212830

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

95%

• Synonym(s): Danishefsky’s diene
• Linear Formula: (CH₃)₃SiOC(=CH₂)CH=CHOCH₃
• CAS Number: 54125-02-9
• Molecular Weight: 172.30
• Beilstein/REAXYS Number: 1616761
• MDL number: MFCD00008498
• UNSPSC Code: 12352100
• PubChem Substance ID: 24852745
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 95%
• form: liquid
• impurities: 2-5% 4-methoxy-3-buten-2-one
• refractive index: n20/D 1.454 (lit.)
• bp: 68-69 °C/14 mmHg (lit.)
• density: 0.885 g/mL at 25 °C (lit.)
• functional group: ether
• storage temp.: 2-8°C
• SMILES string: CO\C=C\C(=C)O[Si](C)(C)C
• InChI: 1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3/b7-6+
• InChI key: SHALBPKEGDBVKK-VOTSOKGWSA-N

Description

General description

trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene is a funtionalized Diels-Alder diene[1][2]. 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[3]. Asymmetric hetero-Diels-Alder cyclization of Danishefsky′s diene with benzaldehyde catalyzed by mesoporous inorganic/metalorganic hybrid materials has been reported[4].

Application

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene was used:

• in the synthesis of sulfone analogues of griseofulvin (sulfogriseofulvins)[5], 4H-1-aminopyrroles[3] and 4,5H-pyrazoles[3]
• as Diels-Alder diene for the synthesis of pyridones[6] and pyranones[7]
• as reagent employed in the Mannich-Michael reaction for preparation of piperidinones[8] and enaminones[9]

Safety Information

• pictograms: GHS02
• signalword: Warning
• hcodes: H226
• pcodes: P210 - P233 - P240 - P241 - P242 - P243
• Hazard Classifications: Flam. Liq. 3
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 138.2 °F - closed cup
• flash_point_c: 59 °C - closed cup
• ppe: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)