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248843

Sigma-Aldrich

Dimethylaluminum chloride solution

1.0 M in hexanes

Synonym(s):

Chlorodimethylaluminum, Dimethylaluminum chloride, Dimethylchloralane, Dimethylchloroalane, Dimethylchloroaluminum

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About This Item

Linear Formula:
(CH3)2AlCl
CAS Number:
1184-58-3
Molecular Weight:
92.50
MDL number:
MFCD00000458
UNSPSC Code:
12352103
PubChem Substance ID:
24854954
NACRES:
NA.22

form

liquid

concentration

1.0 M in hexanes

density

0.701 g/mL at 25 °C

SMILES string

C[Al](C)Cl

InChI

1S/2CH3.Al.ClH/h2*1H3;;1H/q;;+1;/p-1

InChI key

JGHYBJVUQGTEEB-UHFFFAOYSA-M

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General description

Dimethylaluminum chloride (Me2AlCl) is a mild Lewis acid and acts as a proton scavenger. It catalyzes living isobutylene polymerization. Exceptional chelating potential of Me2AlCl, and its companion Lewis acid MeAlCl2, for the chelate-organized carbonyl addition reactions has been investigated. It effectively promotes chelate-controlled aldol and related allylsilane additions.

Application

Dimethylaluminum chloride may be employed as catalyst for the ene reaction of aliphatic and aromatic aldehydes with alkenes having a disubstituted vinylic carbon.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Central nervous system, Nervous system

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

-9.4 °F

Flash Point(C)

-23 °C

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ5219
STBH3034
STBF8979V
STBF4872V
STBC9422V

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D A Evans et al.
Journal of the American Chemical Society, 123(44), 10840-10852 (2001-11-01)
A systematic investigation of the stereoselectivity in Lewis acid-promoted (Mukaiyama) aldol reactions of achiral unsubstituted enolsilanes and chiral beta-hydroxy aldehydes proceeding under conditions favoring chelation control is presented. Good stereocontrol can be realized for enolsilane aldol reactions of beta-alkoxy and
Dimethylaluminum chloride catalyzed ene reactions of aldehydes.
Snider BB, et al.
Journal of the American Chemical Society, 104(2), 555-563 (1982)
Dimethylaluminum chloride catalyzed living isobutylene polymerization.
Bahadur M, et al.
Macromolecules, 33(26), 9548-9552 (2000)

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