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1-Bromo-4-fluorobenzene

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4-Bromofluorobenzene
Skeletal Structure of 4-Bromofluorobenzene
Skeletal Structure of 4-Bromofluorobenzene
Space Filling Model of 4-Bromofluorobenzene
Space Filling Model of 4-Bromofluorobenzene
Names
Preferred IUPAC name
1-Bromo-4-fluorobenzene
Other names
p-Bromofluorobenzene
p-Fluorophenyl bromide
Identifiers
3D model (JSmol)
Abbreviations PBFB
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.638 Edit this at Wikidata
EC Number
  • 207-300-2
UNII
UN number 1993
  • InChI=1S/C6H4BrF/c7-5-1-3-6(8)4-2-5/h1-4H checkY
    Key: AITNMTXHTIIIBB-UHFFFAOYSA-N checkY
  • InChI=1S/C6H4BrF/c7-5-1-3-6(8)4-2-5/h1-4H
    Key: AITNMTXHTIIIBB-UHFFFAOYSA-N
  • c1cc(ccc1F)Br
Properties
C6H4BrF
Molar mass 175.000 g·mol−1
Appearance colorless liquid
Melting point −16 °C (3 °F; 257 K)
Boiling point 150 °C (302 °F; 423 K)
Insoluble
Structure
Planar
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation mark
Warning
H226, H302, H312, H315, H319, H332, H335, H336
P210, P233, P240, P241, P242, P243, P261, P264, P270, P271, P280, P301+P312, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
2
0
Related compounds
Related halobenzenes
1,4-Dichlorobenzene
1,4-Dibromobenzene
1,4-Diiodobenzene
Related compounds
Benzene
1,4-Difluorobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Fluorobromobenzene is a mixed aryl halide (aryl fluoride and aryl bromide) with the formula C6H4BrF. It is a derivative of benzene, with a bromine atom bonded para to a fluorine atom. It has uses as a precursor to some pharmaceuticals, as an agrochemical intermediate, and in organic synthesis.[1] It is a colorless liquid of low acute toxicity.

Production and uses

[edit]

4-Fluorobromobenzene is synthesized via bromination of fluorobenzene in the presence of a Lewis acid catalyst such as iron(III) bromide or aluminium tribromide.[2]

4-Bromofluorobenzene is regarded by the Toxic Substances Control Act as a high production volume chemical, that is, a chemical that 1 million pounds (about 500 tonnes) per year is either produced in or imported to the United States. As of 2002, companies producing or importing this compound reported 10 million (4,536,000 kilograms) used. This is up from 500,000 pounds (226,800 kilograms) used in 1986, as reported in the Inventory Update Rule of the Toxic Substances Control Act.[1] [3]

Reactions

[edit]

4-Bromofluorobenzene is a standard substrate for cross-coupling reactions[4][5] It forms a Grignard reagent used in the synthesis of 4-fluorophenyl containing compounds,[1][6] such as the pesticide Flusilazole.[7]

Drugs List

[edit]
  1. WIN-35428
  2. SCH-57871
  3. Tefludazine & Irindalone
  4. Seganserin
  5. Setoperone
  6. Citalopram
  7. Paroxetine (from arecoline)

Safety

[edit]

This compound is a flammable liquid. It has a flash point of 53 °C.[3]

References

[edit]
  1. ^ a b c "4-Bromofluorobenzene [CAS No. 460-00-4] Review of Toxicological Literature" (PDF). National Toxicology Program. Retrieved 2 January 2015.
  2. ^ Rosenthal, Joel; Schuster, David I. (2003). "The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena". J. Chem. Educ. 80 (6): 679. Bibcode:2003JChEd..80..679R. doi:10.1021/ed080p679.
  3. ^ a b "Material Safety Data Sheet". Acros Organics. Retrieved 2 January 2015.
  4. ^ Tan, Yichen; Hartwig, John F. (2010). "Palladium-Catalyzed Amination of Aromatic C−H Bonds with Oxime Esters". Journal of the American Chemical Society. 132 (11): 3676–3677. doi:10.1021/ja100676r. PMID 20187645.
  5. ^ Liégault, Benoît; Lapointe, David; Caron, Laurence; Vlassova, Anna; Fagnou, Keith (2009). "Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds". The Journal of Organic Chemistry. 74 (5): 1826–1834. doi:10.1021/jo8026565. PMID 19206211.
  6. ^ Patent US4605655 - Neuroleptic agents; no movement disorder side effects - Google Patents
  7. ^ "4-Bromofluorobenzene". Shandong A&Fine Agrochemicals Co., Ltd. Archived from the original on 13 December 2014. Retrieved 2 January 2015.