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{{DISPLAYTITLE:''m''-Phenylenediamine}} |
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{{DISPLAYTITLE:''m''-Phenylenediamine}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| Name = ''m''-Phenylenediamine |
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| Watchedfields = changed |
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| verifiedrevid = 443928316 |
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| Name = ''m''-Phenylenediamine |
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| ImageFile = m-phenylenediamine.png |
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| verifiedrevid = 443930184 |
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| ImageSize = |
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| ImageFile = m-phenylenediamine.png |
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| IUPACName = 1,3-diaminobenzene |
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| OtherNames = MPD |
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| ImageSize = |
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| ImageFileL1 = Meta-phenylenediamine-from-xtal-3D-bs-17.png |
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| Section1 = {{Chembox Identifiers |
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| ImageSizeL1 = 125px |
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| CASNo_Ref = {{cascite}} |
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| ImageFileR1 = Meta-phenylenediamine-from-xtal-3D-sf.png |
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| ImageSizeR1 = 125px |
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| PIN = Benzene-1,3-diamine |
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| OtherNames = 1,3-Diaminobenzene<br />MPD<br />MPDA |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 108-45-2 |
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| CASNo = 108-45-2 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| PubChem = |
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| ChEBI = 8092 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL = 1595914 |
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| KEGG = C02454 |
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| Beilstein = 471357 |
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| PubChem = 7935 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = OE624J2447 |
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| UNII = OE624J2447 |
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| SMILES = Nc1cc(N)ccc1 |
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| RTECS = SS7700000 |
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| UNNumber = 1673 |
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}} |
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| EINECS = 203-584-7 |
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| Section2 = {{Chembox Properties |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Formula = C<sub>6</sub>H<sub>8</sub>N<sub>2</sub> |
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| ChemSpiderID = 13836283 |
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| MolarMass = 108.1 |
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| SMILES = c1cc(cc(c1)N)N |
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| Appearance = White solid |
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| InChI = 1/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2 |
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| Density = |
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| InChIKey = WZCQRUWWHSTZEM-UHFFFAOYAM |
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| MeltingPt = 64 - 66 °C |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| BoilingPt = 282 - 284 °C |
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| StdInChI = 1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2 |
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| Solubility = |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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| StdInChIKey = WZCQRUWWHSTZEM-UHFFFAOYSA-N |
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| Section3 = {{Chembox Hazards |
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}} |
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| MainHazards = |
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| Section2 = {{Chembox Properties |
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| FlashPt = |
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| Formula = C<sub>6</sub>H<sub>8</sub>N<sub>2</sub> |
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| Autoignition = 560 °C |
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| MolarMass = 108.1 g·mol<sup>−1</sup> |
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| RPhrases = {{R23}} {{R24}} {{R25}} {{R36}} {{R37}} {{R38}} {{R40}} {{R42}} {{R43}} |
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| Appearance = White solid |
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| SPhrases = {{S22}} {{S26}} {{S36}} {{S37}} {{S39}} {{S45}} |
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| Density = |
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}} |
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| MeltingPtC = 64 to 66 |
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| MeltingPt_notes = |
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| BoilingPtC = 282 to 284 |
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| BoilingPt_notes = |
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| Solubility = 42.9 g/100 ml (20 °C) |
