2-Chlorobenzaldehyde

Last updated
2-Chlorobenzaldehyde
2-Chlorbenzaldehyd.svg
Names
Preferred IUPAC name
2-Chlorobenzaldehyde
Other names
o-Chlorobenzaldehyde
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.779 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-956-3
PubChem CID
RTECS number
  • CU5075000
UNII
UN number 3265
  • InChI=1S/C7H5ClO/c8-7-4-2-1-3-6(7)5-9/h1-5H
    Key: FPYUJUBAXZAQNL-UHFFFAOYSA-N
  • c1ccc(c(c1)C=O)Cl
Properties
C7H5ClO
Molar mass 140.57 g·mol−1
AppearanceClear colourless to pale yellow oily liquid
Density 1.25
Melting point 9–12 °C (48–54 °F; 282–285 K)
Boiling point 209–215 °C (408–419 °F; 482–488 K)
Insoluble
Solubility Slightly soluble in Acetonitrile, sparingly soluble in DMSO
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
Danger
H290, H302, H314, H317
P234, P260, P261, P264, P270, P272, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P330, P333+P313, P363, P390, P404, P405, P501
Flash point 87 °C (189 °F; 360 K)
385 °C (725 °F; 658 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Chlorobenzaldehyde (o-chlorobenzaldehyde) is an organic compound with the formula ClC5H4CHO. It is one of three isomeric monochlorinated benzaldehyde. 3-Chlorobenzaldehyde and 4-chlorobenzaldehyde are the other isomers. Whereas benzaldehyde is prone to autoxidation, the 2-chloro derivatives are more air-stable.

Synthesis and uses

It is produced by hydrolysis of 2-chlorobenzal chloride: [1]

ClC5H4CHCl2 + H2O → ClC5H4CHO + 2 HCl

2-Chlorobenzaldehyde is used in production of CS gas. It reacts with malononitrile to form CS. [2]

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References

  1. Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_463.pub2. ISBN   978-3-527-30385-4.
  2. "Synthesis of ortho-chlorobenzalmalononitrile".