m-Xylylenediamine

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

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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.575
EC Number
  • 216-032-5
RTECS number
  • PF8970000
UNII
UN number 2735
  • InChI=1S/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2
  • C1=CC(=CC(=C1)CN)CN
Properties
C8H12N2
Molar mass 136.198 g·mol−1
Appearance Colorless liquid
Odor Amine[1]
Density 1.032 g/cm3 (20°C)[2]
Melting point 14 °C; 58 °F; 288 K[2]
Boiling point 247 °C; 477 °F; 520 K[2]
Miscible (20°C)[2]
Vapor pressure 0.03 mmHg (25°C)[2]
Hazards
Flash point 117 °C; 243 °F; 390 K[2]
Lethal dose or concentration (LD, LC):
700 ppm/1 hour (rat, inhalation)[3]
930 mg/kg (rat, oral)[3]
2 g/kg (rabbit, skin)[3]
NIOSH (US health exposure limits):
REL (Recommended)
 C 0.1 mg/m3 [skin][2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Uses and reactions

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

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
  1. "M-Xylylenediamine". PubChem.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0671". National Institute for Occupational Safety and Health (NIOSH).
  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.
  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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