fired clay fragments at 450 - 500℃;

1-bromo-octane (111-83-1) → oct-1-ene (111-66-0)

Conditions	Yield
With potassium hydroxide; triisopropylsilanol In N,N-dimethyl-formamide Ambient temperature;	97%
With 3-(tert-Butylamino)-1,1,1,5,5,5-hexakis(dimethylamino)-3-<amino>-1λ5,3λ5,5λ5-1,4-triphosphazadiene In tetrahydrofuran; xylene for 6h; Ambient temperature;	96%
With lithium diisopropylamide at 0℃; Kinetics;	87%

n-octyne (629-05-0) → octane (111-65-9) + oct-1-ene (111-66-0)

Conditions	Yield
With hydrogen In hexane at 40℃; under 760.051 Torr; for 6h;	A 3% B 97%
With triisobutylaluminum; zirconocene dichloride In benzene for 0.333333h;	A 44% B 51%
With hydrogen In cyclohexane at 150℃; under 75007.5 Torr; for 48h; Autoclave; Glovebox;	A 43% B 47%

2-octyl chloroformate → trans-2-Octene (13389-42-9) + oct-1-ene (111-66-0) + 2-chlorooctane (628-61-5)

Conditions	Yield
With hexabutylguanidinium chloride at 100℃; for 5h; Yields of byproduct given;	A n/a B n/a C 97%

nonanoic acid (112-05-0) → oct-1-ene (111-66-0)

Conditions	Yield
With nickel(II) iodide; 1,1,3,3-Tetramethyldisiloxane; copper(II) bis(trifluoromethanesulfonate); triphenylphosphine In neat (no solvent) at 190℃; for 16h; Reagent/catalyst; Sealed tube; Schlenk technique; Inert atmosphere;	94%
With 1,1'-bis-(diphenylphosphino)ferrocene; bis(1,5-cyclooctadiene)nickel (0); 2,2-dimethylpropanoic anhydride; potassium iodide at 180 - 190℃; for 2h; Inert atmosphere; Glovebox;	78%
With sodium persulfate; sulfuric acid; silver nitrate; copper(II) sulfate 1.) water, reflux, 2.) 5 min, reflux; Yield given. Multistep reaction;

1-hexene (592-41-6) + octane (111-65-9) + hexane (110-54-3) → oct-1-ene (111-66-0)

Conditions	Yield
cobalt(II) naphthenate In nonane Product distribution / selectivity;	93.1%

methanol (67-56-1) + 1-bromo-octane (111-83-1) → 1-methoxyoctane (929-56-6) + oct-1-ene (111-66-0)

Conditions	Yield
With potassium hydroxide; Aliquat 336 at 20℃; for 20h;	A 92% B 7%

1-bromo-octane (111-83-1) + potassium ethoxide (917-58-8) → ethyl octyl ether (929-61-3) + oct-1-ene (111-66-0)

Conditions	Yield
With Aliquat 336 at 20℃; for 20h;	A 92% B 5%

2-(phenylsulfonyl)-1-(trimethylsilyl)octane (84363-56-4) → oct-1-ene (111-66-0)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.666667h; Heating;	92%

heptanal (111-71-7) + (lithiomethyl)dimesitylborane → oct-1-ene (111-66-0)

Conditions	Yield
With trifluoroacetic anhydride	91%

ethene (74-85-1) → 1-hexene (592-41-6) + oct-1-ene (111-66-0)

Conditions	Yield
With CrCl2(tetrahydrofuran)2; N,N'-bis(diphenylphosphino)-N,N'-dimethylpropane-1,3-diamine In methyl cyclohexane at 80℃; under 30003 Torr; for 0.5h; Inert atmosphere;	A 9% B 91%
bis(2-(decylthio)ethyl)amine; chromium chloride In toluene at 90℃; under 33753.4 Torr; for 0.502778 - 0.527778h; Product distribution / selectivity;	A 90.85% B 0.5%
chromium(III)2-ethylhexanoate; trimethylaluminum; N-[bis(2-methoxyphenyl)phosphino]-P,P-bis(2-methoxyphenyl)-N-methylphosphinous amide In methyl cyclohexane; toluene at 60℃; under 36003.6 - 37503.8 Torr; for 0.175h; Product distribution / selectivity;	A 89.7% B 8.5%

