737797-42-1

Basic information

• Product Name: 4-ACETOXYBUTYL ZINC BROMIDE
• Synonyms: 4-ACETOXYBUTYL ZINC BROMIDE
• CAS NO: 737797-42-1
• Molecular Formula: C₆H₁₁BrO₂Zn
• Molecular Weight: 260.44
• Product Categories: Alkyl;Organozinc Halides;Reike and Organozinc Reagents
• Mol File: 737797-42-1.mol

Chemical Properties

• Flash Point: 1 °F
• Appearance: /
• Density: 0.985 g/mL at 25 °C(lit.)
• CAS DataBase Reference: 4-ACETOXYBUTYL ZINC BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ACETOXYBUTYL ZINC BROMIDE(737797-42-1)
• EPA Substance Registry System: 4-ACETOXYBUTYL ZINC BROMIDE(737797-42-1)

Safety Data

• Hazard Codes: F,Xn
• Statements: 14-19-22-36/37/38
• Safety Statements: 16-26-33-36
• RIDADR: UN 3399 4.3/PG 2
• WGK Germany: 1
• Hazardous Substances Data: 737797-42-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H11O2.BrH.Zn/c1-3-4-5-8-6(2)7;;/h1,3-5H2,2H3;1H;/q;;+1/p-1/rC6H11BrO2Zn/c1-6(8)9-4-2-3-5-10-7/h2-5H2,1H3

Upstream product

• 4753-59-7 4-Bromobutyl acetate 
• 7440-66-6 zinc 

Relevant articles and documents

Cobalt-Catalyzed Cross-Coupling of Functionalized Alkylzinc Reagents with (Hetero)Aryl Halides

A combination of 10 % CoCl2 and 20 % 2,2′-bipyridine ligands enables cross-coupling of functionalized primary and secondary alkylzinc reagents with various (hetero)aryl halides. Couplings with 1,3- and 1,4-substituted cycloalkylzinc reagents proceeded diastereoselectively leading to functionalized heterocycles with high diastereoselectivities of up to 98:2. Furthermore, alkynyl bromides react with primary and secondary alkylzinc reagents providing the alkylated alkynes.

Csp3-Csp3 Bond-Forming Reductive Elimination from Well-Defined Copper(III) Complexes

Carbon-carbon bond-forming reductive elimination from elusive organocopper(III) complexes has been considered the key step in many copper-catalyzed and organocuprate reactions. However, organocopper(III) complexes with well-defined structures that can undergo reductive elimination are extremely rare, especially for the formation of Csp3-Csp3 bonds. We report herein a general method for the synthesis of a series of [alkyl-CuIII-(CF3)3]- complexes, the structures of which have been unequivocally characterized by NMR spectroscopy, mass spectrometry, and X-ray crystal diffraction. At elevated temperature, these complexes undergo reductive elimination following first-order kinetics, forming alkyl-CF3 products with good yields (up to 91%). Both kinetic studies and DFT calculations indicate that the reductive elimination to form Csp3-CF3 bonds proceeds through a concerted transition state, with a ΔH? = 20 kcal/mol barrier.

Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N, N-Dimethylacetamide

Monoorganozinc reagents, readily obtained from alkyl bromides, display excellent reactivity with β,β-disubstituted enones and TMSCl in the presence of Cu(I) and Cu(II) salts to synthesize a variety of cyclic functionalized β-quaternary ketones in 38-99% yields and 9:1-20:1 diastereoselectivities. The conjugate addition features a pronounced improvement in DMA using monoorganozinc bromide reagents. A simple one-pot protocol that harnesses in situ generated monoorganozinc reagents delivers comparable product yields.

Continuous flow Negishi cross-couplings employing silica-supported: Pd-PEPPSI - IPr precatalyst

The synthesis of a triethoxysilyl functionalised Pd-PEPPSI-IPr complex prepared via azide-alkyne cycloaddition is described. The complex was immobilised onto silica gel and applied as a heterogeneous catalyst in the Negishi reaction. The catalyst was active in both batch and continuous flow operation and was particularly effective for the coupling of heteroaryl chlorides. Long-term continuous flow experiments demonstrated good catalyst activity over fifteen hours.