2-Chloro-6-fluorobenzaldehyde
{{Chembox
| Name = 2-Chloro-6-fluorobenzaldehyde
| PIN = 2-Chloro-6-fluorobenzaldehyde
| ImageFile = 2-Chloro-6-fluorobenzaldehyde.svg
| ImageSize = 150px
| Section1 = {{Chembox Identifiers
| CASNo = 387-45-1
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 67847
| UNII = 51YJ9BW8W7
| EC_number = 206-860-5
| ChemSpiderID = 61164
| SMILES = C1=CC(=C(C(=C1)Cl)C=O)F
| InChI = 1S/C7H4ClFO/c8-6-2-1-3-7(9)5(6)4-10/h1-4H
| InChIKey = OACPOWYLLGHGCR-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
|C=7 |H=4 |Cl=1 |F=1 |O=1
| Appearance = White solid
| Density =
| MeltingPt = 32–35 °C (89.6-95 °F; 305–308 K)
| BoilingPt = 104–105 °C (219–221 °F; 377–378 K)
| LogP =
| HenryConstant =
| Solubility = Insoluble in water
| SolubleOther = Soluble in methanol, ethanol
}}
| Section7 = {{Chembox Hazards
| MainHazards =
| NFPA-H = 2
| NFPA-F = 0
| NFPA-I = 0
| NFPA-S =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335|401}}
| PPhrases = {{P-phrases|261|264| 271|280|302+352|304+340|305+351+338|321|362+364|403+233|405|501}}
| FlashPt = 101 °C (214 °F; 374 K)
}}
| Section8 = {{Chembox Related
| OtherCompounds = 2-Chloro-6-fluorobenzaldoxime
Chlorobenzaldehyde
Fluorobenzaldehyde
}}
}}
2-Chloro-6-fluorobenzaldehyde is a halogenated benzaldehyde derivative with the formula C6H3ClFCHO. It is an intermediate in the synthesis of halogenated heterocyclic compounds.{{Cite journal |last1=Daniewski |first1=Andrzej R. |last2=Liu |first2=Wen |last3=Püntener |first3=Kurt |last4=Scalone |first4=Michelangelo |date=2002-05-01 |title=Two Efficient Methods for the Preparation of 2-Chloro-6-methylbenzoic Acid |url=https://pubs.acs.org/doi/10.1021/op0102363 |journal=Organic Process Research & Development |language=en |volume=6 |issue=3 |pages=220–224 |doi=10.1021/op0102363 |issn=1083-6160}}{{Cite journal |last1=Naveen |first1=S. |last2=Kavitha |first2=Chandagirikoppal V. |last3=Sarala |first3=G. |last4=Anandalwar |first4=SridharM. |last5=Prasad |first5=J. Shashidhara |last6=Rangappa |first6=Kanchugarakoppal S. |date=2006 |title=Crystal Structure of 3-(2-Chloro-6-fluorophenyl)-2-(4-methoxyphenyl)-acrylonitrile |url=http://www.jstage.jst.go.jp/article/analscix/22/0/22_0_x291/_article |journal=Analytical Sciences: X-ray Structure Analysis Online |language=en |volume=22 |pages=X291–X292 |doi=10.2116/analscix.22.x291 |issn=1348-2238|doi-access=free }}
Preparation, reactions, use
2-Chloro-6-fluorobenzaldehyde is prepared by oxidation of 2-chloro-6-fluorotolulene by chromyl chloride.{{Cite journal |doi=10.1002/cber.19310641019 |title=Über Brom-Addition an substituierte Zimtsäuren |date=1931 |last1=Willstaedt |first1=Harry |journal=Berichte der Deutschen Chemischen Gesellschaft (A and B Series) |volume=64 |issue=10 |pages=2688–2693 }}
It reacts with sodium hydroxide to give a mixture of 2-chloro-6-fluorobenzene and 6-chlorosalicaldehyde.{{Cite journal |last=Bunnett |first=J. F. |last2=Miles |first2=J. H. |last3=Nahabedian |first3=K. V. |date=1961 |title=Kinetics and Mechanism of the Alkali Cleavage of 2,6-Dihalobenzaldehydes 1 |url=https://pubs.acs.org/doi/abs/10.1021/ja01472a022 |journal=Journal of the American Chemical Society |language=en |volume=83 |issue=11 |pages=2512–2516 |doi=10.1021/ja01472a022 |issn=0002-7863}}
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
{{DEFAULTSORT:Chloro-6-fluorobenzaldehyde, 2-}}
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