1,2-octandiol (1117-86-8) → oct-1-ene (111-66-0)

Conditions	Yield
With formic acid at 20 - 240℃; Inert atmosphere;	91%
With methyltrioxorhenium(VII); sodium sulfite at 150℃; for 20h; sealed tube;	60 %Chromat.
With 15-crown-5; tetrabutylammonium perrhenate; sodium sulfite In benzene at 150 - 160℃; for 100h; regiospecific reaction;	68 %Chromat.

rac-octan-2-ol (4128-31-8) → trans-2-Octene (13389-42-9) + oct-1-ene (111-66-0)

Conditions	Yield
at 375℃; under 760.051 Torr; for 0.7h; Reagent/catalyst;	A 5.9% B 90.1%
With copper(II) sulfate In neat (no solvent) at 180℃; under 660 Torr; for 5h; Yield given;

1-Chlorooctane (111-85-3) → oct-1-ene (111-66-0)

Conditions	Yield
With lithium diisopropylamide In tetrahydrofuran; hexane at -78℃;	89%
Multi-step reaction with 2 steps 1: 1.) sodium hydride / 1.) DMF, 20 deg C, 1 h, 2.) 80 deg C, 18 h 2: 1.) NaH / 1.) DMF, 1 h, 2.) 70 deg C, 6 h View Scheme
Multi-step reaction with 2 steps 1: sodium hydride, trifluoroacetamide / dimethylformamide / 18 h / 80 °C 2: 1.) NaH / 1.) DMF, 1 h, 2.) 70 deg C, 6 h View Scheme
Multi-step reaction with 2 steps 1: potassium iodide / methanol / Irradiation 2: methanol / Irradiation View Scheme

heptanal (111-71-7) + C4H11Cl3GeTi (81454-93-5) → oct-1-ene (111-66-0)

Conditions	Yield
In diethyl ether for 15h; from 0 degC to 20 degC;	88%

1-bromo-octane (111-83-1) → 1-Fluoro-octane (463-11-6) + oct-1-ene (111-66-0)

Conditions	Yield
With tetrabutylammomium bromide; cesium fluoride for 1h; Heating;	A 88% B 9.4 % Chromat.
With C12H35N7P2*FH In tetramethylurea; 1,3,5-trimethyl-benzene at 120℃; for 0.416667h; Inert atmosphere;	A 72% B 14%
With 1,1,1-trifluoro-2-(2,2,2-trifluoroethoxy)ethane; 2,2-Dimethylpropyltrimethylammonium fluoride at 25℃;	A 71% B 29%

1-Iodooctane (629-27-6) → oct-1-ene (111-66-0)

Conditions	Yield
With lithium diisopropylamide In tetrahydrofuran; hexane at -78℃;	88%
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 14h;	87%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride at 0 - 20℃; Inert atmosphere;	87%

1-octyl p-toluenesulfonate (3386-35-4) → oct-1-ene (111-66-0)

Conditions	Yield
With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 13h;	88%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride at 0 - 20℃; Inert atmosphere;	88%

2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane (20449-21-2) + tetradec-7-ene (10374-74-0) → oct-1-ene (111-66-0) + 2-((E)-Dec-3-enyl)-2-methyl-[1,3]dioxolane

Conditions	Yield
aluminum oxide; tetramethylstannane; rhenium(VII) oxide In chlorobenzene at 25℃; for 3h; Yields of byproduct given;	A n/a B 87.8%

1-bromo-octane (111-83-1) + sodium methylate (124-41-4) → 1-methoxyoctane (929-56-6) + oct-1-ene (111-66-0)

Conditions	Yield
With Aliquat 336 at 20℃; for 20h;	A 87% B 13%

1-bromo-octane (111-83-1) + sodium ethanolate (141-52-6) → ethyl octyl ether (929-61-3) + oct-1-ene (111-66-0)

Conditions	Yield
With potassium hydroxide; Aliquat 336 at 20℃; for 20h;	A 86% B 10%

di-2-octyl phenylphosphonate (107465-90-7) → 2-octene (111-67-1) + oct-1-ene (111-66-0) + phenylphosphonate (1571-33-1)

Conditions	Yield
With Amberlite 200C In dichloromethane at 40℃; for 72h; Product distribution;	A n/a B n/a C 85%

