M-Phenylenediamine: Difference between revisions

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	{{DISPLAYTITLE:''m''-Phenylenediamine}}		{{DISPLAYTITLE:''m''-Phenylenediamine}}
	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| Name = ''m''-Phenylenediamine
			\| Watchedfields = changed
⚫	\| verifiedrevid = ~~443928316~~
		⚫	\| Name = ''m''-Phenylenediamine
⚫	\| ImageFile = m-phenylenediamine.png
		⚫	\| verifiedrevid = 443930184
	\| ImageSize =
		⚫	\| ImageFile = m-phenylenediamine.png
	\| IUPACName = 1,3-diaminobenzene
	\| ~~OtherNames~~ = ~~MPD~~		\| ImageSize =
			\| ImageFileL1 = Meta-phenylenediamine-from-xtal-3D-bs-17.png
⚫	\| Section1 = {{Chembox Identifiers
			\| ImageSizeL1 = 125px
⚫	\| CASNo_Ref = {{cascite}}
			\| ImageFileR1 = Meta-phenylenediamine-from-xtal-3D-sf.png
			\| ImageSizeR1 = 125px
			\| PIN = Benzene-1,3-diamine
			\| OtherNames = 1,3-Diaminobenzene<br />MPD<br />MPDA
		⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 108-45-2		\| CASNo = 108-45-2
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
⚫	\| PubChem =
			\| ChEBI = 8092
⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| ChEMBL = 1595914
			\| KEGG = C02454
			\| Beilstein = 471357
		⚫	\| PubChem = 7935
		⚫	\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = OE624J2447		\| UNII = OE624J2447
	\| ~~SMILES~~ = ~~Nc1cc(N)ccc1~~		\| RTECS = SS7700000
			\| UNNumber = 1673
⚫	}}
			\| EINECS = 203-584-7
⚫	\| Section2 = {{Chembox Properties
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
⚫	\| Formula = C<sub>6</sub>H<sub>8</sub>N<sub>2</sub>
			\| ChemSpiderID = 13836283
⚫	\| MolarMass = 108.1
			\| SMILES = c1cc(cc(c1)N)N
⚫	\| Appearance = White solid
			\| InChI = 1/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
⚫	\| Density =
			\| InChIKey = WZCQRUWWHSTZEM-UHFFFAOYAM
	\| MeltingPt = 64 - 66 °C
			\| StdInChI_Ref = {{stdinchicite\|changed\|chemspider}}
⚫	\| ~~BoilingPt~~ = 282 - 284 °C
			\| StdInChI = 1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
	\| Solubility =
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
⚫	}}
			\| StdInChIKey = WZCQRUWWHSTZEM-UHFFFAOYSA-N
⚫	\| Section3 = {{Chembox Hazards
		⚫	}}
⚫	\| MainHazards =
		⚫	\| Section2 = {{Chembox Properties
	\| FlashPt =
		⚫	\| Formula = C<sub>6</sub>H<sub>8</sub>N<sub>2</sub>
	\| Autoignition = 560 °C
		⚫	\| MolarMass = 108.1 g·mol<sup>−1</sup>
	\| RPhrases = {{R23}} {{R24}} {{R25}} {{R36}} {{R37}} {{R38}} {{R40}} {{R42}} {{R43}}
		⚫	\| Appearance = White solid
	\| SPhrases = {{S22}} {{S26}} {{S36}} {{S37}} {{S39}} {{S45}}
		⚫	\| Density =
⚫	}}
			\| MeltingPtC = 64 to 66
			\| MeltingPt_notes =
		⚫	\| BoilingPtC = 282 to 284
			\| BoilingPt_notes =
			\| Solubility = 42.9 g/100 ml (20 °C)
			\| pKa = {{ubl
			\| 2.50 (doubly protonated form; 20 °C, H<sub>2</sub>O)
			\| 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>
		⚫	}}
			\| MagSus = -70.53·10<sup>−6</sup> cm<sup>3</sup>/mol
		⚫	}}
		⚫	\| Section3 = {{Chembox Hazards
		⚫	\| MainHazards =
			\| FlashPtC = 187
			\| AutoignitionPtC = 560
			\| AutoignitionPt_notes =
			\| GHSPictograms = {{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}
			\| GHSSignalWord = Danger
			\| HPhrases = {{H-phrases\|301\|311\|317\|319\|331\|341\|410}}
			\| 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}}
			\| 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>
			\| NFPA-H = 3
			\| NFPA-F = 1
			\| NFPA-R = 0
			\| NFPA-S =
			}}
	}}		}}

	'''''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.		'''''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.

	==Production==		==Production==
	''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>		''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>

	==Applications==		==Applications==
	''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		''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>
	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>

	==References==		==References==
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	{{DEFAULTSORT:Phenylenediamine, m-}}		{{DEFAULTSORT:Phenylenediamine, m-}}
	]		]
	]		]


	{{amine-stub}}

	]
	]

Latest revision as of 10:56, 16 November 2023

m-Phenylenediamine

Names

Preferred IUPAC name Benzene-1,3-diamine

Other names 1,3-Diaminobenzene
MPD
MPDA

Identifiers

CAS Number

108-45-2

3D model (JSmol)

Interactive image

Beilstein Reference

471357

ChEBI

CHEBI:8092

ChEMBL

ChEMBL1595914

ChemSpider

13836283

ECHA InfoCard

100.003.259

EC Number

203-584-7

KEGG

C02454

PubChem CID

7935

RTECS number

SS7700000

UNII

OE624J2447

UN number

1673

CompTox Dashboard (EPA)

DTXSID4021137

InChI

InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2Key: WZCQRUWWHSTZEM-UHFFFAOYSA-N
InChI=1/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2Key: WZCQRUWWHSTZEM-UHFFFAOYAM

SMILES

c1cc(cc(c1)N)N

Properties

Chemical formula

C₆H₈N₂

Molar mass

108.1 g·mol

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)

Solubility in water

42.9 g/100 ml (20 °C)

Acidity (pK_a)

2.50 (doubly protonated form; 20 °C, H₂O)
5.11 (conjugate acid; 20 °C, H₂O)

Magnetic susceptibility (χ)

-70.53·10 cm/mol

Hazards

GHS labelling:

Pictograms

Signal word

Danger

Hazard statements

H301, H311, H317, H319, H331, H341, H410

Precautionary 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, P501

NFPA 704 (fire diamond)

3 1 0

Flash point

187 °C (369 °F; 460 K)

Autoignition
temperature

560 °C (1,040 °F; 833 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

N verify (what is ?) Infobox references

Chemical compound

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. Samples often come as colourless flakes and may darken in storage.

Production

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

Applications

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.

References

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, 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

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