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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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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)
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)
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)
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
Trimethylaluminium promoted rearrangements of unsaturated sugars into cyclohexanes
Jia C, et al.
Tetrahedron Asymmetry, 15(4), 699-703 (2004)
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