1586-92-1

Basic information

• Product Name: DIETHYLALUMINUM ETHOXIDE
• Synonyms: Aluminum, ethoxydiethyl-;dlethylaluminumethoxide;ethoxydiethyl-aluminu;ethoxydiethyl-Aluminum;DIETHYLALUMINIUM ETHOXIDE;DIETHYLALUMINUM ETHOXIDE;ethoxydiethylaluminium;DIETHYLALUMINUM ETHOXIDE, 25 WT. % (1.6M ) SOLUTION IN TOLUENE
• CAS NO: 1586-92-1
• Molecular Formula: C₆H₁₅AlO
• Molecular Weight: 130.16
• EINECS: 216-447-1
• Product Categories: Organometallics;AluminumChemical Synthesis;Micro/Nanoelectronics;Organoaluminum;Organometallic Reagents;Solution Deposition Precursors;Chemical Synthesis;Aluminum;Chemical Synthesis;Materials Science;Organometallic Reagents;Solution Deposition Precursors
• Mol File: 1586-92-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 2.5-4.5 °C(lit.)
• Boiling Point: 108-109 °C/10 mmHg(lit.)
• Flash Point: −1 °F
• Appearance: Colorless/Liquid
• Density: 0.862 g/mL at 25 °C
• Vapor Pressure: 5 mm Hg ( 94 °C)
• Storage Temp.: 0-6°C
• Solubility: Soluble in hydrocarbons and ether.
• Sensitive: Air & Moisture Sensitive
• CAS DataBase Reference: DIETHYLALUMINUM ETHOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLALUMINUM ETHOXIDE(1586-92-1)
• EPA Substance Registry System: DIETHYLALUMINUM ETHOXIDE(1586-92-1)

Safety Data

• Hazard Codes: F,T,C
• Statements: 11-14-17-23/24/25-34-14/15-67-65-48/20-63
• Safety Statements: 16-26-36/37/39-45-43-27-62
• RIDADR: UN 3394 4.2/PG 1
• WGK Germany: nwg
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: I
• Hazardous Substances Data: 1586-92-1(Hazardous Substances Data)

Usage

Chemical Properties

colorless liquid

Flammability and Explosibility

Spontaneouslyflammableinair(pyrophoric)

InChI:InChI=1/C2H5O.2C2H5.Al/c1-2-3;2*1-2;/h2H2,1H3;2*1H2,2H3;/q-1;;;+1/rC6H15AlO/c1-4-7(5-2)8-6-3/h4-6H2,1-3H3

Synthetic route

triethylaluminum (97-93-8) + aluminium-triethylate → diethyl(ethoxy)aluminum (1586-92-1)

Conditions	Yield
at 170℃;

triethylaluminum (97-93-8) + sodium ethanolate (141-52-6) → diethyl(ethoxy)aluminum (1586-92-1) + sodium tetraethylaluminate (2397-68-4)

Conditions	Yield
In hexane; n-heptane; toluene at 70℃; for 1h;

triethylaluminum (97-93-8) + aluminum ethoxide (555-75-9) → diethyl(ethoxy)aluminum (1586-92-1)

triethylaluminum (97-93-8) → diethyl(ethoxy)aluminum (1586-92-1)

Conditions	Yield
With ethanol In hexane byproducts: ethane; Ar, ethanol in hexane added dropwise to a soln. of AlEt3 at -30°C; hexane was distilled off; residue was vac. distilled;

hexaethyldialuminum → diethyl(ethoxy)aluminum (1586-92-1)

Conditions	Yield
With O2 In xylene shaking of Al2Et6 soln. with different amts. of dry atm. O2 (mole ratio 3.5/1 - 2/1); spect. anal. {(27)Al-NMR};
With O2 In n-heptane shaking of Al2Et6 soln. with different amts. of dry atm. O2 (mole ratio 3.5/1 - 2/1); spect. anal. {(27)Al-NMR};

nickel(II) acetylacetonate + methyltriphenylphosphonium bromide (106475-72-3) + diethyl(ethoxy)aluminum (1586-92-1) + buta-1,3-diene (106-99-0) → C(x)H(x)Br(x)Ni(x)