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| pKa = {{ubl |
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| 2.50 (doubly protonated form; 20 °C, H<sub>2</sub>O) |
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| 5.11 (conjugate acid; 20 °C, H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = ] | isbn = 978-1498754286 | page=5–89 | title-link = CRC Handbook of Chemistry and Physics }}</ref> |
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}} |
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| MagSus = -70.53·10<sup>−6</sup> cm<sup>3</sup>/mol |
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}} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPtC = 187 |
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| AutoignitionPtC = 560 |
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| AutoignitionPt_notes = |
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| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|311|317|319|331|341|410}} |
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| PPhrases = {{P-phrases|201|202|261|264|270|271|272|273|280|281|301+310|302+352|304+340|305+351+338|308+313|311|312|321|322|330|333+313|337+313|361|363|391|403+233|405|501}} |
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| NFPA_ref= <ref name"fisher>{{cite web|url=https://www.fishersci.com/store/msds?partNumber=AC130570025&productDescription=P-PHENYLENEDIAMINE+99%2B%25+2.5KG&countryCode=US&language=en |title=m-Phenylenediamine MSDS|publisher=Thermo Fisher Scientific}}</ref> |
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| NFPA-H = 3 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-S = |
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}} |
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'''''m''-Phenylenediamine''', also called '''1,3-diaminobenzene''', is an ] with the ] C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub>. It is an isomer of ] and ]. It is a colourless solid. |
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'''''m''-Phenylenediamine''', also called '''1,3-diaminobenzene''', is an ] with the ] C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)<sub>2</sub>. It is an isomer of ] and ]. This ] ] is a colourless solid that appears as needles, but turns red or purple on exposure to air due to formation of oxidation products.<ref>{{cite web|title=1,3-PHENYLENEDIAMINE {{!}} CAMEO Chemicals {{!}} NOAA|url=https://cameochemicals.noaa.gov/chemical/1315|website=CAMEO Chemicals|access-date=27 November 2021}}</ref> Samples often come as colourless flakes and may darken in storage. |
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==Production== |
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==Production== |
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''m''-Phenylenediamine is produced by hydrogenation of 1,3-dinitrobenzene. The dinitrobenzene is prepared by di] of benzene.<ref name=Ullmann>Robert A. Smiley “Phenylene- and Toluenediamines” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a19_405}}</ref> |
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''m''-Phenylenediamine is produced by hydrogenation of ]. The dinitrobenzene is prepared by di] of ].<ref>{{Citation|doi=10.1002/14356007.a19_405|chapter=Phenylene- and Toluenediamines|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2000|last1=Smiley|first1=Robert A.|isbn=3527306730}}</ref> |
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==Applications== |
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==Applications== |
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''m''-Phenylenediamine is used in the preparation various ]s including ] fibers, ]s, wire enamel coatings and polyurea ]s. Other uses for ''m''-phenylenediamine include as an accelerator for adhesive resins, and as a component of dyes for leather and textiles.Basic Brown 1 (Bismarck Brown), Basic Orange |
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''m''-Phenylenediamine is used in the preparation of various ]s including ] fibers, ]s, wire enamel coatings and polyurea ]s. Other uses for ''m''-phenylenediamine include as an accelerator for adhesive resins, and as a component of dyes for leather and textiles. ], Basic Orange 2, Direct Black 38, and Developed Black BH. In hair-dying, ''m''-phenylenediamine is a "coupling agent", used to produce blue colors.<ref>{{Citation|doi=10.1002/14356007.a12_571.pub2|chapter=Hair Preparations|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2006|last1=Clausen|first1=Thomas|last2=Schwan-Jonczyk|first2=Annette|last3=Lang|first3=Günther|last4=Schuh|first4=Werner|last5=Liebscher|first5=Klaus Dieter|last6=Springob|first6=Christian|last7=Franzke|first7=Michael|last8=Balzer|first8=Wolfgang|last9=Imhoff|first9=Sonja|last10=Maresch|first10=Gerhard|last11=Bimczok|first11=Rudolf|isbn=3527306730}}</ref> |
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2, Direct Black 38, and Developed Black BH In hair-dying, ''m''-phenylenediamine is a "coupling agent", used to produce blue colors.<ref>Thomas Clausen et al. “Hair Preparations” in Ullmann’s Encyclopedia of Industrial Chemistry. Wiley-VCH, Weinheim (2006). {{DOI|10.1002/14356007.a12_571.pub2}}</ref> |
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==References== |
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==References== |
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{{DEFAULTSORT:Phenylenediamine, m-}} |
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{{DEFAULTSORT:Phenylenediamine, m-}} |
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{{amine-stub}} |
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