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198048

Sigma-Aldrich

Trimethylaluminum solution

2.0 M in toluene

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Synonym(s):
Trimethylalane
Linear Formula:
(CH3)3Al
CAS Number:
Molecular Weight:
72.09
Beilstein/REAXYS Number:
3587197
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

Quality Level

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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1 of 4

This Item
215007379239268569
Trimethylaluminum solution 2.0 M in toluene

198048

Trimethylaluminum solution

Trimethylaluminum solution 2.0 M in heptane

379239

Trimethylaluminum solution

Trimethylaluminum solution 2.0 M in hexanes

268569

Trimethylaluminum solution

concentration

2.0 M in toluene

concentration

1.0 M in toluene

concentration

2.0 M in heptane

concentration

2.0 M in hexanes

Quality Level

200

Quality Level

200

Quality Level

100

Quality Level

100

form

liquid

form

liquid

form

liquid

form

liquid

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.

Legal Information

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

signalword

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

supp_hazards

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

39.2 °F - closed cup

flash_point_c

4 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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

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