166432-52-6

Basic information

• Product Name: (3E)-undeca-1,3-dien-5-yne
• Synonyms: (3E)-undeca-1,3-dien-5-yne;1,3-Undecadien-5-yne;violettyne mip
• CAS NO: 166432-52-6
• Molecular Formula: C11H16
• Molecular Weight: 148.2447
• EINECS: 417-840-2
• Mol File: 166432-52-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 217°Cat760mmHg
• Flash Point: 75.5°C
• Appearance: /
• Density: 0.813g/cm³
• Vapor Pressure: 0.2mmHg at 25°C
• Refractive Index: 1.469
• CAS DataBase Reference: (3E)-undeca-1,3-dien-5-yne(CAS DataBase Reference)
• NIST Chemistry Reference: (3E)-undeca-1,3-dien-5-yne(166432-52-6)
• EPA Substance Registry System: (3E)-undeca-1,3-dien-5-yne(166432-52-6)

Safety Data

• Hazardous Substances Data: 166432-52-6(Hazardous Substances Data)

Usage

Chemical Properties

1,3-Undecadien-5-yne is a colorless liquid with a nice fruity, green, strong violet-leaf note. It is recommended as an alternative to methyl octynoate and methyl nonynoate.

Synthesis Reference(s)

Synthetic Communications, 24, p. 2273, 1994 DOI: 10.1080/00397919408019052

Trade name

Violettyne MIP (Firmenich).

InChI:InChI=1/C11H16/c1-3-5-7-9-11-10-8-6-4-2/h3,5,7H,1,4,6,8,10H2,2H3/b7-5+

Upstream product

• 628-71-7 1-Heptyne 
• 16503-25-6 1-chloro-1E,3-butadiene 
• 10033-99-5 (1Z)-1-chloro-1,3-butadiene 
• 64146-57-2 1-heptynylzinc chloride 
• 3536-96-7 vinylmagnesium chloride 
• 77973-37-6 (E)-1-chloro-non-1-en-3-yne 
• 1846-68-0 oct-2-ynal 
• 53915-69-8 allenyltributylstannane 
• 13361-64-3 trimethyl(propargyl)silane 
• 78651-47-5 (E)-dec-2-en-4-yn-1-al 
• 19493-09-5 Methylenetriphenylphosphorane 
• 78389-90-9 vinyl zinc chloride 
• 107646-61-7 (E)-1-bromo-3-nonyn-1-ene 
• 66426-94-6 diethyl-undec-2-en-4-ynyl-amine 

Downstream Products

• 85615-64-1 undecatriene-2Z,4Z,6E 

Relevant articles and documents

Stereospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae

Giffordene (=(2Z,4Z,6E,8Z)-2,4,6,8-undecatetraene; 9f) and five stereoisomers are new C11H16 hydrocarbons from the marine brown alga Giffordia mitchellae.Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)-pairs.The uniform enynes (>98percent purity) are then stereospecifically reduced to (Z)-alkenes with Zn(Cu/Ag) in aq.MeOH at r.t. 13C- and 1H-NMR data of the new tetraenes are presented.Biosynthetically, giffordene (9f) originates from dodeca-3,6,9-trienoic acid via an unstable (3Z,5Z,8Z)-1,3,5,8-undecatetraene followed by a thermally allowed antarafacial 1,7-sigmatropic hydrogen shift to the (2Z,4Z,6E,8Z)-isomer 9f.

PROCESS FOR PREPARING DIENE

The present invention relates to the field of organic synthesis and more specifically it concerns a process for preparing compound of formula (I) catalyzed by a nickel complex. The compound of formula (II) is also part of the invention.

An efficient synthesis of stereodefined enynes and dienes via Pd-catalyzed reaction of chloroenynes and chlorodienes with Grignard reagents

In the presence of PdCl2(PPh3)2 and Et3N, chloroenynes and chlorodienes react rapidly under mild conditions with various Grignard reagents to give isomerically pure conjugated enynes, dienes, dienynes and triene