Benzyl chloride

Structural formula
General
Surname	Benzyl chloride
other names	α-chlorotoluene; α-chlorotoluene; Chloromethylbenzene; Phenyl methyl chloride; Tolyl chloride; (Chloromethyl) benzene ( IUPAC );
Molecular formula	C 7 H 7 Cl
Brief description	colorless, pungent smelling liquid
External identifiers / databases
EC number	202-853-6
ECHA InfoCard	100.002.594
PubChem	7503
Wikidata	Q412260
properties
Molar mass	126.58 g mol −1
Physical state	liquid
density	1.10 g cm −3 (20 ° C)
Melting point	−39 ° C
boiling point	179 ° C
Vapor pressure	1.2 hPa (20 ° C); 2.20 hPa (30 ° C); 4.08 hPa (40 ° C); 7.25 hPa (50 ° C);
solubility	slightly soluble in water (110 mg l −1 at 25 ° C); miscible with ethanol and diethyl ether ;
Refractive index	1.5391 (20 ° C)
safety instructions
H and P phrases	H: 302-315-317-318-331-335-340-350-373
	P: 201-260-280-304 + 340 + 311-305 + 351 + 338 + 310-308 + 313
MAK	Switzerland: 0.2 mg m −3
Toxicological data	1230 mg kg −1 ( LD 50 , rat , oral ) ; 1620 mg kg −1 ( LD 50 , mouse , 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

Benzyl chloride is a colorless, tear-irritating, pungent smelling liquid that is one of the aromatic halogenated hydrocarbons . In synthetic chemistry, it is an important intermediate product in the manufacture of benzyl alcohol , plasticizers and dyes .

presentation

Benzyl chloride can be prepared by radical chlorination of toluene . This creates a mixture of the three different toluene derivatives (benzyl chloride, benzal chloride and benzotrichloride ), which are chlorine- substituted in the side chain , from which the benzyl chloride has to be separated.

properties

Physical Properties

Benzyl chloride is a colorless liquid that boils at 179 ° C under normal pressure . The heat of vaporization at the boiling point is 48.6 kJ mol ⁻¹ . According to Antoine, the vapor pressure function results from log ₁₀ (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.68263, B = 1932.142 and C = −39.396 in the temperature range from 295 to 452.6 K.

Safety-related parameters

Benzyl chloride forms flammable vapor-air mixtures above the flash point temperature. The compound has a flash point at 60 ° C. The explosion range is between 1.1 vol.% (55 g / m ³ ) as the lower explosion limit (LEL) and 14 vol.% As the upper explosion limit (UEL). According to the vapor pressure function, there is a lower explosion point of 58 ° C. The ignition temperature is 585 ° C. The substance therefore falls into temperature class T1.

use

Most of the benzyl chloride produced is processed into benzyl alcohol. Benzyl chloride is also a building block for benzylation in the manufacture of plasticizers ( benzyl phthalate ), dyes, drugs , perfumes and vulcanization accelerators . It is used as a reagent for introducing the benzyl protecting group z. B. used for amines , phenols and alcohols .

safety instructions

Benzyl chloride itself is corrosive to the eyes , respiratory tract and skin and breaks down when heated and the like. a. in hydrogen chloride . Benzyl chloride is classified as carcinogenic (Category 1B); The main routes of exposure are the respiratory tract and the skin.

If possible, the less toxic benzyl bromide should be used.

Individual evidence

↑ Benzyl chloride data sheet (PDF) from Merck , accessed on January 19, 2011.

↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on benzyl chloride in the GESTIS substance database of the IFA , accessed on January 25, 2019(JavaScript required) .

↑ Entry on benzyl chloride. In: Römpp Online . Georg Thieme Verlag, accessed on July 23, 2014.

↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-104.

↑ Entry on α-chlorotoluene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 100-44-7 or benzyl chloride ), accessed on November 2, 2015.

↑ RM Stephenson, S. Malanowski: Handbook of the Thermodynamics of Organic Compounds. Springer, 1987, ISBN 94-010-7923-4 , doi: 10.1007 / 978-94-009-3173-2 .

^ DR Stull: Vapor Pressure of Pure Substances. Organic and Inorganic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .

↑ ^a ^b ^c E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.

Web links

Commons : Benzyl chloride - Collection of pictures, videos and audio files

[Merck-1] Benzyl chloride data sheet (PDF) from Merck , accessed on January 19, 2011.

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j ^k ^l ^m ⁿ ^o ^p ^q Entry on benzyl chloride in the GESTIS substance database of the IFA , accessed on January 25, 2019(JavaScript required) .

[3] Entry on benzyl chloride. In: Römpp Online . Georg Thieme Verlag, accessed on July 23, 2014.

[CRC90_3_104-4] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-104.

[CLP_100.002.594-5] Entry on α-chlorotoluene in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .

[6] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 100-44-7 or benzyl chloride ), accessed on November 2, 2015.

[7] RM Stephenson, S. Malanowski: Handbook of the Thermodynamics of Organic Compounds. Springer, 1987, ISBN 94-010-7923-4 , doi: 10.1007 / 978-94-009-3173-2 .

[Stull-8] DR Stull: Vapor Pressure of Pure Substances. Organic and Inorganic Compounds. In: Ind. Eng. Chem. 39, 1947, pp. 517-540, doi: 10.1021 / ie50448a022 .

[Brandes-9] E. Brandes, W. Möller: Safety-related parameters. Volume 1: Flammable Liquids and Gases. Wirtschaftsverlag NW - Verlag für neue Wissenschaft, Bremerhaven 2003.