Conditions	Yield
In further solvent(s) solvent: ethyleneoxide, addn. of (C6H5)2C(Br)CH3 to the react. mixt. at 0-10°C;	99%
In further solvent(s) solvent: ethyleneoxide, addn. of (C6H5)2C(Br)CH3 to the react. mixt. at 0-10°C;	99%
In diethyl ether an orange soln. reacts with phenyl- and halide substituted methane derivative;

nickel(II) acetylacetonate + diethyl(ethoxy)aluminum (1586-92-1) + buta-1,3-diene (106-99-0) + allyl bromide (106-95-6) → C(x)H(x)Br(x)Ni(x)

Conditions	Yield
In diethyl ether -80°C, filtration, addn. of allylbromide to the mixt. at 0°C;	95%
In diethyl ether -80°C, filtration, addn. of allylbromide to the mixt. at 0°C;	95%
In diethyl ether byproducts: (π-C3H5NiBr)2; -80°C, filtration, addn. of allylbromide to the mixt. at -20°C;
In diethyl ether byproducts: (π-C3H5NiBr)2; -80°C, filtration, addn. of allylbromide to the mixt. at -20°C;

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + 1,5-dicyclooctadiene (5259-72-3, 10060-40-9, 111-78-4) → bis(1,5-cyclooctadiene)nickel (0) (1295-35-8)

Conditions	Yield
In benzene molar ratio nickel acetylacetonat : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h;	93.5%
In benzene molar ratio nickel acetylacetonate : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h; washing with cold benzene and ether;	93.5%
In benzene molar ratio nickel acetylacetonate : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h; washing with cold benzene and ether;	93.5%
In benzene molar ratio nickel acetylacetonat : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h;	93.5%

diethyl(ethoxy)aluminum (1586-92-1) + tin(IV) chloride (7646-78-8) → tetraethyltin (597-64-8)

Conditions	Yield
100°C;	93%

(Z)-1-chloro-4-phenylbut-1-en-1-yl acetate (852919-31-4) + diethyl(ethoxy)aluminum (1586-92-1) → ethyl 4-phenylbutyrate (10031-93-3)

Conditions	Yield
In tetrahydrofuran for 1h; Heating;	92%

[2,2]bipyridinyl (366-18-7) + bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) → diethyl(2,2'-bipyridyl)nickel(II) (15218-76-5)

Conditions	Yield
Stage #1: [2,2]bipyridinyl; bis(acetylacetonate)nickel(II) In diethyl ether at 25℃; Inert atmosphere; Schlenk technique; Stage #2: diethyl(ethoxy)aluminum In diethyl ether at -20 - 25℃; for 52h; Inert atmosphere; Schlenk technique;	87%

(E)-1,2-diphenyl-ethene (103-30-0) + bis(triphenylphosphine)ethylenenickel(0) (23777-40-4) + diethyl(ethoxy)aluminum (1586-92-1) → trans-C6H5CHCHC6H5Ni(P(C6H5)3)2 (12151-25-6, 53586-21-3)

Conditions	Yield
With triphenylphosphine In benzene byproducts: methylenecyclopropane, methylenecyclopropane trimers; Ar-atmosphere; molar ratio Ni-complex : olefin = 1:3, stirring (20°C, 22 h); evapn., pptn. with ether, filtration, washing (ether), drying (vac.);	80%

triethylaluminum (97-93-8) + aluminium-triethylate → diethyl(ethoxy)aluminum (1586-92-1)

Conditions	Yield
at 170℃;

triethylaluminum (97-93-8) + sodium ethanolate (141-52-6) → diethyl(ethoxy)aluminum (1586-92-1) + sodium tetraethylaluminate (2397-68-4)

Conditions	Yield
In hexane; n-heptane; toluene at 70℃; for 1h;

triethylaluminum (97-93-8) + aluminum ethoxide (555-75-9) → diethyl(ethoxy)aluminum (1586-92-1)

triethylaluminum (97-93-8) → diethyl(ethoxy)aluminum (1586-92-1)

Conditions	Yield
With ethanol In hexane byproducts: ethane; Ar, ethanol in hexane added dropwise to a soln. of AlEt3 at -30°C; hexane was distilled off; residue was vac. distilled;

hexaethyldialuminum → diethyl(ethoxy)aluminum (1586-92-1)

