2-anilinoethanol

Structural formula
General
Surname	2-anilinoethanol
other names	2- (phenylamino) ethanol; N- phenylethanolamine; N - (2-hydroxyethyl) aniline;
Molecular formula	C 8 H 11 NO
Brief description	yellow-brown, flammable liquid with an amine-like odor
External identifiers / databases
EC number	204-588-1
ECHA InfoCard	100.004.172
PubChem	31235
ChemSpider	28975
Wikidata	Q15632814
properties
Molar mass	137.18 g mol −1
Physical state	liquid
density	1.1 g cm −3
Melting point	−30 ° C
boiling point	284-286 ° C
Vapor pressure	1.46 hPa (100 ° C)
solubility	heavy in water (4.5 g l −1 at 20 ° C)
Refractive index	1.578 (20 ° C)
safety instructions
H and P phrases	H: 310-318-373-412
	P: 273-280-302 + 352-310-305 + 351 + 338
Toxicological data	2230 mg kg −1 ( LD 50 , rat , oral ) ; 69 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-Anilinoethanol is a chemical compound from the group of aminobenzenes and alcohols .

presentation

2-Anilinoethanol can be produced by reacting aniline with 2-haloethanols, for example 2-bromoethanol , or by reacting monoethanolamine with monohalobenzenes in the presence of cupric iodide and potassium hydroxide .

use

2-anilinoethanol can be used to synthesize indole . Poly (2-anilinoethanol) is an organic semiconductor .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 2-anilinoethanol in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
↑ Data sheet N- (2-Hydroxyethyl) aniline from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).
↑ BA Bhanu Prasad, Scott R. Gilbertson: One-Pot Synthesis of Unsymmetrical N-Heterocyclic Carbene Ligands from N- (2-Iodoethyl) arylamine Salts . In: Organic Letters . tape 11 , no. 16 , August 20, 2009, pp. 3710-3713 , doi : 10.1021 / ol901189m .
↑ Yunqi Zhao, Shaofeng Duan, Xing Zeng, Chunjing Liu, Neal M. Davies, Benyi Li, M. Laird Forrest: Prodrug Strategy for PSMA-Targeted Delivery of TGX-221 to Prostate Cancer Cells . In: Molecular Pharmaceutics . tape 9 , no. 6 , June 4, 2012, p. 1705-1716 , doi : 10.1021 / mp3000309 .
↑ Jianjun Yin, Gang Ye, Xiaogong Wang: Star-shaped molecules containing both azo chromophores and carbazole units as a new type of photoresponsive amorphous material . In: Journal of Materials Chemistry C . tape 1 , no. 24 , 2013, p. 3794 , doi : 10.1039 / c3tc30536h .
↑ Huiqing Yin, Ming Jin, Wei Chen, Chen Chen, Likang Zheng, Ping Wei, Shiqing Han: Solvent-free copper-catalyzed N-arylation of amino alcohols and diamines with aryl halides . In: Tetrahedron Letters . tape 53 , no. 10 , March 2012, ISSN 0040-4039 , p. 1265-1270 , doi : 10.1016 / j.tetlet.2011.12.130 .
↑ Jean Afxantidis, Naima Bouchry, Jean-Pierre Aune: Synthesis of indole, benzofuran and benzothiophene by reaction of 2-anilinoethanol, 2-phenoxyethanol and 2- (phenylthio) ethanol on AlPO4 and Pd / AlPO4 catalysts . In: Journal of Molecular Catalysis A: Chemical . tape 102 , no. 1 , September 1995, pp. 49-58 , doi : 10.1016 / 1381-1169 (95) 00082-8 ( PDF ).
↑ E. Ahlatcıoğlu, BF Şenkal, F. Yakuphanoğlu, Sh. A. Mansour: Synthesis of New Organic Semiconductors Based on Poly (2-anilinoethanol) Doped With Different Acids and Investigation of Their Electro-Optical Properties . In: Polymer Engineering & Science . tape 53 , no. 2 , 2012, doi : 10.1002 / pen.23246 ( PDF ).

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 2-anilinoethanol in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .

[Sigma-2] Data sheet N- (2-Hydroxyethyl) aniline from Sigma-Aldrich , accessed on May 22, 2017 ( PDF ).

[DOI10.1021/ol901189m-3] BA Bhanu Prasad, Scott R. Gilbertson: One-Pot Synthesis of Unsymmetrical N-Heterocyclic Carbene Ligands from N- (2-Iodoethyl) arylamine Salts . In: Organic Letters . tape 11 , no. 16 , August 20, 2009, pp. 3710-3713 , doi : 10.1021 / ol901189m .

[DOI10.1021/mp3000309-4] Yunqi Zhao, Shaofeng Duan, Xing Zeng, Chunjing Liu, Neal M. Davies, Benyi Li, M. Laird Forrest: Prodrug Strategy for PSMA-Targeted Delivery of TGX-221 to Prostate Cancer Cells . In: Molecular Pharmaceutics . tape 9 , no. 6 , June 4, 2012, p. 1705-1716 , doi : 10.1021 / mp3000309 .

[DOI10.1039/c3tc30536h-5] Jianjun Yin, Gang Ye, Xiaogong Wang: Star-shaped molecules containing both azo chromophores and carbazole units as a new type of photoresponsive amorphous material . In: Journal of Materials Chemistry C . tape 1 , no. 24 , 2013, p. 3794 , doi : 10.1039 / c3tc30536h .

[DOI10.1016/j.tetlet.2011.12.130-6] Huiqing Yin, Ming Jin, Wei Chen, Chen Chen, Likang Zheng, Ping Wei, Shiqing Han: Solvent-free copper-catalyzed N-arylation of amino alcohols and diamines with aryl halides . In: Tetrahedron Letters . tape 53 , no. 10 , March 2012, ISSN 0040-4039 , p. 1265-1270 , doi : 10.1016 / j.tetlet.2011.12.130 .

[7] Jean Afxantidis, Naima Bouchry, Jean-Pierre Aune: Synthesis of indole, benzofuran and benzothiophene by reaction of 2-anilinoethanol, 2-phenoxyethanol and 2- (phenylthio) ethanol on AlPO4 and Pd / AlPO4 catalysts . In: Journal of Molecular Catalysis A: Chemical . tape 102 , no. 1 , September 1995, pp. 49-58 , doi : 10.1016 / 1381-1169 (95) 00082-8 ( PDF ).

[8] E. Ahlatcıoğlu, BF Şenkal, F. Yakuphanoğlu, Sh. A. Mansour: Synthesis of New Organic Semiconductors Based on Poly (2-anilinoethanol) Doped With Different Acids and Investigation of Their Electro-Optical Properties . In: Polymer Engineering & Science . tape 53 , no. 2 , 2012, doi : 10.1002 / pen.23246 ( PDF ).