tris(2-aminoethyl)amine

• ChemBase ID: 130032
• Molecular Formular: C6H18N4
• Molecular Mass: 146.23392
• Monoisotopic Mass: 146.1531466
• SMILES: NCCN(CCN)CCN
• Canonical SMILES: NCCN(CCN)CCN
• InChI: InChI=1S/C6H18N4/c7-1-4-10(5-2-8)6-3-9/h1-9H2
• InChIKey: MBYLVOKEDDQJDY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tris(2-aminoethyl)amine
• IUPAC Traditional name: tren
• Synonyms: TAEA; Tris(2-aminoethyl)amine; 2,2',2''-Triaminotriethylamine; Tris(2-aminoethyl)amine; 2,2′,2′′-Nitrilotriethylamine; 2,2′,2′′-Triaminotriethylamine; N,N-二(2-氨乙基)-1,2-乙二胺; 三(2-氨乙基)胺; 三(2-氨基乙基)胺; 三(2-氨乙基)胺

Database IDs

• CAS Number: 4097-89-6
• EC Number: 223-857-4
• MDL Number: MFCD00008177
• Beilstein Number: 1739626
• PubChem SID: 24853509; 24858349; 162224317
• PubChem CID: 77731
• CHEBI ID: 30631
• CHEMBL: 19823
• Chemspider ID: 70131
• Gmelin ID: 27074
• MeSH Name: tris(2-aminoethyl)amine
• Wikipedia Title: Tris(2-aminoethyl)amine

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -11.123083
• LogD (pH = 7.4): -8.013978
• Log P: -2.200782
• Molar Refractivity: 43.8375 cm^3
• Polarizability: 17.900114 Å^3
• Polar Surface Area: 81.3 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Miscible in water
• Apperance: Colourless liquid
• Melting Point: -16°C
• Boiling Point: 102°C/0.05mm; 114 °C/15 mmHg(lit.); 265°C
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 0.976 g/mL at 20 °C(lit.); 0.978; 977 mg mL^-1
• Refractive Index: 1.4969; 1.497; n20/D 1.497(lit.)
• Vapor Pressure: 0.02 mmHg ( 20 °C); 3 Pa (at 20 °C)
• Vapor Density: 5 (vs air)
• Partition Coefficient: -2.664
• Odor: Ichtyal, ammoniacal
• Std enthalpy of combustion: -4860.6–-4859.2 kJ mol^-1
• Std enthalpy of formation: -74.3–-72.9 kJ mol^-1

Safety Information

• Storage Warning: Air Sensitive & Hygroscopic
• RTECS: KH8587082
• European Hazard Symbols: Toxic (T)
• UN Number: 2922; UN2922
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 22-24-34; r22, r24, r34
• Safety Statements: 26-36/37/39-45; s26, s36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS corrosion; GHS skull and crossbones; GHS05; GHS06
• GHS Signal Word: DANGER; Danger
• LD50: 117 mg kg^-1 (dermal, rabbit); 246 mg kg^-1 (oral, rat)
• GHS Hazard statements: 301, 310, 314; H301-H310-H314; H301-H310-H314-H318
• GHS Precautionary statements: 280, 302+350, 305+351+338, 310; P280-P301 + P310-P302 + P350-P305 + P351 + P338-P310; P280-P302 + P350-P305 + P351 + P338-P310; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 2

Product Information

• Purity: ~95% (titration); ≥98.0% (T); 96%; 97%
• Grade: purum
• Linear Formula: (NH2CH2CH2)3N

DETAILS

Sigma Aldrich - 225630

Application
Building block for cryptands;1 precursor to a proazaphosphatrane, a stong, nonionic base.2
Packaging
10, 100 mL in glass bottle

REFERENCES

• Reagent for rapid cleavage of the Fmoc group in peptide synthesis, particularly recommended in conjunction with Fmoc-protected acid chlorides as the active species: J. Org. Chem., 55, 1673 (1990). For a review of peptide synthesis via amino acid halides, see: Acc. Chem. Res., 29, 268 (1996). For peptide reagents, see Appendix 6.
• Reaction with aryl isocyanates and isothiocyanates gives tris-urea and -thiourea derivatives which have been evaluated as phosphate and sulfate receptors: Chem. Lett., 759 (1995).