4-Hex-1-ynylbenzaldehyde

Base Information

• Chemical Name: 4-Hex-1-ynylbenzaldehyde
• CAS No.: 175203-90-4
• Molecular Formula: C13H14O
• Molecular Weight: 186.254
• Hs Code.: 2912299000
• DSSTox Substance ID: DTXSID20381409
• Nikkaji Number: J1.686.841H
• Wikidata: Q72482461
• Mol file: 175203-90-4.mol

Synonyms:4-hex-1-ynylbenzaldehyde;175203-90-4;4-(hex-1-yn-1-yl)benzaldehyde;Benzaldehyde, 4-(1-hexyn-1-yl)-;4-(1-Hexynyl)benzaldehyde;4-(hex-1-ynyl)benzaldehyde;SCHEMBL6087379;4-(1-Hexyn-1-yl)benzaldehyde;DTXSID20381409;MFCD00276593;4-hex-1-ynylbenzaldehyde, AldrichCPR;4-PIPERAZINOPHENOLDIHYDROBROMIDE;AKOS006230636;AS-9193;CS-0324160;FT-0618583;A811893

Chemical Property of 4-Hex-1-ynylbenzaldehyde

Chemical Property:

• Vapor Pressure: 0.000852mmHg at 25°C
• Refractive Index: 1.533
• Boiling Point: 304.8 °C at 760 mmHg
• Flash Point: 128.2 °C
• PSA: 17.07000
• Density: 1 g/cm³
• LogP: 3.04080
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 186.104465066
• Heavy Atom Count: 14
• Complexity: 222

Purity/Quality:

98%min ^*data from raw suppliers

4-Hex-1-ynylbenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC#CC1=CC=C(C=C1)C=O

Technology Process of 4-Hex-1-ynylbenzaldehyde

There total 3 articles about 4-Hex-1-ynylbenzaldehyde 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: 95.0%

hex-1-yne (693-02-7) + p-(iodophenyl)carboxaldehyde (15164-44-0) → 4-(hex-1-yn-1-yl)benzaldehyde (175203-90-4)

Guidance literature:

With copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 50 ℃; for 6h;

DOI:10.1002/ejoc.200800633

Reference yield: 93.0%

4-formylphenylboronic acid, (87199-17-5) + hex-1-yne (693-02-7) → 4-(hex-1-yn-1-yl)benzaldehyde (175203-90-4)

Guidance literature:

With caesium carbonate; triphenylphosphine; silver(l) oxide; In dichloromethane; at 35 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.jorganchem.2010.12.038

Reference yield: 91.0%

4-bromo-benzaldehyde (1122-91-4) + hex-1-yne (693-02-7) → 4-(hex-1-yn-1-yl)benzaldehyde (175203-90-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In acetonitrile; at 60 ℃; for 1h;

DOI:10.1021/acs.orglett.9b02455

upstream raw materials:

hex-1-yne

p-(iodophenyl)carboxaldehyde

4-formylphenylboronic acid,

4-bromo-benzaldehyde

Downstream raw materials:

1-(4-(hex-1-ynyl)benzyl)azetidine-3-carboxylic acid

methyl (2E,4E)-4-(4-formylbenzylidene)oct-2-enoate

4-((Z)-hex-1-enyl)benzaldehyde

4-hexylbenzaldehyde

Refernces

• 1、 Ball-Jones, Matthew P.,Tyler, Jasper,Mora-Radó, Helena,Czechtizky, Werngard,Méndez, María,Harrity, Joseph P. A.. "Exploiting Hydrazones to Improve the Efficiency of 6π-Electrocyclization Reactions of 1-Azatrienes". supporting information. p. 6821 - 6824. Retrieved 2019/09/07.
• 2、 Nie, Xiaopeng,Liu, Suli,Zong, Yan,Sun, Peipei,Bao, Jianchun. "Facile synthesis of substituted alkynes by nano-palladium catalyzed oxidative cross-coupling reaction of arylboronic acids with terminal alkynes". experimental part. p. 1570 - 1573. Retrieved 2011/06/17.