1-phenylethanol

Structural formula
	( R ) shape (left) and ( S ) shape (right)
General
Surname	1-phenylethanol
other names	α-methylbenzyl alcohol; Phenylmethylcarbinol; 1-phenylethan-1-ol; 1-hydroxyethylbenzene;
Molecular formula	C 8 H 10 O
Brief description	colorless liquid with a faint floral odor
External identifiers / databases
ECHA InfoCard	100.002.461
PubChem	7409
Wikidata	Q3740715
properties
Molar mass	122.17 g mol −1
Physical state	liquid
density	1.01 g cm −3
Melting point	20 ° C
boiling point	204 ° C
Vapor pressure	0.1 hPa (20 ° C)
solubility	very heavy in water (<1 g l −1 at 20 ° C); soluble in most organic solvents;
Refractive index	1.527 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-319
	P: 301 + 312 + 330-305 + 351 + 338
Toxicological data	400 mg kg −1 ( LD 50 , rat , oral )
	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

1-Phenylethanol is a chemical compound from the group of alcohols and is a structural isomer to 2-phenylethanol .

Occurrence

1-Phenylethanol occurs naturally as part of the aroma of blueberries .

Extraction and presentation

Racemic 1-phenylethanol can be obtained by reducing acetophenone (e.g. with lithium aluminum hydride ), by reacting methyl magnesium chloride with benzaldehyde or by oxidizing ethylbenzene . It is also formed during the hydrolysis of ( S ) -1-bromoethylbenzene , the racemate also being obtained from ( S ) - and ( R ) -1-phenylethanol.

There are also specific syntheses for ( S ) - or ( R ) -1-phenylethanol, which proceed with high enantioselectivity . The enantioselective reduction of acetophenone is the method of choice. Enantioselective catalysts are used in each case .

properties

1-Phenylethanol is a poorly volatile, hardly flammable, colorless liquid with a faint floral odor that is sparingly soluble in water. It reacts with an acidic solution of sodium dichromate to form benzoic acid .

use

1-Phenylethanol is used as a high boiler in coating materials. It is also used to produce styrene .

Safety instructions / toxicology

1-Phenylethanol was included in the EU's ongoing action plan ( CoRAP ) in 2017 in accordance with Regulation (EC) No. 1907/2006 (REACH) as part of substance evaluation . The effects of the substance on human health and the environment are re-evaluated and, if necessary, follow-up measures are initiated. Ingestion of 1-phenylethanol was caused by concerns about consumer use , worker exposure and widespread use, as well as the potential dangers of carcinogenic and mutagenic properties. The re-evaluation has been running since 2019 and is carried out by Italy .

Individual evidence

↑ ^a ^b ^c ^d Entry on 1-phenylethanol in the Hazardous Substances Data Bank , accessed on January 27, 2013.
↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 1-phenylethanol in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .
↑ Data sheet 1-Phenylethanol, 98% from Sigma-Aldrich , accessed on January 27, 2013 ( PDF ).
^ Ralf G. Berger: Flavors and Fragrances . Springer, 2007, ISBN 3-540-49339-5 , pp. 164 ( limited preview in Google Book search).
↑ Joachim Buddrus: Fundamentals of organic chemistry . Walter de Gruyter, 2011, ISBN 3-11-024894-8 , p. 509 ( limited preview in Google Book search).
↑ K. Peter C. Vollhardt, Neil E. Schore: Organic chemistry . John Wiley & Sons, 2011, ISBN 3-527-32754-1 , pp. 282 ( limited preview in Google Book search).
↑ Sabine Wallbaum and Jürgen Martens: Asymmetric Syntheses with Chiral Oxazaborolidines , In: Tetrahedron: Asymmetry 1992 , 3 , 1475-1504, DOI: 10.1016 / S0957-4166 (00) 86044-9 .
↑ Paula Yurkanis Bruice: Organic Chemistry: Study compact . Pearson Deutschland GmbH, 2011, ISBN 3-86894-102-9 , p. 611 ( limited preview in Google Book search).
↑ by Hans-Georg Elias: Macromolecules: Volume 3: Industrial Polymers and Syntheses - Hans-Georg Elias . John Wiley & Sons, 2009, ISBN 3-527-62652-2 , pp. 203 ( limited preview in Google Book search).
↑ Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 1-phenylethanol , accessed on March 26, 2019.Template: CoRAP status / 2019

[HSDB-1] Entry on 1-phenylethanol in the Hazardous Substances Data Bank , accessed on January 27, 2013.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j Entry on 1-phenylethanol in the GESTIS substance database of the IFA , accessed on January 8, 2018(JavaScript required) .

[Sigma-3] Data sheet 1-Phenylethanol, 98% from Sigma-Aldrich , accessed on January 27, 2013 ( PDF ).

[Ralf_G._Berger-4] Ralf G. Berger: Flavors and Fragrances . Springer, 2007, ISBN 3-540-49339-5 , pp. 164 ( limited preview in Google Book search).

[Joachim_Buddrus-5] Joachim Buddrus: Fundamentals of organic chemistry . Walter de Gruyter, 2011, ISBN 3-11-024894-8 , p. 509 ( limited preview in Google Book search).

[K._Peter_C._Vollhardt,_Neil_E._Schore-6] K. Peter C. Vollhardt, Neil E. Schore: Organic chemistry . John Wiley & Sons, 2011, ISBN 3-527-32754-1 , pp. 282 ( limited preview in Google Book search).

[Wallbaum2-7] Sabine Wallbaum and Jürgen Martens: Asymmetric Syntheses with Chiral Oxazaborolidines , In: Tetrahedron: Asymmetry 1992 , 3 , 1475-1504, DOI: 10.1016 / S0957-4166 (00) 86044-9 .

[Paula_Yurkanis_Bruice-8] Paula Yurkanis Bruice: Organic Chemistry: Study compact . Pearson Deutschland GmbH, 2011, ISBN 3-86894-102-9 , p. 611 ( limited preview in Google Book search).

[von_Hans-Georg_Elias-9] y Hans-Georg Elias: Macromolecules: Volume 3: Industrial Polymers and Syntheses - Hans-Georg Elias . John Wiley & Sons, 2009, ISBN 3-527-62652-2 , pp. 203 ( limited preview in Google Book search).

[10] Community rolling action plan ( CoRAP ) of the European Chemicals Agency (ECHA): 1-phenylethanol , accessed on March 26, 2019.Template: CoRAP status / 2019