251615

Sigma-Aldrich

Ethylaluminum dichloride solution

1.0 M in hexanes

Synonym(s):
Dichloro(ethyl)alumane solution
Linear Formula:
CH3CH2AlCl2
CAS Number:
Molecular Weight:
126.95
Beilstein/REAXYS Number:
4123357
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor pressure

5 mmHg ( 60 °C)

concentration

1.0 M in hexanes

density

0.729 g/mL at 25 °C

SMILES string

CC[Al](Cl)Cl

InChI

1S/C2H5.Al.2ClH/c1-2;;;/h1H2,2H3;;2*1H/q;+2;;/p-2

InChI key

UAIZDWNSWGTKFZ-UHFFFAOYSA-L

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Application

Ethylaluminum dichloride is a strong Lewis acid and a proton scavenger that can be used:
  • To catalyze polymerization of isobutylene.
  • To facilitate Diels-Alder reaction of α,β-unsaturated esters.
  • To carry out Pinacol reduction rearrangements.
  • To promote Schmidt rearrangement of diketoazides in the synthesis of indolizidines and pyrroloazepinediones.

Packaging

100, 800 mL in Sure/Seal™

Signal Word

Danger

Target Organs

Central nervous system

Supp Hazards

EUH014

RIDADR

UN 3394 4.3(4.2) / PGI

WGK Germany

WGK 2

Flash Point(F)

-9.4 °F - closed cup

Flash Point(C)

-23 °C - closed cup

Certificate of Analysis
Certificate of Origin
Cyclorearrangement and cycloolefination of keto-bis-sulfones. A sulfone analog of a pinacol reduction-rearrangement.
Trost B M, et al.
Journal of the American Chemical Society, 114(13), 5432-5434 (1992)
Kinetic and Mechanistic Studies of the Polymerization of Isobutylene Catalyzed by EtAlCl2/Bis (2-chloroethyl) Ether Complex in Hexanes.
Banerjee S, et al.
Macromolecules, 48(16), 5474-5480 (2015)
Stereochemical aspects of the intramolecular Diels-Alder reactions of methyl deca-2, 7, 9-trienoates. 1. Thermal cyclizations.
Roush W R, et al.
The Journal of Organic Chemistry, 45(21), 4264-4267 (1980)
Ethylaluminum Dichloride.
Snider B B.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Ethylaluminum Dichloride.
Snider B B.
e-EROS Encyclopedia of Reagents for Organic Synthesis (2001)

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