(E) 2-iodo-1-chloroethylene (28540-81-0) + n-octyne (629-05-0) → oct-1-ene (111-66-0) + (1E,3E)-1-chloro-1,3-decadiene (96251-47-7)

Conditions	Yield
Stage #1: n-octyne With diisobutylaluminium hydride In n-heptane at 50℃; for 4h; Stage #2: With indium(III) chloride In tetrahydrofuran; n-heptane at 0℃; for 0.5h; Stage #3: (E) 2-iodo-1-chloroethylene With trifuran-2-yl-phosphane; Cl2Pd[bis(2-diphenylphosphinophenyl)ether]; diisobutylaluminium hydride In tetrahydrofuran; hexane; n-heptane at 0℃; for 4h;	A 4 % Spectr. B 85%

2-octyl mesylate (924-80-1) → 2-fluorooctane (407-95-4) + oct-1-ene (111-66-0)

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; triphenyltinfluoride In acetonitrile at 85℃; for 10h;	A 83% B 12%

1-fluoropentane (592-50-7) + allyl-trimethyl-silane (762-72-1) → oct-1-ene (111-66-0)

Conditions	Yield
With 2C24BF20(1-)*C21H16N3P(2+) In dichloromethane at 55℃; for 24h; Reagent/catalyst; Inert atmosphere;	83%

(R)-2-octanol trimethylsilyl ether (51003-20-4) → cis-2-octene (7642-04-8) + trans-2-Octene (13389-42-9) + oct-1-ene (111-66-0) + (S)-(+)-2-fluorooctane

Conditions	Yield
With diethylamino-sulfur trifluoride In dichloromethane at -78 - -20℃; for 10h;	A n/a B n/a C n/a D 82%

(E)-1-bromo-2-iodoethylene (56798-08-4) + n-octyne (629-05-0) → oct-1-ene (111-66-0) + (7E,9E)-hexadeca-7,9-diene (71686-99-2) + (1E,3E)-1-bromo-1,3-decadiene (174365-91-4)

Conditions	Yield
Stage #1: n-octyne With diisobutylaluminium hydride In n-heptane at 50℃; for 4h; Stage #2: With indium(III) chloride In tetrahydrofuran; n-heptane at 0℃; for 0.5h; Stage #3: (E)-1-bromo-2-iodoethylene With trifuran-2-yl-phosphane; Cl2Pd[bis(2-diphenylphosphinophenyl)ether]; diisobutylaluminium hydride In tetrahydrofuran; hexane; n-heptane at 0℃; for 4h;	A 7% B 2% C 82%

oct-1-ene (111-66-0) + triphenylstannane (892-20-6) → n-octyltriphenylstannane (23895-44-5)

Conditions	Yield
at 80-100 °C;;	100%
at 80-100 °C;;	100%
In neat (no solvent) other Radiation; under Ar; (60)Co-irradiation; 1.5:1 molar ratio (olefine:Sn-compound) ;25°C; GLC;	74%

oct-1-ene (111-66-0) → octane (111-65-9)

Conditions	Yield
With hydrogen; In dichloromethane at 65℃; for 15h; same yield with a similar catalyst; Pressure (range begins): 120 ;	100%
With {(η6-C6H6)Ru(NCCH3)3}{BF4}2; water; hydrogen In benzene at 90℃; under 30400 Torr; for 4h;	100%
With hydrogen; In dichloromethane at 65℃; for 15h; Product distribution; other catalyst, other substrates; Pressure (range begins): 120 ;	100%

oct-1-ene (111-66-0) → 1,2-octandiol (1117-86-8)

Conditions	Yield
With poly{[CuBa(pyridine-2,5-dicarboxylate)2(H2O)5]*H2O}; dihydrogen peroxide In acetonitrile at 60℃; for 6h; Catalytic behavior; Reagent/catalyst;	100%
With dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate In water; tert-butyl alcohol at 20℃; for 16h;	99%
With 4-methylmorpholine N-oxide; dendritic osmium catalyst In hexane; acetonitrile; tert-butyl alcohol at 20℃; for 36h;	98%

oct-1-ene (111-66-0) → 1,2-dichlorooctane (21948-46-9, 72778-28-0)

