(1E,3Z)-1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene
(1E,3Z)-1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene (CAS: 72486-93-2) is an organosilicon compound with the molecular formula C10H20O2Si and a molecular weight of 200.35 g/mol. This enol ether, often referred to as Danishefsky's diene, serves as a valuable building block in organic synthesis. It is primarily utilised in Diels-Alder reactions and related cycloadditions for the construction of complex molecular architectures, particularly in the synthesis of pharmaceutical intermediates and natural product analogues.
- IUPAC
- (1E,3Z)-1-Methoxy-2-methyl-3-[(trimethylsilyl)oxy]-penta-1,3-diene,[(1-(2-Methoxy-1-methylvinyl)propenyloxy]trimethylsilan
- Synonyms
- 72486-93-2C10H20O2Si(1E,3Z)-1-Methoxy-2-methyl-3-[(trimethylsilyl)oxy]-penta-1,3-diene[(1-(2-Methoxy-1-methylvinyl)propenyloxy]trimethylsilan
Synthesis of Migrastatin Analogues
This compound is employed in the preparation of migrastatin analogues, which are investigated as potential cell migration inhibitors for the treatment of tumour metastasis.
Aza-Diels-Alder Reactions
It acts as a reactant in chlorosilane-promoted aza-Diels-Alder additions for the synthesis of dihydropyridinones.
Stereoselective Cycloadditions
Used in stereoselective Lewis acid-catalyzed aza-Diels-Alder cycloadditions with conjugated dienes for the synthesis of non-proteinogenic amino esters.
| Molecular weight | 200.35 |
|---|---|
| Empirical formula | C10H20O2Si |
| Boiling point | 65 °C/6 mmHg(lit.) |
| Density | 0.899 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.4650(lit.) |
| Storage temperature | 2-8°C |
| Application | Danishefsky diene1 used as a reactant for:Preparation of migrastatin analog as cell migration inhibitor for treatment of tumor metastasis2Preparation of dihydropyridinones by chlorosilane-promoted aza-Diels-Alder addition3Synthesis on non-proteinogenic amino esters via stereoselective Lewis acid-catalyzed aza-Diels-Alder cycloaddition with conjugated (cyclo)dienes4 |
Hazard statements
- H302Harmful if swallowed
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 81 °C / 177.8 °F |
| Transport (UN / ADR) | NA 1993 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xn |
| Risk statements (R) | 22 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is (1E,3Z)-1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene used for?
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(1E,3Z)-1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene is primarily used as a reactant in organic synthesis, particularly in Diels-Alder and aza-Diels-Alder reactions for preparing complex molecules, including pharmaceutical intermediates and analogues.
What are the CAS number and molecular formula for this compound?
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The CAS number is 72486-93-2 and the molecular formula is C10H20O2Si.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical typically at a research or technical grade. We do not represent this product as meeting USP, BP, or EP pharmacopoeial standards unless explicitly stated otherwise.
How should (1E,3Z)-1-Methoxy-2-methyl-3-(trimethylsilyloxy)-1,3-pentadiene be handled safely?
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This compound is classified as harmful if swallowed (H302) and requires appropriate personal protective equipment, including eyeshields, gloves, and a suitable respirator. Handle in a well-ventilated area and store at 2-8°C.
Is this chemical shipped internationally?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including this product, and can arrange international shipments.
How can I request a quote or sample?
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To request a quote or a sample, please visit the Tech Serve Solutions website or contact our sales department directly with your inquiry.
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