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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

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.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class I Designated Chemical Substances

FSL

Group 3: Spontaneously combustible substances and water- reactive materials
Materials containing Organometallic compounds
Hazardous rank I
Class 1

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

673013-5ML:4548173239408
673013-BULK:
673013-50ML:4548173239392
673013-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
49696EK
49396JJ
95898MJ
14912MH
00228HE

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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)

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