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364649

Sigma-Aldrich

tert-Butylmagnesium chloride solution

1.0 M in THF

Synonym(s):

t-Butylmagnesium chloride, tert-Butylchloromagnesium, Chloro(1,1-dimethylethyl)magnesium

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About This Item

Linear Formula:
(CH3)3CMgCl
CAS Number:
677-22-5
Molecular Weight:
116.87
Beilstein:
3535403
MDL number:
MFCD00000465
UNSPSC Code:
12352103
PubChem Substance ID:
24862448

Quality Level

200

reaction suitability

reaction type: Grignard Reaction

concentration

1.0 M in THF

density

0.931 g/mL at 25 °C

SMILES string

CC(C)(C)[Mg]Cl

InChI

1S/C4H9.ClH.Mg/c1-4(2)3;;/h1-3H3;1H;/q;;+1/p-1

InChI key

ZDRJSYVHDMFHSC-UHFFFAOYSA-M

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General description

tert-Butylmagnesium chloride, an organomagnesium compound, is commonly known as Grignard reagent. It is a powerful carbon nucleophile mainly used for C-C bond formation.

Application

tert-Butylmagnesium chloride (1.0 M in THF) has been used in the preparation of tert-butylsulfinyl chloride.
It can be used in:
  • Grignard metathesis reaction of 2,5-dibromo-3-hexylthiophene to form 2-bromo-5-magnesiobromo-3-hexylthiophene.
  • A key step for the asymmetric synthesis of sulfinyl transfer agents using cinchona alkaloids quinine and quinidine as chiral auxiliaries.

Other Notes

Storage below 25°C may cause formation of crystalline magnesium salts. Moving container to a warm location and ocassional gentle swirling should redissolve the solid.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Pyr. Liq. 1 - Skin Corr. 1B - Water-react 1

Supplementary Hazards

EUH019

Storage Class Code

4.2 - Pyrophoric and self-heating hazardous materials

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °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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Organic Chemistry, 542-542 (2008)
New general sulfinylating process for asymmetric synthesis of enantiopure sulfinates and sulfoxides.
Lu B Z, et al.
Organic Letters, 7(8), 1465-1468 (2005)
Facile synthesis of end-functionalized regioregular poly (3-alkylthiophene) s via modified Grignard metathesis reaction.
Jeffries-El M, et al.
Macromolecules, 38(25), 10346-10352 (2005)
"Tert-butylsulfonyl (Bus), a new protecting group for amines"
Sun P, et al.
The Journal of Organic Chemistry, 62(24), 8604-8608 (1997)

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