Conditions	Yield
With O2 In xylene shaking of Al2Et6 soln. with different amts. of dry atm. O2 (mole ratio 3.5/1 - 2/1); spect. anal. {(27)Al-NMR};
With O2 In n-heptane shaking of Al2Et6 soln. with different amts. of dry atm. O2 (mole ratio 3.5/1 - 2/1); spect. anal. {(27)Al-NMR};

nickel(II) acetylacetonate + methyltriphenylphosphonium bromide (106475-72-3) + diethyl(ethoxy)aluminum (1586-92-1) + buta-1,3-diene (106-99-0) → C(x)H(x)Br(x)Ni(x)

Conditions	Yield
In further solvent(s) solvent: ethyleneoxide, addn. of (C6H5)2C(Br)CH3 to the react. mixt. at 0-10°C;	99%
In further solvent(s) solvent: ethyleneoxide, addn. of (C6H5)2C(Br)CH3 to the react. mixt. at 0-10°C;	99%
In diethyl ether an orange soln. reacts with phenyl- and halide substituted methane derivative;

nickel(II) acetylacetonate + diethyl(ethoxy)aluminum (1586-92-1) + buta-1,3-diene (106-99-0) + allyl bromide (106-95-6) → C(x)H(x)Br(x)Ni(x)

Conditions	Yield
In diethyl ether -80°C, filtration, addn. of allylbromide to the mixt. at 0°C;	95%
In diethyl ether -80°C, filtration, addn. of allylbromide to the mixt. at 0°C;	95%
In diethyl ether byproducts: (π-C3H5NiBr)2; -80°C, filtration, addn. of allylbromide to the mixt. at -20°C;
In diethyl ether byproducts: (π-C3H5NiBr)2; -80°C, filtration, addn. of allylbromide to the mixt. at -20°C;

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + 1,5-dicyclooctadiene (5259-72-3, 10060-40-9, 111-78-4) → bis(1,5-cyclooctadiene)nickel (0) (1295-35-8)

Conditions	Yield
In benzene molar ratio nickel acetylacetonat : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h;	93.5%
In benzene molar ratio nickel acetylacetonate : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h; washing with cold benzene and ether;	93.5%
In benzene molar ratio nickel acetylacetonate : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h; washing with cold benzene and ether;	93.5%
In benzene molar ratio nickel acetylacetonat : cyclooctadiene = 1 : 2.5-5, benzene free from air, reduction between 0 and 5°C, 2 h, and room temp. 15 h;	93.5%

diethyl(ethoxy)aluminum (1586-92-1) + tin(IV) chloride (7646-78-8) → tetraethyltin (597-64-8)

Conditions	Yield
100°C;	93%

(Z)-1-chloro-4-phenylbut-1-en-1-yl acetate (852919-31-4) + diethyl(ethoxy)aluminum (1586-92-1) → ethyl 4-phenylbutyrate (10031-93-3)

Conditions	Yield
In tetrahydrofuran for 1h; Heating;	92%

[2,2]bipyridinyl (366-18-7) + bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) → diethyl(2,2'-bipyridyl)nickel(II) (15218-76-5)

Conditions	Yield
Stage #1: [2,2]bipyridinyl; bis(acetylacetonate)nickel(II) In diethyl ether at 25℃; Inert atmosphere; Schlenk technique; Stage #2: diethyl(ethoxy)aluminum In diethyl ether at -20 - 25℃; for 52h; Inert atmosphere; Schlenk technique;	87%

(E)-1,2-diphenyl-ethene (103-30-0) + bis(triphenylphosphine)ethylenenickel(0) (23777-40-4) + diethyl(ethoxy)aluminum (1586-92-1) → trans-C6H5CHCHC6H5Ni(P(C6H5)3)2 (12151-25-6, 53586-21-3)

Conditions	Yield
With triphenylphosphine In benzene byproducts: methylenecyclopropane, methylenecyclopropane trimers; Ar-atmosphere; molar ratio Ni-complex : olefin = 1:3, stirring (20°C, 22 h); evapn., pptn. with ether, filtration, washing (ether), drying (vac.);	80%