Conditions	Yield
With tetraethylammonium trichloride In dichloromethane	100%
With chlorine In chloroform at 20℃; for 1.5h;	97%
With oxone||potassium monopersulfate triple salt; potassium chloride; N-(n-butyl)-2-methylbenzamide In dichloromethane; water at 20℃; for 0.25h;	91%

oct-1-ene (111-66-0) → 1,2-Epoxyoctane (2984-50-1)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid; iron(III) perchlorate In acetonitrile at -10℃; for 0.0833333h;	100%
With 3-chloro-benzenecarboperoxoic acid; (Cl8TPP)FeIII(ClO4) In acetonitrile at -10℃; for 0.0833333h; Product distribution; invetigation of the iron(III) perchlorate-catalyzed epoxidation of olefins and oxidative cleavage of diols by m-chloroperbenzoic acid and pentafluoroiodobenzene;	100%
With oxygen; isobutyraldehyde In acetonitrile at 60℃; for 18h;	99%

oct-1-ene (111-66-0) + Triethoxysilane (998-30-1) → triethoxy(octyl)silane (2943-75-1)

Conditions	Yield
at 90℃; for 5h; Inert atmosphere;	100%
at 90℃; for 5h; Inert atmosphere;	100%
With graphene nanoplates-supported platinum nanoparticles In neat (no solvent) at 80℃; for 2h; Catalytic behavior;	99%

oct-1-ene (111-66-0) + Diethyl phosphonate (762-04-9, 123-22-8) → diethyl octylphosphonate (1068-07-1)

Conditions	Yield
With triethyl borane; oxygen In cyclohexane at 20℃;	100%
at 30℃; for 17h; (γ-irradiation);

oct-1-ene (111-66-0) + carbon monoxide (201230-82-2) → nonan-1-al (124-19-6)

Conditions	Yield
With 2-pyridylpropylimine rhodium(I)chlorocarbonyl; hydrogen In toluene at 95℃; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave; chemoselective reaction;	100%
With hydrogen In dichloromethane at 45℃; under 51716.2 Torr; for 16h; Autoclave; Inert atmosphere; Green chemistry; regioselective reaction;	100%
With hydrogen In cyclohexane at 120℃; under 37503.8 Torr; for 4h; Autoclave;	99%

oct-1-ene (111-66-0) + thexylchloroborane * dimethylsulfide (75067-06-0) → octanol (111-87-5) + rac-octan-2-ol (4128-31-8) + 2,3-dimethylbutan-2-ol (594-60-5)

Conditions	Yield
With methanol; dihydrogen peroxide Product distribution; different solvents; other olefins;	A 99.2% B 0.8% C 100%

oct-1-ene (111-66-0) → oenanthic acid (111-14-8)

Conditions	Yield
With dihydrogen peroxide; 6-molybdo-6-tungstophosphoric acid/Al/C In tert-butyl alcohol at 60℃; for 4h;	100%
With [Me(n-Oct)3N]3{PO4[WO(O2)2]4}; dihydrogen peroxide In water; 1,2-dichloro-ethane at 95℃; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Concentration; Reflux; Green chemistry;	97%
With jones reagent; osmium(VIII) oxide In water; acetone for 20h; Ambient temperature;	85%

oct-1-ene (111-66-0) + Trichloroacetyl chloride (76-02-8) → 2,2-Dichloro-3-hexyl-cyclobutanone (217805-08-8)

Conditions	Yield
With zinc In diethyl ether at 15 - 20℃; for 1.5h; sonication;	100%
With zinc/copper couple; trichlorophosphate In diethyl ether Reflux;
With zinc-copper couple; trichlorophosphate In diethyl ether Reflux; Inert atmosphere;
With zinc/copper couple; trichlorophosphate In diethyl ether at 0℃; Inert atmosphere; Reflux;

oct-1-ene (111-66-0) + 1,1,1,3,5,5,5-heptamethyltrisiloxan (1873-88-7) → 3-n-octyl-1,1,1,3,5,5,5-heptamethyltrisiloxane (17955-88-3)

