Tribromofluoromethane
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470613245
| ImageFile = Fluorotribromomethane Formula V1.svg
| ImageSize = 120px
| PIN = Tribromo(fluoro)methane
| OtherNames = Tribromofluoromethane
Tribromo-fluoro-methane
Fluorotribromomethane
Halon 1103
FC-11B3
R 11B3
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 61026
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/CBr3F/c2-1(3,4)5
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = IHZAEIHJPNTART-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 353-54-8
| EINECS = 206-535-8
| PubChem = 67707
| SMILES = BrC(Br)(Br)F
| InChI = 1/CBr3F/c2-1(3,4)5
}}
|Section2={{Chembox Properties
| Formula = CBr3F
| MolarMass = 270.72{{nbsp}}g/mol
| Appearance = Clear yellow liquid
| Density = {{ubl
| 2.7650{{nbsp}}g/cm{{sup|3}} at 25{{nbsp}}°C
| 1.8211{{nbsp}}g/cm{{sup|3}} at 0{{nbsp}}°C
}}
| MeltingPtC = -73
| MeltingPt_notes =
| BoilingPtC = 108
| BoilingPt_notes =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards = Irritant
| FlashPt =
| AutoignitionPt =
}}
}}
Tribromofluoromethane{{Cite web |last=PubChem |title=Tribromofluoromethane |url=https://pubchem.ncbi.nlm.nih.gov/compound/67707 |access-date=2022-11-25 |website=pubchem.ncbi.nlm.nih.gov |language=en}} also known as Halon 1103 or R 11B3, is a fully halogenated mixed halomethane or, more exactly, a bromofluorocarbon (BFC). It is a colorless to yellow liquid{{Cite web |title=Tribromofluoromethane 98.0 %, TCI America, Quantity: 5g {{!}} Fisher Scientific |url=https://www.fishersci.com/shop/products/tribromofluoromethane-tci-america/T23045G |access-date=2022-11-25 |website=www.fishersci.com}}
Tribromofluoromethane can be used in fire extinguishers.
Table of physical properties
| class="wikitable"
! Property ! Value |
| Refractive index, n, at 20{{nbsp}}°C
| 1.5216 |
| Surface tension at 20{{nbsp}}°C
| 31.68{{nbsp}}mN·m−1 |
| Viscosity at 0{{nbsp}}°C
| 2.09{{nbsp}}mPa·s, 2.09{{nbsp}}cP |
History
Tribromofluoromethane was first synthesised in 1919 by Hans Rathburg.{{cite thesis|degree=Graduate|last=Finch|first=Charles Richard|year=1955|title=A Study of Methods for the Production of Bromotrifluoromethane and Dibromodifluoromethane|publisher=University of Maryland}} It was later prepared by reacting carbon tetrabromide with antimony trifluoride and elemental bromine{{cite journal|first1=J. M.|last1=Birchall|first2=R. N.|last2=Haszeldine|journal=Journal of the Chemical Society|title=Polyfluoroarenes. Part I. Pentafluorophenol|year=1959|pages=13-17}} by heating at {{convert|120|to|130|C|F K}} for 1 hour and having the tribromofluormethane distill off.{{cite book |last=Armarego |first=W.L.F. |title=Purification of Laboratory Chemicals |date=March 14, 2017 |publisher=Elsevier Science |isbn=9780128054567 |page=217}}
Chemistry
Pyrolysis of tribromofluoromethane yields hexafluorobenzene at up to a 45 percent yield,{{cite journal |last1=Hellmann |first1=Margaret |last2=Peters |first2=Ernest |last3=Pummer |first3=Walter J. |last4=Wall |first4=Leo A. |title=Hexafluorobenzene from the Pyrolysis of Tribromofluoromethane |journal=Journal of the American Chemical Society |date=April 10, 1957 |volume=79 |issue=21 |pages=5654-5656}} plus bromine, alongside small quantities of bromopentafluorobenzene.{{cite journal|date=June 1961|volume=65A|issue=3|pages=239–242|title=Preparation of Fluoro- and Bromofluoroaryl Compounds by Copyrolysis of Bromofluoroalkanes|journal=Journal of Research of the National Bureau of Standards for Physical Chemistry|first1=Leo A.|last1=Wall|first2=James E.|last2=Fearn|first3=Walter J|last3=Pummer|first4=Robert E|last4=Lowry}}
The bromines in tribromofluoromethane can be substituted by reactive metals like lithium and zinc using organometallic compounds, ultimately creating fluorinated alcohols by addition of carbonyl compounds.{{cite thesis|title=Title Studies on the Synthetic Aspects of Fluoromethylmetal Reagents Derived from Tribromofluoromethane|author=Hata Takeshi|publisher=Kyoto University|page=4|date=23 March 2000|url=http://dx.doi.org/10.11501/3167283}}
Tribromofluoromethane also forms phosphorus ylides which can be used to synthesise bromofluoro-substituted terminal alkenes.{{cite book |last1=Barlow |first1=M.G. |last2=Taylor |first2=D.R. |editor1-last=Banks |editor1-first=R.E. |editor2-last=Barlow |editor2-first=M.G. |title=Fluorocarbon and Related Chemistry: Volume 2 |date=1974 |page=47 |chapter=Per- and Poly-fluorinated Olefins, Dienes, Heterocumulenes and Acetylenes}} Similar loss of bromine takes place through cyclisation with hydrazones to form 4-fluoro pyrazoles.{{cite journal |last1=Prieto |first1=Alexis |last2=Bouyssi |first2=Didier |last3=Monteiro |first3=Nuno |title=Ruthenium-Catalyzed Tandem C–H Fluoromethylation/Cyclization of N-Alkylhydrazones with CBr3F: Access to 4-Fluoropyrazoles |journal=Journal of Organic Chemistry |date=2017 |volume=82 |issue=6 |pages=3311-3316}}
References
{{reflist}}
External links
- [https://archive.today/20121210092803/http://www3.interscience.wiley.com/cgi-bin/abstract/110457839/ABSTRACT?CRETRY=1&SRETRY=0 Raman and infrared spectra of solid tribromofluoromethane]
- [https://archive.today/20070729190728/http://www.chem007.com/specification_d/chemicals/supplier/cas/Tribromofluoromethane.asp Entry at chem007.com]
{{Halomethanes}}
{{fluorine compounds}}
Category:Fire suppression agents
Category:Tribromomethyl compounds
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