1647-16-1

Basic information

• Product Name: 1,9-DECADIENE
• Synonyms: 1,9-DECADIENE;TIMTEC-BB SBB008889;decadiene-1,9;1,9-Decadien;deca-1,9-diene;1,9-Decadiene,97%;1,9-DECADIENE FOR SYNTHESIS 25 ML;1,9-DECADIENE FOR SYNTHESIS 5 ML
• CAS NO: 1647-16-1
• Molecular Formula: C₁₀H₁₈
• Molecular Weight: 138.25
• EINECS: 216-711-6
• Product Categories: Acyclic;Alkenes;Organic Building Blocks
• Mol File: 1647-16-1.mol
• Article Data: 39

Chemical Properties

• Melting Point: -69.6°C (estimate)
• Boiling Point: 169 °C(lit.)
• Flash Point: 107 °F
• Appearance: /Liquid
• Density: 0.75 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.09mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: Flammables area
• Solubility: It is soluble in organic solvents.
• Explosive Limit: 0.7%(V)
• BRN: 1697870
• CAS DataBase Reference: 1,9-DECADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,9-DECADIENE(1647-16-1)
• EPA Substance Registry System: 1,9-DECADIENE(1647-16-1)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3295 3/PG 3
• WGK Germany: 3
• F: 9
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1647-16-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to slightly yellow liquid

Uses

It is widely used in the manufacturers and suppliers of pharmaceuticals and intermediates in the preparation of fine chemicals. 1,9-decadiene is also used as a starting material in ADMET polymerizations .

General Description

1,9-Decadiene acts as comonomer and undergoes acyclic diene metathesis (ADMET) copolymerization with 1, 5-hexadiene to form random linear polybutadiene –polyoctenamer copolymers. It undergoes ADMET copolymerization with divinyltetraethoxydisiloxane to yield siloxylene–vinylene–alkenylene copolymer.

InChI:InChI=1/C10H18/c1-3-5-7-9-10-8-6-4-2/h3-4H,1-2,5-10H2

Synthetic route

C24H34Se2 → 1,10-decadiene (1647-16-1) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7) + toluene (108-88-3)

Conditions	Yield
at 600℃; under 20 Torr; for 0.0333333h;	A 93% B 31% C 57%

ethene (74-85-1) + 1,2-cyclooctene (931-88-4, 22770-27-0, 3958-30-3) → 1,10-decadiene (1647-16-1)

Conditions	Yield
Mo(NC6H3(CH(CH3)2)2)(CHC(CH3)2C6H5)(NC4H2(CH3)2)(OC10H9BrC10H9BrOSi(CH3)2C(CH3)3) In 1,3,5-trimethyl-benzene under 7600.51 Torr; for 16h; Product distribution / selectivity; Inert atmosphere; Sealed system;	90%
Re2O7/B2O3/Al2O3; tetramethylstannane In toluene under 3750.38 - 4500.45 Torr; for 92.5h; Product distribution / selectivity;
Re2O7/B2O3/Al2O3; tetramethylstannane In toluene under 3750.38 - 4500.45 Torr; Product distribution / selectivity;
With Mo[N(2,6-(i-Pr)2Ph)](CHCMe2Ph)(Me2Pyr)(OBitet) at 20℃; under 15201 Torr; for 20h; Inert atmosphere;	93 %Chromat.

1,10-Decanediol (112-47-0) → 1,10-decadiene (1647-16-1) + 9-Decen-1-ol (13019-22-2)

Conditions	Yield
With 1-hexadecylcarboxylic acid at 340℃; for 6h; Molecular sieve;	A n/a B 88%

1,12-dodecandiol (5675-51-4) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With methoxy(cyclooctadiene)rhodium(I) dimer; N,N-Dimethylacrylamide; 3-Methoxybenzoic acid; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 90℃; for 24h; Inert atmosphere; Glovebox; Sealed tube; chemoselective reaction;	88%

10-undecenoic acid (112-38-9) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With nickel(II) iodide; triphenylphosphine In neat (no solvent) for 16h; Reagent/catalyst; Inert atmosphere; Sealed tube;	85%
With bis-triphenylphosphine-palladium(II) chloride; 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In neat (no solvent) at 132℃; for 3h; Inert atmosphere;	59%
Stage #1: 10-undecenoic 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;

