173602-43-2

Basic information

• Product Name: methyl (E)-10-cyano-9-decenoate
• Synonyms: methyl (E)-10-cyano-9-decenoate
• CAS NO: 173602-43-2
• Molecular Weight: 209.288
• Mol File: 173602-43-2.mol

Chemical Properties

• CAS DataBase Reference: methyl (E)-10-cyano-9-decenoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (E)-10-cyano-9-decenoate(173602-43-2)
• EPA Substance Registry System: methyl (E)-10-cyano-9-decenoate(173602-43-2)

Safety Data

• Hazardous Substances Data: 173602-43-2(Hazardous Substances Data)

Upstream product

• 112-62-9 Methyl oleate 
• 107-13-1 acrylonitrile 
• 13481-97-5 dimethyl 9-octadecen-1,18-dioate 
• 4494-16-0 1,18-octadec-9-enedioic acid 
• 13481-97-5 dimethyl (Z)-octadec-9-ene-1,18-dioate 

Relevant articles and documents

USE OF RUTHENIUM COMPLEXES IN OLEFIN METATHESIS REACTION

The invention relates to the use of ruthenium complexes, which are homogeneous catalysts and/or precatalysts of the olefin metathesis reaction, which lead to the production of alkenes containing an internal (non-terminal) double C=C bond.

CROSS METATHESIS APPROACH TO C11-C13 FATTY-CHAIN AMINO ESTERS FORM OLEIC ACID DERIVATIVES

A concise method of producing nylon 11, 12, or 13 precursors from oleic acid or an ester of oleic acid is described. The method involves cross-metathesis reactions as the key C-C bond formation step. Subsequent steps are provided to convert the metathesis product to the corresponding nylon precursors. Also provided are the products of the method.

Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: A key step toward long-chain bifunctional and amino acid compounds

The ruthenium catalysed cross-metathesis of fatty-esters arising from plant oils with acrylonitrile is presented. The resulting linear nitrile ester products have potential as new intermediates for polyamides synthesis. A series of commercially available catalysts are able to promote the transformation of methyl 10-undecenoate 1, dimethyl octadec-9-en-1,18-dioate 5 and methyl ricinoleate 9 with acrylonitrile and a protocol based on the slow addition of catalyst allowed TONs as high as 1900 (92% yield) to be reached for cross-metathesis with acrylonitrile. These cross-metathesis conditions have been applied to methyl acrylate and TONs up to 7600 were obtained.

Alkylidene-ruthenium-tin catalysts for the formation of fatty nitriles and esters via cross-metathesis of plant oil derivatives

The reaction of SnCl2 with the Ru-Cl bond of the Grubbs I catalyst RuCl2(=CHPh)(PCy3)2 (1) gives the complex {[Ru(=CHPh)(SnCl3)(PCy3)]2(μ-Cl) 3}-[HPCy3]+ (2), but containing two diethyl ether solvate molecules. The formal insertion of SnCl2 into one Ru-Cl bond of the Hoveyda II catalyst RuCl2(=CH-C 6H4OPri)(H2IMes) (3) (H 2IMes = N,N′-dimesityl-4,5-dihydroimidazol-2-ylidene) results in formation of the new complex RuCl(SnCl3)(=CH-C6H 4OPri)(H2IMes) (4). The X-ray analyses of 2 and 4 show the presence of very short Ru-Sn bonds (2.5834(9) A mean bond for 2 and 2.5925(12) A for 4) and the retention of short Ru=C bonds (1.895(10) and 1.825(8) A, respectively). Complex 4 shows an excellent catalytic activity for the cross-metathesis of plant oil derivatives, the C11 ω-unsaturated ester and aldehyde and the unsaturated C18 diester with acrylonitrile, and a good activity for their cross-metathesis with methyl acrylate. Good to excellent yield of α,ω-bifunctional compounds, precursors of polyesters and polyamides, were obtained. Complex 2 shows catalytic activity for the self-metathesis of C11 ω-unsaturated aldehyde at low concentration to produce C20 α,ω-dialdehyde.