2-Chloro-6-fluorobenzaldehyde

2-Chloro-6-fluorobenzaldehyde
Names
	Preferred IUPAC name 2-Chloro-6-fluorobenzaldehyde
Identifiers
CAS Number	387-45-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	61164;
ECHA InfoCard	100.006.237
EC Number	206-860-5;
PubChem CID	67847;
UNII	51YJ9BW8W7;
CompTox Dashboard (EPA)	DTXSID4022028 ;
	InChI InChI=1S/C7H4ClFO/c8-6-2-1-3-7(9)5(6)4-10/h1-4H Key: OACPOWYLLGHGCR-UHFFFAOYSA-N;
	SMILES C1=CC(=C(C(=C1)Cl)C=O)F;
Properties
Chemical formula	C7H4ClFO
Molar mass	158.56 g·mol−1
Appearance	White solid
Melting point	32–35 °C (89.6-95 °F; 305–308 K)
Boiling point	104–105 °C (219–221 °F; 377–378 K)
Solubility in water	Insoluble in water
Solubility	Soluble in methanol, ethanol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335, H401
Precautionary statements	P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P321, P362+P364, P403+P233, P405, P501
NFPA 704 (fire diamond)	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). Infobox references

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

^ 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.
^ 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.
^ 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.
^ 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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[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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