2-(oct-7-en-1-yl)oxirane (85721-25-1) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With bis(acetylacetonate)nickel(II); diethylzinc In hexane; toluene at 110℃; for 48h; Inert atmosphere;	85%

C24H30O4 (94160-13-1) → 1,10-decadiene (1647-16-1)

Conditions	Yield
at 330℃; for 8h;	82%

1,10-decanediol diacetate (26118-61-6) → 1,10-decadiene (1647-16-1)

Conditions	Yield
at 350℃; for 8h;	80%
at 565℃;
at 600℃;

tetrabromo-1,1,10,10 decane (82176-56-5) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With n-butyllithium In diethyl ether at -30 - -25℃;	78%

n-Decandiyl-dipropionat (42236-22-6) → 1,10-decadiene (1647-16-1)

Conditions	Yield
at 340℃; for 8h;	78%

bromopentene (1119-51-3) + (E)-4-(phenylthio)-3-octene (217803-17-3) → 1,10-decadiene (1647-16-1) + (E)-6-butyl-1,6-nonadiene

Conditions	Yield
Stage #1: bromopentene With magnesium Stage #2: (E)-4-(phenylthio)-3-octene With 1,2-bis(diphenylphosphino)ethane nickel(II) chloride In diethyl ether at 20℃; for 15h;	A n/a B 76%

C26H34O4 → 1,10-decadiene (1647-16-1)

Conditions	Yield
at 350℃; for 8h;	70%

1,3-dioxoisoindolin-2-yl hex-5-enoate → 1,10-decadiene (1647-16-1)

Conditions	Yield
With C55H46N4O4W; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 3h; Irradiation;	41%

1,4-dibromo-butane (110-52-1) + allylmagnesium bromide (1730-25-2) → 1,10-decadiene (1647-16-1) + 7-bromo-hept-1-ene (4117-09-3)

Conditions	Yield
With lithium chloride; copper dichloride In tetrahydrofuran at 0℃; for 2.5h;	A n/a B 40%

1,4-dibromo-butane (110-52-1) + allylmagnesium bromide (1730-25-2) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With dilithium tetrachlorocuprate In tetrahydrofuran at 25℃; for 20h;	38%

(Z)-Cyclooctene (931-88-4, 931-87-3) + ethene (74-85-1) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With C27H29Cl2FN2ORu at 60℃; under 7757.43 Torr; Pressure; Inert atmosphere; Glovebox;	34%
With aluminum oxide; tetramethylstannane; rhenium(VII) oxide at 90℃; under 37503 Torr;
With C41H46Cl2F9N2PRu In toluene at 35℃; under 7500.75 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Glovebox;	20 %Chromat.

(Z)-Cyclooctene (931-88-4, 931-87-3) + ethene (74-85-1) → 1,10-decadiene (1647-16-1) + C19H34

Conditions	Yield
With C44H59Cl2F2N2PRu In toluene at 35℃; under 7500.75 Torr; for 0.0833333h; Catalytic behavior; Reagent/catalyst; Time; Temperature; Glovebox;	A 15% B 9%
With C37H52Cl2F3N2PRu In toluene at 35℃; under 7500.75 Torr; for 5h; Catalytic behavior; Reagent/catalyst; Temperature; Autoclave; Glovebox;	A 50 %Chromat. B 11 %Chromat.

1,4-Diiodobutane (628-21-7) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With diethyl ether; magnesium durch Einw. von Allylbromid auf die entstehende Loesung von Tetramethylen-bismagnesiumjodid;

1,9-decadiyne (1720-38-3) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With ammonium sulfate; ammonia; sodium
With copper(II)-citrate; hexamethylenetetramine; hypophosphorous acid In water; N,N-dimethyl-formamide at 130℃; for 24h; Inert atmosphere; Green chemistry; chemoselective reaction;	88 %Chromat.

