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682101

Sigma-Aldrich

Bis(trimethylaluminum)-1,4-diazabicyclo[2.2.2]octane adduct

Synonym(s):

Bis(trimethylaluminum)-DABCO® adduct, DABAL-Me3, DABAL-trimethylaluminum, Triethylenediaminine bis(trimethylaluminum)

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About This Item

Linear Formula:
(CH3)3Al · C6H12N2 · Al(CH3)3
CAS Number:
137203-34-0
Molecular Weight:
256.34
MDL number:
MFCD09265160
UNSPSC Code:
12352103
PubChem Substance ID:
24885678
NACRES:
NA.22

mp

>250 °C

Quality Level

100

SMILES string

C[Al-](C)(C)[N+]12CC[N+](CC1)(CC2)[Al-](C)(C)C

InChI

1S/C6H12N2.6CH3.2Al/c1-2-8-5-3-7(1)4-6-8;;;;;;;;/h1-6H2;6*1H3;;

InChI key

WSTAITCRSVOCTK-UHFFFAOYSA-N

General description

Product is air and moisture sensitive. Handle and store under a dry, inert atmosphere.

Application

DABAL-Me3: An Air Stable "Methyl Anion"
A more stable 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.

Legal Information

DABCO is a registered trademark of Air Products & Chemicals, Inc.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H260,H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3 - Water-react 1

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Woodward, S.
Synlett, 1490-1490 (2007)

Articles

DABAL-Me3 - Non-pyrophoric Methyl Anion Equivalent

DABAL-Me3 is an adduct of trimethylaluminum and DABCO® that is a free-flowing solid that can be manipulated without the need for an inert atmosphere.

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