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Dimethylaluminium chloride

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Dimethylaluminium chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.335 Edit this at Wikidata
EC Number
  • 214-668-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/2CH3.Al.ClH/h2*1H3;;1H/q;;+1;/p-1Key: JGHYBJVUQGTEEB-UHFFFAOYSA-M
SMILES
  • C(C)Cl
Properties
Chemical formula C4H12Al2Cl2
Molar mass 185.00 g·mol
Appearance colorless liquid
Density 0.996 g cm−3
Melting point −21 °C (−6 °F; 252 K)
Boiling point 126–127 °C (259–261 °F; 399–400 K)
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS05: Corrosive
Signal word Danger
Hazard statements H225, H250, H260, H314
Precautionary statements P210, P222, P223, P231, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P402+P404, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Dimethylaluminium chloride is an organoaluminium compound with the chemical formula 2. It behaves similarly to diethylaluminium chloride but is more expensive. Hence, it is less commonly used.

Like other organoaluminium chlorides, dimethylaluminium chloride is a Lewis acid. This property is exploited by the use of dimethylaluminium chloride to induce some Diels-Alder reactions.

Structure and bonding

Compounds of the empirical formula AlR2Cl (R = alkyl, aryl) usually exist as dimers with the formula (R2Al)2(μ-Cl)2. The bridging ligands, indicated by the prefix "μ-", are halides, not the organic substituents. The aluminium adopts a tetrahedral geometry and follows the octet rule. By contrast, triethylaluminium and trimethylaluminium feature bridging alkyl groups and these compounds violate the octet rule.

Safety

Dimethylaluminium chloride is not only flammable but pyrophoric.

References

  1. "Aluminum, chlorodimethyl-". pubchem.ncbi.nlm.nih.gov.
  2. Snider, Barry B. (2001). "Dimethylaluminum Chloride". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd297. ISBN 0-471-93623-5.
  3. Danheiser, Rick L.; Renslo, Adam R.; Amos, David T.; Wright, Graham T. (2003). "Preparation of Substituted Pyridines Via Regiocontrolled [4 + 2] Cycloadditions of Oximinosulfonates: Methyl 5-Methylpyridine-2-Carboxylate". Organic Syntheses. 80: 133. doi:10.15227/orgsyn.080.0133.
  4. Brendhaugen, Kristen; Haaland, Arne; Novak, David P.; Østvold, Terje; Bjørseth, Alf; Powell, D. L. (1974). "The Molecular Structure of Dimethylaluminium Chloride Dimer, [(CH3)2AlCl]2 Redetermined by Gas Phase Electron Diffraction". Acta Chemica Scandinavica. 28a: 45–47. doi:10.3891/acta.chem.scand.28a-0045.
  5. McMahon, C. Niamh; Francis, Julie A.; Barron, Andrew R. (1997). "Molecular Atructure of 2". Journal of Chemical Crystallography. 27 (3): 191–194. doi:10.1007/BF02575988. S2CID 195242291.
Aluminium compounds
Al(I)
Organoaluminium(I) compoundsAl(C5(CH3)5)
Al(II)
Al(III)
Alums
Organoaluminium(III) compounds
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