Isopropylmagnesium chloride

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Isopropylmagnesium chloride
IPrMgCl.png
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.012.680 Edit this at Wikidata
EC Number
  • 213-947-1
UNII
  • InChI=1S/C3H7.ClH.Mg/c1-3-2;;/h3H,1-2H3;1H;/q-1;;+2/p-1
    Key: IUYHWZFSGMZEOG-UHFFFAOYSA-M
  • C[CH-]C.[Mg+2].[Cl-]
Properties
C3H7ClMg
Molar mass 102.84 g·mol−1
Solubility Ethyl ether
Hazards
GHS labelling:
GHS02: FlammableGHS05: Corrosive
Danger
H225, H260, H314
P210, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, 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 [77 °F], 100 kPa).

Isopropylmagnesium chloride is an organometallic compound with the general formula (CH3)2HCMgCl. This highly flammable, colorless, and moisture sensitive material is the Grignard reagent derived from isopropyl chloride. It is commercially available, usually as a solution in tetrahydrofuran. This reagent is used to prepare Grignard reagents by transmetalation reactions as well as installing isopropyl groups.[1] An illustrative generic reaction involves the generation of the Grignard reagent derived from bromo-3,5-bis(trifluoromethyl)benzene:[2]

(CH3)2HCMgCl + (CF3)2C6H3Br → (CH3)2HCCl + (CF3)2C6H3MgBr

Isopropylmagnesium chloride is also used to prepare other isopropyl compounds, such as chlorodiisopropylphosphine:[3]

PCl3 + 2 (CH3)2CHMgCl → [(CH3)2CH]2PCl + 2 MgCl2

This reaction exploits the bulky nature of the isopropyl substituent.

References[edit]

  1. ^ Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. (2003). "Highly Functionalized Organomagnesium Reagents Prepared through Halogen–Metal Exchange". Angewandte Chemie International Edition. 42 (36): 4302–4320. doi:10.1002/anie.200300579. PMID 14502700.{{cite journal}}: CS1 maint: uses authors parameter (link)
  2. ^ Johnnie L. Leazer, Jr, Raymond Cvetovich (2005). "A Practical and Safe Preparation of 3,5-Bis(trifluoromethyl)acetophenone". Org. Synth. 82: 115. doi:10.15227/orgsyn.082.0115.{{cite journal}}: CS1 maint: uses authors parameter (link)
  3. ^ W. Voskuil and J. F. Arens (1968). "Chlorodiisopropylphosphine". Org. Synth. 48: 47. doi:10.15227/orgsyn.048.0047.{{cite journal}}: CS1 maint: uses authors parameter (link)