4-Ethynylbenzaldehyde

Base Information

• Chemical Name: 4-Ethynylbenzaldehyde
• CAS No.: 63697-96-1
• Molecular Formula: C9H6O
• Molecular Weight: 130.146
• Hs Code.: 29122990
• European Community (EC) Number: 627-348-1
• DSSTox Substance ID: DTXSID10377992
• Nikkaji Number: J1.244.380C
• Wikidata: Q72477707
• Mol file: 63697-96-1.mol

Synonyms:4-Ethynylbenzaldehyde;63697-96-1;4-ethynyl-benzaldehyde;BENZALDEHYDE, 4-ETHYNYL-;Benzaldehyde,4-ethynyl-;MFCD05664348;p-Ethynylbenzaldehyde;4-ethynyl benzaldehyde;4-acetylenylbenzaldehyde;SCHEMBL92340;4-Ethynylbenzaldehyde, 97%;YSZC680;AMY1259;DTXSID10377992;BGMHQBQFJYJLBP-UHFFFAOYSA-N;BBL100385;STL554179;AKOS005216979;CS-W008115;PS-3048;SY008404;E0987;FT-0600812;A19007;EN300-115689;Z1203159515

Chemical Property of 4-Ethynylbenzaldehyde

Chemical Property:

• Vapor Pressure: 0.0946mmHg at 25°C
• Melting Point: 89-93 °C
• Refractive Index: 1.554
• Boiling Point: 223.8 °C at 760 mmHg
• Flash Point: 86.8 °C
• PSA: 17.07000
• Density: 1.07 g/cm³
• LogP: 1.48040
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 130.041864811
• Heavy Atom Count: 10
• Complexity: 155

Purity/Quality:

98%, ^*data from raw suppliers

4-?Ethynylbenzaldehyde ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CC1=CC=C(C=C1)C=O
• Uses: 4-?Ethynylbenzaldehyde is commonly used in solar cells as the acceptor unit.

Technology Process of 4-Ethynylbenzaldehyde

There total 23 articles about 4-Ethynylbenzaldehyde 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: 98.0%

4-[(trimethylsilyl)ethynyl]bezaldehyde (77123-57-0) → 4-Ethynylbenzaldehyde (63697-96-1)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ja806663h

Reference yield: 94.0%

N-cyclohexyl-4-ethynylbenzamide (1244044-85-6) → 4-Ethynylbenzaldehyde (63697-96-1)

Guidance literature:

N-cyclohexyl-4-ethynylbenzamide; With 2-fluoropyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -78 - 0 ℃; Inert atmosphere;

With triethylsilane; In dichloromethane; at 0 - 25 ℃; Inert atmosphere;

With citric acid; In tetrahydrofuran; dichloromethane; water; at 45 ℃; for 2h; chemoselective reaction;

DOI:10.1021/ja105194s

Reference yield: 85.1%

4-bromo-benzaldehyde (1122-91-4) + trimethylsilylacetylene (1066-54-2) → 4-Ethynylbenzaldehyde (63697-96-1)

Guidance literature:

4-bromo-benzaldehyde; With triethylamine; In tetrahydrofuran; for 0.75h; Inert atmosphere;

trimethylsilylacetylene; With copper(l) iodide; triphenylphosphine hydrochloride; In tetrahydrofuran; for 10h; Inert atmosphere;

With potassium carbonate; In methanol; at 20 ℃; for 5h;

upstream raw materials:

4-[(trimethylsilyl)ethynyl]bezaldehyde

4-bromo-1-ethynylbenzene

N,N-dimethyl-formamide

1-Formyl-4-ethynyl-1,4-cyclohexadiene

Downstream raw materials:

(Z)-HCCC₆H₄CH=CHC₆H₄NO₂

4-( p-nitrostyryl)phenylacetylene

4-[2-(3,4-dicyanophenyl)ethynyl]benzaldehyde

2-(4-ethynyl-phenyl)-[1,3]dioxane

Refernces

• 1、 Eisterhold, Andrew M.,Puangsamlee, Thamon,Otterbach, Steffen,Br?se, Stefan,Weis, Patrick,Wang, Xiqu,Kutonova, Ksenia V.,Miljani?, Ognjen ?.. "Expanded Cyclotetrabenzoins". . p. 781 - 785. Retrieved 2021.
• 2、 Ravikanth,Strachan, Jon-Paul,Li, Feirong,Lindsey, Jonathan S.. "Trans-substituted porphyrin building blocks bearing iodo and ethynyl groups for applications in bioorganic and materials chemistry". . p. 7721 - 7734. Retrieved 1998.
• 3、 Yu, Mingfeng,Wong, Joseph K.-H.,Tang, Cyril,Turner, Peter,Todd, Matthew H.,Rutledge, Peter J.. "Efficient deprotection of F-BODIPY derivatives: Removal of BF2 using bronsted acids". . p. 37 - 41. Retrieved 2014.
• 4、 Chen, Yanli,Gao, Wen,Kong, Xia,Li, Xiyou,Liu, Qi,Liu, Xue,Shen, Jingshun,Sun, Qiqi,Xing, Chuanwang,Zhang, Yuexing. "A high-performance photoelectrochemical sensor for the specific detection of H2O2and glucose based on an organic conjugated microporous polymer". supporting information. p. 26216 - 26225. Retrieved 2021/12/13.
• 5、 -. "CONJUGATED OLIGOMER-BASED MACROCYCLES FOR LIVE CELL IMAGING". Paragraph 0046-0047. . Retrieved 2020/12/29.