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251615

Sigma-Aldrich

Ethylaluminum dichloride solution

1.0 M in hexanes

Synonym(s):

Dichloro(ethyl)alumane solution

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About This Item

Linear Formula:
CH3CH2AlCl2
CAS Number:
563-43-9
Molecular Weight:
126.95
Beilstein/REAXYS Number:
4123357
MDL number:
MFCD00000457
UNSPSC Code:
12352103
PubChem Substance ID:
24855143
NACRES:
NA.22

vapor pressure

5 mmHg ( 60 °C)

Quality Level

100

form

liquid

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.

signalword

Danger

Hazard Classifications

Aquatic Chronic 2 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 2 - Repr. 2 - Skin Corr. 1B - STOT RE 1 Inhalation - STOT SE 3 - Water-react 2

target_organs

Central nervous system, Nervous system

Storage Class

4.2 - Pyrophoric and self-heating hazardous materials

wgk_germany

WGK 3

flash_point_f

-9.4 °F - closed cup

flash_point_c

-23 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6571
STBJ5686
STBJ5685
SHBK6672
STBG6856

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Concise access to indolizidine and pyrroloazepine skeleta via intramolecular Schmidt reactions of azido 1, 3-diketones.
Lertpibulpanya D and Marsden S P
Organic & Biomolecular Chemistry, 4(18), 3498-3504 (2006)
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)
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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