76927-70-3

Basic information

• Product Name: 3,6,9,12,15,18-Hexaoxaeicosane-1,20-diamine
• Synonyms: 3,6,9,12,15,18-Hexaoxaeicosane-1,20-diamine;Amino-PEG6-amine;3,6,9,12,15,18-Hexaoxaicosane-1,20-diamine
• CAS NO: 76927-70-3
• Molecular Formula: C₁₄H₃₂N₂O₆
• Molecular Weight: 324.41368
• Mol File: 76927-70-3.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Solubility: Soluble in Water, DMSO, DCM, DMF
• CAS DataBase Reference: 3,6,9,12,15,18-Hexaoxaeicosane-1,20-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6,9,12,15,18-Hexaoxaeicosane-1,20-diamine(76927-70-3)
• EPA Substance Registry System: 3,6,9,12,15,18-Hexaoxaeicosane-1,20-diamine(76927-70-3)

Safety Data

• Hazardous Substances Data: 76927-70-3(Hazardous Substances Data)

Usage

Description

Amino-PEG6-Amine is a PEG linker with two amino groups. The amino groups are reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc.

Uses

3,6,9,12,15,18-Hexaoxaeicosane-1,20-diamine is an intermediate in the synthesis of O-(2-Aminoethyl)-O’-[2-(Boc-amino)ethyl]pentaethylene Glycol (A608865), a heterobifunctional polyethyleneglycol (PEG) derivative used in the preparation of intramolecular linking agents.

Upstream product

• 56930-39-3 1,20-dichloro-3,6,9,12,15,18-hexaoxatetradecane 
• 76927-71-4 1,20-Diphthalimido-3,6,9,12,15,18-hexaoxaeicosane 

Relevant articles and documents

Catalysis in Aprotic Solvents. Inter- and Intramolecular Hydrogen Bonding Complexation

A mechanistic investigation is reported of aminolysis reactions of 2-hydroxy-5-nitro-α-toluenesulfonic acid sultone (1) in aprotic solvents.The n-butylaminolysis of 1 in acetonitrile and in toluene requires two and three molecules of amine, respectively.In the latter solvent, general bases strongly catalyze the reaction, and their catalytic constants are well correlated by the hydrogen bonding parameter pKHB.These results are interpreted by a multistep mechanism where each intermediate can be stabilized via hydrogen bonding by general bases.The mechanistic features depend on the stability of the intermediates and on the solvent characteristics.When diamines such as polyoxyethylenediamines H2NCH2(CH2OCH2)nCH2NH2 (2, n=2; 3, n=4; 4, n=6) are used as nucleophiles for the reaction with sultone 1 in toluene, much higher reactivities are observed when compared to reactions of monoamines and alkylenediamines.This represents a novel type of intramolecular catalysis due to intramolecular hydrogen bonding complexation between oxygen atoms and the ammonium group of the reaction intermediates (Scheme III).In toluene 2-4 also display a large basicity.