16695-35-5

Basic information

• Product Name: (E)-1-Bromo-4-nonene
• Synonyms: (E)-1-Bromo-4-nonene
• CAS NO: 16695-35-5
• Molecular Formula: C₉H₁₇Br
• Molecular Weight: 205.14
• Mol File: 16695-35-5.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-1-Bromo-4-nonene(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-Bromo-4-nonene(16695-35-5)
• EPA Substance Registry System: (E)-1-Bromo-4-nonene(16695-35-5)

Safety Data

• Hazardous Substances Data: 16695-35-5(Hazardous Substances Data)

Upstream product

• 97-99-4 Tetrahydrofurfuryl alcohol 
• 3003-84-7 Tetrahydrofurfuryl chloride 
• 98955-39-6 alcool α-butyltetrahydrofurfurylique 
• 54173-32-9 2-(1-chloro-pentyl)-tetrahydro-furan 
• 693-02-7 hex-1-yne 
• 66270-63-1 [(1E)-1-iodo-hex-1-enyl]-trimethyl-silane 
• 3844-94-8 1-(trimethylsilyl)-1-hexyne 
• 110-87-2 3,4-dihydro-2H-pyran 
• 5390-04-5 pent-1-yn-5-ol 
• 31535-08-7 2-butyl-3-chloro-tetrahydro-pyran 
• 5631-95-8 2,3-dichlorotetrahydro-2H-pyran 
• 69361-38-2 ethyl (4E)-non-4-enoate 
• 4938-52-7 1-hepten-3-ol 
• 74962-48-4 1-chloro-3-iodoheptane 

Downstream Products

• 16424-55-8 (E)-dec-5-enoic acid 
• 56578-18-8 (E)-5-decen-1-ol 
• 53042-79-8 1-acetoxyhexadeca-7Z,11E-diene 
• 23192-82-7 (E)-tetradec-9-en-1-yl acetate 
• 64275-71-4 (Z,E)-5,10-Pentadecadiensaeure 
• 64275-58-7 pentadeca-5c,10t-dienal 
• 64275-60-1 (Z,E)-5,10-Pentadecadien-1-ol 
• 53963-09-0 (7Z,11E)-hexadeca-7,11-dien-1-ol 
• 38421-90-8 (E)-5-decen-1-yl acetate 
• 59512-90-2 <(E)-4-Nonenyl>-triphenylphosphonium-bromid 
• 64275-59-8 (E)-10-pentadecen-5-yn-1-ol 

Relevant articles and documents

Preparation of Geometrical Isomers of 2,7-Dodecadienal, 2,7-Dodecadienyl Formate, and Other 1,6-Diene System-containing Compounds and Their Electroantennography Activities toward Male Eri-Silk Moths

We measured the electroantennography (EAG) activities of the geometrical isomers of several pheromone-related compounds towards male eri-silk moths (Samia cynthia richini) using EAG-gas chromatography (GC).C16-aldehyde and formyl ester, with the same chain length as C16-aldehyde, were found to be much more active than other compounds with a shorter chain.For the compounds with (1Z,6Z)- or (1E,6E)-configuration, the activity in decreasing order was C14-formyl ester > C16-aldehyde > C14-aldehyde > C12-formyl ester, while that for the compounds with (1Z,6E)- or (1E,6Z)-configuration is C16-aldehyde > C14-formyl ester > other compounds with a shorter C14 chain.

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Coupling reactions of lithium compounds, (Z)-carbonyl olefination of phosphonium ylides and 'crossed' Wittig olefination of bisylides are the key reaction steps in the synthesis principle for nonconjugated, bisolefinic Lepidoptera pheromones and structural analogs. Double unsaturated (E,Z)- and (E,E)-1-vinyl halides are converted into the corresponding (E,Z)- and (E,E)-1-vinyl lithium compounds and coupled selectively to (E,Z)- and (E,E)-alkadienols, alkadienals and alkadienyl acetates with different carbon chain length, geometry and relative positions of double bonds. 'Crossed' Wittig reactions of 1,ω-alkylidene bisylides with two different alkanals gives rise to the formation of corresponding (Z,Z)-dienic sex attractants and derivatives. A monounsaturated (E)-1-vinyl iodide is the synthon for the preparation of an (E)-alkenyl bromide which is converted to an (E)-alkenyl phosphonium salt and (Z)-selectively olefinated to (Z,E)-isomers of moth sex pheromones.

A Convenient Synthesis of (E)-9-Tetradecen-1-yl Acetate, a Sex Pheromone of Gelechiid Moth and (E)-5-Decenol, a Sex Pheromone of Peach Twig Borer

n-Butyllithium reacts with dihydropyran to give (E)-4-nonenyl alcohol (IV).The alcohol (IV) is converted into the corresponding bromide (V).The Grignard reagent of the bromide (V) on coupling with the bromide (VI) in the presence of Li2CuCl4, followed by hydrolysis yields the alcohol (III).This on acetylation gives the pheromone (I).The formylation of the Grignard reagent prepared from V gives the pheromone (II).