1,10-decanediol diacetate (26118-61-6) → 1,10-decadiene (1647-16-1) + 9-decen-1-yl acetate (50816-18-7)

Conditions	Yield
at 565℃;

2,13-dioxa-tetradecanedioic acid diethyl ester (96536-94-6) → 1,10-decadiene (1647-16-1) + 1,10-Decanediol (112-47-0) + 9-Decen-1-ol (13019-22-2) + carbonic acid ethyl ester-(10-hydroxy-decyl ester) (100528-96-9)

Conditions	Yield
at 500℃; Produkt 5-7:Aethanol,Kohlensaeure-aethylester-dec-9-enylester,Aethylen.Pyrolysis;

butanediyl dimagnesium (2+); iodide + allyl bromide (106-95-6) → 1,10-decadiene (1647-16-1)

3,3'-(butane-1,4-disulfonyl)-bis-propene (99174-56-8) → 1,10-decadiene (1647-16-1)

Conditions	Yield
at 195 - 260℃; under 150 - 250 Torr; (pyrolysis);

5-hexenoic acid (1577-22-6) → 1,10-decadiene (1647-16-1)

Conditions	Yield
With sodium methylate In methanol (electrolysis);

acetoxycyclodecane (7386-24-5) → 1,10-decadiene (1647-16-1) + (Z)-cyclodecene (935-31-9) + trans-cyclodecene (2198-20-1)

Conditions	Yield
at 500℃;

1,4-dibromo-butane (110-52-1) + allyl bromide (106-95-6) → 1,10-decadiene (1647-16-1) + 1,5-Hexadien (592-42-7) + 7-bromo-hept-1-ene (4117-09-3) + tetradeca-1,13-diene (21964-49-8)

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 605308/; Multistep reaction. Further byproducts given;

1,4-dibromo-butane (110-52-1) + allyl bromide (106-95-6) + 3-Chloro-2-methylpropene (563-47-3) → 1,10-decadiene (1647-16-1) + 2,9-dimethyl-deca-1,9-diene (22080-34-8) + 2-methyl-deca-1,9-diene (13286-07-2)

Conditions	Yield
(i) Mg, THF, (ii) /BRN= 605308/, /BRN= 878160/; Multistep reaction;

1,10-dibromodecane (4101-68-2) → 1,10-decadiene (1647-16-1) + 1,10-difluorodecane (334-63-4) + 1-bromo-10-fluorodecane (334-61-2)

Conditions	Yield
With tetrabutylammonium hydrogen bifluoride In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at 95℃; for 3.5h;	A 2 % Chromat. B 76 % Chromat. C 22 % Chromat.

1,10-decadiene (1647-16-1) + carbon monoxide (201230-82-2) → 2,9-dimethyldecanedioic acid

Conditions	Yield
With hydrogenchloride; oxygen; copper dichloride; palladium dichloride In tetrahydrofuran under 760 Torr; for 19h; Ambient temperature;	100%

1,10-decadiene (1647-16-1) + 2,4,4-trimethyl-1-pentyl hypophosphorous acid (144900-28-7) → {10-(hydroxy-(2,4,4-trimethylpentyl)phosphinoyl)decyl}(2,4,4-trimethylpentyl)phosphinic acid (1189189-08-9)

Conditions	Yield
With di-tert-amyl peroxide at 140℃; for 6h; Inert atmosphere;	100%

1,10-decadiene (1647-16-1) + 6-methyl-1,10-undecadiene → poly(6-methyl-1,10-undecadiene-co-1,9-decadiene) copolymer, 7.1 methyl groups/1000 total carbons, Mw=35000, Mw/Mn=1.8; Monomer(s): 6-methyl-1,10-undecadiene; 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	98%

1,10-decadiene (1647-16-1) + 6-methyl-1,10-undecadiene → poly(6-methyl-1,10-undecadiene-co-1,9-decadiene) copolymer, 1.5 methyl groups/1000 total carbons, Mw=30100, Mw/Mn=1.9; Monomer(s): 6-methyl-1,10-undecadiene; 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	98%

1,10-decadiene (1647-16-1) → poly(1,9-decadiene), linear, Mw=27600, Mw/Mn=1.8; Monomer(s): 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	98%

1,10-decadiene (1647-16-1) + methyl vinyl ketone (78-94-4) → (3E,11E)-tetradeca-3,11-diene-2,13-dione (1231149-74-8)

Conditions	Yield
With copper(l) iodide; C39H52Cl2N2O3Ru In diethyl ether at 35℃; for 16h; Cross Metathesis; Inert atmosphere;	98%

1,10-decadiene (1647-16-1) + 6-methyl-1,10-undecadiene → poly(6-methyl-1,10-undecadiene-co-1,9-decadiene) copolymer, 25.0 methyl groups/1000 total carbons, Mw=60200, Mw/Mn=2.4; Monomer(s): 6-methyl-1,10-undecadiene; 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	97%

