Benzal chloride

Benzal chloride

Names
IUPAC name Dichloromethylbenzene
Systematic IUPAC name (Dichloromethyl)benzene
Other names benzyl dichloride benzylidene chloride α,α-Dichlorobenzenea
Identifiers
CAS Number	98-87-3 N
Beilstein Reference	1099407
ChemSpider	13882337 Y
EC Number	249-854-8
Jmol interactive 3D	Image
KEGG	C19165 Y
MeSH	Compounds Benzylidene Compounds
PubChem	7411
RTECS number	CZ5075000
UNII	222447TR16 N
UN number	1886
InChI InChI=1S/C7H6Cl2/c8-7(9)6-4-2-1-3-5-6/h1-5,7H Y Key: CAHQGWAXKLQREW-UHFFFAOYSA-N Y
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/cm3, 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 @10 mm Hg)
Solubility in water	0.25 g/L at 39 °C
Vapor pressure	0.6 kPa (45 °C)
Hazards
EU classification (DSD)	Toxic (T), Carc. Cat. 2B, Dangerous for the environment (N)
R-phrases	22-23-37/38-40-41
S-phrases	36/37-38-45
Flash point	93 °C (199 °F; 366 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Benzal chloride is an organic compound with the formula C₆H₅CHCl₂.^[1] 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:^[2]

C₆H₅CHCl₂ + H₂O → C₆H₅CHO + 2 HCl

References

1. ↑ "BENZAL CHLORIDE". International Programme on Chemical Safety. Retrieved 2007-10-30. 
2. ↑ Karl-August Lipper and Eckhard Löser “Benzyl Chloride and Other Side-Chain Chlorinated Aromatic Hydrocarbons" in Ullmann’s Encyclopedia of Industrial Chemistry, 2011, Wiley-VCH, Weinheim. doi:10.1002/14356007.o04_o01