Basic information
- CAS
54125-02-9- Standard SMILES
C=C(/C=C/OC)O[Si](C)(C)C- InChIKey
SHALBPKEGDBVKK-VOTSOKGWSA-N- Molecular formula
- C8H16O2Si
- Average molar mass
- 172.3 g/mol
- Monoisotopic mass
- 172.09195628
Names & identifiers
- Preferred name
- trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene
- IUPAC
- [(3E)-4-methoxybuta-1,3-dien-2-yl]oxy-trimethylsilane
- English name
- 1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE
- Molecular formula
- C8H16O2Si
- Molecular weight
- 172.3
Names & synonyms
Silane, [[(2E)-3-methoxy-1-methylene-2-propenyl]oxy]trimethyl-[[(2E)-3-Methoxy-1-methylene-2-propen-1-yl]oxy]trimethylsilane(((2E)-3-Methoxy-1-methylene-2-propen-1-yl)oxy)trimethylsilaneSilane, (((2E)-3-methoxy-1-methylene-2-propenyl)oxy)trimethyl-RefChem:898715trans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene54125-02-91-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE(E)-((4-methoxybuta-1,3-dien-2-yl)oxy)trimethylsilaneDanishefsky's diene59414-23-2MFCD00008498
Show more names
DK814DKSI071Danishefsky-Kitahara diene.1-METHOXY-3-(TRIMETHYLSILOXY)BUTADIENETRANS-1-METHOXY-3-TRIMETHYLSILOXY- &1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE1-Methoxy-3-trimethylsiloxy-1,3-butadiene ,95%1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE, 98+%
(E)-1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene(E)-(4-Methoxybuta-1,3-dien-2-yloxy)trimethylsilaneUNII-1ZOR63U51OTRANS-1-METHOXY-3-(TRIMETHYLSILOXY)-1,3-BUTADIENE1ZOR63U51O[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy-trimethylsilane(E)-1-Methoxy-3-trimethylsiloxy-1,3-butadiene1-Methoxy-3-(trimethylsilyloxy)-1,3-butadiene, (E)-
Properties
Computed structural properties
- Topological polar surface area
- 18.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 156
Physicochemical properties
- Boiling point
- 68 · 68-69 °C/14 mmHg (lit.)
- Density
- 0.885 g/mL · 0.885 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.454(lit.)
- Flash point
- 113 °F · 113 °F
- storage temp.
- 2 · 2-8°C
- form
- liquid
- Specific Gravity
- 0.89 · 0.89
- Appearance
- Colorless to light yellow Liquid
- Water Solubility
- Miscible with most organic solvents. Immiscible with water.
- Hydrolytic Sensitivity
- 8 · 8: reacts rapidly with moisture, water, protic solvents
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,6001
- BRN
- 1616761 · 1616761
- InChI
- 1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3/b7-6+
- InChIKey
- SHALBPKEGDBVKK-VOTSOKGWSA-N
- SMILES
- CO\C=C\C(=C)O[Si](C)(C)C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Informationtrans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene: Does not have an individual approval but may be used under an appropriate group standard
Regulatory information
Regulatory Informationtrans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
- wgk
- 3
- tsca
- No
- ridadr
- UN 1993 3/PG 3
- hs_code
- 2931900090
- risk_code
- 10
- Signal word
- Warning
- Symbol(GHS)
- GHS02
- safety_code
- 23-24/25
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H226
- Hazard Classifications
- Flam. Liq. 3
- Precautionary statements
- P210-P233-P240-P241-P242-P243
Chemistry & industry
Applications
Uses1-Methoxy-3-trimethylsiloxy-1,3-butadiene is employed as a reagent in Mannich-Michael reaction for the synthesis of piperidinones and enaminones. As Diels-Alder diene, it is used in the synthesis of pyridones and pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins) and 4H-1-aminopyrroles and 4, 5H-pyrazoles.
General Descriptiontrans-1-methoxy-3-trimethylsiloxy-1,3-butadiene is a funtionalized Diels-Alder diene. Mukaiyama-Michael-type addition/heterocyclization of trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky′s diene) with 1,2-diaza-1,3-butadiene has been investigated. Asymmetric hetero-Diels-Alder cyclization of Danishefsky′s diene with benzaldehyde catalyzed by mesoporous inorganic/metalorganic hybrid materials has been reported.
Upstream & downstream products
Upstream raw materials
Related reactions
17 records
Compound notes
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