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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
NACRES:
NA.22

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 - STOT SE 3 - Water-react 1

Target Organs

Respiratory system

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

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
1st spontaneously combustible materials and water reactive materials

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

364649-PZ:
364649-100ML:4548173140162
364649-4X25ML:4548173373263
364649-VAR:
364649-800ML:4548173140179
364649-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
SHBM7866
SHBM6823
SHBD6651V
SHBC7324V
SHBC5004V

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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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