3-methyltetrahydrofuran (13423-15-9) + vanadium(III) bromide (13470-26-3) + sodium tetraphenyl borate (143-66-8) + diethyl(ethoxy)aluminum (1586-92-1) → {V2(μ-Br)3(3-methyltetrahydrofuran)6}BPh4

Conditions	Yield
In further solvent(s) (Ar); VBr3 and 3-methyltetrahydrofuran refluxed for 12 h; cooled (room temp.); addn. of soln. of AlEt2OEt in toluene; stirred (10 days; room temp.); filtration through Celite onto NaBPh4; stirred for 12 h at room temp.;; filtration (Celite); hexane placed on top of soln.; soln. allowed to stand for several days; crystals filtered, washed (hexane) and dried (vacuum);;	76.5%

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + (1E,5E,9E)-cyclododeca-1,5,9-triene (676-22-2) → (trans,trans,trans-1,5,9-cyclododecatriene)nickel

Conditions	Yield
In diethyl ether at about 0°C; recrystn. from ether;	75%
In diethyl ether at about 0°C;	57%
In diethyl ether at about 0°C;	57%

5-methyl-2-furanone (591-12-8) + diethyl(ethoxy)aluminum (1586-92-1) + benzaldehyde (100-52-7) → (4S,5S)-4-Acetyl-5-phenyl-dihydro-furan-2-one (95891-75-1) + β-acetyl-γ-phenyl-γ-butyrolactone (95891-76-2) + 3-(hydroxy-phenyl-methyl)-4-oxo-pentanoic acid ethyl ester

Conditions	Yield
In tetrahydrofuran at 0℃; for 4h; crossed aldol reaction;	A 74% B n/a C n/a

nickel(II) acetylacetonate + 1,3,5,7-cycloocatetraene + diethyl(ethoxy)aluminum (1586-92-1) → cyclooctatetraene nickel

Conditions	Yield
In benzene 0-20°C;	71%
In benzene 0-20°C;	71%
In benzene 0-5°C;	60%
In benzene 0-5°C;	60%

[2,2]bipyridinyl (366-18-7) + iron(III) acetylacetonate + diethyl(ethoxy)aluminum (1586-92-1) → (C2H5)2Fe(2,2'-bipyridyl)2

Conditions	Yield
In diethyl ether from -20°C to 10°C, under N2, Ar or in vac.;	70%
In diethyl ether from -20°C to 10°C, under N2, Ar or in vac.;	50%

bis(acetylacetonato)palladium(II) + diethyl(ethoxy)aluminum (1586-92-1) → (2,2'-bipyridine)diethylpalladium(II) (102150-17-4) + Al(3+)*OC2H5(1-)*2CH(COCH3)2(1-)=Al(OC2H5)(CH(COCH3)2)2

Conditions	Yield
With [2,2]bipyridinyl In diethyl ether under Ar; Pd(acac)2 and 2,2'-bipyridine were suspensed; addition of Al(C2H5)2(OC2H5); stirred for 4 d at 22°C; filtered; washed 3 times with Et2O; dried in vacuo; crystals extracted (acetone) under reduced pressure; solid separated; dried in vacuo; elem.anal.;	A 67% B n/a

3-phenyl-propionaldehyde (104-53-0) + 5-methyl-2-furanone (591-12-8) + diethyl(ethoxy)aluminum (1586-92-1) → (4R,5S)-4-Acetyl-5-phenethyl-dihydro-furan-2-one + (4S,5S)-4-Acetyl-5-phenethyl-dihydro-furan-2-one + 3-acetyl-4-hydroxy-6-phenyl-hexanoic acid ethyl ester

Conditions	Yield
In tetrahydrofuran at -10℃; for 4h; crossed aldol reaction;	A 61% B n/a C n/a

tetrahydrofuran (109-99-9) + vanadium(III) bromide (13470-26-3) + sodium tetraphenyl borate (143-66-8) + diethyl(ethoxy)aluminum (1586-92-1) → {V2(μ-Br)3(tetrahydrofuran)6}BPh4

