230111

Isopropylmagnesium chloride solution

2.0 M in THF

• Synonym(s): Chloro 1-methylethyl magnesium, Chloroisopropylmagnesium, Isopropylmagnesium chloride, iPrMgCl
• Linear Formula: (CH₃)₂CHMgCl
• CAS Number: 1068-55-9
• Molecular Weight: 102.85
• Beilstein/REAXYS Number: 4124221
• MDL number: MFCD00000466
• UNSPSC Code: 12352103
• PubChem Substance ID: 24853775
• NACRES: NA.22

Properties

• Quality Level: 200
• reaction suitability: reaction type: Grignard Reaction
• concentration: 2.0 M in THF
• density: 0.975 g/mL at 25 °C
• SMILES string: CC(C)[Mg]Cl
• InChI: 1S/C3H7.ClH.Mg/c1-3-2;;/h3H,1-2H3;1H;/q;;+1/p-1
• InChI key: GPIBKUJXKCEZOH-UHFFFAOYSA-M

Description

General description

Isopropylmagnesium chloride is a highly reactive organomagnesium halide formed by the reaction of magnesium metal with isopropyl chloride. It is used in the Grignard reaction to form new carbon-carbon bonds.

Application

Isopropylmagnesium chloride solution (2.0 M in THF) can be used as a reagent to synthesize:      

• 2,6-Diiodobenzaldehyde derivatives via regioselective metal-iodine exchange of 5-substituted 1,2,3-triiodobenzene in the presence of ethyl formate as a formylating agent.      
• Arene and heteroarene sulfonamides from aryl and heteroaryl bromides via the formation of corresponding Grignard reagents.
• Symmetrical pyridyl monoselenides by treating with bromo/iodopyridines followed by quenching with selenyl chloride, SeCl₂.

Packaging

The 25 mL Sure/Seal^™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Legal Information

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Safety Information

• pictograms: GHS02,GHS08,GHS05,GHS07
• signalword: Danger
• hcodes: H225,H260,H314,H335,H336,H351
• pcodes: P210 - P231 + P232 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3 - Water-react 1
• target_organs: Central nervous system, Respiratory system
• supp_hazards: EUH014,EUH019
• Storage Class: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• wgk_germany: WGK 1
• flash_point_f: 1.4 °F - closed cup
• flash_point_c: -17 °C - closed cup