m-Xylylenediamine

m-Xylylenediamine
Names
	Preferred IUPAC name 1,1′-(1,3-Phenylene)di(methanamine)
	Other names m-Xylene-α,α'-diamine; 1,3-Benzenedimethanamine; MXDA; m-Phenylenebis(methylamine); 1,3-Bis(aminomethyl)benzene; 1,3-Phenylenedimethanamine; 1,3-Xylylenediamine; m-Xylylenediamine; 1,3-Xylenediamine; m-Xylenediamine; 1,3-Bis(aminomethyl)benzene
Identifiers
CAS Number	1477-55-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	14404;
ECHA InfoCard	100.014.575
EC Number	216-032-5;
PubChem CID	15133;
RTECS number	PF8970000;
UNII	1E84B9YLJD ;
UN number	2735
CompTox Dashboard (EPA)	DTXSID9029649 ;
	InChI InChI=1S/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2;
	SMILES C1=CC(=CC(=C1)CN)CN;
Properties
Chemical formula	C8H12N2
Molar mass	136.198 g·mol−1
Appearance	Colorless liquid
Odor	Amine
Density	1.032 g/cm3 (20°C)
Melting point	14 °C; 58 °F; 288 K
Boiling point	247 °C; 477 °F; 520 K
Solubility in water	Miscible (20°C)
Vapor pressure	0.03 mmHg (25°C)
Hazards
Flash point	117 °C; 243 °F; 390 K
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	700 ppm/1 hour (rat, inhalation); 930 mg/kg (rat, oral); 2 g/kg (rabbit, skin)
	NIOSH (US health exposure limits):
REL (Recommended)	C 0.1 mg/m3 [skin]
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

m-Xylylenediamine is an organic compound with the formula C₆H₄(CH₂NH₂)₂. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.^[4]

Uses and reactions[edit]

m-Xylylenediamine (MXDA) is used in a variety of industrial applications including amine based curing agents for epoxy resins^[5] which may then be formulated into coatings, adhesives, sealants, and elastomers.^[1]

m-Xylylenediamine undergoes to Sommelet reaction to give isophthalaldehyde.^[6]

Hazards[edit]

Exposure to m-xylylenediamine may occur by inhalation, skin contact, eye exposure, or ingestion. It can cause chemical burns, tissue damage, delayed pulmonary edema, shock, and skin sensitization. Symptoms of inhalation include a burning sensation in the respiratory tract, cough, sore throat, labored breathing, and dyspnea (shortness of breath). It is also flammable and produces toxic fumes when burned. m-Xylylenediamine reacts with acids, acid chlorides, and acid anhydrides.^[1]^[7]

References[edit]

^ ^a ^b ^c "M-Xylylenediamine". PubChem.
^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0671". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b ^c "RTECS PF88DF10". NIOSH.
^ Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 978-3527306732.
^ "MXDA│Epoxy Resin Curing Agents│MITSUBISHI GAS CHEMICAL CO.,INC". www.aromaticchemicals.com. Retrieved 2018-08-19.
^ Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.
^ "1,3-BIS(AMINOMETHYL)BENZENE". International Chemical Safety Cards.

External links[edit]

[PubChem-1] "M-Xylylenediamine". PubChem.

[NPG-2] ^ ^a ^b ^c ^d ^e ^f ^g NIOSH Pocket Guide to Chemical Hazards. "#0671". National Institute for Occupational Safety and Health (NIOSH).

[RTECS-3] "RTECS PF88DF10". NIOSH.

[4] Pollak, Peter; Romeder, Gérard; Hagedorn, Ferdinand; Gelbke, Heinz-Peter (2000). "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_363. ISBN 978-3527306732.

[5] "MXDA│Epoxy Resin Curing Agents│MITSUBISHI GAS CHEMICAL CO.,INC". www.aromaticchemicals.com. Retrieved 2018-08-19.

[6] Ackerman, J. H.; Surrey, A. R. (1967). "Isophthalaldehyde". Organic Syntheses. 47: 76. doi:10.15227/orgsyn.047.0076.

[7] "1,3-BIS(AMINOMETHYL)BENZENE". International Chemical Safety Cards.

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