Conditions	Yield
With tetradecyl(tributyl)phosphonium bis(trifluoromethylsulfonyl)amide; C24H20Cl2P2Pt at 100℃; for 1h; Reagent/catalyst;	100%
With tetradecyl(tributyl)phosphonium bis(trifluoromethylsulfonyl)amide; bis(cyclooctadiene (μ-silyloxytrimethyl) rhodium(I)) at 110℃; for 1h; Catalytic behavior; Reagent/catalyst; Time;	100%
With nickel 2-ethylhexanoate; 1,4-bis(2,6-diisopropylphenyl)-2,3-dimethyl-1,4-diazabuta-1,3-diene In neat (no solvent) at 23℃; for 6h; regioselective reaction;	99%

oct-1-ene (111-66-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-octyl-[1,3,2]dioxaborolane (66217-56-9)

Conditions	Yield
With sodium triethylborohydride at 23℃; for 3h; Catalytic behavior; Reagent/catalyst; Inert atmosphere;	100%
Wilkinson's catalyst In dichloromethane 25°C, 10 min;	99%
With chlorocarbonylbis(triphenylphosphine)rhodium(I) In dichloromethane at 0 - 20℃; for 1.83333h; Inert atmosphere;	99%

oct-1-ene (111-66-0) → n-octylphosphonic acid (4724-48-5)

Conditions	Yield
With hypophosphorous acid; palladium; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In water; N,N-dimethyl-formamide at 110℃; for 24h;	100%
With tris-(dibenzylideneacetone)dipalladium(0); hypophosphorous acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; oxygen In N,N-dimethyl-formamide at 110℃; for 20h;
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 9 h / 70 °C 2: sodium hydroxide; potassium permanganate / water / 5 h / 15 °C / Cooling with ice View Scheme

oct-1-ene (111-66-0) + tri-n-butyl-tin hydride (688-73-3) → tributyl(octyl)stannane (14775-14-5)

Conditions	Yield
With diisobutylaluminium hydride 75-80°C;;	100%
With (iso-C4H9)2AlH 75-80°C;;	100%
With diisobutylaluminium hydride 75-80°C;;	100%

Phenylselenyl chloride (5707-04-0) + oct-1-ene (111-66-0) → C14H21ClSe (1401238-31-0)

Conditions	Yield
In dichloromethane at 20℃; for 4h; Inert atmosphere;	100%

oct-1-ene (111-66-0) → (2S)-2-hexyloxirane (2984-50-1, 50418-68-3, 77495-66-0, 77549-73-6)

Conditions	Yield
With titanium(IV) isopropylate; Pentafluorobenzoic acid; C32H22F10N2O2; dihydrogen peroxide In water; 1,2-dichloro-ethane at 20℃; for 45h; Inert atmosphere; enantioselective reaction;	100%
With titanium(IV) isopropylate; C46H40N2O2; dihydrogen peroxide In dichloromethane; water; 1,2-dichloro-ethane at 20℃; for 100h; Reagent/catalyst; Inert atmosphere;	82%
With oxygen; isobutyraldehyde In acetonitrile at 25℃; for 8h; Catalytic behavior; Green chemistry; enantioselective reaction;	70 %Chromat.

oct-1-ene (111-66-0) + dimethylsulfide borane complex (13292-87-0) → trioctylborane (3248-78-0)

Conditions	Yield
In Petroleum ether at -10 - 0℃; for 1h; Inert atmosphere;	100%
at 0 - 20℃; for 3h; Inert atmosphere; Further stages;
In tetrahydrofuran at 20℃; for 1h; Cooling with ice;
In diethyl ether Inert atmosphere; Reflux;

oct-1-ene (111-66-0) + phenylsilane (694-53-1) → octan-2-yl(phenyl)silane

Conditions	Yield
With MesPDI; cobalt(II) stearate In tetrahydrofuran at 60℃; for 5h; Reagent/catalyst;	100%
With C22H31Cl2CoN2P In neat (no solvent) at 60℃; for 24h; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere; regioselective reaction;	92%
With 2,6-bis[1-(2,4,6-trimethylimino)ethyl]pyridine; C10H14CoO5 In toluene at 60℃; for 24h; Reagent/catalyst; Temperature; regioselective reaction;	91%
With 2,6-bis[1-(2,4,6-trimethylimino)ethyl]pyridine; cobalt(II) tetrafluoroborate hexahydrate In tetrahydrofuran at 20℃; for 4h; Catalytic behavior; Reagent/catalyst; regioselective reaction;	72 %Spectr.

oct-1-ene (111-66-0) + triisobutylaluminum (100-99-2) → trioctylaluminum (1070-00-4)

