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198048

Sigma-Aldrich

Trimethylaluminum solution

2.0 M in toluene

Synonym(s):

Trimethylalane

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About This Item

Linear Formula:
(CH3)3Al
CAS Number:
75-24-1
Molecular Weight:
72.09
Beilstein:
3587197
MDL number:
MFCD00008252
UNSPSC Code:
12352103
PubChem Substance ID:
24851857
NACRES:
NA.22

form

liquid

Quality Level

200

concentration

2.0 M in toluene

density

0.81 g/mL at 25 °C

SMILES string

C[Al](C)C

InChI

1S/3CH3.Al/h3*1H3;

InChI key

JLTRXTDYQLMHGR-UHFFFAOYSA-N

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Application

Trimethylaluminum solution can be used as a reagent in the synthesis of:
  • Polyhydroxylated cyclohexanes by stereoselective rearrangement of unsaturated glycosides.
  • Partially hydrolyzed trimethylaluminum (PHT) catalyst for the polymerization of olefins.
  • Methyl benzene by methylation of anisole derivatives using nickel-1,3-dicyclohexylimidazol-2-ylidene catalyst system.

Used in a recently reported Al-catalyzed oxidation based on Oppenauer chemistry providing excellent yields of aldehydes and ketones. As a (1:1) complex with binol catalyzes the dynamic kinetic resolution of secondary alcohols with Novozym 435.

Packaging

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
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Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Classifications

Aquatic Chronic 3 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Repr. 2 - Skin Corr. 1B - STOT RE 2 - STOT SE 3 - Water-react 1

Target Organs

Central nervous system

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

39.2 °F - closed cup

Flash Point(C)

4 °C - closed cup

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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Partially hydrolyzed trimethylaluminum (PHT) as heterogeneous cocatalyst for the polymerization of olefins with metallocene complexes
Koppl A, et al.
Journal of Applied Polymer Science, 80(3), 454-466 (2001)
Nickel-catalyzed cross-coupling of anisole derivatives with trimethylaluminum through the cleavage of carbon-oxygen bonds
Morioka T, et al.
Chemistry Letters (Jpn), 44(12), 1729-1731 (2015)
Lipase/aluminum-catalyzed dynamic kinetic resolution of secondary alcohols.
Albrecht Berkessel et al.
Angewandte Chemie (International ed. in English), 45(39), 6567-6570 (2006-09-05)
Trimethylaluminium promoted rearrangements of unsaturated sugars into cyclohexanes
Jia C, et al.
Tetrahedron Asymmetry, 15(4), 699-703 (2004)
Christopher R Graves et al.
Journal of the American Chemical Society, 128(39), 12596-12597 (2006-09-28)
A highly active and selective Al-based catalytic Oppenauer (O) oxidation is reported. Quantitative and selective oxidations of a variety of benzylic, propargylic, allylic, and aliphatic primary and secondary alcohols were achieved using nitrobenzaldehyde derivatives as the oxidant and simple aluminum
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