13688-67-0

Basic information

• Product Name: 1,10-UNDECADIENE
• Synonyms: 1,10-undexadiene;undecadiene;1,10-UNDECADIENE;1,10-UNDECADIENE 90+%;Undeca-1,10-diene
• CAS NO: 13688-67-0
• Molecular Formula: C₁₁H₂₀
• Molecular Weight: 152.28
• Mol File: 13688-67-0.mol

Chemical Properties

• Boiling Point: 187 °C
• Flash Point: 55.7°C
• Appearance: /
• Density: 0.77
• Vapor Pressure: 1.05mmHg at 25°C
• Refractive Index: 1.4350 to 1.4380
• CAS DataBase Reference: 1,10-UNDECADIENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,10-UNDECADIENE(13688-67-0)
• EPA Substance Registry System: 1,10-UNDECADIENE(13688-67-0)

Safety Data

• RIDADR: 3295
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13688-67-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Industry:
1,10-Undecadiene is used as a chemical intermediate for the production of polymers, plastics, and other industrial chemicals. Its versatile reactivity and solubility in organic solvents make it a valuable component in the synthesis of a variety of compounds.
Used in Specialty Chemicals and Pharmaceuticals:
1,10-Undecadiene is used as a monomer in the synthesis of specialty chemicals and pharmaceuticals. Its ability to participate in addition reactions enables the creation of new compounds with specific therapeutic or functional properties.
Used in Research and Development:
Due to its reactivity and the potential for creating various derivatives, 1,10-Undecadiene is also utilized in research and development settings to explore new chemical reactions and the development of novel materials and compounds.

InChI:InChI=1/C11H20/c1-3-5-7-9-11-10-8-6-4-2/h3-4H,1-2,5-11H2

Upstream product

• 106-95-6 allyl bromide 
• 1224431-85-9 C₁₆H₂₅NSe 
• 3937-56-2 1,9-Nonanediol 
• 51651-40-2 nonanedial 
• 19493-09-5 Methylenetriphenylphosphorane 
• 505-52-2 brassylic acid 
• 111-81-9 Methyl 10-undecenoate 
• 112-38-9 10-undecenoic acid 
• 112-43-6 10-Undecen-1-ol 
• 112-46-9 9-undecenol 
• 89968-59-2 ethyl 2-(diphenylmethylsilyl)-10-undecenoate 
• 692-86-4 ethyl 10-undecenenoate 
• 111-24-0 1,5-dibromo-pentane 
• 1730-25-2 allylmagnesium bromide 

Downstream Products

• 123-99-9 azelaic acid 
• 36219-73-5 undec-10-en-2-one 
• 6974-31-8 11-(acetylthio)undecanoic acid 
• 71310-21-9 11-mercaptounadecanoic acid 
• 2834-05-1 11-bromoundecanoic acid 
• 1611-56-9 1-Bromo-11-hydroxyundecane 
• 765-04-8 undecane-1,11-diol 

Relevant articles and documents

Dilithium tetrachlorocuprate catalyzed coupling of allylmagnesium bromide with α,ω-dihaloalkanes

Allylmagnesium bromide has been shown to cross-couple with α,ω- dihaloalkanes in the presence of dilithium tetrachlorocuprate to yield, depending on reaction conditions, mono-coupled haloalkenes or di-coupled alkadienes. The order of the reactivity of the dihalides is I > Br >> CI and secondary halides show greater reactivity than primary halides.

Oxidation of terminal diols using an oxoammonium salt: A systematic study

A systematic study of the oxidation of a range of terminal diols is reported, employing the oxoammonium salt 4-acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+ BF4-) as the oxidant. For substrates bearing a hydrocarbon chain of seven carbon atoms or more, the sole product is the dialdehyde. A series of post-oxidation reactions have been performed showing that the product mixture resulting from the oxidation step can be taken on directly to a subsequent transformation. For diols containing four to six carbon atoms, the lactone product is the major product upon oxidation. In the case of 1,2-ethanediol and 1,3-propanediol, when using a 1 : 0.5 stoichiometric ratio of substrate to oxidant, the corresponding monoaldehyde is formed which reacts rapidly with further diol to yield the acetal product. This is of particular synthetic value given both the difficulty of their preparation using other approaches and also their potential application in further reaction chemistry.

Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes

The biocatalytic oxidative tandem decarboxylation of C7–C18dicarboxylic acids to terminal C5–C16dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene; scale-up allowed the isolation of 1,15-hexadecadiene and 1,11-dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.

Absolute configuration for 1, n-glycols: A nonempirical approach to long-range stereochemical determination

The absolute configurations of 1,n-glycols (n = 2-12, 16) bearing two chiral centers were rapidly determined via exciton-coupled circular dichroism (ECCD) using a tris(pentafluorophenyl)porphyrin (TPFP porphyrin) tweezer system in a nonempirical fashion devoid of chemical derivatization. A unique "side-on" approach of the porphyrin tweezer relative to the diol guest molecule is suggested as the mode of complexation.

Reaction of Dess-Martin periodinane with 2-(alkylselenyl)pyridines. Dehydration of primary alcohols under extraordinarily mild conditions

Dess-Martin periodinane oxidizes very rapidly 2-pyridylseleno derivatives RR′CHCH2SePy in CHCl3 or CH2Cl2 and more chemoselectively than mCPBA. Tetravalent selenanes, RR′CHCH2Se(OAc)2Py, se

Semivolatile and volatile compounds in combustion of polyethylene

The evolution of semivolatile and volatile compounds in the combustion of polyethylene (PE) was studied at different operating conditions in a horizontal quartz reactor. Four combustion runs at 500 and 850°C with two different sample mass/air flow ratios and two pyrolytic runs at the same temperatures were carried out. Thermal behavior of different compounds was analyzed and the data obtained were compared with those of literature. It was observed that α,ω-olefins, α-olefins and n-paraffins were formed from the pyrolytic decomposition at low temperatures. On the other hand, oxygenated compounds such as aldehydes were also formed in the presence of oxygen. High yields were obtained of carbon oxides and light hydrocarbons, too. At high temperatures, the formation of polycyclic aromatic hydrocarbons (PAHs) took place. These compounds are harmful and their presence in the combustion processes is related with the evolution of pyrolytic puffs inside the combustion chamber with a poor mixture of semivolatile compounds evolved with oxygen. Altogether, the yields of more than 200 compounds were determined. The collection of the semivolatile compounds was carried out with XAD-2 adsorbent and were analyzed by GC-MS, whereas volatile compounds and gases were collected in a Tedlar bag and analyzed by GC with thermal conductivity and flame ionization detectors.

Hydroboration. 86. Convenient Conversion of Aldehydes and Ketones into the Corresponding Alkenes via Hydroboration of their Enamines. A Remarkably Simple Synthesis of Either (Z)- or (E)-Alkenes

Aldehydes and ketones are converted into the corresponding alkenes via hydroboration of their enamines.Hydroboration of aldehyde enamines by 9-borabicyclononane (9-BBN), followed by methanolysis, affords the corresponding terminal alkenes in 75-90percent yields.Unsaturated aldehyde enamines produce the corresponding dienes under these conditions.Enamines derived from substituted cyclic ketones and heterocyclic ketones are readily accommodated in this reaction to afford the corresponding alkenes in very good yields.The synthesis of pure (Z)- or (E)-alkenes is readily achieved from the same acyclic ketone enamine by modification of the hydroboration-elimination procedure: (A) hydroboration by 9-BBN followed by methanolysis or (B) hydroboration by borane methyl sulfide (BMS) followed by methanolysis and hydrogen peroxide oxidation.Mechanistic rationale is provided.