4266-66-4

Basic information

• Product Name: 1,8-Diazacyclotetradecane-2,7-dione
• Synonyms: 1,8-Diazacyclotetradecane-2,7-dione
• CAS NO: 4266-66-4
• Molecular Formula: C₁₂H₂₂N₂O₂
• Molecular Weight: 226
• Mol File: 4266-66-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 263 °C
• Boiling Point: 497.8 °C at 760 mmHg
• Flash Point: 204.1 °C
• Appearance: /
• Density: 0.969 g/cm³
• Vapor Pressure: 4.81E-10mmHg at 25°C
• Refractive Index: 1.446
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Sparingly, Heated), Methanol (Slightly)
• PKA: 16.01±0.20(Predicted)
• CAS DataBase Reference: 1,8-Diazacyclotetradecane-2,7-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-Diazacyclotetradecane-2,7-dione(4266-66-4)
• EPA Substance Registry System: 1,8-Diazacyclotetradecane-2,7-dione(4266-66-4)

Safety Data

• Hazardous Substances Data: 4266-66-4(Hazardous Substances Data)

Usage

Uses

1.8-Diazacyclotetradecane-2,7-dione is a polymer additive present in textile fibers.

InChI:InChI=1/C12H22N2O2/c15-11-7-3-4-8-12(16)14-10-6-2-1-5-9-13-11/h1-10H2,(H,13,15)(H,14,16)

Synthetic route

1,6-Hexanediamine (124-09-4) + 1,6-Bis-(2-thioxo-thiazolidin-3-yl)-hexane-1,6-dione (74058-83-6) → 1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4) + 1,8,15,22-tetraaza-cyclooctacosane-2,7,16,21-tetraone (4238-35-1)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	A 34% B 37%

N-(6-amino-hexyl)-adipamic acid methyl ester; hydrochloride (108903-95-3) → 1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4)

Conditions	Yield
ueber das Hydrazid und Azid;

1,6-Hexanediamine (124-09-4) + Adipic acid dichloride (111-50-2) → 1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4)

Conditions	Yield
With benzene

1,6-Hexanediamine (124-09-4) → 1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: dioxane 2: hydrogen chloride 3: ueber das Hydrazid und Azid View Scheme

adipic acid monomethyl ester (627-91-8) → 1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: dioxane 2: hydrogen chloride 3: ueber das Hydrazid und Azid View Scheme

N-(6-amino-hexyl)-adipamic acid (5136-16-3) → 1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen chloride 2: ueber das Hydrazid und Azid View Scheme

1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4) → 1,8-diazacyclotetradecane (295-29-4)

Conditions	Yield
With lithium aluminium tetrahydride

1,8-diaza-cyclotetradecane-2,7-dione (4266-66-4) + aqueous HCl (7.7 n) → Adipic acid (124-04-9)

Conditions	Yield
at 110℃; Rate constant; Hydrolysis;

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 111-50-2 Adipic acid dichloride 
• 74058-83-6 1,6-Bis-(2-thioxo-thiazolidin-3-yl)-hexane-1,6-dione 
• 5136-16-3 N-(6-amino-hexyl)-adipamic acid 
• 627-91-8 adipic acid monomethyl ester 
• 108903-95-3 N-(6-amino-hexyl)-adipamic acid methyl ester; hydrochloride 

Downstream Products

• 124-04-9 Adipic acid 

Relevant articles and documents

MONITORED AMINOLYSIS OF 3-ACYLTHIAZOLIDINE-2-THIONE: A NEW SYNTHESIS OF MACROCYCLIC AMIDES

A new efficient procedure for synthesis of macrocyclic amides has been exploited by aminolysis of thiazolidine-2-thione amide (1) of dicarboxylic acid with diamines (4), or spermidine (7).A variety of macrocyclic diamides (5 and 8) and/or tetramides (6, 9, 12, and 13) have been synthesized in high yields.One can monitor the reaction, since the original yellow color of the starting material (1) disappears at the end of the reaction.