| Identification | Back Directory | [Name]
1,3-Butadienyl-2-magnesium Chloride | [CAS]
32657-89-9 | [Synonyms]
1,3-Butadienyl-2-magnesium Chloride | [Molecular Formula]
C4H5ClMg | [MDL Number]
MFCD16876610 | [MOL File]
32657-89-9.mol | [Molecular Weight]
112.841 |
| Hazard Information | Back Directory | [Uses]
1,3-Butadienyl-2-magnesium Chloride is used as a reagent for a variety of carbon-carbon bond forming reactions with carbonyls, epoxides, and alkyl and aryl halides; precursor of organotin and organosilicon compounds via transmetalation reactions.
| [Synthesis Reference(s)]
1. Aufdermarsh, Jr., C. A. JOC 1964, 29, 1994.
2. Sultanov, N. T.; Mekhtiev, S. D.; Efendieva, T. G.; Kodzhaeva, Sh. Ya.; Aleieva M. A.; Mamedov, F. A. CA 1971, 74, 142.
| [Synthesis]
1,3-butadienyl-2-magnesium chloride is synthesized by Grignard reaction of 4-chloro-1,2-butadiene with Magnesium in ether (eq 1)1 or 2-chloro-1,3-butadiene (chloroprene) with magnesium in the presence of 1,2-Dibromoethane and a catalytic amount of Zinc Chloride in THF (eq 2).2The experimental procedure is as follows: to a flask equipped with a mechanical stirrer under nitrogen were charged magnesium turnings, well activated by scratching (0.15 mol), 0.5 mL of 1,2-dibromoethane, and 5 mL of THF. On cooling, ZnCl2 (3 mol%) was added. To this mixture was added a small amount of freshly distilled chloroprene (ca. 1 g), and the solution was stirred vigorously with heating until initiation occurred. Several drops of dibromoethane may be added to assist initiation. After initiation occurred, chloroprene (100 mmol) in THF (100 mL) was added dropwise at a rate to maintain gentle reflux. An additional 3 h of reflux ensured complete reaction. 1,3-Butadienyl-2-magnesium chloride is generally used directly for further reactions as the solution.
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