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673013

2-Benzyloxyphenylmagnesium bromide solution

1.0 M in THF

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About This Item

Empirical Formula (Hill Notation):
C13H11BrMgO
CAS Number:
328000-16-4
Molecular Weight:
287.43
NACRES:
NA.22
PubChem Substance ID:
24885138
UNSPSC Code:
12352103
MDL number:
MFCD08705262
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reaction suitability

reaction type: Grignard Reaction

Quality Level

100

packaging

Sure/Seal™ of

concentration

1.0 M in THF

density

1.047 g/mL at 25 °C

functional group

phenyl

SMILES string

Br[Mg]c1ccccc1OCc2ccccc2

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/p-1

InChI key

VELKJPFZDYXBDE-UHFFFAOYSA-M

Application

2-Benzyloxyphenylmagnesium bromide can be used:
  • As a substrate in the iron-catalyzed coupling reaction of aryl Grignard reagents with unprotected bromophenols.
  • As a substrate in the cross-coupling of Grignard reagents using diaryl titanates and ferric chloride.
  • In one of the key synthetic steps for the total synthesis of an antibiotic caboxamycin.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

signalword

Danger

supp_hazards

EUH014,EUH019

Storage Class

3 - Flammable liquids

flash_point_f

-4.0 - 5.0 °F - closed cup

flash_point_c

-20 - -15 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

target_organs

Central nervous system, Respiratory system

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SHBR1128
49696EK
49396JJ
95898MJ
14912MH

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Iron catalyzed oxidative assembly of N-heteroaryl and aryl metal reagents using oxygen as an oxidant
Liu KM, et al.
Chemical Communications (Cambridge, England), 51(6), 1124-1127 (2015)
Iron-Catalyzed Room Temperature Cross-Couplings of Bromophenols with Aryl Grignard Reagents
Xu L, et al.
Advanced Synthesis & Catalysis, 361(23), 5421-5427 (2019)
Iron-Catalyzed Room Temperature Cross-Couplings of Bromophenols with Aryl Grignard Reagents
Xu L, et al.
advanced synthesis and catalysis, 361(23), 5421-5427 (2019)
View All Related Papers

Global Trade Item Number

SKUGTIN
673013-50ML04061837845055