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70384-51-9 - Tris(3,6-dioxaheptyl)amine, 95% - TDA-1 - Tris[2-(2-methoxyethoxy)ethyl]amine - L13544 - Alfa Aesar

L13544 Tris(3,6-dioxaheptyl)amine, 95%

CAS Number
70384-51-9
Synonyms
TDA-1
Tris[2-(2-methoxyethoxy)ethyl]amine

Size Price ($) Quantity Availability
5g 22.04
25g 33.03
100g 86.40
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Tris(3,6-dioxaheptyl)amine, 95%

MDL
MFCD00010748
EINECS
274-590-5

Chemical Properties

Formula
N(CH2CH2OCH2CH2OCH3)3
Formula Weight
323.43
Melting point
<-100°
Boiling Point
163-171°/1mm
Flash Point
162°(323°F)
Density
1.011
Refractive Index
1.4486
Sensitivity
Air Sensitive & Hygroscopic
Solubility
Miscible with water.

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.

Notes

Air sensitive and hygroscopic. Incompatible strong oxidizing agents and strong acids.

Literature 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 Cyclopropyl­triphenyl­phosphonium 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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319

Causes skin irritation. Causes serious eye irritation.

Precautionary Statements: P280-P264-P305+P351+P338-P362-P321-P332+P313-P337+P313-P302+P352

Wear protective gloves/protective clothing/eye protection/face protection. Wash thoroughly after handling. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Take off contaminated clothing and wash before reuse. Specific treatment (see label). If skin irritation occurs: Get medical advice/attention. If eye irritation persists: IF ON SKIN: Wash with plenty of soap and water.

Other References

Beilstein
2369296
Harmonized Tariff Code
2922.19
TSCA
Yes

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