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1-Bromo-4-fluorobenzene
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4-Bromofluorobenzene 4-Fluorobromobenzene.svg 90px Skeletal Structure of 4-Bromofluorobenzene Bromofluorobenzene space filling re-edit.png 120px Space Filling Model of 4-Bromofluorobenzene 1-Bromo-4-fluorobenzene p-Bromofluorobenzenep-Fluorophenyl bromide 13875180 141551 1876826 9993 207-300-2 1993 A7ZH69I3KH 1S/C6H4BrF/c7-5-1-3-6(8)4-2-5/h1-4H c1cc(ccc1F)Br AITNMTXHTIIIBB-UHFFFAOYSA-N correct chemspider 1S/C6H4BrF/c7-5-1-3-6(8)4-2-5/h1-4H correct chemspider AITNMTXHTIIIBB-UHFFFAOYSA-N PBFB correct CAS 460-00-4
6 4 1 1 colorless liquid Insoluble -16 150
Planar
1 2 0 02 07 Warning 226 302 312 315 319 332 335 336 210 233 240 241 242 243 261 264 270 271 280 301+312 302+352 303+361+353 304+312 304+340 305+351+338 312 321 322 330 332+313 337+313 362 363 370+378 403+233 403+235 405 501
1,4-Dichlorobenzene1,4-Dibromobenzene1,4-Diiodobenzene halobenzenes Benzene1,4-Difluorobenzene
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.4-Bromofluorobenzene [CAS No. 460-00-4] Review of Toxicological Literature http://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/4-bfb_508.pdf https://web.archive.org/web/20141213021151/http://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/4-bfb_508.pdf dead December 13, 2014 National Toxicology Program 2 January 2015 It is a colorless liquid of low acute toxicity.
Production and uses
4-Fluorobromobenzene is synthesized via bromination of fluorobenzene in the presence of a Lewis acid catalyst such as iron(III) bromide or aluminium tribromide.The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena Joel Rosenthal David I. Schuster J. Chem. Educ. 2003 80 6 679 10.1021/ed080p679 2003JChEd..80..679R
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.
Material Safety Data Sheet https://www.fishersci.ca/viewmsds.do?catNo=AC107011000 Acros Organics 2 January 2015
Reactions
4-Bromofluorobenzene is a standard substrate for cross-coupling reactions10.1021/ja100676r Palladium-Catalyzed Amination of Aromatic C−H Bonds with Oxime Esters 2010 Tan Yichen Hartwig John F. Journal of the American Chemical Society 132 11 3676–3677 20187645 10.1021/jo8026565 Establishment of Broadly Applicable Reaction Conditions for the Palladium-Catalyzed Direct Arylation of Heteroatom-Containing Aromatic Compounds 2009 Liégault Benoît Lapointe David Caron Laurence Vlassova Anna Fagnou Keith The Journal of Organic Chemistry 74 5 1826–1834 19206211 It forms a Grignard reagent used in the synthesis of 4-fluorophenyl containing compounds,Patent US4605655 - Neuroleptic agents; no movement disorder side effects - Google Patents such as the pesticide Flusilazole.4-Bromofluorobenzene http://www.afineagro.com/cgi/search-en.cgi?f=product_en1+product_en_1_+company_en_1_+contact_en&id=576084&t=product_en_1_ Shandong A&Fine Agrochemicals Co., Ltd 2 January 2015 13 December 2014 https://web.archive.org/web/20141213024740/http://www.afineagro.com/cgi/search-en.cgi?f=product_en1+product_en_1_+company_en_1_+contact_en&id=576084&t=product_en_1_ dead
Drugs List
WIN-35428
SCH-57871
Tefludazine & Irindalone
Seganserin
Setoperone
Citalopram
Paroxetine (from arecoline)
Safety
This compound is a flammable liquid. It has a flash point of 53 °C.
References
Category:Bromobenzene derivatives
Category:Fluorobenzene derivatives
Category:Mixed halobenzenes