364649

tert-Butylmagnesium chloride solution

1.0 M in THF

• Synonym(s): t-Butylmagnesium chloride, tert-Butylchloromagnesium, Chloro(1,1-dimethylethyl)magnesium
• Linear Formula: (CH₃)₃CMgCl
• CAS Number: 677-22-5
• Molecular Weight: 116.87
• Beilstein/REAXYS Number: 3535403
• MDL number: MFCD00000465
• UNSPSC Code: 12352103
• PubChem Substance ID: 24862448
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H250,H260,H302,H314,H335,H336,H351
• pcodes: P210 - P231 + P232 - P280 - P303 + P361 + P353 - P305 + P351 + P338 - P370 + P378
• 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
• supp_hazards: EUH019
• Storage Class: 4.2 - Pyrophoric and self-heating hazardous materials
• wgk_germany: WGK 3
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup
• ppe: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter