3-TRIETHYLSILOXY-1,4-PENTADIENE

3-TRIETHYLSILOXY-1,4-PENTADIENE structure

CAS No.: 62418-65-9

Chemical Name:: 3-TRIETHYLSILOXY-1,4-PENTADIENE

Synonyms: 3-TRIETHYLSILOXY-1,4-PENTADIENE;3-(triethylsilyloxy)-1,4-pentadiene;1,4-Pentadien-3-yloxy-triethylsilane;Silane, [(1-ethenyl-2-propen-1-yl)oxy]triethyl-

CBNumber:: CB8497811

Molecular Formula:: C11H22OSi

Molecular Weight:: 198.38

MDL Number:: MFCD00043055

MOL File:: 62418-65-9.mol

Last updated:2023-05-04 15:15:24

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3-TRIETHYLSILOXY-1,4-PENTADIENE Properties

Boiling point	74-75 °C/14 mmHg
refractive index	n20/D 1.439
Flash point	58 °C
storage temp.	2-8°C
solubility	sol pentane, benzene, THF, ether, CH2Cl2.

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS02
Signal word	Warning
Hazard statements	H226
Safety Statements	23-24/25
RIDADR	1993
HazardClass	3.2
PackingGroup	III

3-TRIETHYLSILOXY-1,4-PENTADIENE Chemical Properties,Uses,Production

Physical properties

bp 140°C; n20D 1.4390.

Uses

3-Triethylsilyloxy-1,4-pentadiene is used as a masked vinyl ketone synthon; a precursor for either the diene or dienophile in the intramolecular Diels–Alder reaction.) It may be used to prepare the useful 3-triethylsilyloxypentadienyl anion via metalation with sec-butyllithium (eq 1).
A wide variety of electrophiles may be used and the selectivity is based on kinetics.The method has been used to prepare intermediates for intramolecular Diels–Alder reactions (eqs 4 and 5).

Preparation

3-Triethylsilyloxy-1,4-pentadiene is by silylation of 3-hydroxy-1,4-pentadiene with chlorotriethylsilane.1,2 Other relatives of the title compound are available by silylation with chlorotrimethylsilane2 or t-butyldimethylchlorosilane3 3-Trimethylsilyloxy- 1,4-pentadiene is usually prepared and used in situ. Storage of 3-trimethylsilyl-1,4-pentadiene at ?30°C is recommended. The dianion of the parent 3-hydroxy-1,4-pentadiene can also be prepared.

Purification Methods

Dissolve it in pentane, wash this with H2O, dry (Na2SO4), evaporate, and distil it under vacuum. RF values on Kieselgel 60 are 0.15 (pentane) and 0.60 (*C6H6). [IR, NMR, MS: Oppolzer et al. Helv Chim Acta 64 2002 1981.]

3-TRIETHYLSILOXY-1,4-PENTADIENE Preparation Products And Raw materials

Raw materials

Preparation Products

3-TRIETHYLSILOXY-1,4-PENTADIENE Suppliers

Global( 2)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Riedel-de Haen AG	--		United States	6825	87
SIGMA-RBI	--		Switzerland	6913	91

Supplier	Advantage
Riedel-de Haen AG	87
SIGMA-RBI	91

62418-65-9(3-TRIETHYLSILOXY-1,4-PENTADIENE)Related Search:

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3-TRIETHYLSILOXY-1,4-PENTADIENE 3-(triethylsilyloxy)-1,4-pentadiene 1,4-Pentadien-3-yloxy-triethylsilane Silane, [(1-ethenyl-2-propen-1-yl)oxy]triethyl- 62418-65-9