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212830 Aldrich

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

95%

Synonym: Danishefsky’s diene

  • CAS Number 54125-02-9

  • Linear Formula (CH3)3SiOC(=CH2)CH=CHOCH3

  • Molecular Weight 172.30

  •  Beilstein Registry Number 1616761

  •  MDL number MFCD00008498

  •  PubChem Substance ID 24852745

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Properties

Related Categories Building Blocks, Chemical Synthesis, Enol Ethers, Organic Building Blocks, Oxygen Compounds More...
InChI Key   SHALBPKEGDBVKK-VOTSOKGWSA-N
assay   95%
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.)
storage temp.   2-8°C

Description

Packaging

1, 5 g in ampule

Application

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene was used:
• in the synthesis of sulfone analogues of griseofulvin (sulfogriseofulvins), 4H-1-aminopyrroles and 4,5H-pyrazoles
• as Diels-Alder diene for the synthesis of pyridones and pyranones
• as reagent employed in the Mannich-Michael reaction for preparation of piperidinones and enaminones

General description

trans-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.

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Warning
Hazard statements 
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
3
Flash Point(F) 
138.2 °F
Flash Point(C) 
59 °C

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Protocols & Articles

Articles

Reagents for C–C Bond Formation

Aldrich carries a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

Peer-Reviewed Papers
15

References

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94791 SnapIT Ampule Opener, Regular, for 1-2ml, 5-10ml, 10-15ml ampoules
43917 SnapIT Ampule Opener, large, for 5-10ml, 10-15ml, 20-25ml ampoules
08168 Timestrip Plus 8 °C

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