Description

(E,Z)-1-Methoxy-2-Methyl-3-(Trimethylsilyloxy)-1,3-Pentadiene is a versatile silyl enol ether intermediate of significant importance in advanced organic synthesis. Its core value lies in its role as a highly reactive diene component for Diels-Alder cycloadditions and as a protected enolate equivalent for regioselective alkylation and acylation reactions. This compound is essential for research chemists and process development scientists in the pharmaceutical, agrochemical, and fine chemical industries seeking to construct complex molecular architectures with high stereocontrol.

Application

• Diels-Alder Reactions: Serves as a reactive diene for the synthesis of substituted cyclohexene derivatives, a key step in natural product and active pharmaceutical ingredient (API) synthesis.
• Regioselective Alkylation: Acts as a masked enolate for the controlled introduction of alkyl groups at the α-position of carbonyl equivalents.
• Acylation and Aldol Reactions: Used as a nucleophile in reactions with acyl chlorides, anhydrides, and aldehydes to form new carbon-carbon bonds.
• Pharmaceutical Intermediate: A critical building block in the multi-step synthesis of complex drug candidates, particularly those containing six-membered carbocycles.
• Agrochemical Synthesis: Employed in the research and development of novel herbicides, fungicides, and insecticides requiring specific stereochemistry.
• Material Science Precursor: Used in the development of specialty polymers and organic electronic materials where precise molecular structure is crucial.
• Academic & Process R&D: A valuable tool for methodology development and scaling novel synthetic routes in laboratory and pilot plant settings.

Basic Information

Product Name	(E,Z)-1-Methoxy-2-Methyl-3-(Trimethylsilyloxy)-1,3-Pentadiene
CAS No.	72486-93-2
Molecular Formula	C10H20O2Si
Molecular Weight	200.35 g/mol
Synonyms	1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene; (E,Z)-1-Methoxy-2-methyl-3-(trimethylsiloxy)-1,3-pentadiene; 3-(Trimethylsilyloxy)-1-methoxy-2-methyl-1,3-pentadiene; Danishefsky's Diene (related); TMS enol ether of 1-methoxy-2-methyl-1,3-pentadien-3-one; Silyl enol ether of 1-methoxy-2-methyl-1,3-pentadien-3-one
EINECS	Contact for details

Quality Control

Our (E,Z)-1-Methoxy-2-Methyl-3-(Trimethylsilyloxy)-1,3-Pentadiene is produced and handled under strict quality management protocols. Each batch undergoes rigorous analytical testing, including GC, HPLC, and NMR analysis, to ensure identity, purity, and consistency. Certificates of Analysis (COA) detailing all specifications are provided and can be tailored to meet specific customer requirements for research or cGMP applications.

Storage

Preserve in a tightly closed container, protected from light. Store in a cool, dry, and well-ventilated area. Due to its hygroscopic and moisture-sensitive nature, containers should be kept sealed under an inert atmosphere (e.g., nitrogen or argon) after opening. Recommended long-term storage temperature is 2-8°C. Allow the container to reach room temperature before opening to prevent moisture condensation.

Specification

Item	Specification
Appearance	Colorless to pale yellow liquid
Identification (IR)	Conforms to structure
Purity (GC)	≥ 95.0% (E/Z mixture)
Water Content (KF)	≤ 0.5%

Note: Specifications can be tailored. Please contact us for the detailed technical data sheet of a specific grade.