triallylamine

{{Chembox

| ImageFile = Triallylamine.png

| ImageSize =

| ImageAlt =

| IUPACName = N,N-bis(prop-2-enyl)prop-2-en-1-amine

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo = 102-70-5

| ChEMBL = 3188834

| ChemSpiderID = 7335

| EC_number = 203-048-2

| PubChem = 7617

| RTECS = XX5950000

| UNNumber = 2610

| UNII = B6N19XC04R

| StdInChI=1S/C9H15N/c1-4-7-10(8-5-2)9-6-3/h4-6H,1-3,7-9H2

| StdInChIKey = VPYJNCGUESNPMV-UHFFFAOYSA-N

| SMILES = C=CCN(CC=C)CC=C

}}

| Section2 = {{Chembox Properties

| C=9|H=15|N = 1

| MolarMass =

| Appearance = colorless liquid

| Density = 0.809 g/cm³

| MeltingPt =

| BoilingPtC = 155.5

| Solubility = }}

| Section3 = {{Chembox Hazards

| GHS_ref={{cite web |title=Triallylamine |url=https://pubchem.ncbi.nlm.nih.gov/compound/7617#section=Safety-and-Hazards |website=pubchem.ncbi.nlm.nih.gov |access-date=3 April 2022 |language=en}}

| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|226|302|311|312|314|331|332|412}}

| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|273|280|301+317|301+330+331|302+352|302+361+354|303+361+353|304+340|305+354+338|316|317|321|330|361+364|362+364|363|370+378|403+233|403+235|405|501}}

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

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Triallylamine is the organic compound with the formula N(CH₂CH=CH₂)₃. It is a colorless liquid with an ammonia-like odor. It is multifunctional, featuring a tertiary amine and three alkene groups. Triallylamine (and mono- and diallyl amines) is produced by the treating allyl chloride with ammonia.{{Ullmann|doi=10.1002/14356007.a02_001|title=Amines, Aliphatic|year=2000|last1= Eller|first1=Karsten|last2=Henkes|first2=Erhard|last3=Rossbacher|first3=Roland|last4=Höke|first4=Hartmut|isbn=3527306730}}

Allylamines have particularly weak α-CH bonds, being near 80 kcal/mol.{{cite journal |doi=10.1021/JO9813843|title=Α-C−H Bond Dissociation Energies of Some Tertiary Amines|year=1999|last1=Dombrowski|first1=G. W.|last2=Dinnocenzo|first2=J. P.|last3=Farid|first3=S.|last4=Goodman|first4=J. L.|last5=Gould|first5=I. R.|journal=The Journal of Organic Chemistry|volume=64|issue=2|pages=427–431}}