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673013

Sigma-Aldrich

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
MDL number:
MFCD08705262
UNSPSC Code:
12352103
PubChem Substance ID:
24885138
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

100

concentration

1.0 M in THF

density

1.047 g/mL at 25 °C

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.

Signal Word

Danger

Hazard Statements

H225,H302,H314,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014,EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-4.0 - 5.0 °F - closed cup

Flash Point(C)

-20 - -15 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Iron-catalyzed oxidative biaryl cross-couplings via mixed diaryl titanates: significant influence of the order of combining aryl Grignard reagents with titanate
Liu KM, et al.
Chemical Communications (Cambridge, England), 51(22), 4655-4658 (2015)

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