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562076

Sigma-Aldrich

3,5-Dimethylphenylmagnesium bromide solution

0.5 M in THF

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About This Item

Linear Formula:
(CH3)2C6H3MgBr
CAS Number:
34696-73-6
Molecular Weight:
209.37
MDL number:
MFCD01311497
UNSPSC Code:
12352103
PubChem Substance ID:
24880004
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

Quality Level

100

concentration

0.5 M in THF

bp

65 °C

density

0.950 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

Cc1cc(C)cc([Mg]Br)c1

InChI

1S/C8H9.BrH.Mg/c1-7-4-3-5-8(2)6-7;;/h4-6H,1-2H3;1H;/q;;+1/p-1

InChI key

XPXQQJMQESWIKM-UHFFFAOYSA-M

Application

3,5-Dimethylphenylmagnesium bromide solution can be used:
  • As a starting material for the synthesis of diarylborinic acids, which on Suzuki coupling with vinyl triflate yield penultimate methyl ester.
  • To prepare 3,5-dimethyl-p-terphenyl by reacting with biphenylsulfonate in the presence of dppfNiCl2 catalyst.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-0.0 °F - closed cup

Flash Point(C)

-17.78 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM7584
SHBM3465
SHBM1717
SHBG6843V
SHBF3229V

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Preparation of unsymmetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents
Cho C, et al.
Tetrahedron, 60(21), 4589-4599 (2004)
Suzuki reaction of a diarylborinic acid: one-pot preparation and cross-coupling of bis (3, 5-dimethylphenyl) borinic acid
Winkle DD and Schaab KM
Organic Process Research & Development, 5(4), 450-451 (2001)

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