185416-14-2

Basic information

• Product Name: 4-N-BUTYLPHENYLMAGNESIUM BROMIDE
• Synonyms: 4-N-BUTYLPHENYLMAGNESIUM BROMIDE;4-n-Butylphenylmagnesium Bromide 0.5 M In Tetrhydrofuran
• CAS NO: 185416-14-2
• Molecular Formula: C₁₀H₁₃BrMg
• Molecular Weight: 237.42
• Mol File: 185416-14-2.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• CAS DataBase Reference: 4-N-BUTYLPHENYLMAGNESIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-N-BUTYLPHENYLMAGNESIUM BROMIDE(185416-14-2)
• EPA Substance Registry System: 4-N-BUTYLPHENYLMAGNESIUM BROMIDE(185416-14-2)

Safety Data

• Hazardous Substances Data: 185416-14-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H13.BrH.Mg/c1-2-3-7-10-8-5-4-6-9-10;;/h5-6,8-9H,2-3,7H2,1H3;1H;/q;;+1/p-1/rC10H13BrMg/c1-2-3-4-9-5-7-10(12-11)8-6-9/h5-8H,2-4H2,1H3

Upstream product

• 41492-05-1 p-bromobutylbenzene 
• 7439-95-4 magnesium 

Downstream Products

• 185416-25-5 [2-(4-Butyl-phenyl)-6-methoxy-benzo[b]thiophen-3-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone 
• 404872-01-1 1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-β-D-erythro-hex-2-enopyranosyl]-4-n-butylbenzene 
• 406951-48-2 C₄₃H₅₂O₂S₂ 
• 265098-44-0 C₅₀H₆₆O₂S₂ 
• 406951-46-0 C₅₄H₇₄O₂S₂ 
• 792924-51-7 (2-amino-5-bromo-phenyl)-(4-butyl-phenyl)-methanone 
• 1033595-33-3 C₂₃H₂₂N₂O₂ 

Relevant articles and documents

Facile Hydrogenolysis of C(sp3)–C(sp3) σ Bonds

The modification of benzylic quaternary, tertiary, and secondary carbon centers through palladium-catalyzed hydrogenolysis of C(sp3)–C(sp3) σ bonds is presented. When benzyl Meldrum's acid derivatives bearing quaternary benzylic centers are treated under mild hydrogenolysis conditions – palladium on carbon and atmospheric pressure of hydrogen – aromatics substituted with tertiary benzylic centers and Meldrum's acid are obtained with good to excellent yield. Analogously, substrates containing tertiary or secondary benzylic centers yield aromatics substituted with secondary benzylic centers or toluene derivatives, respectively. Furthermore, this strategy is used for the high yielding synthesis of diarylmethanes. The scope of the reductive dealkylation reaction is explored and the limitations with respect to steric and electronic factors are determined. A mechanistic analysis of the reaction is described that consisted of deuterium labelling experiments and hydrogenolysis of enantioenriched derivatives. The investigation shows that the C(sp3)–C(sp3) σ bond-cleaving events occur through a hybrid SN1/SN2 mechanism, in which the palladium center displaces a carbon-based leaving group, namely Meldrum's acid, with inversion of configuration, followed by reductive elimination of palladium to furnish a C?H bond. (Figure presented.).

Facile synthesis of a series of liquid crystalline 2-(4'-alkylphenyl)-5-cyanopyridines

The invention relates to a facile synthesis of a series of 2-(4′-alkylphenyl)-5-cyanopyridine liquid crystal compounds which are represented by the following formula (I): wherein Cn is a linear alkyl having 1-12 carbon atoms. The synthesis of the liquid crystalline 2-(4′-alkylphenyl)-5-cyanopyridine is completed in a two-step reaction. First, a Grignard reagent (such as 4-alkylphenylmagnesium bromide) is added to a 3-cyanopyridinium salt (such as N-phenyloxycarbonyl-3-cyanopyridinium chloride) to get a 1,2-dihydropyridine. Then the 1,2-dihydropyridine is oxidized with o-chloronil to obtain the 2-(4′-alkylphenyl)-5-cyanopyridine.