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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:
17573-94-3
Molecular Weight:
145.20
NACRES:
NA.22
PubChem Substance ID:
24881401
UNSPSC Code:
12352100
MDL number:
MFCD00168816
Assay:
97%
Form:
solid
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Quality Level

200

assay

97%

form

solid

mp

49-53 °C (lit.)

functional group

amine

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000522806
0000522806
0000488092
0000294703
0000294704

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Tetrahedron Letters, 44(27), 5011-5013 (2003)
?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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Global Trade Item Number

SKUGTIN
592609-1G04061832643632
592609-5G04061833356593