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Nysted Reagent

Nysted Reagent Structure
CAS No.
41114-59-4
Chemical Name:
Nysted Reagent
Synonyms
nysted;Nysted Reag;NystedReagen;NYSTED REAGENT;Nystead reagent;Nysted(20% in THF);Nysted reagent 20% THF;Nysted Reagent ISO 9001:2015 REACH;Nysted Reagent, 20% w/w suspension in THF;Nysted Reagent 20 wt. % suspension in THF
CBNumber:
CB0352930
Molecular Formula:
C6H12Br2OZn3
Molecular Weight:
456.11
MOL File:
41114-59-4.mol
Modify Date:
2022/8/15 17:40:01

Nysted Reagent Properties

Density 1.186 g/mL at 25 °C(lit.)
Flash point −15 °F
InChIKey CCTHTLJWXPUNGT-UHFFFAOYSA-L
CAS DataBase Reference 41114-59-4

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS02,GHS07,GHS08
Signal word  Danger
Hazard statements  H225-H319-H335-H336-H351
Precautionary statements  P201-P202-P210-P233-P305+P351+P338-P308+P313
Hazard Codes  F,Xn
Risk 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

Nysted Reagent price More Price(2)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) 381985 Nysted Reagent 20?wt. % suspension in THF 41114-59-4 100G ₹7285.23 2022-06-14 Buy
Sigma-Aldrich(India) 381985 Nysted Reagent 20?wt. % suspension in THF 41114-59-4 1KG ₹68403.18 2022-06-14 Buy
Product number Packaging Price Buy
381985 100G ₹7285.23 Buy
381985 1KG ₹68403.18 Buy

Nysted Reagent Chemical Properties,Uses,Production

Chemical Properties

The Nysted reagent is a reagent used in organic synthesis for the methenylation of a carbonyl group. It was discovered in 1975 by Leonard N. Nysted in Chicago, Illinois. It was originally prepared by reacting dibromomethane and activated zinc in THF.
A similar reagent is Tebbe's reagent.In the Nysted olefination, the Nysted reagent reacts with TiCl to methylenate a carbonyl group. The biggest problem with these reagents are that the reactivity has not been well documented. It is believed that the TiCl acts as a mediator in the reaction. Nysted reagent can methylenate different carbonyl groups in the presence of different mediators. For example, in the presence of BF•OEt, the reagent will methylenate aldehydes. On the other hand, in the presence of TiCl, TiCl or TiCl and BF•OEt, the reagent can methylenate ketones. Most commonly, it is used to methylenate ketones because of their general difficulty to methylenate due to crowding around the carbonyl group. The Nysted reagent is able to overcome the additional steric hinderance found in ketones, and more easily methylenate the carbonyl group.
There is little research on Nysted reagent because of the hazards and high reactivity and the difficulty of keeping the reagent stable while it is in use. More specifically, it can form explosive peroxides when exposed to air and is extremely flammable. Also, it reacts violently with water. These make this reagent very dangerous to work with.

Uses

The cyclo-dibromo-di-m-methylene-(m-tetrahydrofuran)-trizinc is known as the Nysted reagent. This reagent is prepared by treatment of dibromomethane with activated zinc-lead couple or hydrogen chloride-activated zinc dust in THF. This reagent is useful for converting a carbonyl group into a methylene group, and such transformation is known as the Nysted methylenation or Nysted olefination. The study finds that this reagent is superior to the Tebbe reagent.

Application

Useful reagent for the methylenation of ketones and α-ketols.
Reactant for:
Synthesis of amphidinolide T3 using a ring-closing metathesis and asymmetric dihydroxylation strategy
Methylenation of carbonyl compounds
Olefination reactions

Reactions

Reactions of 41114-59-4
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.

Nysted Reagent Preparation Products And Raw materials

Raw materials

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Preparation Products

Nysted Reagent Suppliers

Global( 110)Suppliers
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CLEARSYNTH LABS LTD. +91-22-45045900 Hyderabad, India 6351 58 Inquiry
Capot Chemical Co.,Ltd. 571-85586718 +8613336195806 China 29798 60 Inquiry
career henan chemical co +86-0371-86658258 +8613203830695 China 29901 58 Inquiry
Chongqing Chemdad Co., Ltd +86-023-6139-8061 +86-86-13650506873 China 39916 58 Inquiry
SIMAGCHEM CORP +86-13806087780 China 17367 58 Inquiry
Hefei TNJ Chemical Industry Co.,Ltd. 0551-65418671 China 34571 58 Inquiry
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Shaanxi Dideu Medichem Co. Ltd +86-029-89586680 +86-18192503167 China 9030 58 Inquiry
AFINE CHEMICALS LIMITED +86-0571-85134551 China 15395 58 Inquiry
ZHEJIANG JIUZHOU CHEM CO., LTD +86-0576225566889 +86-13454675544 China 19947 58 Inquiry
Nysted Reagent,cyclo-Dibromodi-μ-methylene[μ-(tetrahydrofuran)]trizinc Nysted Reagent, 20% w/w suspension in THF Nysted reagent (20% wet suspension in THF) Nysted Reagent 20 wt. % suspension in THF Nysted Reagent, 20% solution in THF, SpcSeal Nystead reagent bis(bromozinciomethyl)zinc (20% tetrahydrofuran solution) Nysted reagent 20% THF Nysted(20% in THF) NYSTED REAGENT nysted NYSTED REAGENT, 20 WT. % SUSPENSION IN T ETRAHYDROFURAN cyclo-dibromodi-μ-methylene[μ-(tetrahydrofuran)]trizinc CYCLO-DIBROMODI-MU-METHYLENE[MU-(TETRAHYDROFURAN)TRIZINC] Nysted Reag Nysted Reagent ISO 9001:2015 REACH Zinc, dibromodi-μ-methylene[μ-(tetrahydrofuran)]tri-, cyclo (9CI, ACI) NystedReagen 41114-59-4 C4H8OC2H4Br2Zn3 C6H12Br2OZn3 C-C Bond Formation Others Olefination Synthetic Reagents API intermediates