Conditions	Yield
In tetrahydrofuran (Ar); VBr3 and tetrahydrofuran refluxed for 12 h; cooled (room temp.); addn. of soln. of AlEt2OEt in toluene; stirred (10 days; room temp.); filtration through Celite onto NaBPh4; stirred for 12 h at room temp.;; filtration (Celite); hexane placed on top of soln.; soln. allowed to stand for several days; crystals filtered, washed (hexane) and dried (vacuum);;	61%

2,2-[μ-(N,N'-piperazindiyl)dimethyl]-bis(4,6-di-tert-butyl-phenol) (110546-20-8) + diethyl(ethoxy)aluminum (1586-92-1) → ethoxy aluminium-N,N-bis(benzyl-3,5-di-tert-butyl-phenol)piperazine (1214751-50-4)

Conditions	Yield
In diethyl ether; toluene in atm. of N2 or Ar using Schlenk technique; AlEt2OEt in Et2O added dropwise to piperazine deriv. soln. in toluene at 50°C, stirred at 50°C ca. 30 min; mixt. refluxed at 110°C for 5 h; solvent removed in vacuo, solid washed with pentane 3 times; pumped dry;elem. anal.;	59%

[2,2]bipyridinyl (366-18-7) + iron(III)-acetylacetonate (14024-18-1) + diethyl(ethoxy)aluminum (1586-92-1) → (C2H5)2Fe(2,2'-bipyridyl)2

Conditions	Yield
In diethyl ether under Ar; a mixt. of Fe-contg. compd. (12.9 mmol) and a ligand (30.3 mmol) in Et2O was treated dropwise at ca. -20°C with Al-contg. compd. (36.7 mmol); the mixt. was allowed to warm up to room temp.; stirring for 12 h at room temp.; the solid was filtered off, washed with Et2O, C7H16 and dried in vac.; IR-, NMR spectra;	55%

iron(III)-acetylacetonate (14024-18-1) + diethyl(ethoxy)aluminum (1586-92-1) + buta-1,3-diene (106-99-0) + Dimethyl(phenyl)phosphine (672-66-2) → (1,3-butadiene)tris(dimetylphenylphosphine)iron(0) (88242-44-8)

Conditions	Yield
In not given reaction of Fe(acac)3 with AlEt2OEt in the presence of PPhMe2, excess of 1,3-butadiene, 0°C;	52%

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + methylene cyclopropane (6142-73-0) → (η2-methylenecyclopropane)bis(triphenylphosphine)nickel (89606-46-2)

Conditions	Yield
With triphenylphosphine In benzene Ar-atmosphere; molar ratio Ni : PPh3 : Al : olefin = 1:2:3:4; stirring (20°C, 9 h, pptn.); filtration, washing (ether), drying (vac.);	44%

diphenyl dicyclopentadienyl-zirconium (51177-89-0) + diethyl(ethoxy)aluminum (1586-92-1) → (C5H5)2Zr(C6H4Al(C2H5)2OC2H5) (169617-72-5)

Conditions	Yield
In tetrahydrofuran; toluene Ar or N2-atmosphere; 80°C (18 h); evapn. (vac., room temp.), toluene addn., evapn. (vac.), pptn. on pentane addn. (sonicating, 30 min), filtering, pptn. on concg., decanting, drying (vac.); elem. anal.;	44%

C14H12Mg*3.3C4H8O + diethyl(ethoxy)aluminum (1586-92-1) → magnesium-μ-(9,10-dihydro-9,10-anthrylen)ethoxidiethylaluminate*3THF

Conditions	Yield
In tetrahydrofuran under Ar to C14H10Mg*nTHF in THF stirring at 20°C added during 30 min dropwise CH3CH2OAl(C2H5)2H in THF; after standing 1-2 d warmed to50-60°C, filtrated warm; crystn. in any h at -20°C; filtrated, washed with cooled ether,dried at 20°C/1E-3 torr; elem. anal.;	43%

bis-(cinnamaldehyde-N,N'-propylenediimine)-bis-acetylacetonatonickel(II) + diethyl(ethoxy)aluminum (1586-92-1) → bis{bis(cinnamic aldehyde)-propylenediimine-nickel(0)} + acetylacetonato(ethoxy)ethylaluminum

