1,4-Diazabicyclo[2.2.2]octane;trimethylalumane

Base Information

• Chemical Name: 1,4-Diazabicyclo[2.2.2]octane;trimethylalumane
• CAS No.: 137203-34-0
• Molecular Formula: (CH3)3AlC6H12N2Al(CH3)3
• Molecular Weight: 256.347
• European Community (EC) Number: 628-951-2
• DSSTox Substance ID: DTXSID20586917
• Mol file: 137203-34-0.mol

Synonyms:137203-34-0;1,4-diazabicyclo[2.2.2]octane;trimethylalumane;DABAL-Me3;SCHEMBL173954;DTXSID20586917;MFCD09265160;AKOS025294430;J-006979;1,4-Diazabicyclo[2.2.2]octane--trimethylalumane (1/2);Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum)

Chemical Property of 1,4-Diazabicyclo[2.2.2]octane;trimethylalumane

Chemical Property:

• Melting Point: >250 °C
• Flash Point: 23°C (73°F)
• PSA: 6.48000
• LogP: 3.98500
• Storage Temp.: Hygroscopic, Room Temperature, Under inert atmosphere
• Solubility.: Benzene (Slightly), DMSO (Slightly)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 256.203976
• Heavy Atom Count: 16
• Complexity: 69.5

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,4-Diazabicyclo[2.2.2]OctaneBis(Trimethylaluminum)Complex ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 14-15-22-36/37/38
• Safety Statements: 16-26-43

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Al](C)C.C[Al](C)C.C1CN2CCN1CC2
• Uses: Bis(trimethylaluminum)-DABCO(R) adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum) is a non-pyrophoric alternative to trimethylaluminum for use in numerous reactions including methylations of aldehydes and imines, methylations of aryl and vinyl halides, conjugate addition to enones, and amide bond formation.1 DABAL-Me3: An Air Stable "Methyl Anion"

Technology Process of 1,4-Diazabicyclo[2.2.2]octane;trimethylalumane

There total 2 articles about 1,4-Diazabicyclo[2.2.2]octane;trimethylalumane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9,88935-43-7) + trimethylaluminium dimer → bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct (137203-34-0)

Guidance literature:

In diethyl ether; addn. of (AlMe3)2 in Et2O to a soln. of dabco in Et2O, immediate pptn., refluxing (1.5 h); Schlenk techniques;; removal of solvent (vac.), removal of excess dabco by sublimation (20°C, 1E-2 torr), recrystn. (refluxing benzene, cooling to 20°C); elem. anal.;

Reference yield: 60.0%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9,88935-43-7) + trimethylaluminum (75-24-1) → bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct (137203-34-0)

Guidance literature:

In toluene; at 0 ℃;

Reference yield: 90.0%

bis(trimethylaluminum)–1,4-diazabicyclo[2.2.2]octane adduct (137203-34-0) + 1-Iodonaphthalene (90-14-2) → 1-Methylnaphthalene (90-12-0,34475-76-8)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); dicyclohexyl(2',6'-diisopropyl-4'-sulfobiphenyl-2-yl)phosphonium hydrogen sulfate; In tetrahydrofuran; at 65 ℃; for 2h; chemoselective reaction; Inert atmosphere; Ionic liquid;

DOI:10.1016/j.apcata.2010.04.005

upstream raw materials:

1,4-diaza-bicyclo[2.2.2]octane

trimethylaluminum

Downstream raw materials:

1-Phenylethanol

(R)-1-phenylethanol

(2R,3E)-4-phenyl-3-buten-2-ol

(S)-trans-4-phenyl-3-buten-2-ol

Refernces

• 1、 -. "IMPROVED METHOD FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED SECONDARY ALCOHOLS BY THE ADDITION OF ORGANOALUMINIUM REAGENTS TO CARBONYL COMPOUNDS". Page/Page column 25. . Retrieved 2008/06/13.
• 2、 Bradford, Arleen M.,Bradley, Donald C.,Hursthouse, Michael B.,Motevalli, Majid. "Interactions of 1,4-diazabicyclo[2.2.2]octane with group III metal trimethyls: Structures of Me3M·N(C2H4) 3N·MMe3 (M = Al, Ga)". . p. 111 - 115. Retrieved 2008/10/08.