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    Aniline

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    triana
    Aniline is an organic compound consisting of a phenyl group attached to an amino group, making it the simplest aromatic amine. It is a colorless liquid that is flammable and toxic. Aniline is industrially significant as it is used to make precursors for polyurethane, dyes, and other industrial chemicals. It readily undergoes electrophilic aromatic substitution and oxidation reactions due to being electron-rich relative to benzene.

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    Aniline

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    triana
    21 views8 pages
    Aniline is an organic compound consisting of a phenyl group attached to an amino group, making it the simplest aromatic amine. It is a colorless liquid that is flammable and toxic. Aniline is industrially significant as it is used to make precursors for polyurethane, dyes, and other industrial chemicals. It readily undergoes electrophilic aromatic substitution and oxidation reactions due to being electron-rich relative to benzene.

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    Aniline is an organic compound consisting of a phenyl group attached to an amino group, making it the simplest aromatic amine. It is a colorless liquid that is flammable and toxic. Aniline is industrially significant as it is used to make precursors for polyurethane, dyes, and other industrial chemicals. It readily undergoes electrophilic aromatic substitution and oxidation reactions due to being electron-rich relative to benzene.

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    © All Rights Reserved
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    Download as pdf or txt
    21 views8 pages

    Aniline

    Uploaded by

    triana
    Aniline is an organic compound consisting of a phenyl group attached to an amino group, making it the simplest aromatic amine. It is a colorless liquid that is flammable and toxic. Aniline is industrially significant as it is used to make precursors for polyurethane, dyes, and other industrial chemicals. It readily undergoes electrophilic aromatic substitution and oxidation reactions due to being electron-rich relative to benzene.

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    of 8

    Aniline

    Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group
    attached to an amino group, aniline is the simplest aromatic amine. It is an industrially
    significant commodity chemical, as well as a versatile starting material for fine chemical
    synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other
    industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily,
    burning with a smoky flame characteristic of aromatic compounds.[6] It is toxic to humans.
    Aniline

    Names

    Preferred IUPAC name


    Aniline[1]

    Systematic IUPAC name


    Benzenamine

    Other names
    Phenylamine

    Aminobenzene

    Benzamine

    Identifiers

    CAS Number 62-53-3 (https://commonchemistry.cas.org/detai


    l?cas_rn=62-53-3)  

    142-04-1 (https://commonchemistry.cas.org/deta
    il?cas_rn=142-04-1) (HCl) 

    3D model (JSmol) Interactive image (https://chemapps.stolaf.edu/j


    mol/jmol.php?model=Nc1ccccc1)

    Interactive image (https://chemapps.stolaf.edu/j


    mol/jmol.php?model=c1ccc%28cc1%29N)

    3DMet B00082 (http://www.3dmet.dna.affrc.go.jp/cgi/sh


    ow_data.php?acc=B00082)

    Beilstein Reference 605631


    ChEBI CHEBI:17296 (https://www.ebi.ac.uk/chebi/searc
    hId.do?chebiId=17296)  

    ChEMBL ChEMBL538 (https://www.ebi.ac.uk/chembldb/in


    dex.php/compound/inspect/ChEMBL538)  

    ChemSpider 5889 (https://www.chemspider.com/Chemical-Str


    ucture.5889.html)  

    DrugBank DB06728 (https://www.drugbank.ca/drugs/DB0


    6728)  

    ECHA InfoCard 100.000.491 (https://echa.europa.eu/substance-i


    nformation/-/substanceinfo/100.000.491)

    EC Number 200-539-3

    Gmelin Reference 2796

    KEGG C00292 (https://www.kegg.jp/entry/C00292)  

    PubChem CID 6115 (https://pubchem.ncbi.nlm.nih.gov/compou


    nd/6115)

    8870 (https://pubchem.ncbi.nlm.nih.gov/compou
    nd/8870)  (HCl)

    RTECS number BW6650000

    UNII SIR7XX2F1K (https://fdasis.nlm.nih.gov/srs/srsdi


    rect.jsp?regno=SIR7XX2F1K)  

    576R1193YL (https://fdasis.nlm.nih.gov/srs/srsdi
    rect.jsp?regno=576R1193YL)  (HCl) 

