41114-59-4

Basic information

• Product Name: Nysted Reagent
• Synonyms: CYCLO-DIBROMODI-MU-METHYLENE[MU-(TETRAHYDROFURAN)TRIZINC];NYSTED REAGENT;nysted;NYSTED REAGENT, 20 WT. % SUSPENSION IN T ETRAHYDROFURAN;cyclo-dibromodi-μ-methylene[μ-(tetrahydrofuran)]trizinc;Nysted(20% in THF);Nysted Reagent,cyclo-Dibromodi-μ-methylene[μ-(tetrahydrofuran)]trizinc;Nysted Reagent, 20% w/w suspension in THF
• CAS NO: 41114-59-4
• Molecular Formula: C6H12Br2OZn3
• Molecular Weight: 456.14
• Product Categories: API intermediates;NULL
• Mol File: 41114-59-4.mol
• Article Data: 0

Chemical Properties

• Flash Point: −15 °F
• Appearance: /
• Density: 1.186 g/mL at 25 °C(lit.)
• CAS DataBase Reference: Nysted Reagent(CAS DataBase Reference)
• NIST Chemistry Reference: Nysted Reagent(41114-59-4)
• EPA Substance Registry System: Nysted Reagent(41114-59-4)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-14-19-22-36/37/38-40-36/37
• Safety Statements: 16-26-36-36/37
• RIDADR: UN 3399 4.3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 41114-59-4(Hazardous Substances Data)

Usage

Description

Nysted Reagent, also known as cyclo-dibromo-di-m-methylene-(m-tetrahydrofuran)-trizinc, is a reagent used in organic synthesis for the methylenation of carbonyl groups. It was discovered in 1975 by Leonard N. Nysted in Chicago, Illinois. The reagent is prepared by treating dibromomethane with activated zinc-lead couple or hydrogen chloride-activated zinc dust in THF. Nysted Reagent is known for its ability to convert a carbonyl group into a methylene group, a transformation referred to as Nysted methylenation or Nysted olefination. It is considered superior to the Tebbe reagent in certain applications.

Uses

Used in Organic Synthesis:
Nysted Reagent is used as a reagent for the methylenation of ketones and aldehydes, particularly useful for converting a carbonyl group into a methylene group. This transformation is known as Nysted methylenation or Nysted olefination.
Used in Pharmaceutical Industry:
Nysted Reagent is used as a reagent in the synthesis of Entacvir, an antiviral medication.
Used in Chemical Research:
Nysted Reagent is employed in various chemical research applications, such as the synthesis of amphidinolide T3 using a ring-closing metathesis and asymmetric dihydroxylation strategy, methylenation of carbonyl compounds, and olefination reactions.

Reactions

This commerically available reagent is capable of methyenylation alone or in concert with TiCl4. While information on the reactivity of the reagent exists, the mechanistic basis of its function has yet to be elucidated.

InChI:InChI=1/C4H8O.2CH2.2BrH.3Zn/c1-2-4-5-3-1;;;;;;;/h1-4H2;2*1H2;2*1H;;;/q;;;;;;2*+1/p-2/rC4H8O.C2H4Br2Zn3/c1-2-4-5-3-1;3-6-1-5-2-7-4/h1-4H2;1-2H2