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m-Phenylenediamine

m-Phenylenediamine, also called 1,3-diaminobenzene, is an organic compound with the formula C6H4(NH2)2. It is an isomer of o-phenylenediamine and p-phenylenediamine. This aromatic diamine is a colourless solid that appears as needles, but turns red or purple on exposure to air due to formation of oxidation products.[3] Samples often come as colourless flakes and may darken in storage.

m-Phenylenediamine
Names
Preferred IUPAC name
Benzene-1,3-diamine
Other names
1,3-Diaminobenzene
MPD
MPDA
Identifiers
  • 108-45-2 Y
3D model (JSmol)
  • Interactive image
471357
ChEBI
  • CHEBI:8092 N
ChEMBL
  • ChEMBL1595914
ChemSpider
  • 13836283 N
ECHA InfoCard 100.003.259
EC Number
  • 203-584-7
KEGG
  • C02454
  • 7935
RTECS number
  • SS7700000
UNII
  • OE624J2447 Y
UN number 1673
  • DTXSID4021137
  • InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2 N
    Key: WZCQRUWWHSTZEM-UHFFFAOYSA-N N
  • InChI=1/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
    Key: WZCQRUWWHSTZEM-UHFFFAOYAM
  • c1cc(cc(c1)N)N
Properties
C6H8N2
Molar mass 108.1 g·mol−1
Appearance White solid
Melting point 64 to 66 °C (147 to 151 °F; 337 to 339 K)
Boiling point 282 to 284 °C (540 to 543 °F; 555 to 557 K)
42.9 g/100 ml (20 °C)
Acidity (pKa)
  • 2.50 (doubly protonated form; 20 °C, H2O)
  • 5.11 (conjugate acid; 20 °C, H2O)[1]
-70.53·10−6 cm3/mol
Hazards
GHS labelling:
Danger
H301, H311, H317, H319, H331, H341, H410
P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
Flash point 187 °C (369 °F; 460 K)
560 °C (1,040 °F; 833 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Production edit

m-Phenylenediamine is produced by hydrogenation of 1,3-dinitrobenzene. The dinitrobenzene is prepared by dinitration of benzene.[4]

Applications edit

m-Phenylenediamine is used in the preparation of various polymers including aramid fibers, epoxy resins, wire enamel coatings and polyurea elastomers. 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, Basic Orange 2, Direct Black 38, and Developed Black BH. In hair-dying, m-phenylenediamine is a "coupling agent", used to produce blue colors.[5]

References edit

  1. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89. ISBN 978-1498754286.
  2. ^ "m-Phenylenediamine MSDS". Thermo Fisher Scientific.
  3. ^ "1,3-PHENYLENEDIAMINE | CAMEO Chemicals | NOAA". CAMEO Chemicals. Retrieved 27 November 2021.
  4. ^ Smiley, Robert A. (2000), "Phenylene- and Toluenediamines", Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a19_405, ISBN 3527306730
  5. ^ Clausen, Thomas; Schwan-Jonczyk, Annette; Lang, Günther; Schuh, Werner; Liebscher, Klaus Dieter; Springob, Christian; Franzke, Michael; Balzer, Wolfgang; Imhoff, Sonja; Maresch, Gerhard; Bimczok, Rudolf (2006), "Hair Preparations", Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a12_571.pub2, ISBN 3527306730

phenylenediamine, also, called, diaminobenzene, organic, compound, with, formula, c6h4, isomer, phenylenediamine, phenylenediamine, this, aromatic, diamine, colourless, solid, that, appears, needles, turns, purple, exposure, formation, oxidation, products, sam. m Phenylenediamine also called 1 3 diaminobenzene is an organic compound with the formula C6H4 NH2 2 It is an isomer of o phenylenediamine and p phenylenediamine This aromatic diamine is a colourless solid that appears as needles but turns red or purple on exposure to air due to formation of oxidation products 3 Samples often come as colourless flakes and may darken in storage m Phenylenediamine NamesPreferred IUPAC name Benzene 1 3 diamineOther names 1 3 DiaminobenzeneMPDMPDAIdentifiersCAS Number 108 45 2 Y3D model JSmol Interactive imageBeilstein Reference 471357ChEBI CHEBI 8092 NChEMBL ChEMBL1595914ChemSpider 13836283 NECHA InfoCard 100 003 259EC Number 203 584 7KEGG C02454PubChem CID 7935RTECS number SS7700000UNII OE624J2447 YUN number 1673CompTox Dashboard EPA DTXSID4021137InChI InChI 1S C6H8N2 c7 5 2 1 3 6 8 4 5 h1 4H 7 8H2 NKey WZCQRUWWHSTZEM UHFFFAOYSA N NInChI 1 C6H8N2 c7 5 2 1 3 6 8 4 5 h1 4H 7 8H2Key WZCQRUWWHSTZEM UHFFFAOYAMSMILES c1cc cc c1 N NPropertiesChemical formula C6H8N2Molar mass 108 1 g mol 1Appearance White solidMelting point 64 to 66 C 147 to 151 F 337 to 339 K Boiling point 282 to 284 C 540 to 543 F 555 to 557 K Solubility in water 42 9 g 100 ml 20 C Acidity pKa 2 50 doubly protonated form 20 C H2O 5 11 conjugate acid 20 C H2O 1 Magnetic susceptibility x 70 53 10 6 cm3 molHazardsGHS labelling PictogramsSignal word DangerHazard statements H301 H311 H317 H319 H331 H341 H410Precautionary statements P201 P202 P261 P264 P270 P271 P272 P273 P280 P281 P301 P310 P302 P352 P304 P340 P305 P351 P338 P308 P313 P311 P312 P321 P322 P330 P333 P313 P337 P313 P361 P363 P391 P403 P233 P405 P501NFPA 704 fire diamond 2 310Flash point 187 C 369 F 460 K Autoignitiontemperature 560 C 1 040 F 833 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesProduction editm Phenylenediamine is produced by hydrogenation of 1 3 dinitrobenzene The dinitrobenzene is prepared by dinitration of benzene 4 Applications editm Phenylenediamine is used in the preparation of various polymers including aramid fibers epoxy resins wire enamel coatings and polyurea elastomers 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 Basic Orange 2 Direct Black 38 and Developed Black BH In hair dying m phenylenediamine is a coupling agent used to produce blue colors 5 References edit Haynes William M ed 2016 CRC Handbook of Chemistry and Physics 97th ed CRC Press p 5 89 ISBN 978 1498754286 m Phenylenediamine MSDS Thermo Fisher Scientific 1 3 PHENYLENEDIAMINE CAMEO Chemicals NOAA CAMEO Chemicals Retrieved 27 November 2021 Smiley Robert A 2000 Phenylene and Toluenediamines Ullmann s Encyclopedia of Industrial Chemistry doi 10 1002 14356007 a19 405 ISBN 3527306730 Clausen Thomas Schwan Jonczyk Annette Lang Gunther Schuh Werner Liebscher Klaus Dieter Springob Christian Franzke Michael Balzer Wolfgang Imhoff Sonja Maresch Gerhard Bimczok Rudolf 2006 Hair Preparations Ullmann s Encyclopedia of Industrial Chemistry doi 10 1002 14356007 a12 571 pub2 ISBN 3527306730 Retrieved from https en wikipedia org w index php title M Phenylenediamine amp oldid 1185384547, wikipedia, wiki, book, books, library,

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