Conditions	Yield
In benzene suspn. of Ni-compd. in benzene is treated with the Al compd. at room temp. (under Ar) with stirring, further stirring for 3 d; filtn., evapn. (vac.), addn. of THF, filtn., addn. of ether to the filtrate and extn. with benzene; elem. anal.;	A 40% B n/a

(Z)-1-chloro-4-phenylbut-1-en-1-yl acetate (852919-31-4) + diethyl(ethoxy)aluminum (1586-92-1) → ethyl 3-oxo-6-phenyl-2-(2-phenylethyl)hexanoate

Conditions	Yield
With dimethyl sulfoxide In tetrahydrofuran at 0 - 20℃; for 15h; Claisen condensation;	38%

4,4'-dimethyl-2,2'-bipyridines (1134-35-6) + bis(acetylacetonato)palladium(II) + diethyl(ethoxy)aluminum (1586-92-1) → diethyl(4,4'-dimethyl-2,2'-bipyridine)palladium(II)

Conditions	Yield
In diethyl ether addn. of 11.0mmol (C2H5O)Al(C2H5)2 to 3.6mmol Pd-compound and 7.2mmol bipyridine in 50ml ether, stirring at 22°C for 6d, filtration, extractn. of residue with ethylether, concn. of ether extract, crystn. on cooling to -18°C (7d);; filtration under Ar, washing with ether, drying in vac.; elem. anal.;;	32%

cis-3-benzyl-4-p-tolyl-oxetan-2-one + diethyl(ethoxy)aluminum (1586-92-1) → 2-benzyl-3-hydroxy-3-p-tolyl-propionic acid ethyl ester + 1-methyl-4-(3-phenyl-1-propen-1-yl)benzene (134539-87-0, 62056-37-5)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 15h;	A 27% B 16%

1,10-Phenanthroline (66-71-7) + bis(acetylacetonato)palladium(II) + diethyl(ethoxy)aluminum (1586-92-1) → diethyl(1.10-phenanthroline)palladium(II) (109298-81-9)

Conditions	Yield
In tetrahydrofuran addn. of 11.54mmol (C2H5O)Al(C2H5)2 to 3.84mmol Pd-compound and 7.88mmol phenanthroline in 30ml dry THF, stirring at room temp. for 160h, filtration, concn. of filtrate, crystn. on cooling to -18°C for several days; Ar atm.;; filtration under Ar, washing with ether, drying in vac.; elem. anal.;;	17%

iron(III)-acetylacetonate (14024-18-1) + diethyl(ethoxy)aluminum (1586-92-1) + Dimethyl(phenyl)phosphine (672-66-2) → bis(ethylene)tris(dimetylphenylphosphine)iron(0) (88326-00-5)

Conditions	Yield
In diethyl ether addn. of AlEt2OEt to soln. of Fe(acac)3 and PPhMe2, -39°C, warmed up to -5°C, stirred 30min, concd. up, soln. cooled down to -78°C, pptn., under deoxygenated Ar; recrystn. from ether below 0°C under Ar; elem. anal.;	16%

diethyl ether (60-29-7) + diethyl(ethoxy)aluminum (1586-92-1) + nickel(II) acetylacetonate (3264-82-2) → Ni(C2H5)2(((C6H5)2PCH2)2)*0.5(C2H5)2O

Conditions	Yield
With bis-(diphenylphosphino)-ethane In diethyl ether AlEt2(OEt) added to mixt. of Ni(acac)2 and diphosphine in Et2O at -50°C, stirred at -20°C for 10 h; ppt. sepd. by filtration, washed with Et2O, dried in vac.; elem. anal.;	12%

bis(acetylacetonate)nickel(II) + diethyl(ethoxy)aluminum (1586-92-1) + 1,5-dicyclooctadiene (5259-72-3, 10060-40-9, 111-78-4) → cyclo-C8H12NiC5H7O2

