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590630

Sigma-Aldrich

2-Ethynylbenzaldehyde

97%

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About This Item

Fórmula lineal:
HC≡CC6H4CHO
Número de CAS:
38846-64-9
Peso molecular:
130.14
MDL number:
MFCD04039985
UNSPSC Code:
12352100
PubChem Substance ID:
24881289
NACRES:
NA.22

Quality Level

100

assay

97%

form

solid

mp

64-67 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)c1ccccc1C#C

InChI

1S/C9H6O/c1-2-8-5-3-4-6-9(8)7-10/h1,3-7H

InChI key

ZEDSAJWVTKUHHK-UHFFFAOYSA-N

Application

2-Ethynylbenzaldehyde may be used in the synthesis of the following:
  • iodoisoquinoline-fused benzimidazoles obtained via tandem iodocyclization of 2-ethynylbenzaldehyde with o-benzenediamine and iodine in the presence of copper(I)iodide
  • N-[(7,7a-dihydroisoquinolino[2,1-a]perimidin-13-yl)methyl]-N-isopropylpropan-2-amine obtained via a multi-step process
It may also be used in the synthesis of the following substituted 2-alkynylbenzaldehydes by Sonogashira coupling:
  • 2-[(2-bromophenyl)ethynyl]benzaldehyde
  • 2-[(2-bromo-5-fluorophenyl)ethynyl]benzaldehyde
  • 2-[(2-bromo-5-methylphenyl)ethynyl]benzaldehyde
  • 2-(phenylethynyl)benzaldehyde
  • 2-[(4-methylphenyl)ethynyl]benzaldehyde

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
MKCF4921
MKBK1117V
MKBH5639V
03997LJ
55196LJ

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?CuI/I2-Promoted Electrophilic Tandem Cyclization of 2 Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of
Iodoisoquinoline-Fused Benzimidazoles?
Ouyang C-H, et al.
The Journal of Organic Chemistry, 76(01), 223-228 (2010)
?Direct synthesis of highly fused perimidines by copper(I)-catalyzed
hydroamination of 2-ethynylbenzaldehydes?
Tokimizu Y, et al.
Tetrahedron, 67(29), 5168-5175 (2011)
Nishant Singh et al.
Biomaterials science, 7(10), 4099-4111 (2019-07-30)
Many debilitating infections result from persistent microbial biofilms that do not respond to conventional antibiotic regimens. A potential method to treat such chronic infections is to combine agents which interfere with bacterial biofilm development together with an antibiotic in a

Artículos

New Aromatic Terminal Alkynes

The terminal alkyne functionality has a wide range of applications including most recently the synthesis of spiropyran substituted 2,3-dicyanopyrazines and (±)-asteriscanolide, as well as conversion to enamines using resin-bound 2° amines.

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