Search Thermo Fisher Scientific
Element Search
Structure Search
Thermo Scientific Chemicals
Tris(3,6-dioxaheptyl)amine, 95%, Thermo Scientific Chemicals
Have Questions?
Change view
Price (USD)/ Each
22.30
Tris(3,6-dioxaheptyl)amine, 95%, Thermo Scientific Chemicals
Catalog numberL13544.06
Price (USD)/ Each
22.30
-
Chemical Identifiers
CAS70384-51-9
IUPAC Name8-[2-(2-methoxyethoxy)ethyl]-2,5,11,14-tetraoxa-8-azapentadecane
Molecular FormulaC15H33NO6
InChI KeyXGLVDUUYFKXKPL-UHFFFAOYSA-N
SMILESCOCCOCCN(CCOCCOC)CCOCCOC
View more
Specifications
Specification Sheet
Specification SheetFormLiquid
Refractive Index1.4465-1.4490 @ 20?C
Appearance (Color)Clear pale yellow to yellow to orange to brown
Assay (GC)≥94.0%
Tris(3,6-dioxaheptyl)amine acts as a phase transfer catalyst used in the preparation of 1,3-dideaza-2'-deoxyadenosine and related benzimidazole 2'-deoxyribonucleosides. It is also used as an intermediate in the synthesis of telithromycin. Further, it is used in the oxidation of arylmethanols under phase-transfer conditions. In addition to this, it acts as a cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Tris(3,6-dioxaheptyl)amine acts as a phase transfer catalyst used in the preparation of 1,3-dideaza-2′-deoxyadenosine and related benzimidazole 2′-deoxyribonucleosides. It is also used as an intermediate in the synthesis of telithromycin. Further, it is used in the oxidation of arylmethanols under phase-transfer conditions. In addition to this, it acts as a cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine.
Solubility
Miscible with water.
Notes
Air sensitive and hygroscopic. Incompatible strong oxidizing agents and strong acids.
Tris(3,6-dioxaheptyl)amine acts as a phase transfer catalyst used in the preparation of 1,3-dideaza-2′-deoxyadenosine and related benzimidazole 2′-deoxyribonucleosides. It is also used as an intermediate in the synthesis of telithromycin. Further, it is used in the oxidation of arylmethanols under phase-transfer conditions. In addition to this, it acts as a cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine.
Solubility
Miscible with water.
Notes
Air sensitive and hygroscopic. Incompatible strong oxidizing agents and strong acids.
RUO – Research Use Only
General References:
- Acyclic solid-liquid phase-transfer catalyst (see Appendix 2).
- 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).
- Forms isolable 2:1 complexes with Grignard reagents: Tetrahedron, 45, 171 (1989).
- Accelerates dehydrobromination of alkyl halides in the presence of KOH: Org. Synth. Coll., 9, 539 (1998). For use in the Wittig reaction, see Cyclopropyl triphenyl phosphonium bromide, B25102.
- Has been used in a number of aromatic nucleophilic substitution reactions:
- In studies of solvent-free SNAr 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).
- Quick, M. P.; Wünsch, B. Synthesis of hydrogenated 2-benzazepin-1-ones by the addition of aryllithium intermediates to isocyanates. Tetrahedron: Asymmetry 2015, 26 (5-6), 276-280.
- Li, H.; Pang, Z.; Gao, P.; Wang, L. Fe(III)-catalyzed grafting copolymerization of lignin with styrene and methyl methacrylate through AGET ATRP using triphenyl phosphine as a ligand. RSC Adv. 2015, 5 (67), 54387-54394.