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425508

Sigma-Aldrich

2,6-Dimethylphenylmagnesium bromide solution

1.0 M in THF

Synonym(s):

2,6-Xylylmagnesium bromide, Bromo(2,6-dimethylphenyl)magnesium

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About This Item

Linear Formula:
(CH3)2C6H3MgBr
CAS Number:
21450-64-6
Molecular Weight:
209.37
MDL number:
MFCD00192083
UNSPSC Code:
12352103
PubChem Substance ID:
24866639
NACRES:
NA.22

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

bp

65-67 °C

density

0.998 g/mL at 25 °C

SMILES string

Cc1cccc(C)c1[Mg]Br

InChI

1S/C8H9.BrH.Mg/c1-7-4-3-5-8(2)6-7;;/h3-5H,1-2H3;1H;/q;;+1/p-1

InChI key

BIGUVDUZGAJWQK-UHFFFAOYSA-M

Application

2,6-Dimethylphenylmagnesium bromide can be used:
  • As an intermediate in the synthesis of dibutyl(5,10-dihydro-1,9-di-p-toluoyl-5-p-tolyldipyrrinato)tin(IV), which is further used in the preparation of zinc-based porphyrin.
  • As a substrate in the preparation of substituted fluorenes by reacting with 2-substituted arenesulfonates and dihaloarenes.

Signal Word

Danger

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

-2.2 °F - closed cup

Flash Point(C)

-19 °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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Pd (OAc) 2-catalyzed domino reactions of 1, 2-dihaloarenes and 2-haloaryl arenesulfonates with Grignard reagents: efficient synthesis of substituted fluorenes
Dong C and Hu Q
Tetrahedron, 64(11), 2537-2552 (2008)
Nearly Chromatography-Free Synthesis of the A3B-Porphyrin 5-(4-Hydroxymethylphenyl)-10, 15, 20-tri-p-tolylporphinatozinc (II).
Zaidi SHH, et al.
Organic Process Research & Development, 10(2), 304-314 (2006)

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