1,8-Diazacyclotetradecane-2,9-dione

Base Information

• Chemical Name: 1,8-Diazacyclotetradecane-2,9-dione
• CAS No.: 56403-09-9
• Molecular Formula: C12H22N2O2
• Molecular Weight: 226.319
• European Community (EC) Number: 611-385-5
• UNII: LIJ968E05S
• DSSTox Substance ID: DTXSID90204974
• Nikkaji Number: J450.663D
• Wikidata: Q27102157
• Metabolomics Workbench ID: 50722
• Mol file: 56403-09-9.mol

Synonyms:6-aminohexanoic acid cyclic dimer;nylon oligomer

Chemical Property of 1,8-Diazacyclotetradecane-2,9-dione

Chemical Property:

• Vapor Pressure: 4.81E-10mmHg at 25°C
• Melting Point: 341 °C
• Refractive Index: 1.446
• Boiling Point: 497.766 °C at 760 mmHg
• PKA: 16.05±0.20(Predicted)
• Flash Point: 204.11 °C
• PSA: 65.18000
• Density: 0.97 g/cm³
• LogP: 1.90500
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 226.168127949
• Heavy Atom Count: 16
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

1,8-Diaza-2,9-diketocyclotetradecane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=O)NCCCCCC(=O)NCC1
• Uses: 1,8-Diaza-2,9-diketocyclotetradecane is a dimer of Caprolactam (C175665), an amonomer used in the production of nylon-6 and other synthetic polymers.

Technology Process of 1,8-Diazacyclotetradecane-2,9-dione

There total 21 articles about 1,8-Diazacyclotetradecane-2,9-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

6-aminohexanoic acid (60-32-2,93208-38-9) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / 4 M NaOH / 4 h / 0 - 20 °C

2: DCC / dioxane / 24 h / 0 °C

3: aq. NaHCO₃ / 1,2-dimethoxy-ethane / 5 h / 20 °C

4: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C

5: 33percent HBr / acetic acid / 2 h / 20 °C

6: pyridine / dimethylformamide / 4 h / 60 °C

With pyridine; sodium hydroxide; hydrogen bromide; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; 1,2-dimethoxyethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1007/BF00473947

Reference yield:

N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester (51513-80-5) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 94 percent / 1,2-dimethoxy-ethane / 3 h

2: 100 percent / H₂, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr

3: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C

4: 0.25 h / 50 °C

5: Et₃N / dimethylformamide / 4 h / 60 °C

With hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1007/BF00473947

Reference yield:

6-(tert-butoxycarbonylamino)hexanoic acid (6404-29-1) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C

2: 94 percent / 1,2-dimethoxy-ethane / 3 h

3: 100 percent / H₂, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr

4: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C

5: 0.25 h / 50 °C

6: Et₃N / dimethylformamide / 4 h / 60 °C

With hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; 1,2-dimethoxyethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1007/BF00473947

upstream raw materials:

13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid hydrazide

6-(6-aminohexanamido)hexanoic acid

chloroformic acid ethyl ester

6-(6-amino-hexanoylamino)-hexanoic acid-(4-nitro-phenyl ester); hydrobromide

Downstream raw materials:

6-aminohexanoic acid

6-(6-aminohexanamido)hexanoic acid

caprolactam

1,8-bis-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane

Refernces