821-95-4

Basic information

• Product Name: 1-UNDECENE
• Synonyms: alpha-nonylethylene;alpha-Undecene;alpha-undecylene;n-1-Undecene;Undec-1-ene;Undecene-1;1-UNDECENE;TIMTEC-BB SBB009051
• CAS NO: 821-95-4
• Molecular Formula: C₁₁H₂₂
• Molecular Weight: 154.29
• EINECS: 212-483-7
• Product Categories: 1-Olefins (GC Standard);Analytical Chemistry;Standard Materials for GC;OlefinsVolatiles/ Semivolatiles;T-ZAnalytical Standards;Alpha Sort;Alphabetic;Chemical Class;Hydrocarbons;NeatsGasoline, Diesel,&Petroleum;Substance classes;U;Acyclic;Alkenes;Organic Building Blocks
• Mol File: 821-95-4.mol

Chemical Properties

• Melting Point: −49 °C(lit.)
• Boiling Point: 192-193 °C(lit.)
• Flash Point: 145 °F
• Appearance: /
• Density: 0.75 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.426(lit.)
• Water Solubility: Solunle in ether, chloroform and ligroin. Insoluble in water.
• BRN: 1740044
• CAS DataBase Reference: 1-UNDECENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-UNDECENE(821-95-4)
• EPA Substance Registry System: 1-UNDECENE(821-95-4)

Safety Data

• Hazard Codes: Xn,F
• Statements: 20/22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 821-95-4(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
1-Undecene is used as a pharmaceutical intermediate for the synthesis of various drugs and pharmaceutical compounds. Its unique chemical structure allows it to be easily modified and incorporated into complex molecules, making it a valuable building block in the development of new medications.
2. Used in Organic Synthesis:
1-Undecene is used as a reagent in organic synthesis for the preparation of various organic compounds. Its alkene functional group can participate in a wide range of chemical reactions, such as addition, oxidation, and reduction, enabling the formation of diverse chemical products.
3. Used in Pd-Catalyzed Aerobic Oxidative Amination Reaction:
1-Undecene is used as a reactant in the Pd-catalyzed aerobic oxidative amination reaction with nitrogen nucleophiles. This reaction allows for the production of useful amine analogs, which are important building blocks in the synthesis of various pharmaceuticals and organic compounds.
4. Used in the Total Synthesis of (+)-Deoxoprosopinine:
1-Undecene serves as a key intermediate in the total synthesis of (+)-deoxoprosopinine, a naturally occurring alkaloid with potential biological activities. Its involvement in this synthesis highlights its utility in the preparation of complex organic molecules with potential applications in medicine and other fields.

Synthesis Reference(s)

Chemistry Letters, 7, p. 1155, 1978The Journal of Organic Chemistry, 47, p. 876, 1982 DOI: 10.1021/jo00344a024Tetrahedron, 49, p. 7104, 1993 DOI: 10.1016/S0040-4020(01)87982-5

Health Hazard

Recommended Personal Protective Equipment: Goggles or face shield; rubber gloves; Symptoms Following Exposure: Aspiration hazard if ingested. Slight skin and eye irritation. No inhalation hazard expected; General Treatment for Exposure: INHALATION: remove victim to fresh air. INGESTION: do NOT lavage or induce vomiting; give vegetable oil and demulcents; call a doctor. EYES: flush with water for 15 min. SKIN: wipe off, wash with soap and water; Toxicity by Inhalation (Threshold Limit Value): Data not available; Short-Term Exposure Limits: Data not available; Toxicity by Ingestion: Data not available; Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: Slight smarting of eyes and respiratory system at high concentrations. The effect is temporary; Liquid or Solid Irritant Characteristics: Minimum hazard. If spilled on clothing and allowed to remain, may cause smarting and reddening of the skin; Odor Threshold: Data not available.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: No reactions; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

InChI:InChI=1/C11H22/c1-3-5-7-9-11-10-8-6-4-2/h3H,1,4-11H2,2H3

Upstream product

• 67-56-1 methanol 
• 10124-65-9 potassium laurate 
• 64-17-5 ethanol 
• 2473-03-2 1-chloroundecane 
• 112-46-9 9-undecenol 
• 17049-49-9 octylmagnesium bromide 
• 106-95-6 allyl bromide 
• 67-64-1 acetone 
• 107-05-1 3-chloroprop-1-ene 
• 592-76-7 1-Heptene 
• 143-07-7 lauric acid 
• 112-16-3 n-dodecanoyl chloride 
• 112-31-2 caprinaldehyde 
• 2065-66-9 methyl-triphenylphosphonium iodide 

