Cyclohexylallene

Base Information

• Chemical Name: Cyclohexylallene
• CAS No.: 5664-17-5
• Molecular Formula: C9H14
• Molecular Weight: 122.21
• European Community (EC) Number: 625-333-4
• Nikkaji Number: J109.025I
• Mol file: 5664-17-5.mol

Synonyms:Cyclohexylallene;5664-17-5;Cyclohexalallene;Cyclohexane, propadienyl-;CYCLOHEXYLALLENE, 97%;Cyclohexane, 1,2-propadienyl-;1,2-PROPADIENYLCYCLOHEXANE;propa-1,2-dienylcyclohexane;(1,2-Propadienyl)cyclohexane;propa-1,2-dienyl-cyclohexane;1,2-Propadienylcyclohexane #;1-Cyclohexyl-1,2-propadiene;CQHBBSICMXUMIB-UHFFFAOYSA-N;MFCD00190199;AKOS015907014;FT-0635799

Chemical Property of Cyclohexylallene

Chemical Property:

• Vapor Pressure: 2.85mmHg at 25°C
• Refractive Index: n20/D 1.483
• Boiling Point: 162.3°Cat760mmHg
• Flash Point: 35.1°C
• PSA: 0.00000
• Density: 0.857g/cm³
• LogP: 2.90780
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 1
• Exact Mass: 122.109550447
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cyclohexylallene 97% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: N
• Statements: 10-50/53
• Safety Statements: 16-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C=CC1CCCCC1

Technology Process of Cyclohexylallene

There total 15 articles about Cyclohexylallene 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: 91.0%

(Cy)Ti(O-i-Pr)3 (135303-54-7) + propargyl bromide (106-96-7) → cyclohexylallene (5664-17-5)

Guidance literature:

With nickel dichloride; tricyclohexylphosphine; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c4ob00677a

Reference yield: 88.0%

1-cyclohexylprop-2-yn-1-yl acetate (108104-21-8,16169-86-1) → (R)-1-cyclohexylprop-2-yn-1-yl acetate (936638-45-8) + cyclohexylallene (5664-17-5) + (S)-1-cyclohexyl-2-propyn-1-ol acetate (108104-21-8)

Guidance literature:

With [(R)-(+)-2,2'-Bis(di-2-furanylphosphino)-6,6'-dimethoxy-1,1'-biphenyl]palladium(II) dichloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; at 60 ℃; for 6.5h; Inert atmosphere;

DOI:10.1002/adsc.201300720

Reference yield: 80.0%

cyclohexylmagnesiumchloride (931-51-1) + propargyl bromide (106-96-7) → cyclohexylallene (5664-17-5)

Guidance literature:

With copper(I) bromide; lithium bromide; In tetrahydrofuran; diethyl ether; at -60 - 20 ℃;

DOI:10.1080/00397919708005448

upstream raw materials:

quinoline

(2,3-dibromo-propyl)-cyclohexane

2-methyl-but-2-ene

(3-chloroprop-1-yn-1-yl)cyclohexane

Downstream raw materials:

1-cyclohexyl-2-methylenecyclopropane

<1-Aethinyl-cyclohexyl>-essigsaeure

4-cyclohexyl-butan-2-one

Refernces

• 1、 Endo, Takeshi,Takagi, Koji,Tomita, Ikuyoshi. "Design and synthesis of polymerizable cumulated double bond system. - Living coordination polymerization of alkylallenes by Π-allylnickel catalyst-". . p. 15187 - 15196. Retrieved 1997.
• 2、 Geng, Hui-Qing,Wu, Xiao-Feng,Zhang, Youcan. "Palladium-Catalyzed Carbonylative Four-Component Synthesis of β-Perfluoroalkyl Amides". supporting information. p. 17682 - 17687. Retrieved 2021/10/25.
• 3、 Brochetta, Massimo,Borsari, Tania,Gandini, Andrea,Porey, Sandip,Deb, Arghya,Casali, Emanuele,Chakraborty, Arka,Zanoni, Giuseppe,Maiti, Debabrata. "Trifluoromethylation of Allenes: An Expedient Access to α-Trifluoromethylated Enones at Room Temperature". supporting information. p. 750 - 753. Retrieved 2019/01/04.