Conditions	Yield
at 110℃; Inert atmosphere; Schlenk technique;	100%

oct-1-ene (111-66-0) → bis-(2-bromooctyl)selenide

Conditions	Yield
With selenium dibromide In tetrachloromethane at -20 - 20℃; for 18h; regioselective reaction;	100%
With selenium dibromide In chloroform at 20 - 25℃; for 18h; regioselective reaction;	95%
Stage #1: oct-1-ene With selenium(IV) oxide; hydrogen bromide In diethyl ether; water at 0 - 25℃; for 0.5h; Stage #2: With sodium metabisulfite In benzene at 5 - 25℃; for 2h;	84%

oct-1-ene (111-66-0) → trichloro(2-chlorooctyl)-λ4-tellane

Conditions	Yield
With tellurium tetrachloride In chloroform at 20 - 25℃; for 20h; regioselective reaction;	100%

methanol (67-56-1) + oct-1-ene (111-66-0) → trichloro(2-methoxyoctyl)-λ4-tellane

Conditions	Yield
With tellurium tetrachloride In chloroform at 20 - 25℃; for 20h; regioselective reaction;	100%

methanol (67-56-1) + oct-1-ene (111-66-0) → tribromo(2-methoxyoctyl)-λ4-tellane

Conditions	Yield
With tellurium(IV) tetrabromide at 55 - 60℃; for 6h; regioselective reaction;	100%

oct-1-ene (111-66-0) → bis-(2-chlorooctyl)selenide

Conditions	Yield
With selenium(II) chloride In chloroform at -60 - 20℃; for 18h; regioselective reaction;	100%
Stage #1: oct-1-ene With hydrogenchloride; selenium(IV) oxide In diethyl ether; water at 0 - 25℃; for 7h; Stage #2: With sodium metabisulfite In benzene at 5 - 25℃; for 2h;	80%

ethanol (64-17-5) + oct-1-ene (111-66-0) → trichloro(2-ethoxyoctyl)-λ4-tellane

Conditions	Yield
Stage #1: oct-1-ene With tellurium tetrachloride In chloroform at 0 - 20℃; for 14h; Stage #2: ethanol In chloroform for 5h; Reflux;	100%

ethyl methyl disulfide (20333-39-5) + oct-1-ene (111-66-0) → 1-ethylsulfanyl-2-methylsulfanyl-octane

Conditions	Yield
for 2h; UV-irradiation; cooling;	99.6%

oct-1-ene (111-66-0) + Triethoxysilane (998-30-1) → β-octylltriethoxysilane (1233710-95-6)

Conditions	Yield
With Wilkinson's catalyst at 80℃; for 6h; Reagent/catalyst;	99.3%
With graphite oxide-supported Karstedt catalyst at 60℃; for 1h;
With rhodium(III) chloride trihydrate; diphenyl(3-triethylsilylphenyl)phosphine at 90℃; for 5h; Inert atmosphere; Schlenk technique;

Upstream product

• 74-85-1 ethene 
• 152212-49-2 1,2-dibromooctane 
• 36971-14-9 dec-1-en-4-ol 
• 109-72-8 n-butyllithium 
• 111-83-1 1-bromo-octane 
• 55553-85-0 potassium 2,2-dimethyl-1-propanolate 
• 111-65-9 octane 
• 1455-13-6 deuteromethanol 
• 90886-04-7 14-n-octyl-5,6,8,9-tetrahydro-7-phenyl-dibenzoacridinium tetrafluoroborate 
• 4468-61-5 hexylcyclopropane 
• 38841-98-4 n-octylmagnesium chloride 
• 4145-75-9 octylidenebis(diisobutylaluminium) 
• 89232-08-6 1-iodo-[1,1-D₂]octane 
• 97567-68-5 octan-2-yl phenyl telluride 

Downstream Products

• 1070-27-5 1,1,1,3-tetrachlorononane 
• 5929-67-9 dibutyl octylphosphonate 
• 6172-97-0 octyl-phosphonic acid dimethyl ester 
• 627-97-4 2-methyl-2-heptene 
• 2432-34-0 S-octyl thioacetate 
• 3001-66-9 octane-2-thiol 
• 1117-86-8 1,2-octandiol 
• 2984-50-1 1,2-Epoxyoctane 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 98-86-2 acetophenone 
• 67-64-1 acetone 
• 108-95-2 phenol 
• 102462-53-3 diphenyl-dithiophosphinic acid-(1-methyl-heptyl ester) 
• 18415-18-4 (1-octyl)(phenyl)silane 

