| Identification | More | [Name]
4-ETHYNYLANILINE | [CAS]
14235-81-5 | [Synonyms]
1-AMINO-4-ETHYNYLBENZENE
4-AMINOPHENYLACETYLENE
4-ETHYNYLANILINE
4-ETHYNYLPHENYLAMINE
P-ETHYNYLANILINE
4-ethenylbenzenamine
4-Ethynyl aniline (4-aminophenylacetylene)
4-ETHYNYLANILINE 97%
Benzenamine, 4-ethynyl-(9CI) | [Molecular Formula]
C8H7N | [MDL Number]
MFCD00168824 | [Molecular Weight]
117.15 | [MOL File]
14235-81-5.mol |
| Chemical Properties | Back Directory | [Melting point ]
98-102 °C (dec.) (lit.) | [Boiling point ]
99-101 °C(Press: 13 Torr) | [density ]
1.05±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Crystalline Powder | [pka]
3.11±0.10(Predicted) | [color ]
Yellow to brown | [BRN ]
2205181 | [InChI]
InChI=1S/C8H7N/c1-2-7-3-5-8(9)6-4-7/h1,3-6H,9H2 | [InChIKey]
JXYITCJMBRETQX-UHFFFAOYSA-N | [SMILES]
C1(N)=CC=C(C#C)C=C1 | [CAS DataBase Reference]
14235-81-5(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [F ]
8-10-23 | [HS Code ]
29214990 |
| Questions And Answer | Back Directory | [Reaction]
4-Ethynylaniline, also known as p-ethynylaniline, is a terminal alkyne. Its synthesis using 2-methyl-3-butyn-2-ol (MEBYNOL) has been reported. The transition metal catalyzed polymerization of 4-ethynylaniline to afford poly(4-ethynylaniline) has been reported.[3]The impact of the surface functionalization with 4-ethynylaniline on the thermal behavior of multi-walled carbon nanotubes (MWNTs) and graphene has been investigated. | [Uses]
4-Ethynylaniline may be used in the synthesis of N-methyliminodiethyl 4-(4-ethynylphenyliminomethyl) benzeneboronate. It can also be used to prepare an acetylene ligand, HC2-NDI (NDI= 1,4,5,8-naphthalenediimide).It can be used as an alkyne component in a synthesis of indoles from nitroarenes in the presence of a palladium-phenantroline catalyst.
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| Hazard Information | Back Directory | [Chemical Properties]
White or light yellow solid | [Definition]
ChEBI: 4-ethynylaniline is a substituted aniline. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 59, p. 5818, 1994 DOI: 10.1021/jo00098a051 | [General Description]
4-Ethynylaniline, also known as p-ethynylaniline, is a terminal alkyne. Its synthesis using 2-methyl-3-butyn-2-ol (MEBYNOL) has been reported. The transition metal catalyzed polymerization of 4-ethynylaniline to afford poly(4-ethynylaniline) has been reported. The impact of the surface functionalization with 4-ethynylaniline on the thermal behavior of multi-walled carbon nanotubes (MWNTs) and graphene has been investigated. | [reaction suitability]
reaction type: click chemistry | [Synthesis]
General procedure for the synthesis of 4-ethynylaniline from 4-[(trimethylsilyl)ethynyl]aniline: To a stirred solution of potassium hydroxide (1.34 g, 23.8 mmol) in methanol (6 mL) was slowly added a solution of 4-[(trimethylsilyl)ethynyl]aniline (1.10 g, 5.86 mmol) in tetrahydrofuran (5 mL). The reaction mixture was heated to reflux overnight. Upon completion of the reaction, the mixture was cooled to room temperature and filtered to remove insoluble impurities. The filtrate was concentrated under reduced pressure to remove the solvent. The residue was dissolved in dichloromethane (50 mL), filtered and dried using anhydrous magnesium sulfate. The dried solution was concentrated under reduced pressure to give a yellow solid product in 98% yield. The structure of the product was confirmed by nuclear magnetic resonance hydrogen (1H NMR) and carbon (13C NMR) spectra: 1H NMR (400 MHz, CDCl3, Me4Si): δ 7.32 (d, J = 2.4 Hz, 2H), 6.61 (d, J = 2.4 Hz, 2H), 3.83 (s, 2H), 2.98 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 147.0, 133.5, 114.6, 111.3, 84.4, 77.4, 77.1, 76.7, 74.9. | [References]
[1] Organometallics, 2014, vol. 33, # 18, p. 4947 - 4963
[2] RSC Advances, 2016, vol. 6, # 95, p. 92845 - 92851
[3] Tetrahedron, 2011, vol. 67, # 37, p. 7096 - 7100
[4] Chemical Communications, 2013, vol. 49, # 80, p. 9197 - 9199
[5] Dalton Transactions, 2013, vol. 42, # 2, p. 338 - 341 |
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