Downstream Products

• 76964-70-0 dimethyl undecylphosphonate 
• 693-67-4 bromoundecane 
• 1120-21-4 n-Undecane 
• 39563-54-7 2-bromo-n-undecane 
• 116296-31-2 2-(undecylthio)acetic acid 
• 4536-88-3 α-methyldecylbenzene 
• 66022-14-8 2-undecylcyclohexanone 
• 3007-53-2 N,N-dimethyldodecanamide 
• 111-82-0 methyl n-dodecanoate 
• 55955-69-6 2-methylundecanoic acid methyl ester 
• 50-00-0 formaldehyd 
• 112-31-2 caprinaldehyde 
• 17322-97-3 1,2-epoxyundecane 
• 177698-19-0 Beta-pinene 

Relevant articles and documents

Oxidative Decarboxylase UndA Utilizes a Dinuclear Iron Cofactor

UndA is a nonheme iron enzyme that activates oxygen to catalyze the decarboxylation of dodecanoic acid to undecene and carbon dioxide. We report the first optical and M?ssbauer spectroscopic characterization of UndA, revealing that the enzyme harbors a coupled dinuclear iron cluster. Single turnover studies confirm that the reaction of the diferrous enzyme with dioxygen produces stoichiometric product per cluster. UndA is the first characterized example of a diiron decarboxylase, thus expanding the repertoire of reactions catalyzed by dinuclear iron enzymes.

Preparation of Primary and Secondary Dialkylmagnesiums by a Radical I/Mg-Exchange Reaction Using sBu2Mg in Toluene

The treatment of primary or secondary alkyl iodides with sBu2Mg in toluene (25–40 °C, 2–4 h) provided dialkylmagnesiums that underwent various reactions with aldehydes, ketones, acid chlorides or allylic bromides. 3-Substituted secondary cyclohexyl iodides led to all-cis-3-cyclohexylmagnesium reagents under these exchange conditions in a highly stereoconvergent manner. Enantiomerically enriched 3-silyloxy-substituted secondary alkyl iodides gave after an exchange reaction with sBu2Mg stereodefined dialkylmagnesiums that after quenching with various electrophiles furnished various 1,3-stereodefined products including homo-aldol products (99 % dr and 98 % ee). Mechanistic studies confirmed a radical pathway for these new iodine/magnesium-exchange reactions.

Unexpected Reactions of α,β-Unsaturated Fatty Acids Provide Insight into the Mechanisms of CYP152 Peroxygenases

CYP152 peroxygenases catalyze decarboxylation and hydroxylation of fatty acids using H2O2 as cofactor. To understand the molecular basis for the chemo- and regioselectivity of these unique P450 enzymes, we analyze the activities of three CYP152 peroxygenases (OleTJE, P450SPα, P450BSβ) towards cis- and trans-dodecenoic acids as substrate probes. The unexpected 6S-hydroxylation of the trans-isomer and 4R-hydroxylation of the cis-isomer by OleTJE, and molecular docking results suggest that the unprecedented selectivity is due to OleTJE’s preference of C2?C3 cis-configuration. In addition to the common epoxide products, undecanal is the unexpected major product of P450SPα and P450BSβ regardless of the cis/trans-configuration of substrates. The combined H218O2 tracing experiments, MD simulations, and QM/MM calculations unravel an unusual mechanism for Compound I-mediated aldehyde formation in which the active site water derived from H2O2 activation is involved in the generation of a four-membered ring lactone intermediate. These findings provide new insights into the unusual mechanisms of CYP152 peroxygenases.

Piperazine-promoted gold-catalyzed hydrogenation: The influence of capping ligands

Gold nanoparticles (NPs) combined with Lewis bases, such as piperazine, were found to perform selective hydrogenation reactions via the heterolytic cleavage of H2. Since gold nanoparticles can be prepared by many different methodologies and using different capping ligands, in this study, we investigated the influence of capping ligands adsorbed on gold surfaces on the formation of the gold-ligand interface. Citrate (Citr), poly(vinyl alcohol) (PVA), polyvinylpyrrolidone (PVP), and oleylamine (Oley)-stabilized Au NPs were not activated by piperazine for the hydrogenation of alkynes, but the catalytic activity was greatly enhanced after removing the capping ligands from the gold surface by calcination at 400 °C and the subsequent adsorption of piperazine. Therefore, the capping ligand can limit the catalytic activity if not carefully removed, demonstrating the need of a cleaner surface for a ligand-metal cooperative effect in the activation of H2 for selective semihydrogenation of various alkynes under mild reaction conditions.