Conditions	Yield
In benzene byproducts: Al(C5H7O2)3; 0°C; molar ratio of NiC5H7O2)2:1,5-cyclooctadiene:(C2H5)2AlOC2H5=1:2.5:2.3; 2.5h; solvolyse with ethanol and 2nHCl below 5°C; distn. in high vac. at 40-50°C; cooling and crystn.;	10%

diethyl(ethoxy)aluminum (1586-92-1) + methyl (2E)-penta-2,4-dienoate (2409-87-2) → (Z)-3-carbomethoxy 4-(2-carbomethoxy vinyl) cyclohexene + (Z)-3-carbomethoxy 4-(2-carboethoxy vinyl) cyclohexene + (Z)-cycloocta-3,7-diene-1,2-dicarboxylate de methyle + (Z)-1-carbomethoxy-2-carboethoxy cycloocta-3,7-diene

Conditions	Yield
With Ni(acac); threophos In toluene at 40℃; for 48h; Yield given. Further byproducts given. Yields of byproduct given;

Upstream product

• 97-93-8 triethylaluminum 
• 555-75-9 aluminum ethoxide 
• 141-52-6 sodium ethanolate 

Downstream Products

• 10031-93-3 ethyl 4-phenylbutyrate 
• 134539-87-0 1-methyl-4-(3-phenyl-1-propen-1-yl)benzene 
• 17230-09-0 2-ethoxy-5-methyltetrahydropyran 
• 823-22-3 5-hexanolide 
• 165727-45-7 tert-butyl ((2S,3S)-4-chloro-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 1295-35-8 bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ 
• 7440-02-0 nickel 
• 88242-44-8 (1,3-butadiene)tris(dimetylphenylphosphine)iron⁽⁰⁾ 
• 75108-68-8 trans-diethylbis(EtPh₂phosphine)palladium(II) 
• 75108-73-5 trans-diethylbis(Et₂Phphosphine)palladium(II) 

Relevant articles and documents

37Al NMR spectroscopy of triethylaluminum. A direct method to the determination of the proportion of monomer in solution

The sole 27Al NMR signal of triethylaluminum (TEA) is shifted significantly to lower field with: (1) decreasing concentration; (2) increasing temperature; and (3) increasing polarity of the solvent; that is, in each case with an increase in the amount of the monomeric form. 27Al NMR chemical shifts of Al2Et6 and AlEt3 are estimated as 153 +/- 2 and 265 +/- 10 ppm, respectively.By use of these and observed values, thermodynamic data Kd, ΔHd and ΔSd were calculated for the dissociation of Al2Et6.The dependence of the monomer-dimer equilibria on the concentration of TEA in the solvents used indicated the participation of an intermolecular process in the exchange of bridging and terminal ethyl groups not only in aromatic solvents but also, in contrast to previous reports, in aliphatic hydrocarbons.

Antiperspirants

Compounds represented by the formula wherein m and n each are 1 or 2 and the sum of m and n is 3; R1 is alkyl; R2 is substituted and unsubstituted alkyl, cycloalkyl, alkenyl, cycloalkenyl, aryl, alkanoyl, alkenoyl or aroyl; wherein the substituents on R2 when R2 is alkyl, alkenyl, alkanoyl and alkenoyl are one or more of cycloalkyl, cycloalkenyl, alkyl substituted cycloalkenyl, or aryl, alkoxy, cycloalkoxy, cycloalkenyloxy, aryloxy or alkyl and/or alkoxy substituted aryl, alkoxy, cycloalkoxy, cycloalkenyloxy or aryloxy; and wherein the substituents on R2 when R2 is cycloalkyl, cycloalkenyl, aryl and aroyl are one or more of alkyl, alkoxy or aryl; and when R2 is phenyl two adjacent alkyl and/or alkoxy substituents on the phenyl can be joined to form a 5 or 6-membered saturated ring; when m is 2 and n is 1, R2 can be wherein R1 has the significance above and each R1 can be the same or different, R3 is a straight chain alkylene of 2 to 4 carbons and p is 0, 1 or 2; when m is 1 and n is 2, R2 has the significance above and each R2 can be the same or different or when one R2 is alkyl the other R2 can be STR1 WHEREIN R1 has the significance above and R4 is alkyl; are disclosed as having activity as antiperspirants. Antiperspirant/deodorant compositions containing one or more of the compounds as active ingredients and methods for preparing the compounds are also disclosed.