:Benzal chloride

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 460122078

| ImageFileL1 = Benzal chloride.svg

| ImageNameL1 = Skeletal formula of benzal chloride

| ImageFileR1 = Benzal chloride 3D.png

| ImageNameR1 = Ball-and-stick model of benzal chloride

| PIN = (Dichloromethyl)benzene

| OtherNames = {{unbulleted list|Benzyl dichloride|Benzylidene chloride|α,α-Dichlorotoluene|PhCl2H}}

|Section1={{Chembox Identifiers

| CASNo = 98-87-3

| CASNo_Ref = {{cascite|changed|??}}

| ChemSpiderID = 13882337

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| EINECS = 249-854-8

| KEGG = C19165

| KEGG_Ref = {{keggcite|correct|kegg}}

| MeSHName = Benzylidene Compounds

| ChEBI = 82273

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1412576

| PubChem = 7411

| UNNumber = 1886 2810

| RTECS = CZ5075000

| StdInChI = 1S/C7H6Cl2/c8-7(9)6-4-2-1-3-5-6/h1-5,7H

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = CAHQGWAXKLQREW-UHFFFAOYSA-N

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| SMILES = ClC(Cl)c1ccccc1

| SMILESOther = C1=CC=C(C=C1)C(Cl)Cl

| Beilstein = 1099407

| UNII_Ref = {{fdacite|changed|FDA}}

| UNII = 222447TR16

}}

|Section2={{Chembox Properties

| Formula = C7H6Cl2

| MolarMass = 161.03 g/mol

| Appearance = Colorless liquid

| Density = 1.254 g/cm3, liquid

| MeltingPtC = −17 to −15

| BoilingPtC = 205

| BoilingPt_notes = (82 °C at 10 mmHg)

| Solubility = 0.25 g/L at 39 °C

| LogP =

| VaporPressure = 0.6 kPa (45 °C)

| HenryConstant =

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|Section3={{Chembox Structure

| CrystalStruct =

| Coordination =

| MolShape = }}

|Section4={{Chembox Hazards

| GHSPictograms = {{GHS03}}{{GHS06}}{{GHS07}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|302|315|318|331|335|351}}

| PPhrases = {{P-phrases|201|202|261|264|270|271|280|281|301+312|302+352|304+340|305+351+338|308+313|310|311|312|321|330|332+313|362|403+233|405|501}}

| MainHazards =

| NFPA-H =

| NFPA-F =

| NFPA-R =

| NFPA-S =

| FlashPtC = 93

| AutoignitionPtC =

}}

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Benzal chloride is an organic compound with the formula C6H5CHCl2.{{cite web

| url =http://www.inchem.org/documents/icsc/icsc/eics0101.htm

| title =BENZAL CHLORIDE

| publisher =International Programme on Chemical Safety

| accessdate =2007-10-30

}} 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:{{cite encyclopedia|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|url=https://onlinelibrary.wiley.com/doi/abs/10.1002/14356007.o04_o01.pub2|first1=Karl-August|last1=Lipper|first2=Eckhard|last2=Löser|title=Benzyl Chloride and Other Side-Chain Chlorinated Aromatic Hydrocarbons|year=2011 |doi=10.1002/14356007.o04_o01|isbn=978-3527306732 |url-access=subscription}}

: C6H5CHCl2 + H2O → C6H5CHO + 2 HCl

References