2-Chloro-6-fluorobenzaldehyde

Last updated
2-Chloro-6-fluorobenzaldehyde
2-Chloro-6-fluorobenzaldehyde.svg
Names
Preferred IUPAC name
2-Chloro-6-fluorobenzaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.006.237 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 206-860-5
PubChem CID
UNII
  • InChI=1S/C7H4ClFO/c8-6-2-1-3-7(9)5(6)4-10/h1-4H
    Key: OACPOWYLLGHGCR-UHFFFAOYSA-N
  • C1=CC(=C(C(=C1)Cl)C=O)F
Properties
C7H4ClFO
Molar mass 158.56 g·mol−1
AppearanceWhite solid
Melting point 32–35 °C (89.6-95 °F; 305–308 K)
Boiling point 104–105 °C (219–221 °F; 377–378 K)
Insoluble in water
Solubility Soluble in methanol, ethanol
Hazards
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H315, H319, H335, H401
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P321, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
Flash point 101 °C (214 °F; 374 K)
Related compounds
Related compounds
 2-Chloro-6-fluorobenzaldoxime
Chlorobenzaldehyde
Fluorobenzaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

2-Chloro-6-fluorobenzaldehyde is a halogenated benzaldehyde derivative with the formula C6H3ClFCHO. It is an intermediate in the synthesis of halogenated heterocyclic compounds. [1] [2]

Preparation, reactions, use

2-Chloro-6-fluorobenzaldehyde is prepared by oxidation of 2-chloro-6-fluorotolulene by chromyl chloride. [3]

It reacts with sodium hydroxide to give a mixture of 2-chloro-6-fluorobenzene and 6-chlorosalicaldehyde. [4]

2-Chloro-6-fluorobenzaldehyde is used in the production of the antiseptics dicloxacillin and flucloxacillin. Additionally it is used in the production of pesticides.

References

  1. ↑ Daniewski, Andrzej R.; Liu, Wen; Püntener, Kurt; Scalone, Michelangelo (2002-05-01). "Two Efficient Methods for the Preparation of 2-Chloro-6-methylbenzoic Acid" . Organic Process Research & Development. 6 (3): 220–224. doi:10.1021/op0102363. ISSN   1083-6160.
  2. ↑ Naveen, S.; Kavitha, Chandagirikoppal V.; Sarala, G.; Anandalwar, SridharM.; Prasad, J. Shashidhara; Rangappa, Kanchugarakoppal S. (2006). "Crystal Structure of 3-(2-Chloro-6-fluorophenyl)-2-(4-methoxyphenyl)-acrylonitrile". Analytical Sciences: X-ray Structure Analysis Online. 22: X291 –X292. doi: 10.2116/analscix.22.x291 . ISSN   1348-2238.
  3. ↑ Willstaedt, Harry (1931). "Über Brom-Addition an substituierte Zimtsäuren". Berichte der Deutschen Chemischen Gesellschaft (A and B Series). 64 (10): 2688–2693. doi:10.1002/cber.19310641019.
  4. ↑ Bunnett, J. F.; Miles, J. H.; Nahabedian, K. V. (1961). "Kinetics and Mechanism of the Alkali Cleavage of 2,6-Dihalobenzaldehydes 1" . Journal of the American Chemical Society. 83 (11): 2512–2516. doi:10.1021/ja01472a022. ISSN   0002-7863.


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