8-[2-(2-methoxyethoxy)ethyl]-2,5,11,14-tetraoxa-8-azapentadecane

• ChemBase ID: 89662
• Molecular Formular: C15H33NO6
• Molecular Mass: 323.42562
• Monoisotopic Mass: 323.23078778
• SMILES: N(CCOCCOC)(CCOCCOC)CCOCCOC
• Canonical SMILES: COCCOCCN(CCOCCOC)CCOCCOC
• InChI: InChI=1S/C15H33NO6/c1-17-10-13-20-7-4-16(5-8-21-14-11-18-2)6-9-22-15-12-19-3/h4-15H2,1-3H3
• InChIKey: XGLVDUUYFKXKPL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-[2-(2-methoxyethoxy)ethyl]-2,5,11,14-tetraoxa-8-azapentadecane
• IUPAC Traditional name: 8-[2-(2-methoxyethoxy)ethyl]-2,5,11,14-tetraoxa-8-azapentadecane
• Synonyms: Tris(3,6-dioxaheptyl)amine; TDA-1; Tris(3,6-dioxaheptyl)amine; Tris[2-(2-methoxyethoxy)ethyl]amine; Tris[2-(2-methoxyethoxy)ethyl]amine; Tris(3,6-dioxaheptyl)amine; Tris(2-(2-methoxyethoxy)ethyl)amine; 三(3,6-二氧庚基)胺; 三(3,6-二氧杂庚基)胺; 三[2-(2-甲氧基乙氧基)乙基]胺

Database IDs

• CAS Number: 70384-51-9
• EC Number: 274-590-5
• MDL Number: MFCD00010748
• Beilstein Number: 2369296
• PubChem SID: 162076525; 24889862; 24858174
• PubChem CID: 112414

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): -2.751921
• LogD (pH = 7.4): -0.9779692
• Log P: -0.09168358
• Molar Refractivity: 86.2491 cm^3
• Polarizability: 34.08694 Å^3
• Polar Surface Area: 58.62 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: <-100°C
• Boiling Point: 163-171°C/1mm
• Flash Point: 162 °C; 162°C(323°F); 323.6 °F
• Density: 1.011; 1.011 g/mL at 25 °C(lit.)
• Refractive Index: 1.4486; n20/D 1.4486(lit.)

Safety Information

• Storage Warning: Air Sensitive & Hygroscopic; Corrosive
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 2735
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 34; 36/38
• Safety Statements: 26-36/37/39-45; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H315-H319
• GHS Precautionary statements: P280-P305 + P351 + P338-P310; P280-P305+P351+P338-P302+P352-P321-P362-P332+P313
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2735 8/PG 3

Product Information

• Purity: ≥90% (T); 95%; 95+%
• Grade: technical
• Linear Formula: (CH3OCH2CH2OCH2CH2)3N

DETAILS

Sigma Aldrich - 301248

Packaging
5, 100, 500 g in glass bottle

Sigma Aldrich - 93373

Other Notes
This tripodand shows good complexing characteristics with sodium, potassium and rubidium (log K: Na 2.2; K 2.2; Rb 2.0)1; PTC useful for many reactions2,3,4; Preparation of solid Grignard reagents used in hydrocarbon solvent5

REFERENCES

• Acyclic solid-liquid phase-transfer catalyst (see Appendix 2).
• Forms isolable 2:1 complexes with Grignard reagents: Tetrahedron, 45, 171 (1989).
• Has been used in a number of aromatic nucleophilic substitution reactions:
• Solubilizes salts of alkali metals and of transition metals, e.g. PdCl₂, RuCl₃ and RhCl₃, allowing these to be used in hydrogenation reactions: Synth. Commun., 19, 2833 (1989).
• Accelerates dehydrobromination of alkyl halides in the presence of KOH: Org. Synth. Coll., 9, 539 (1998). For use in the Wittig reaction, see Cyclopropyltriphenylphosphonium bromide, B25102.
• In studies of solvent-free S_NAr reactions, TDA-1 was found to be the best catalyst: Synth. Commun., 20, 2855 (1990); Heterocycles, 32, 1947 (1991). In combination with CuCl, is also a useful catalyst in the Ullmann aryl ether synthesis: J. Org. Chem., 50, 3717 (1985). An improved N-arylation of amides utilizes a catalyst combination of CuCl and TDA-1 (5:1): Synthesis, 312 (1989).
• For use in a stereospecific glycosylation reaction of a pyrimidine base, see: Helv. Chim. Acta, 71, 1573 (1988).