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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Alkyl aluminum
Hazardous rank II
2nd spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

252662-VAR:
252662-BULK:
252662-PZ:
252662-100ML:4548173124971
252662-800ML:4548173124988

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Certificates of Analysis (COA)

Lot/Batch Number
SHBN7441
STBK3940
STBK2174
STBJ9748
SHBL8927

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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)
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)
Copper-Catalyzed Asymmetric Conjugate Addition of Alkenyl-and Alkylalanes to ?, ?-Unsaturated Lactams.
Cottet P, et al.
Organic Letters, 15(4), 828-831 (2013)
Aliphatic Claisen rearrangement promoted by organoaluminium reagents.
Takai K, et al.
Bulletin of the Chemical Society of Japan, 57(2), 446-451 (1984)

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