Misplaced Pages

Benzal chloride

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
Benzal chloride
Skeletal formula of benzal chloride
Skeletal formula of benzal chloride
Ball-and-stick model of benzal chloride
Ball-and-stick model of benzal chloride
Names
Preferred IUPAC name (Dichloromethyl)benzene
Other names
  • Benzyl dichloride
  • Benzylidene chloride
  • α,α-Dichlorotoluene
  • PhCl2H
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1099407
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.463 Edit this at Wikidata
EC Number
  • 249-854-8
KEGG
MeSH Compounds Benzylidene Compounds
PubChem CID
RTECS number
  • CZ5075000
UNII
UN number 1886 2810
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6Cl2/c8-7(9)6-4-2-1-3-5-6/h1-5,7HKey: CAHQGWAXKLQREW-UHFFFAOYSA-N
SMILES
  • ClC(Cl)c1ccccc1
  • C1=CC=C(C=C1)C(Cl)Cl
Properties
Chemical formula C7H6Cl2
Molar mass 161.03 g/mol
Appearance Colorless liquid
Density 1.254 g/cm, liquid
Melting point −17 to −15 °C (1 to 5 °F; 256 to 258 K)
Boiling point 205 °C (401 °F; 478 K) (82 °C at 10 mmHg)
Solubility in water 0.25 g/L at 39 °C
Vapor pressure 0.6 kPa (45 °C)
Hazards
GHS labelling:
Pictograms GHS03: OxidizingGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Signal word Danger
Hazard statements H302, H315, H318, H331, H335, H351
Precautionary statements P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501
Flash point 93 °C (199 °F; 366 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Benzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis.

Preparation and usage

Benzal chloride is produced by the free radical chlorination of toluene, being preceded in the process by benzyl chloride (C6H5CH2Cl) and followed by benzotrichloride (C6H5CCl3):

C6H5CH3 + Cl2 → C6H5CH2Cl + HCl
C6H5CH2Cl + Cl2 → C6H5CHCl2 + HCl
C6H5CHCl2 + Cl2 → C6H5CCl3 + HCl

Benzylic halides are typically strong alkylating agents, and for this reason benzal chloride is treated as a hazardous compound.

Treatment of benzal chloride with sodium gives stilbene.

Most benzal chloride main industrial use is as a precursor to benzaldehyde. This conversion involves hydrolysis in the presence of base:

C6H5CHCl2 + H2O → C6H5CHO + 2 HCl

References

  1. "BENZAL CHLORIDE". International Programme on Chemical Safety. Retrieved 2007-10-30.
  2. Lipper, Karl-August; Löser, Eckhard (2011). "Benzyl Chloride and Other Side-Chain Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o04_o01. ISBN 978-3527306732.
Categories: