17589-14-9

Basic information

• Product Name: bis(1-methylpropyl)magnesium
• Synonyms: bis(1-methylpropyl)magnesium;Bis-sec-butylmagnesium;Di(sec-butyl) magnesium;Di-sec-butylmagnesium;Einecs 241-558-7;Magnesium, bis(1-methylpropyl)-
• CAS NO: 17589-14-9
• Molecular Formula: C₈H₁₈Mg
• Molecular Weight: 138.53352
• EINECS: 241-558-7
• Mol File: 17589-14-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Vapor Pressure: 1920mmHg at 25°C
• CAS DataBase Reference: bis(1-methylpropyl)magnesium(CAS DataBase Reference)
• NIST Chemistry Reference: bis(1-methylpropyl)magnesium(17589-14-9)
• EPA Substance Registry System: bis(1-methylpropyl)magnesium(17589-14-9)

Safety Data

• Hazardous Substances Data: 17589-14-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Bis(1-methylpropyl)magnesium is utilized as a reagent in organic synthesis, particularly for Grignard reactions, which are widely used to form carbon-carbon bonds and introduce functional groups into organic molecules.
Used in Pharmaceutical Production:
It is employed as an important intermediate in the production of various pharmaceuticals, where its reactivity allows for the creation of complex organic molecules that are integral to drug structures.
Used in Agrochemical Manufacturing:
Bis(1-methylpropyl)magnesium also plays a role in the manufacturing of agrochemicals, contributing to the synthesis of compounds that are used in the development of pesticides and other agricultural products.
Used in Fine Chemicals Industry:
bis(1-methylpropyl)magnesium is used as an intermediate in the production of fine chemicals, which are high-purity chemicals used in various applications, including the fragrance, flavor, and specialty chemical industries.
Used in Polymer Production:
Bis(1-methylpropyl)magnesium is utilized in the manufacturing of polymers, where it may contribute to the formation of specific polymer structures or properties.
Used in Preparation of Complex Organic Molecules:
It is employed in the preparation of complex organic molecules, where its reactivity is harnessed to facilitate the synthesis of intricate molecular architectures that are challenging to produce through conventional methods.

InChI:InChI=1/2C4H9.Mg/c2*1-3-4-2;/h2*3H,4H2,1-2H3;/q2*-1;+2

Upstream product

• 78-86-4 s-butyl chloride 
• 15366-08-2 s-butylmagnesium chloride 
• 7439-93-2 lithium 
• 598-30-1 sec.-butyllithium 

Downstream Products

• 98-52-2 4-(1,1-dimethylethyl)-cyclohexanol 
• 21862-63-5 trans-4-tert-butylcyclohexanol 
• 75724-20-8 1-sec-Butyl-4-tert-butyl-cyclohexanol 
• 75724-21-9 1-sec-Butyl-4-tert-butyl-cyclohexanol 

Relevant articles and documents

Preparation of Polyfunctionalized Aromatic Nitriles from Aryl Oxazolines

A selective ortho,ortho’-functionalization of readily available aryl oxazolines by two successive magnesiations with sBu2Mg in toluene followed by trapping reactions with electrophiles, such as (hetero)aryl iodides or bromides, iodine, tosyl cyanide, ethyl cyanoformate or allylic bromides (39 examples, 62–99 % yield) is reported. Treatment of these aryl oxazolines with excess oxalyl chloride and catalytic amounts of DMF (50 °C, 4 h) provided the corresponding nitriles (36 examples, 73–99 % yield). Conversions of these nitriles to valuable heterocycles are reported, and a tentative mechanism is proposed.

Preparation of Functionalized Diorganomagnesium Reagents in Toluene via Bromine or Iodine/Magnesium-Exchange Reactions

A wide range of polyfunctionalized di(hetero)aryl- and dialkenyl-magnesium reagents are prepared in toluene within 10 to 120 minutes between 78 C and 25 C via an I/Mg- or Br/Mg-exchange reaction using reagents of the general formula R2Mg (R = sBu, Mes). Highly sensitive functional groups, such as triazene or nitro, are tolerated in these exchange reactions, enabling the synthesis of various functionalized (hetero)arene and alkene derivatives after quenching with several electrophiles including allyl bromides, acyl chlorides, aldehydes, ketones, and aryl iodides.

Untangling the Complexity of Mixed Lithium/Magnesium Alkyl/Alkoxy Combinations Utilised in Bromine/Magnesium Exchange Reactions

While it is known that the addition of Group 1 alkoxides to s-block organometallics can have an activating effect on reactivity, the exact nature of this effect is not that well understood. Here we describe the activation of sBu2Mg towards substituted bromoarenes by adding one equivalent of LiOR (R=2-ethylhexyl), where unusually both sBu groups can undergo efficient Br/Mg exchange. Depending on the substitution pattern on the bromoarene two different types of organometallic intermediates have been isolated, either a mixed aryl/alkoxide [{LiMg(2-FG-C6H4)2(OR)}2] (FG=OMe; NMe2) or a homoaryl [(THF)4Li2Mg(4-FG-C6H4)4] (FG=OMe, F). Detailed NMR spectroscopic studies have revealed that these exchange reactions and the formation of their intermediates are controlled by a new type of bimetallic Schlenk-type equilibrium between heteroleptic [LiMgsBu2(OR)], alkyl rich [Li2MgsBu4] and Mg(OR)2, with [Li2MgsBu4] being the active species performing the Br/Mg exchange process.

Method for Preparing Diorganomagnesium-Containing Synthesis Means

A diorganomagnesium-containing synthesis means, a method for its preparation and its use.