Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

590630

Sigma-Aldrich

2-Ethynylbenzaldehyde

97%

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
HC≡CC6H4CHO
CAS Number:
38846-64-9
Molecular Weight:
130.14
MDL number:
MFCD04039985
UNSPSC Code:
12352100
PubChem Substance ID:
24881289
NACRES:
NA.22

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000187181
0000187156
MKCF4921
MKBK1117V
MKBH5639V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

?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)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service