592609
4-Ethynyl-N,N-dimethylaniline
97%
Synonym(s):
1-Ethynyl-4-dimethylaniline, 4-Dimethylaminophenylacetylene
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About This Item
Linear Formula:
CH≡CC6H4N(CH3)2
CAS Number:
Molecular Weight:
145.20
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
97%
form
solid
mp
49-53 °C (lit.)
SMILES string
CN(C)c1ccc(cc1)C#C
InChI
1S/C10H11N/c1-4-9-5-7-10(8-6-9)11(2)3/h1,5-8H,2-3H3
InChI key
ZWMAYLMVFSCMMS-UHFFFAOYSA-N
General description
4-Ethynyl-N,N-dimethylaniline can be prepared via hydrolysis of 4-(3-methyl-3-hydroxy-1-butynyl)-N,N-dimethylaniline using potassium hydroxide in toluene.
Application
4-Ethynyl-N,N-dimethylaniline may be used to synthesize the following:
- copper(I) arylacetylide via reaction with copper(II)acetate
- N,N-dimethyl-4-(3-pyridinylethynyl)aniline via Sonogashira–Hagihara coupling with 3-iodopyridine
- [[5,15-bis[(40-dimethylamino)phenyl]ethynyl]-10,20-bis[(triisopropylsilyl)ethynyl]porphyrinato]magnesium(II) via reaction with dibromo magnesium porphyrin
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Beletskaya P.I, et al.
Tetrahedron Letters, 44(27), 5011-5013 (2003)
"Soluble porphyrin donors for small molecule bulk heterojunction solar cells"
Hatano J, et al.
Journal of Materials Chemistry, 22(36), 19258-19263 (2012)
"Synthesis and crystal structures of phenylethynylpyridinium derivatives for second-order nonlinear optics"
Umezawa H, et al.
Bulletin of the Chemical Society of Japan, 78(02), 344-348 (2005)
?Donor-substituted 1,1,4,4-tetracyanobutadienes (TCBDs): new chromophores with efficient intramolecular charge-transfer interactions by atom-economic synthesis?
Michinobu T, et al.
Chemistry?A European Journal , 12(07), 1889-1905 (2006)
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