2-Benzyloxyphenylmagnesium bromide,1m &

Name: 2-Benzyloxyphenylmagnesium bromide,1m &
SKU: ACM328000164-1
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Catalog NumberACM328000164-1

CAS Number328000-16-4

CategorySalt

IUPAC Name

magnesium;phenylmethoxybenzene;bromide

Molecular Weight

287.43g/mol

Molecular Formula

C13H11BrMgO

Canonical SMILES

C1=CC=C(C=C1)COC2=CC=CC=[C-]2.[Mg+2].[Br-]

InChI

InChI=1S/C13H11O.BrH.Mg/c1-3-7-12(8-4-1)11-14-13-9-5-2-6-10-13;;/h1-9H,11H2;1H;/q-1;;+2/p-1

InChI Key

WHVIUIJRSBHYEZ-UHFFFAOYSA-M

Application

The 2-Benzyloxyphenylmagnesium bromide, 1m, serves as a versatile reagent used prominently in Grignard reactions for various applications. It acts as a substrate in the iron-catalyzed coupling reactions involving aryl Grignard reagents and unprotected bromophenols, facilitating the formation of complex organic compounds. Additionally, it plays a critical role in cross-coupling reactions using diaryl titanates and ferric chloride, highlighting its importance in the synthesis of diverse chemical structures. Notably, 2-Benzyloxyphenylmagnesium bromide is essential in one of the key synthetic steps in the total synthesis of the antibiotic caboxamycin, underscoring its significance in medicinal chemistry.

Complexity

265

Covalently-Bonded Unit Count

Exact Mass

285.98437g/mol

Formal Charge

Heavy Atom Count

Monoisotopic Mass

285.98437g/mol

Rotatable Bond Count

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