Benzaldehyde, 5-ethynyl-2-hydroxy- (9CI)

Base Information

• Chemical Name: Benzaldehyde, 5-ethynyl-2-hydroxy- (9CI)
• CAS No.: 252771-08-7
• Molecular Formula: C9H6 O2
• Molecular Weight: 146.145
• Mol file: 252771-08-7.mol

Synonyms:5-Ethynyl-2-hydroxybenzaldehyde;5-Ethynylsalicylaldehyde

Chemical Property of Benzaldehyde, 5-ethynyl-2-hydroxy- (9CI)

Chemical Property:

• Melting Point: 115-118 °C
• Boiling Point: 245.6±30.0 °C(Predicted)
• PKA: 7.02±0.18(Predicted)
• PSA: 37.30000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 1.18600

Purity/Quality:

98% ^*data from raw suppliers

5-Ethynyl-2-hydroxybenzaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzaldehyde, 5-ethynyl-2-hydroxy- (9CI)

There total 4 articles about Benzaldehyde, 5-ethynyl-2-hydroxy- (9CI) 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: 92.0%

2-hydroxy-5-(2-(trimethylsilyl)ethynyl)benzaldehyde (727375-48-6) → 5‐ethynyl‐2‐hydroxybenzaldehyde (252771-08-7)

Guidance literature:

2-hydroxy-5-(2-(trimethylsilyl)ethynyl)benzaldehyde; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

With water; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo100309r

Reference yield: 40.0%

5-bromosalicyclaldehyde (1761-61-1) + trimethylsilylacetylene (1066-54-2) → 5‐ethynyl‐2‐hydroxybenzaldehyde (252771-08-7)

Guidance literature:

5-bromosalicyclaldehyde; trimethylsilylacetylene; With copper(l) iodide; cis-dichlorobis(triphenylphosphine)platinum(II); diisopropylamine; for 4h; Inert atmosphere; Reflux;

With potassium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 12h;

DOI:10.1021/acs.inorgchem.7b00475

Reference yield:

5-bromosalicyclaldehyde (1761-61-1) → 5‐ethynyl‐2‐hydroxybenzaldehyde (252771-08-7)

Guidance literature:

Multi-step reaction with 2 steps

1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / 12 h / 85 - 90 °C

2: potassium hydroxide / methanol; dichloromethane / 3 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; potassium hydroxide; In methanol; dichloromethane;

DOI:10.1016/j.polymer.2011.10.034

upstream raw materials:

2-hydroxy-5-(2-(trimethylsilyl)ethynyl)benzaldehyde

5-bromosalicyclaldehyde

trimethylsilylacetylene

Downstream raw materials:

2-hydroxy-5-((perfluorophenyl)ethynyl)benzaldehyde

5-(4-hexyloxy-phenylethynyl)-2-hydroxy-benzaldehyde

5-(4-dodecyloxy-phenylethynyl)-2-hydroxy-benzaldehyde

C₄H₂S(C₂C₆H₃(OH)CHO)2

Refernces

• 1、 More,Pawal,Lolage,Chavan. "Syntheses, structural characterization, luminescence and optical studies of Ni(II) and Zn(II) complexes containing salophen ligand". . p. 419 - 427. Retrieved 2017.
• 2、 Pawal,Lolage,Chavan. "Coordination-organometallic hybrid materials based on the trinuclear M(II)-Ru(II) (M=Ni and Zn) complexes: Synthesis, structural characterization, luminescence and electrochemical properties". . p. 131 - 139. Retrieved 2018.
• 3、 Zhang, Chunyu,Zhang, Yu,Zhang, Hexin,Hu, Yanming,Zhang, Xuequan,Masuda, Toshio. "Synthesis and ion responsiveness of optically active polyacetylenes containing salicylidene Schiff-base moieties". . p. 46 - 52. Retrieved 2015.
• 4、 He, Xifeng,Ma, Jie,Zhang, Hongbo,Zhang, Yizhi. "Near infrared absorption/emission perylenebisimide fluorophores with geometry relaxation-induced large Stokes shift". . p. 35840 - 35847. Retrieved 2020/10/27.