143-14-6

Basic information

• Product Name: 10-UNDECENAL
• Synonyms: 9-UNDECENAL;ALDEHYDE C11 ENIC/UNDECYLENIC ALDEHYDE;ALDEHYDE C-11 UNDECYLENIC;N-UNDECYLENIC ALDEHYDE;UNDECYLIC ALDEHYDE;UNDECENAL-10;undec-9-enal;9-Hendecenaldehyde
• CAS NO: 143-14-6
• Molecular Formula: C₁₁H₂₀O
• Molecular Weight: 168.28
• EINECS: 203-973-1
• Mol File: 143-14-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 7 °C
• Boiling Point: 98-100 °C3 mm Hg(lit.)
• Flash Point: 199 °F
• Appearance: /
• Density: 0.84 g/mL at 25 °C(lit.)
• Vapor Density: >1 (vs air)
• Vapor Pressure: 0.0333mmHg at 25°C
• Refractive Index: n20/D 1.4427(lit.)
• CAS DataBase Reference: 10-UNDECENAL(CAS DataBase Reference)
• NIST Chemistry Reference: 10-UNDECENAL(143-14-6)
• EPA Substance Registry System: 10-UNDECENAL(143-14-6)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37/39-26
• WGK Germany: 2
• RTECS: YQ2835000
• Hazardous Substances Data: 143-14-6(Hazardous Substances Data)

Usage

Chemical Properties

9-Undecenal has an orange peel-like, sweet odor with a sweet, citrus flavor.

InChI:InChI=1/C11H20O/c1-2-3-4-5-6-7-8-9-10-11-12/h2-3,11H,4-10H2,1H3/b3-2+

Upstream product

• 112-45-8 10-Undecenal 
• 201230-82-2 carbon monoxide 
• 35345-72-3 11-hydroxyundecan-2-one 

Relevant articles and documents

Rhodium versus iridium catalysts in the controlled tandem hydroformylation-isomerization of functionalized unsaturated fatty substrates

The hydroformylation of 10-undecenitrile (1) and related unsaturated fatty substrates (H2C=CH(CH2)7CH2R; R=CO2Me, CH2Br, CHO) has been studied with rhodium, iridium, ruthenium, and palladium biphephos catalysts. The reactions proceeded effectively with all four systems, with high selectivities for the linear aldehyde (ratio of linear/branched aldehydes=99:1). The biphephos-bis[chloro(cyclooctadiene)iridium] system showed a non-optimized hydroformylation turnover frequency (TOFHF) of 770h-1 that was only approximately 5times lower than that of the rhodium-based system (TOFHF=3320h-1); the palladium and ruthenium biphephos systems were less active (TOFHF=210 and 310h-1, respectively). Upon recycling, remarkable productivities were achieved in both cases (TON≈58-000mol(1/1-int)-mol(Ir)-1 and 250-000mol(1/1-int)-mol(Rh)-1, in which int=internal olefin). Competitive isomerization of terminal to internal olefins occurred with these catalysts. Iridium biphephos systems allowed slightly better control of the distribution of the internal isomers than the rhodium biphephos catalyst, with higher ratios of 9-/8-undecenitrile (1-int). Place your bets now: Iridium-biphephos catalysts are highly effective in the controlled tandem isomerization-hydroformylation of 10-undecenitrile and related functionalized unsaturated fatty substrates.