1,10-decadiene (1647-16-1) + 6-methyl-1,10-undecadiene → poly(6-methyl-1,10-undecadiene-co-1,9-decadiene) copolymer, 13.6 methyl groups/1000 total carbons, Mw=57500, Mw/Mn=2.0; Monomer(s): 6-methyl-1,10-undecadiene; 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	97%

1,10-decadiene (1647-16-1) + C16H36O4Si4 → C56H108O4Si4

Conditions	Yield
With C69H57N2*C8H18OSi2*Pt In toluene at 95℃; for 3.95h; Inert atmosphere; regioselective reaction;	97%

1,10-decadiene (1647-16-1) + 2-hydroxyethanethiol (60-24-2) → thiadenol (6964-20-1)

Conditions	Yield
With tert-butyl peroxypivalate In acetonitrile at 75℃; for 2h;	96%

1,10-decadiene (1647-16-1) + 2,3-dimethyl-buta-1,3-diene (513-81-5) → C22H38 (1254327-46-2)

Conditions	Yield
With cobalt(II) bromide-[1,2-bis(diphenylphosphino)ethane]; zinc(II) iodide; zinc In dichloromethane for 20h;	96%

1,10-decadiene (1647-16-1) + 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane (697-45-0) → 2,2'-[decane-2,9-diylbis(thio)]bis(5,5-dimethyl-1,3,2-dioxaphosphorinane)2,2'-disulfide (1034024-87-7)

Conditions	Yield
In toluene at 80℃; for 12h;	96%

1,10-decadiene (1647-16-1) + 2,2,4,6-tetraphenoxy-4,6-bis-undec-10-enyloxy-2λ5,4λ5,6λ5-[1,3,5,2,4,6]triazatriphosphinine → polymer; monomer(s): 1,9-decadiene; 2,2,4,6-tetraphenoxy-4,6-di(10-undecenyloxy)-1,3,5,2λ5,4λ5,6λ5-triazatriphosphinine

Conditions	Yield
Grubbs catalyst first generation at 20 - 60℃; under 10 Torr; for 24h; Product distribution; Further Variations:; Reagents; ratio of the input monomer; copolymerization;	95%

1,10-decadiene (1647-16-1) → polymer, acyclic diene metathesis; monomer(s): 1,9-decadiene

Conditions	Yield
With trifluorormethanesulfonic acid; (η6-p-cymene)Ru(P(cyclohexyl)3)(CCC(phenyl)2)Cl triflate In dichloromethane-d2 at 0℃; for 12h;	94%

tetrakis(dimethylsiloxy)octaphenylsilsesquioxane (674298-98-7) + 1,10-decadiene (1647-16-1) → C96H140O14Si12

Conditions	Yield
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex In toluene at 65℃; for 20h; Schlenk technique; Inert atmosphere;	93%

1,10-decadiene (1647-16-1) + (E)-1-phenyl-N-(1-phenylethylidene)methanamine (14428-98-9, 98325-59-8, 98359-08-1) → 1-(2-decyl-phenyl)-ethanone

Conditions	Yield
Stage #1: 1,10-decadiene; (E)-1-phenyl-N-(1-phenylethylidene)methanamine 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	92%
Stage #1: 1,10-decadiene; (E)-1-phenyl-N-(1-phenylethylidene)methanamine; [RhCl(PPh3)3]Cl In toluene at 150℃; for 2h; Stage #2: With hydrogenchloride Stage #3: With hydrogen; palladium on activated charcoal Further stages.;	92%

1,10-decadiene (1647-16-1) + 6-methyl-1,10-undecadiene → poly(6-methyl-1,10-undecadiene-co-1,9-decadiene) copolymer, 43.3 methyl groups/1000 total carbons, Mw=69400, Mw/Mn=1.8; Monomer(s): 6-methyl-1,10-undecadiene; 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	92%

1,10-decadiene (1647-16-1) → 1,10-dibromodecane (4101-68-2)

Conditions	Yield
With 2,2,4-trimethylpentane; tetradecafluorohexane; bromine at 20℃; for 2h; Irradiation;	92%
With HBr gas; sodium hydrogencarbonate; dibenzoyl peroxide In diethyl ether; hexane; water	58 mol %

1,10-decadiene (1647-16-1) → 1,10-Decanediol (112-47-0)