Relevant articles and documents

Iridium complexes of new NCP pincer ligands: Catalytic alkane dehydrogenation and alkene isomerization

Iridium complexes of novel NCP pincer ligands containing pyridine and phosphinite arms have been synthesized. One Ir complex shows good catalytic activity for alkane dehydrogenation, and all complexes are highly active for olefin isomerization. A combination of the Ir complex and a (PNN)Fe pincer complex catalyzes the formation of linear alkylboronates selectively from internal olefins via sequential olefin isomerization-hydroboration. This journal is the Partner Organisations 2014.

Photocatalytic properties of new cyclopentadienyl and indenyl rhodium(I) carbonyl complexes with water-soluble 1,3,5-triaza-7-phosphaadamantane (PTA) and tris(2-cyanoethyl)phosphine

Reactions of [(η5-R)Rh(CO)2] (R = cp, ind) with water-soluble phosphines (L = 1,3,5-triaza-7-phosphaadamantane and tris(2-cyanoethyl)phosphine) give the new rhodium(I) complexes of the types [Rh(η5-cp)(CO)(PTA)] (1), [Rh(η5-cp)(CO)(P(CH 2CH2CN)3)] (2), [Rh(η5-ind)(CO) (PTA)] (3) and [Rh(η5-ind)(CO)(P(CH2CH 2CN)3)] (4) in isolated yields of 52-75%. All these compounds have been fully characterized by IR, 1H, 31P{1H} and 13C{1H} NMR, FAB-MS spectroscopies and elemental analyses. Reactivity for the substitution of phosphine is greater for [(η5-ind)Rh(CO)(L)] comparing to [(η5-cp)Rh(CO)(L)] because of a flexibility of the indenyl ligand to undergo facile η5-η3 coordinative isomerizations. The obtained complexes are active catalyst precursors for the dehydrogenation of propan-2-ol, octane and cyclooctane under photoassisted conditions without any organic hydrogen transfer acceptors, giving TOFs of 26-56 using 3 as precatalyst.

The First Successful Direct Metallation of Ethene

Vinyl potassium was formed directly from ethene by use of a new butyl-lithium-potassium t-butoxide-tetramethylethylenediamine metallating reagent; typical products were obtained with 1-bromo-octane and after addition of LiBr in tetrahydrofuran, with benzaldehyde and diphenyl disulphide.

Influence of elevated temperature and pressure on the chromium-catalysed tetramerisation of ethylene

A catalyst system comprising a diphenylphosphineamine (PNP) ligand, chromium(III) acetylacetonate and a methylaluminoxane-based activator was studied for the selective tetramerisation of ethylene. The reaction was investigated over a broad temperature and pressure range and the resulting product mixture was interpreted in the light of the recently published, enlarged metallacycle mechanism. Vapour-liquid equilibrium (VLE) data were calculated for the binary ethylene-cyclohexane mixture over the relevant temperature and pressure ranges to deconvolute the influence of ethylene concentration and temperature. Good agreement of the experimental data with the proposed mechanism was found. Enlargement of the metallacycloheptane ring by insertion of ethylene was found to be dependent on the ethylene concentration, albeit to a lesser extent than assumed. The 1-octene selectivity, which reaches a maximum of 72-74 mass %, thus seems to be primarily dependent on the temperature. The formation of the cyclic side products methyl- and methylenecyclopentane was in effect independent of the ethylene concentration. This is in good accordance with the proposed mechanism, since it indicates that the formation of the products occurs via rearrangement of a metallacycle intermediate.

Synthesis of Pincer Hydrido Ruthenium Olefin Complexes for Catalytic Alkane Dehydrogenation

A series of new hydrido Ru(II) olefin complexes supported by isopropyl-substituted pincer ligands have been synthesized and characterized. These complexes are thermally robust and active for catalytic transfer and acceptorless alkane dehydrogenation. Notably, the alkane dehydrogenation catalysts are tolerant of a number of polar functional species.

