Isopropylmagnesium chloride

Isopropylmagnesium chloride
Identifiers
CAS Number	1068-55-9;
3D model (JSmol)	Interactive image;
ChemSpider	10620969;
ECHA InfoCard	100.012.680
EC Number	213-947-1;
PubChem CID	101955;
CompTox Dashboard (EPA)	DTXSID6061444 ;
	InChI InChI=1S/C3H7.ClH.Mg/c1-3-2;;/h3H,1-2H3;1H;/q-1;;+2/p-1 Key: IUYHWZFSGMZEOG-UHFFFAOYSA-M;
	SMILES C[CH-]C.[Mg+2].[Cl-];
Properties
Chemical formula	C3H7ClMg
Molar mass	102.84 g·mol−1
Solubility	Ethyl ether
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H260, H314
GHS precautionary statements	P210, P223, P231+232, P233, P240, P241, P242, P243, P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P335+334, P363, P370+378, P402+404, P403+235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

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

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: 4302–4320. doi:10.1002/anie.200300579. PMID 14502700.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)
W. Voskuil and J. F. Arens (1968). "Chlorodiisopropylphosphine". Org. Synth. 48: 47. doi:10.15227/orgsyn.048.0047.CS1 maint: uses authors parameter (link)

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[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: 4302–4320. doi:10.1002/anie.200300579. PMID 14502700.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.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.CS1 maint: uses authors parameter (link)