5-Phenyl-1-pentyne

Base Information

• Chemical Name: 5-Phenyl-1-pentyne
• CAS No.: 1823-14-9
• Molecular Formula: C11H12
• Molecular Weight: 144.216
• Hs Code.: 2902909090
• European Community (EC) Number: 217-352-8
• NSC Number: 102794
• UNII: B4QV76Z86Q
• DSSTox Substance ID: DTXSID50171279
• Nikkaji Number: J199.641J
• Wikidata: Q27274371
• ChEMBL ID: CHEMBL1743362
• Mol file: 1823-14-9.mol

Synonyms:5-phenyl-1-pentyne;pent-4-ynylbenzene

Chemical Property of 5-Phenyl-1-pentyne

Chemical Property:

• Appearance/Colour: liquid
• Vapor Pressure: 6.17E-05mmHg at 25°C
• Melting Point: 103-106 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• Refractive Index: 1.5165
• Boiling Point: 213 °C at 760 mmHg
• Flash Point: 72 °C
• PSA: 0.00000
• Density: 0.927 g/cm³
• LogP: 2.64250
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 144.093900383
• Heavy Atom Count: 11
• Complexity: 131

Purity/Quality:

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

5-Phenyl-1-Pentyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53-36
• Safety Statements: 26-36/37/39-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCCC1=CC=CC=C1
• Uses: 5-Phenyl-1-pentyne is also used as an intermediate in organic synthesis and pharmaceuticals. It is also used to make other chemicals.

Technology Process of 5-Phenyl-1-pentyne

There total 25 articles about 5-Phenyl-1-pentyne 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: 89.0%

1-Bromo-3-phenylpropane (637-59-2) + acetylene (74-86-2,25067-58-7) → 5-phenyl-1-pentyne (1823-14-9)

Guidance literature:

acetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h; Inert atmosphere;

1-Bromo-3-phenylpropane; In tetrahydrofuran; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; hexane; at -78 - 0 ℃; for 10h; Inert atmosphere;

DOI:10.1021/ja209553f

Reference yield: 77.0%

CBr4 + 3-benzyl propionaldehyde (18328-11-5) → 5-phenyl-1-pentyne (1823-14-9)

Guidance literature:

With n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; chloroform;

Reference yield: 57.02%

trimethyl(5-phenylpent-1-yn-1-yl)silane (110211-35-3) → 5-phenyl-1-pentyne (1823-14-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1h;

upstream raw materials:

5-phenyl-1-pentanal

1-Bromo-3-phenylpropane

lithium acetylenide N,N,N'N'-tetramethylethylenediamine complex

(+/-)-1-(2-Phenylethyl)-3-propynyl acetate

Downstream raw materials:

7-phenyl-3-heptyn-2-ol

5-phenyl-2-pentanone

hex-4-yn-1-ylbenzene

(4-methylpent-4-en-1-yl)benzene

Refernces

• 1、 Munteanu, Charissa,Frantz, Doug E.. "Palladium-Catalyzed Synthesis of Alkynes via a Tandem Decarboxylation/Elimination of (E)-Enol Triflates". supporting information. p. 3937 - 3939. Retrieved 2016/08/30.
• 2、 Li, Da-Peng,Pan, Xiang-Qiang,An, Li-Tao,Zou, Jian-Ping,Zhang, Wei. "Manganese(III)-mediated selective diphenylphosphinoyl radical reaction of 1,4-diaryl-1-butynes for the synthesis of 2-phosphinoylated 3,4- dihydronaphathalenes". . p. 1850 - 1855. Retrieved 2014/03/21.