Conditions	Yield
Stage #1: 1,10-decadiene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 40℃; for 0.0666667h; Stage #2: With dihydrogen peroxide; sodium hydroxide In ethanol; water at 20℃; for 0.0488333h;	91%
Stage #1: 1,10-decadiene With sodium tetrahydroborate; iodine; ethylene dibromide In 1,2-dimethoxyethane at 25℃; for 20h; Stage #2: With dihydrogen peroxide; sodium hydroxide In water at 0 - 25℃; for 0.333333h;	69%

1,10-decadiene (1647-16-1) → rac/meso-1,2,9,10-diepoxydecane (24854-67-9)

Conditions	Yield
With peracetic acid; manganese(II) perchlorate; ammonium bicarbonate In water; acetic acid; acetonitrile at 20℃; for 0.666667h;	90%
With peracetic acid; C8H18N(1+)*MnO4(1-); sodium hydrogencarbonate In water at 20℃; for 0.5h;	82%
With Perbenzoic acid; chloroform
With peracetic acid; 1-methyl-1-propylpyrrolidinium dodecyl sulfate; manganese(II) acetate; sodium hydrogencarbonate In water; acetic acid at 20℃; for 0.5h;	88 %Chromat.

1,10-decadiene (1647-16-1) + 6-methyl-1,10-undecadiene → poly(6-methyl-1,10-undecadiene-co-1,9-decadiene) copolymer, 55.6 methyl groups/1000 total carbons, Mw=26100, Mw/Mn=1.7; Monomer(s): 6-methyl-1,10-undecadiene; 1,9-decadiene

Conditions	Yield
With bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum	90%

2,2-dimethyl-3-butyne (917-92-0) + 1,10-decadiene (1647-16-1) → 1,4-di-tert-butyl-5-(7-octenyl)-1,3-cyclohexadiene (1239513-47-3)

Conditions	Yield
With tris-(trimethylsilyl)silane; niobium pentachloride In 1,2-dichloro-ethane at 40℃; for 3h; Inert atmosphere; chemoselective reaction;	90%
With NbCl3(DME) In 1,2-dichloro-ethane at 40℃; for 2h; Inert atmosphere; regioselective reaction;	81%

bromoborane-dimethyl sulfide complex (55652-52-3) + 1,10-decadiene (1647-16-1) → (CH2)10BOCH3

Conditions	Yield
With MeOH In dichloromethane N2-atmosphere; addn. of H2BrB*SMe2 to olefin, then MeOH addn. (pptn.);	88%

1,10-decadiene (1647-16-1) → 2-(oct-7-en-1-yl)oxirane (85721-25-1)

Conditions	Yield
With oxygen In acetonitrile at 60℃; under 760.051 Torr; for 1.5h; Catalytic behavior; chemoselective reaction;	85%
With p-chloroperbenzoic acid In dichloromethane
With oxygen In acetonitrile under 760.051 Torr; for 1h; Kinetics;	90 %Chromat.

Upstream product

• 1720-38-3 1,9-decadiyne 
• 96536-94-6 2,13-dioxa-tetradecanedioic acid diethyl ester 
• 106-95-6 allyl bromide 
• 110-52-1 1,4-dibromo-butane 
• 563-47-3 3-Chloro-2-methylpropene 
• 4101-68-2 1,10-dibromodecane 
• 7386-24-5 acetoxycyclodecane 
• 151309-96-5 4-nitrophenyl ω-undecenoate 
• 931-88-4 cis-Cyclooctene 
• 74-85-1 ethene 
• 112-47-0 1,10-Decanediol 
• 42236-22-6 n-Decandiyl-dipropionat 
• 94160-13-1 C₂₄H₃₀O₄ 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 32362-97-3 2-pentylcyclohexanone 
• 112-47-0 1,10-Decanediol 
• 4203-48-9 decan-1,5-diol 
• 16538-91-3 decane-2,9-dione 
• 97963-22-9 3-chloro-2,9-decanedione 
• 6964-20-1 thiadenol 
• 31948-18-2 1,10-bis(4-benzoylphenyl)decane 
• 4101-68-2 1,10-dibromodecane 
• 931-88-4 cis-Cyclooctene 
• 628-92-2 Cycloheptene 
• 110-83-8 cyclohexene 
• 112-43-6 10-Undecen-1-ol 
• 39770-04-2 8-nonen-1-al 
• 190966-17-7 N₁,N₁₂-diphenyldodecane-1,12-diamine 