Normal Alpha Olefin Synthesis Using Dehydroformylation or Dehydroxymethylation

The present invention discloses processes for producing normal alpha olefins, such as 1-hexene, 1-octene, 1-decene, and 1-dodecene in a multistep synthesis scheme from another normal alpha olefin. Also disclosed are reactions for converting aldehydes, primary alcohols, and terminal vicinal diols into normal alpha olefins.

Oxidative Dehydroxymethylation of Alcohols to Produce Olefins

Catalyst compositions for the conversion of aldehyde compounds and primary alcohol compounds to olefins are disclosed herein. Reactions include oxidative dehydroxymethylation processes and oxidative dehydroformylation methods, which are beneficially conducted in the presence of a sacrificial acceptor of H2 gas, such as N,N-dimethylacrylamide.

An Engineered Self-Sufficient Biocatalyst Enables Scalable Production of Linear α-Olefins from Carboxylic Acids

Fusing the decarboxylase OleTJE and the reductase domain of P450BM3 creates a self-sufficient protein, OleT-BM3R, which is able to efficiently catalyze oxidative decarboxylation of carboxylic acids into linear α-olefins (LAOs) under mild aqueous conditions using O2 as the oxidant and NADPH as the electron donor. The compatible electron transfer system installed in the fusion protein not only eliminates the need for auxiliary redox partners, but also results in boosted decarboxylation reactivity and broad substrate scope. Coupled with the phosphite dehydrogenase-based NADPH regeneration system, this enzymatic reaction proceeds with improved product titers of up to 2.51 g L-1 and volumetric productivities of up to 209.2 mg L-1 h-1 at low catalyst loadings (～0.02 mol%). With its stability and scalability, this self-sufficient biocatalyst offers a nature-friendly approach to deliver LAOs.

Chemoselective deoxygenation of ether-substituted alcohols and carbonyl compounds by B(C6F5)3-catalyzed reduction with (HMe2SiCH2)2

B(C6F5)3-catalyzed deoxygenation of ether-substituted alcohols and carbonyl compounds has been developed using (HMe2SiCH2)2 as the reductant. This unique reagent shows distinct superiority over traditional one silicon-centered hydrosilanes, giving the corresponding alkanes in high yields with good tolerance of ethers, aryl halides and alkenes. The control experiments suggest that (HMe2SiCH2)2 might facilitate the approach in an intramolecular Si/O activation manner.

Tandem Catalysis: Transforming Alcohols to Alkenes by Oxidative Dehydroxymethylation

We report a Rh-catalyst for accessing olefins from primary alcohols by a C-C bond cleavage that results in dehomologation. This functional group interconversion proceeds by an oxidation-dehydroformylation enabled by N,N-dimethylacrylamide as a sacrificial acceptor of hydrogen gas. Alcohols with diverse functionality and structure undergo oxidative dehydroxymethylation to access the corresponding olefins. Our catalyst protocol enables a two-step semisynthesis of (+)-yohimbenone and dehomologation of feedstock olefins.

A durable nanocatalyst of potassium-doped iron-carbide/alumina for significant production of linear alpha olefins via Fischer-Tropsch synthesis

Improvement of activity, selectivity, and stability of the catalyst used in Fischer-Tropsch synthesis (FTS) to produce targeted hydrocarbon products has been a major challenge. In this work, the potassium-doped iron-carbide/alumina (K-Fe5C2/Al2O3), as a durable nanocatalyst containing small iron-carbide particles (～ 10 nm), was applied to high-temperature Fischer-Tropsch synthesis (HT-FTS) to optimize the production of linear alpha olefins. The catalyst, suitable under high space velocity reaction conditions (14–36 N L gcat?1 h?1) based on the well-dispersed potassium as an efficient base promoter on the active iron-carbide surface, shows very high CO conversion (up to ～90%) with extremely high activity (1.41 mmolCO gFe?1 s?1) and selectivity for C5–C13 linear alpha olefins.