pentachloroaniline
{{Chembox
| Name = Pentachloroaniline
| ImageFile = Pentachloroaniline.svg
| ImageSize = 120px
| ImageAlt =
| PIN = 2,3,4,5,6-pentachloroaniline
| OtherNames = Benzenamine, pentachloroaminobenzene{{cite web |last1=Informatics |first1=NIST Office of Data and |title=2,3,4,5,6-Pentachloroaniline |url=https://webbook.nist.gov/cgi/cbook.cgi?ID=C527208&Mask=200 |website=webbook.nist.gov |access-date=23 April 2025 |language=en}}
| Section1 = {{Chembox Identifiers
| CASNo = 527-20-8
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UW5QVL647I
| DTXSID = DTXSID4037584
| PubChem = 10693
| ChemSpiderID =
| EINECS = 208-410-3
| SMILES = C1(=C(C(=C(C(=C1Cl)Cl)Cl)Cl)Cl)N
| StdInChI= InChI=1S/C6H2Cl5N/c7-1-2(8)4(10)6(12)5(11)3(1)9/h12H2
| StdInChIKey= KHCZSJXTDDHLGJ-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=6|H=2|Cl=5|N=1
| Appearance = yellow crystalline solid
| Density = 1.75 g/cm³
| Solubility = practically insoluble
| MeltingPtC = -43.8
| BoilingPtC = 81.6
| VaporPressure =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| GHSPictograms = {{GHS07}}{{GHS02}}{{cite web |title=Pentachloroaniline |url=https://www.accustandard.com/prod0010207.html |publisher=accustandard.com |access-date=23 April 2025 |language=en}}
| GHSSignalWord = DANGER
| HPhrases =
| PPhrases =
| FlashPtC =
| AutoignitionPt =
}}
}}
Pentachlorotoluene is a chemical compound from the group of chloroanilines. Its chemical formula is {{chem2|C6H2Cl5N}}.{{cite web |title=NCATS Inxight Drugs — PENTACHLOROANILINE |url=https://drugs.ncats.io/drug/UW5QVL647I |publisher=drugs.ncats.io |access-date=23 April 2025 |language=en}} Pentachloroaniline occurs as a derivative of pentachloronitrobenzene.{{cite web |title=Pentachloroaniline |url=https://sitem.herts.ac.uk/aeru/ppdb/en/Reports/949.htm |publisher=sitem.herts.ac.uk |access-date=23 April 2025}}{{cite web |title=Pentachloroaniline |url=https://www.sigmaaldrich.com/RU/en/product/sial/46012?srsltid=AfmBOorUejTh89JMteOrHMdHdfSwMMHGz2Lu5PjxBugSYMN2DYRVEAur |publisher=Sigma Aldrich |access-date=23 April 2025}}
Synthesis
Pentachloroaniline can be obtained by reducing pentachloronitrobenzene with tin, hydrochloric acid, and ethanol. It is also formed by the action of chlorine on an ethereal solution of symmetrical m-dichloroaniline.{{cite book |last1=Erlenmeyer |first1=Emil |title=Lehrbuch der organischen Chemie |date=1894 |publisher=C.F. Winter'sche Verlagshandlung |page=743 |url=https://books.google.de/books?id=L-s-AAAAYAAJ&pg=PA743#v=onepage&q&f=false |access-date=23 April 2025 |language=de}}
Physical characteristics
Pentachloroaniline is a yellow crystalline solid, practically insoluble in water, but readily dissolves in organic solvents. Highly flammable.
Uses
Pentachloroaniline is highly important in the industrial field, where it is utilized in various ways. Belonging to the aniline group, which comprises substances such as aniline and chloroanilines, it is employed as a dye and as an intermediate in the synthesis of plasticizers and pesticides. Additionally, it is involved in rubber production and functions as a flame retardant.{{cite web |title=Pentachloroaniline {{!}} CAS 527-20-8 {{!}} SCBT - Santa Cruz Biotechnology |url=https://www.scbt.com/p/pentachloroaniline-527-20-8?srsltid=AfmBOoo4t-_LrnQBK0sGTq5y4L3jAy04oByleypvFGMz7x8sgSSE3c9V |publisher=scbt.com |access-date=23 April 2025 |language=en}}