10405-84-2

Usage

Uses

Used in Chemical Synthesis:
CIS-4-NONENE is used as a key intermediate in the synthesis of various organic compounds, particularly in the preparation of specialty chemicals and pharmaceuticals. Its ability to undergo addition reactions and serve as a building block for more complex molecules makes it a valuable component in the chemical industry.
Used in Immobilized Metal Alkylidene Imidazolidene Carbene Alkoxide Catalysts:
CIS-4-NONENE is employed as a crucial component in the preparation of Immobilized metal Alkylidene Imidazolidene Carbene Alkoxide (IMIC) catalysts. These catalysts are essential in the field of olefin metathesis, a type of chemical reaction that involves the redistribution of carbon-carbon double bonds in olefins.
Used in Olefin Metathesis:
CIS-4-NONENE plays a significant role in olefin metathesis, a reaction that is widely used in the production of polymers, pharmaceuticals, and advanced materials. The use of IMIC catalysts, which incorporate CIS-4-NONENE, enhances the efficiency and selectivity of olefin metathesis reactions, leading to the development of novel materials with improved properties.

Health Hazard

Recommended Personal Protective Equipment: Respiratory organic vapor canister or air-supplied mask; face splash shield; Symptoms Following Exposure: High vapor concentrations irritate eyes and respiratory tract and act as an anesthetic; General Treatment for Exposure: INHALATION: remove patient to fresh air; if breathing stops, apply artificial respiration and administer oxygen; call a physician. INGESTION: do NOT induce vomiting because of aspiration hazard; Toxicity by Inhalation (Threshold Limit Value): Data not available; Short-Term Inhalation Limits: Data not available; Toxicity by Ingestion: Data not available; Late Toxicity: Data not available; Vapor (Gas) Irritant Characteristics: Vapors cause a slight smarting of the eyes or respiratory system if present 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 reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

InChI:InChI=1/C9H18/c1-3-5-7-9-8-6-4-2/h7,9H,3-6,8H2,1-2H3/b9-7-

Upstream product

• 65950-00-7 (+/-)-1-propylhexyl 4-methylbenzenesulfonate 
• 85102-22-3 (4R,5R)-4,5-Dibromo-nonane 
• 85102-22-3 (4S,5R)-4,5-Dibromo-nonane 
• 119105-48-5 5-nonyl fluoride 
• 29541-98-8 pentylidenetriphenylphosphorane 
• 502-56-7 nonanone-5 
• 13532-22-4 5-dimethylaminononane 
• 623-93-8 5-nonanol 
• 110684-91-8 4-(1-butyl-1(E)-pentenyl)morpholine 

Downstream Products

• 14850-23-8 trans-4-Octene 
• 7433-78-5 cis-5-decene 
• 7433-56-9 (E)-5-decene 
• 7642-15-1 (Z)-oct-4-ene 
• 592-99-4 4-octene 
• 10405-85-3 (E)-non-4-ene 
• 19689-19-1 5-decene 
• 2198-23-4 4-nonene 

Relevant academic research and scientific papers

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.

BASE-PROMOTED ELIMINATION OF HYDROGEN FLUORIDE FROM ALKYL FLUORIDES: REACTIVITY AND STEREOCHEMISTRY

- The alcoholate-promoted dehydrohalogenation of 5-nonyl fluoride and cyclododecyl fluoride, typical straight-chain and, respectively, medium-size cyclic substrates, leads to cis- and trans-alkenes in an approximate ratio of 1:3.With bulky bases such as lithium diisopropylamide the trans isomer may be obtained almost exclusively.In general, the elimination of hydrogen fluoride proceeds very slowly.Increase of the base strength has only a moderate effect on the rates.Electrophilic assistance as provided by lithium cations in media of low polarity can, however, considerably accelerate the reaction. - Cyclododecyl fluoride cannot be prepared from cyclododecanol.It is, however, readily accessible by bromofluorination of cyclododecene and subsequent reduction of the adduct with stannane.

Double Bond Geometry of the Alkenes produced by Oxidative Elimination of Alkyl Phenyl Selenides and Tellurides

Treatment of secondary-alkyl phenyl selenides with various oxidants affords the corresponding trans-alkene highly selectively irrespective of the amount of oxidant, while in the case of the tellurium analogues the double bond geometry of the product alkene depends markedly on the amount of oxidant, the trans-isomer being formed highly selectively with 1 equiv. oxidant and the proportion of the cis-isomer being increased with excess (2-10 equiv.) of oxidant.

THE EFFECT OF CROWN ETHER ON STERIC HINDRANCE TO BASE APPROACH IN BIMOLECULAR ELIMINATION: EVIDENCE AGAINST CLUMP AGGREGATE MODEL OF ION-PAIRED ALKOXIDE BASE

The effect of 18-crown-6-ether upon geometrical orientation and rates was investigated in tert-C4H9OK-tert-C4H9OH promoted anti-elimination from two homologous series of tosylates, RCH2CHOTsC5H11 and RCHOTsCH2C5H11 (R = H, CH3, C2H5, n-C3H5, iso-C3H7, tert-C4H9).Steric requirements of the cis- and trans-stereoselective base species operating in the reaction in the absence and in the presence of the crown ether, respectively, have been assessed.An unambiguous distinction has been made between two pending models of the cis-stereoselective (ion-paired) base.