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252662

Sigma-Aldrich

Triethylaluminum solution

1.0 M in hexanes

Synonym(s):

Aluminumtriethanide

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About This Item

Linear Formula:
Al(C2H5)3
CAS Number:
97-93-8
Molecular Weight:
114.16
Beilstein:
3587229
MDL number:
MFCD00009015
UNSPSC Code:
12352103
PubChem Substance ID:
24855229
NACRES:
NA.22

form

liquid

Quality Level

100

concentration

1.0 M in hexanes

density

0.692 g/mL at 25 °C

SMILES string

CC[Al](CC)CC

InChI

1S/3C2H5.Al/c3*1-2;/h3*1H2,2H3;

InChI key

VOITXYVAKOUIBA-UHFFFAOYSA-N

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Application

Triethylaluminum solution can be used:
  • As a reagent in Alumino-Mannich reaction, where it reacts with iminium ion substrates for which the corresponding Petasis borono-Mannich reaction is unsuccessful.
  • In the synthesis of macrocyclic binuclear aluminum complexes with efficient activities toward ring-opening polymerization of ε-caprolactone.
  • To promote Claisen rearrangement of allyl vinyl ether derivatives along with the transfer of ethyl group to aldehydic carbon.
  • As a reagent for copper-catalyzed asymmetric conjugate addition of alkenyl- and alkylalanes to α,β-unsaturated lactams.
  • As a precursor to synthesize diethylaluminium cyanide, which is used as hydrocyanating reagent.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH014

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

-0.4 °F - closed cup

Flash Point(C)

-18 °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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Aliphatic Claisen rearrangement promoted by organoaluminium reagents.
Takai K, et al.
Bulletin of the Chemical Society of Japan, 57(2), 446-451 (1984)
Copper-Catalyzed Asymmetric Conjugate Addition of Alkenyl-and Alkylalanes to ?, ?-Unsaturated Lactams.
Cottet P, et al.
Organic Letters, 15(4), 828-831 (2013)
Binuclear aluminum complexes with amine?imine type ligands derived from 1, 3-benzenedialdehyde: synthesis, structures and their catalytic properties in ring-opening polymerization.
Wu C, et al.
Journal of Coordination Chemistry, 69(6), 1066-1075 (2016)
Hydrocyanation. IV. New hydrocyanation methods using hydrogen cyanide and an alkylaluminum, and an alkylaluminum cyanide.
Nagata W, et al.
Journal of the American Chemical Society, 94(13), 4635-4643 (1972)
An Alumino?Mannich Reaction of Organoaluminum Reagents, Silylated Amines, and Aldehydes.
Tarasewicz A, et al.
Chemistry?A European Journal , 24(23), 6071-6074 (2018)

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