m-Xylylenediamine

{{DISPLAYTITLE:m-Xylylenediamine}}

{{Chembox

| Name = m-Xylylenediamine

| ImageFile = M-Xylylenediamine.svg

| ImageSize = 200px

| PIN = 1,1′-(1,3-Phenylene)di(methanamine)

| OtherNames = 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

| Section1 = {{Chembox Identifiers

| CASNo = 1477-55-0

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 1E84B9YLJD

| EINECS = 216-032-5

| PubChem = 15133

| SMILES = C1=CC(=CC(=C1)CN)CN

| ChemSpiderID = 14404

| RTECS = PF8970000

| InChI = 1S/C8H12N2/c9-5-7-2-1-3-8(4-7)6-10/h1-4H,5-6,9-10H2

| UNNumber = 2735

}}

| Section2 = {{Chembox Properties

| C=8|H=12|N=2

| Appearance = Colorless liquid

| Odor = Amine{{cite web |url = https://pubchem.ncbi.nlm.nih.gov/compound/15133 |title = M-Xylylenediamine |publisher = PubChem}}

| Density = 1.032 g/cm3 (20°C)

| MeltingPtF = 58

| MeltingPt_ref =

| BoilingPtF = 477

| BoilingPt_ref =

| Solubility = Miscible (20°C)

| VaporPressure = 0.03 mmHg (25°C)

}}

| Section3 = {{Chembox Hazards

| FlashPtF = 243

| FlashPt_ref =

| REL = C 0.1 mg/m3 [skin]{{PGCH|0671}}

| LD50 = 700 ppm/1 hour (rat, inhalation){{cite web |url = https://www.cdc.gov/niosh-rtecs/PF88DF10.html |title = RTECS PF88DF10 |publisher = NIOSH}}
930 mg/kg (rat, oral)
2 g/kg (rabbit, skin)

}}

}}

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.{{Ullmann|doi=10.1002/14356007.a17_363|title=Nitriles|year=2000|last1=Pollak|first1=Peter|last2=Romeder|first2=Gérard|last3=Hagedorn|first3=Ferdinand|last4=Gelbke|first4=Heinz-Peter|isbn=3527306730}}

Uses and reactions

m-Xylylenediamine (MXDA) is used in a variety of industrial applications including amine based curing agents for epoxy resins{{Cite web|url=http://www.aromaticchemicals.com/prfAmn/mxda.html|title=MXDA│Epoxy Resin Curing Agents│MITSUBISHI GAS CHEMICAL CO., INC|website=www.aromaticchemicals.com|language=en|access-date=2018-08-19}} which may then be formulated into coatings, adhesives, sealants, and elastomers.

m-Xylylenediamine undergoes the Sommelet reaction to give isophthalaldehyde.{{cite journal|first1=J. H. |last1=Ackerman|first2=A. R. |last2=Surrey|doi=10.15227/orgsyn.047.0076|title=Isophthalaldehyde|journal=Organic Syntheses|year=1967|volume=47|pages=76}}

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.{{cite web |url = https://www.cdc.gov/niosh/ipcsneng/neng1462.html |title = 1,3-BIS(AMINOMETHYL)BENZENE |work = International Chemical Safety Cards}}

References