    UN number 1547

    CompTox Dashboard (EPA) DTXSID8020090 (https://comptox.epa.gov/dashb


    oard/chemical/details/DTXSID8020090)

    InChI
    InChI=1S/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2 
    Key: PAYRUJLWNCNPSJ-UHFFFAOYSA-N 
    InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
    Key: PAYRUJLWNCNPSJ-UHFFFAOYAP
    SMILES
    Nc1ccccc1
    c1ccc(cc1)N

    Properties

    Chemical formula C6H7N

    Molar mass 93.129 g·mol−1

    Appearance Colorless liquid

    Density 1.0297 g/mL

    Melting point −6.30 °C (20.66 °F; 266.85 K)

    Boiling point 184.13 °C (363.43 °F; 457.28 K)

    Solubility in water 3.6 g/100 mL at 20 °C

    Vapor pressure 0.6 mmHg (20° C)[2]

    Acidity (pKa) 4.63 (conjugate acid; H2O)[3]

    Magnetic susceptibility (χ) −62.95·10−6 cm3/mol

    Refractive index (nD) 1.58364

    Viscosity 3.71 cP (3.71 mPa·s at 25 °C)

    Thermochemistry

    Std enthalpy of
    −3394 kJ/mol
    combustion (ΔcH⦵298)

    Hazards

    Occupational safety and health (OHS/OSH):

    Main hazards potential occupational carcinogen

    GHS labelling:

    Pictograms

    Signal word Danger


    Hazard statements H301, H311, H317, H318, H331, H341, H351,
    H372, H400

    Precautionary statements P201, P202, P260, P261, P264, P270, P271, P272,
    P273, P280, P281, P301+P310, P302+P352,
    P304+P340, P305+P351+P338, P308+P313,
    P310, P311, P312, P314, P321, P322, P330,
    P333+P313, P361, P363, P391, P403+P233,
    P405, P501

    NFPA 704 (fire diamond) [5]

    2
    3 0

    Flash point 70 °C (158 °F; 343 K)

    Autoignition
    770 °C (1,420 °F; 1,040 K)
    temperature

    Explosive limits 1.3–11%[2]

    Lethal dose or concentration (LD, LC):

    LDLo (lowest published) 195 mg/kg (dog, oral)

    250 mg/kg (rat, oral)

    464 mg/kg (mouse, oral)

    440 mg/kg (rat, oral)

    400 mg/kg (guinea pig, oral)[4]

    LC50 (median concentration) 175 ppm (mouse, 7 h)[4]

    LCLo (lowest published) 250 ppm (rat, 4 h)

    180 ppm (cat, 8 h)[4]

    NIOSH (US health exposure limits):

    PEL (Permissible) TWA 5 ppm (19 mg/m3) [skin][2]

    REL (Recommended) Ca [potential occupational carcinogen][2]

    IDLH (Immediate danger) 100 ppm[2]

    Related compounds

    Related aromatic amines 1-Naphthylamine

    2-Naphthylamine

    Related compounds Phenylhydrazine

    Nitrosobenzene

    Nitrobenzene

    Supplementary data page

    Aniline (data page)

    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F],
    100 kPa).
     verify (https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=443390967&page2=
    Aniline)  (what is   ?)
    Infobox references

    Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic


    substitution reactions. Likewise, it is also prone to oxidation: while freshly purified aniline is an
    almost colorless oil, exposure to air results in gradual darkening to yellow or red, due to the
    formation of strongly colored, oxidized impurities. Aniline can be diazotized to give a diazonium
    salt, which can then undergo various nucleophilic substitution reactions.

    “Aniline” is ultimately from Portuguese anil which means "the indigo shrub", with suffix -ine
    indicating "derived substance".[7]

    Like other amines, aniline is both a base (pKaH = 4.6) and a nucleophile, although less so than
    structurally similar aliphatic amines.

    Because an early source of the benzene from which they are derived was coal tar, aniline dyes
    are also called coal tar dyes.

    Structure

    Production

    Reactions

    Uses
    History

    Toxicology and testing

    Notes

    References

    External links

    Retrieved from
    "https://en.wikipedia.org/w/index.php?
    title=Aniline&oldid=1123033439"


    Last edited 16 days ago by InvalidOS

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