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1-Methoxy-3-trimethylsiloxy-1,3-butadiene

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1-Methoxy-3-trimethylsiloxy-1,3-butadiene Basic information
Product Name:1-Methoxy-3-trimethylsiloxy-1,3-butadiene
Synonyms:TRANS-1-METHOXY-3-TRIMETHYLSILOXY-1,3-BUTADIENE;TRANS-1-METHOXY-3-(TRIMETHYLSILYLOXY)-1,3-BUTADIENE;DANISHEFSKY'S DIENE;1-METHOXY-3-(TRIMETHYLSILOXY)BUTADIENE;1-METHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE;TRANS-1-METHOXY-3-TRIMETHYLSILOXY- &;1-Methoxy-3-(trimethylsiloxy)butadiene(Danishefsky`sDiene);Silane, (2E)-3-methoxy-1-methylene-2-propenyloxytrimethyl-
CAS:54125-02-9
MF:C8H16O2Si
MW:172.3
EINECS:629-035-5
Product Categories:
Mol File:54125-02-9.mol
1-Methoxy-3-trimethylsiloxy-1,3-butadiene Structure
1-Methoxy-3-trimethylsiloxy-1,3-butadiene Chemical Properties
Boiling point 68-69 °C/14 mmHg (lit.)
density 0.885 g/mL at 25 °C (lit.)
refractive index n20/D 1.454(lit.)
Fp 113 °F
storage temp. 2-8°C
form liquid
Specific Gravity0.89
AppearanceColorless to light yellow Liquid
Water Solubility Miscible with most organic solvents. Immiscible with water.
Hydrolytic Sensitivity8: reacts rapidly with moisture, water, protic solvents
Sensitive Moisture Sensitive
Merck 14,6001
BRN 1616761
InChI1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3/b7-6+
InChIKeySHALBPKEGDBVKK-VOTSOKGWSA-N
SMILESCO\C=C\C(=C)O[Si](C)(C)C
CAS DataBase Reference54125-02-9(CAS DataBase Reference)
Safety Information
Risk Statements 10
Safety Statements 23-24/25
RIDADR UN 1993 3/PG 3
WGK Germany 3
10-21
TSCA No
HazardClass 3
PackingGroup III
HS Code 2931900090
Storage Class3 - Flammable liquids
Hazard ClassificationsFlam. Liq. 3
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
1-Methoxy-3-trimethylsiloxy-1,3-butadiene Usage And Synthesis
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.
Purification MethodsIt may contain up to 1% of the precursor 4-methoxybut-4-ene-2-one. It is easily purified by distilling through a Vigreux column (p 11) in a vacuum and taking the middle fraction. [Danishefsky & Kitihara J Am Chem Soc 96 7807 1974, Danishefsky Acc Chem Res 14 400 1981.]
Tag:1-Methoxy-3-trimethylsiloxy-1,3-butadiene(54125-02-9) Related Product Information
Triethoxysilane Octamethylcyclotetrasiloxane Vinyltrimethoxysilane 2-(Trimethylsiloxy)-1,3-butadiene ISOPROPENYLOXYTRIMETHYLSILANE 1-METHOXY-1,3-BUTADIENE Ethoxytrimethylsilane 1-Methoxy-3-trimethylsiloxy-1,3-butadiene 1-Methoxy-3-trimethylsiloxy-1,3-butadiene Dimethylethoxysilane Allyloxytrimethylsilane Methoxytrimethylsilane Vinyloxytrimethylsilane (E,Z)-1-Methoxy-2-methyl-3- (trimethylsilyloxy)-1,3-pentadiene DIMETHYLMETHOXYSILANE Silane, methoxy- TRANS-3-(TERT-BUTYLDIMETHYLSILYLOXY)-1-METHOXY-1,3-BUTADIENE (1Z)-1-(Benzyloxy)-3-methoxy-1-(trimethylsiloxy)-1,3-butadiene