Highly active chromium-based selective ethylene tri-/tetramerization catalysts supported by N,N-diphospholylamines

We have developed novel Cr(III) catalysts supported by asymmetic N,N-diphospholylamine ligands bearing a phenoxaphosphine group. Upon activation with MMAO-3A, the Cr(III) catalysts supported by the PNP ligands are highly active for ethylene tri-/tetramerization with considerable selectivity. The ligand substitution and oligomerization conditions are found to be essential to achieve high activity and controllable selectivity. The catalytic system with asymmetric diphospholylamine ligands exhibited higher activity than that supported by symmetric ligands. Asymmetric diphospholylamine ligand with a N-cyclohexyl group achieved the highest activity of 282.2?kg/(g?Cr/h) with a high total selectivity of 83.2% toward valuable 1-hexene (28.7%) and 1-octent (54.5%) at 35?bar under 80?°C.

Semihydrogenation of Alkynes Catalyzed by a Pyridone Borane Complex: Frustrated Lewis Pair Reactivity and Boron–Ligand Cooperation in Concert

The metal-free cis selective hydrogenation of alkynes catalyzed by a boroxypyridine is reported. A variety of internal alkynes are hydrogenated at 80 °C under 5 bar H2 with good yields and stereoselectivity. Furthermore, the catalyst described herein enables the first metal-free semihydrogenation of terminal alkynes. Mechanistic investigations, substantiated by DFT computations, reveal that the mode of action by which the boroxypyridine activates H2 is reminiscent of the reactivity of an intramolecular frustrated Lewis pair. However, it is the change in the coordination mode of the boroxypyridine upon H2 activation that allows the dissociation of the formed pyridone borane complex and subsequent hydroboration of an alkyne. This change in the coordination mode upon bond activation is described by the term boron-ligand cooperation.

A NEW METHOD FOR THE in Situ GENERATION OF Cp2Zr(H)Cl (SCHWARTZ' REAGENT)

Treatment of Cp2ZrCl2 with LiEt3BH in THF leads to formation of Cp2Zr(H)Cl.Subsequently introduced terminal acetylenes undergo hydrozirconation without compromising acid-sensitive functionality present in the alkyne.

Switching a catalyst system from ethene polymerization to ethene trimerization with a hemilabile ancillary ligand

A drastic ligand effect was observed in the catalytic ethene conversion by the substituted mono(cyclopentadienyl)titaniumtrichloride/methylalumoxane (MAO) catalysts shown. The catalyst with R = Me produces polyethene, whereas the catalyst with R = Ph selectively trimerizes ethene to 1-hexene. This switch in catalyst performance appears to be the result of a hemilabile behavior of the cyclopentadienyl ligand with the pendant arene group, involving reversible coordination of the arene moiety.

Phospholane-Based Ligands for Chromium-Catalyzed Ethylene Tri- And Tetramerization

Chromium complexes with bis(phospholane) ligands were synthesized and evaluated for ethylene tetramerization in a high-throughput reactor. Three ligand parameters - the phospholane substituent, the ligand backbone, and the type of phosphine (cyclic vs acyclic) - were investigated. The size of the phospholane substituent was found to impact the selectivity of the resulting catalysts, with smaller substituents leading to the production of larger proportions of 1-octene. Changing the ligand backbone from 1,2-phenylene to ethylene did not impact catalysis, but the use of acyclic phosphines in place of the cyclic phospholanes had a detrimental effect on catalytic activity. Selected phospholane-chromium complexes were evaluated in a 300 mL Parr reactor at 70 °C and 700 psi of ethylene pressure, and the ethylene oligomerization performance was consistent with that observed in the smaller, high-throughput reactor. MeDuPhos-CrCl3(THF) (MeDuPhos = 1,2-bis(2,5-dimethylphospholano)benzene; THF = tetrahydrofuran) gave activity and selectivity for 1-octene (54.8 wt %) similar to the state-of-the-art i-PrPNP-CrCl3(THF) (64.0 wt %) (PNP = bis(diphenylphosphino)amine), while EtDuPhos-CrCl3(THF) (EtDuPhos = 1,2-bis(2,5-diethylphospholano)benzene) exhibited even higher activity, with catalyst selectivity shifted toward 1-hexene production (90 wt %). These results are surprising, given the prevalence of the aryl phosphine motif in ligands used in ethylene oligomerization catalysts and the inferior performance of previously reported catalysts with alkyl phosphine-containing ligands.