cis-3-Nonene

Base Information

• Chemical Name: cis-3-Nonene
• CAS No.: 20237-46-1
• Molecular Formula: C9H18
• Molecular Weight: 126.242
• Hs Code.: 2901299090
• European Community (EC) Number: 243-624-0
• NSC Number: 97534
• UNII: UH93O11YFQ
• DSSTox Substance ID: DTXSID301015976
• Nikkaji Number: J87.942H
• Wikidata: Q27291075
• Mol file: 20237-46-1.mol

Synonyms:cis-3-Nonene;20237-46-1;(Z)-Non-3-ene;3-Nonene, (3Z)-;(Z)-3-Nonene;(3Z)-non-3-ene;3-Nonene, (Z)-;(3Z)-3-Nonene;UNII-UH93O11YFQ;UH93O11YFQ;EINECS 243-624-0;(Z)-3-C9H18;NSC-97534;NSC97534;.GAMMA.-CIS-NONENE;YCBSHDKATAPNIA-ALCCZGGFSA-N;DTXSID301015976;MFCD00067490;Q27291075

Chemical Property of cis-3-Nonene

Chemical Property:

• Boiling Point: 145.7°Cat760mmHg
• Flash Point: 32.2°C
• PSA: 0.00000
• Density: 0.739g/cm³
• LogP: 3.53290
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 5
• Exact Mass: 126.140850574
• Heavy Atom Count: 9
• Complexity: 62.4

Purity/Quality:

99% ^*data from raw suppliers

cis-3-Nonene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC
• Isomeric SMILES: CCCCC/C=C\CC
• Uses: cis-3-Nonene is derived from Hexanal (H292130), which is an alkyl aldehyde used in the flavor industry to produce fruity flavors.

Technology Process of cis-3-Nonene

There total 11 articles about cis-3-Nonene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

S-p-toluenesulfonic acid-1-ethylheptyl ester (65950-02-9) → cis-3-nonene (20237-46-1) + (E)-3-nonene (20063-92-7) + 2-nonene (6434-78-2) + cis-2-nonene (6434-77-1)

Guidance literature:

With 18-crown-6 ether; potassium tert-butylate; In tert-butyl alcohol; at 25.4 ℃; Product distribution; Rate constant;

Reference yield:

n-propyltriphenylphosphonium bromide (6228-47-3) + hexanal (66-25-1) → cis-3-nonene (20237-46-1) + (E)-3-nonene (20063-92-7)

Guidance literature:

n-propyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Schlenk technique; Inert atmosphere;

hexanal; In tetrahydrofuran; hexane; at 0 - 25 ℃; for 16h; Overall yield = 38 percent; Overall yield = 239.4 mg; Schlenk technique; Inert atmosphere;

DOI:10.1002/chem.202004946

Reference yield:

rac-pent-1-en-3-yl acetate (10500-11-5) + dibutylmagnesium (1191-47-5) → cis-3-nonene (20237-46-1) + (E)-3-nonene (20063-92-7)

Guidance literature:

copper acetylacetonate; triphenylphosphine; In tetrahydrofuran; at 40 ℃; for 4h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1007/BF01157358

upstream raw materials:

3-nonyne

rac-pent-1-en-3-yl acetate

dibutylmagnesium

(+/-)-1-propylhexyl 4-methylbenzenesulfonate

Refernces

• 1、 Dalpozzo, Renato,De Nino, Antonio,Tagarelli, Antonio,Bartoli, Giuseppe,Bellucci, M. Cristina,Bosco, Marcella,Sambri, Letizia. "Reactivity of organocerium compounds with allyl alcohols". . p. 9559 - 9560. Retrieved 2007/10/03.
• 2、 Tolstikov, G. A.,Dzhemilev, U. M.. "CROSS-COUPLIN REACTIONS BETWEEN SOME ALLYL, HOMOALLYL, AND HOMOPROPARGYL SUBSTRATES AND TRIALKYLALANES OR DIALKYL- AND DIARYL-MAGNESIUM DERIVATIVES". . p. 133 - 144. Retrieved 2007/10/02.