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The barrier domain solubility-diffusion theory of lipid bilayer permeability relates the permeability coefficient (Pm) to the solute's partition coefficient (PCbarrier/w) and diffusion coefficient (Dbarrier) in the ordered chain region of the bilayer that serves as the barrier region for po...detailed

ADMET copolymerization of divinyltetraethoxydisiloxane with 1,9-DECADIENE (cas 1647-16-1) catalyzed by Grubbs’ catalyst08/09/2019

The acyclic diene metathesis (ADMET) copolymerization of divinyltetraethoxydisiloxane with 1,9-decadiene, catalyzed by RuCl2(CHPh)(PCy3)2, is the first example of a siloxylene–vinylene–alkenylene copolymer reported in the literature. This copolymer was isolated and characterized by 1H, and 1...detailed

Copolymerisation of 1,9-DECADIENE (cas 1647-16-1) and propylene with binary and isolated metallocene systems08/08/2019

1,9-Decadiene/propylene copolymers were obtained with isolated metallocenes and with a binary metallocene catalyst system activated by methylaluminoxane. The metallocenes under investigation were syndiospecific diphenylmethyl(cyclopentadienyl)(9-fluorenyl)zirconium dichloride (1) and isospecific...detailed

Karstedt Catalyst – Catalyzed stepgrowth co-polyaddition of 1,9-DECADIENE (cas 1647-16-1) and 1,1,3,3-tetramethyldisiloxane08/07/2019

Low to medium molecular weight H–Si-terminating and alkyl–Si-terminating co-polyadducts of 1,9-decadiene and 1,1,3,3-tetramethyldisiloxane have been synthesized. Molecular weight determination from 1H NMR data is described. Product features indicate that this novel class of siloxane-modified p...detailed

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Ethenolysis reactions catalyzed by imido alkylidene monoaryloxide monopyrrolide (MAP) complexes of molybdenum

(Chemical Equation Presented) Monoaryloxide-pyrrolide (MAP) olefin metathesis catalysts of molybdenum that contain a chiral bitetralin-based aryloxide ligand are efficient for ethenolysis of methyl oleate, cyclooctene, and cyclopentene. Ethenolysis of 5000 equiv of methyl oleate produced 1-decene (1D) and methyl-9-decenoate (M9D) with a selectivity of >99%, yields up to 95%, and a TON (turnover number) of 4750 in 15 h. Tungstacyclobutane catalysts gave yields approximately half those of molybdenum catalysts, either at room temperature or at 50 °C, although selectivity was still >99%. Ethenolysis of 30000 equiv of cyclooctene to 1,9-decadiene could be carried out with a TON of 22500 at 20 atm (75% yield), while ethenolysis of 10000 equiv of cyclopentene to 1,6-heptadiene could be carried out with a TON of 5800 at 20 atm (58% yield). There is no reason to propose that the efficiency of ethenolysis has been maximized with the most successful catalyst reported here.

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Luminescent tungsten(vi) complexes as photocatalysts for light-driven C-C and C-B bond formation reactions

The realization of photocatalysis for practical synthetic application hinges on the development of inexpensive photocatalysts which can be prepared on a large scale. Herein an air-stable, visible-light-absorbing photoluminescent tungsten(vi) complex which can be conveniently prepared at the gram-scale is described. This complex could catalyse photochemical organic transformation reactions including borylation of aryl halides, such as aryl chloride, reductive coupling of benzyl bromides for C-C bond formation, reductive coupling of phenacyl bromides, and decarboxylative coupling of redox-active esters of alkyl carboxylic acid with high product yields and broad functional group tolerance.

Nickel-catalyzed deoxygenation of oxiranes: Conversion of epoxides to alkenes

Deoxygenation of epoxides takes place under the catalysis of nickel in the presence of diethylzinc as a deoxygenation agent to yield alkenes. Epoxides with a wide variety of substitution patterns are deoxygenated in this catalytic system to give terminal, 1,1-disubstituted, 1,2-disubstituted, trisubstituted, and tetrasubstituted alkenes in high yields. Reactions of 1,2-disubstituted epoxides we examined proceeded in an E-stereoselective manner. High compatibility with other functional groups through this transformation was also observed.

Oxidative Dehydroxymethylation of Alcohols to Produce Olefins

Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.