Pentabromotoluene
{{Chembox
| Name = Pentabromotoluene
| ImageFile = 1,2,3,4,5-pentabromo-6-methylbenzene.svg
| ImageSize = 120px
| ImageAlt =
| PIN = 1,2,3,4,5-pentabromo-6-methylbenzene
| OtherNames = Pentabromomethylbenzene, 2,3,4,5,6-Pentabromotoluene, PBT
| Section1 = {{Chembox Identifiers
| CASNo = 87-83-2
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 87007N97G5
| DTXSID = DTXSID3025833
| PubChem = 6906
| ChemSpiderID = 6640
| EINECS = 201-774-4
| SMILES = Cc1c(Br)c(Br)c(Br)c(Br)c1Br
| StdInChI= 1S/C7H3Br5/c1-2-3(8)5(10)7(12)6(11)4(2)9/h1H3
| StdInChIKey= OZHJEQVYCBTHJT-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=7|H=3|Br=5
| Appearance = white crystals
| Density = 1.67 g/cm³
| Solubility = soluble
| MeltingPtC = 290
| BoilingPtC =
| VaporPressure =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = WARNING
| HPhrases = {{HPhrases|315|319|335}}
| PPhrases =
| FlashPtC =
| AutoignitionPt =
}}
}}
Pentachlorotoluene is a synthetic organobromine compound with the molecular formula {{chem2|C6Br5CH3}}.{{cite web |title=2,3,4,5,6-Pentabromotoluene 98.0+%, TCI America - Chemicals, Organic compounds |url=https://www.fishersci.com/shop/products/2-3-4-5-6-pentabromotoluene-98-0-tci-america/P082725G |publisher=Fisher Scientific |access-date=22 April 2025 |language=en}}{{cite web |title=Pentabromotoluene |url=https://drugs.ncats.io/drug/87007N97G5 |publisher=drugs.ncats.io |access-date=22 April 2025}}
Synthesis
Pentabromotoluene is a derivative of toluene and is synthesized from it.{{cite journal |last1=Nevile |first1=R. H. C. |last2=Winther |first2=A. |title=Die sechs Tribromtoluole, die drei Tetrabromtoluole und das Pentabromtoluol |journal=Berichte der deutschen chemischen Gesellschaft |date=1880 |volume=13 |issue=1 |pages=974–976 |doi=10.1002/cber.188001301273 |url=https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/cber.188001301273 |access-date=22 April 2025 |language=en |issn=1099-0682}}
Physical properties
The compound forms white crystalline powder. Its crystals are of monoclinic system.{{cite journal |last1=Krigbaum |first1=W. R. |last2=Wildman |first2=G. C. |title=The crystal structure of pentabromotoluene |journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry |date=15 December 1971 |volume=27 |issue=12 |pages=2353–2358 |doi=10.1107/S0567740871005879 |url=https://journals.iucr.org/paper?a08426 |access-date=22 April 2025 |language=en |issn=0567-7408}} Due to the substitution with five bromine atoms on the aromatic ring, pentabromotoluene has a significantly lower volatility than toluene.
Uses
Pentabromotoluene is widely used as a flame retardant in textiles, rubber, unsaturated polyesters, polyethylene, SBR latex, etc.{{cite web |title=2,3,4,5,6-Pentabromotoluene |url=https://www.sigmaaldrich.com/RU/en/product/sial/07444?srsltid=AfmBOooAK0W9Rwx3ucEm8tpnPHCjBaFx6fF-YL1yi5CENwsZODqBKH09 |publisher=Sigma Aldrich |access-date=22 April 2025}}{{cite book |last1=Milne |first1=G. W. A. |title=Gardner's Commercially Important Chemicals: Synonyms, Trade Names, and Properties |date=19 August 2005 |publisher=John Wiley & Sons |isbn=978-0-471-73661-5 |page=474 |url=https://www.google.ru/books/edition/Gardner_s_Commercially_Important_Chemica/oWdc2qcb3QsC?hl=en&gbpv=1&dq=Pentabromotoluene&pg=PA474&printsec=frontcover |access-date=22 April 2025 |language=en}}