Просмотр кода страницы Английская Википедия:Bromochlorobenzene

{{Английская Википедия/Панель перехода}}
'''Bromochlorobenzene''' is any of three different [[positional isomer]]s consisting of a [[bromine]] atom and a [[chlorine]] atom as [[substituent]]s on a [[benzene]] ring.

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! {{Chemical datatable header}}  align="center" colspan="4" | Isomers of Bromochlorobenzene
|-
| [[Skeletal formula]]
| [[File:1-bromo-2-chlorobenzene 200.svg|center|80px]]
| [[File:1-bromo-3-chlorobenzene 200.svg|center|105px]]
| [[File:1-bromo-4-chlorobenzene 200.svg|center|80px]]
|-
! {{Chemical datatable header}} align="center" colspan="4" | General
|-
| Common names
| '''''o''-bromochlorobenzene'''<br>''ortho''-bromochlorobenzene
| '''''m''-bromochlorobenzene'''<br>''meta''-bromochlorobenzene
| '''''p''-bromochlorobenzene'''<br>''para''-bromochlorobenzene
|-
| [[IUPAC nomenclature|Systematic name]]
| 1-bromo-2-chlorobenzene
| 1-bromo-3-chlorobenzene
| 1-bromo-4-chlorobenzene
|-
| [[Chemical formula|Molecular formula]]
| align="center" colspan="3" | BrC<sub>6</sub>H<sub>4</sub>Cl
|-
| [[Molar mass]]
| align="center" colspan="3" |  191.45&nbsp;g/mol
|-
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| [[CAS registry number|CAS number]]
| {{Chembox CASNo/format|localValue=694-80-4}}
| {{Chembox CASNo/format|localValue=108-37-2}}
| {{Chembox CASNo/format|localValue=106-39-8}}
|-
| [[ChemSpider]]
| {{Chembox ChemSpiderID/format|localValue=12230}}
| {{Chembox ChemSpiderID/format|localValue=13875377}}
| {{Chembox ChemSpiderID/format|localValue=7518}}
|-
| [[PubChem]] {{abbr|CID|Compound ID}}
| {{Chembox PubChem/format|localValue=12754}}
| {{Chembox PubChem/format|localValue=7928}}
| {{Chembox PubChem/format|localValue=7806}}
|-
! {{Chemical datatable header}} align="center" colspan="4" | Properties
|-
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|  g/cm<sup>3</sup>, solid
|  g/cm<sup>3</sup>, liquid
|  g/cm<sup>3</sup>, liquid
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| [[Soluble|Solubility]] in [[Water (molecule)|pure water]]<br /> at 20−25&nbsp;°C
|  g/100 ml
|  g/100 ml
|  g/100 ml
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| [[Melting point]]
|  {{convert|-13|°C|K}}
|  {{convert|-22|°C|K}}
|  {{convert|63-67|°C|K}}
|-
| [[Boiling point]]
| {{convert|203-205|°C|K}}
| {{convert|195-196|°C|K}}
| {{convert|196|°C|K}}
|-
<!--
! {{Chemical datatable header}} align="center" colspan="4" | Structure
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| [[Dipole#Molecular dipoles|Dipole moment]]
|  [[Debye|D]]
|  [[Debye|D]]
|  [[Debye|D]]
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|-
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{{clear}}<!-- wide chembox forces the bullet-list below the box on narrow monitors; want to keep the intro sentence to it close to it -->
All three have been synthesized by various routes:
* [[1-Bromo-2-chlorobenzene]]: from 2-[[chloroaniline]], via [[diazotization]] followed by a [[Sandmeyer reaction]]<ref>{{OrgSynth |first= Jonathan L. |last= Hartwell |year=1944 |title= ''o''-Chlorobromobenzene |volume= 24 |pages= 22 |prep= CV3P0185 }}</ref>
* [[1-Bromo-3-chlorobenzene]]: by (3-chlorophenyl)trimethylgermanium by [[electrophilic substitution]]<ref>{{cite journal |doi=10.1021/jo00380a031|title=Use of aryltrimethylgermanium substrates for facile aromatic chlorination, bromination, and iodination|journal=The Journal of Organic Chemistry|volume=52|issue=4|pages=664–667|year=1987|last1=Moerlein|first1=S. M.}}</ref>{{better source needed|date=January 2019}}
* [[1-Bromo-4-chlorobenzene]]:
**From a derivative of (4-bromophenyl)silane using [[N-Bromosuccinimide|''N''-bromosuccinimide]]<ref>{{cite journal |doi=10.1246/cl.1981.243|title=Carbon–silicon bond cleavage of organotrialkoxysilanes and organosilatranes with ''m''-chloroperbenzoic acid and ''N''-bromosuccinimide. New route to phenols, primary alcohols and bromides|journal=Chemistry Letters|volume=10|issue=2|pages=243–246|year=1981|last1=Hosomi|first1=Akira|last2=Iijima|first2=Susumu|last3=Sakurai|first3=Hideki}}</ref>
**From [[4-Chlorophenol|4-chlorophenol]] using [[triphenylphosphine dibromide]]<ref>{{cite journal|doi=10.1021/ja01059a073|title = Studies in Organophosphorus Chemistry. I. Conversion of Alcohols and Phenols to Halides by Tertiary Phosphine Dihalides|journal = Journal of the American Chemical Society|volume = 86|issue = 5|pages = 964–965|year = 1964|last1 = Wiley|first1 = G. A.|last2 = Hershkowitz|first2 = R. L.|last3 = Rein|first3 = B. M.|last4 = Chung|first4 = B. C.}}</ref> or [[phenylphosphorus tetrachloride]]<ref>{{cite journal |doi=10.1021/jo00297a087|title=Preparation of aryl chlorides from phenols|journal=The Journal of Organic Chemistry|volume=55|issue=10|pages=3415–3417|year=1990|last1=Bay|first1=Elliott|last2=Bak|first2=David A.|last3=Timony|first3=Peter E.|last4=Leone-Bay|first4=Andrea}}</ref>

== References ==
{{reflist}}

{{Chemistry index}}
{{Authority control}}

[[Category:Chlorobenzene derivatives]]
[[Category:Bromobenzene derivatives]]
[[Category:Multiple compounds, tabular|C]]
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