56403-09-9

Basic information

• Product Name: 1,8-diazacyclotetradecane-2,9-dione
• Synonyms: 1,8-diazacyclotetradecane-2,9-dione;7,14-diazacyclotetradecane-1,8-dione
• CAS NO: 56403-09-9
• Molecular Formula: C₁₂H₂₂N₂O₂
• Molecular Weight: 226.32
• Mol File: 56403-09-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 341 °C
• Boiling Point: 497.766 °C at 760 mmHg
• Flash Point: 204.11 °C
• Appearance: /
• Density: 0.97 g/cm³
• Vapor Pressure: 4.81E-10mmHg at 25°C
• Refractive Index: 1.446
• PKA: 16.05±0.20(Predicted)
• CAS DataBase Reference: 1,8-diazacyclotetradecane-2,9-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1,8-diazacyclotetradecane-2,9-dione(56403-09-9)
• EPA Substance Registry System: 1,8-diazacyclotetradecane-2,9-dione(56403-09-9)

Safety Data

• Hazardous Substances Data: 56403-09-9(Hazardous Substances Data)

Usage

Description

1,8-Diazacyclotetradecane-2,9-dione, also known as 1,8-Diaza-2,9-diketocyclotetradecane, is a chemical compound that is a dimer of Caprolactam (C175665). It is characterized by its unique molecular structure, which consists of a cyclic structure with two nitrogen atoms and two carbonyl groups. 1,8-Diazacyclotetradecane-2,9-dione is widely used in various industries due to its versatile properties and applications.

Uses

Used in Polymer Industry:
1,8-Diazacyclotetradecane-2,9-dione is used as a monomer in the polymer industry for the production of nylon-6 and other synthetic polymers. Its unique molecular structure allows it to form strong and durable polymers with excellent mechanical properties, making it a valuable component in the manufacturing of various plastic products, fibers, and resins.
Used in Chemical Synthesis:
In the field of chemical synthesis, 1,8-Diazacyclotetradecane-2,9-dione serves as an important intermediate compound. It can be used to synthesize a wide range of other chemicals, including pharmaceuticals, dyes, and specialty chemicals. Its versatility as a building block in chemical synthesis makes it a valuable asset in the development of new and innovative products.
Used in Research and Development:
Due to its unique properties and potential applications, 1,8-Diazacyclotetradecane-2,9-dione is also used in research and development for the exploration of new materials and processes. Scientists and researchers utilize this compound to study its properties, investigate its potential applications, and develop new methods for its synthesis and utilization.

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

Synthetic route

13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid hydrazide (112507-71-8) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
ueber 6-<6-Amino-hexanoylamino>-hexansaeure-hydrazid-hydrobromid und das entsprechende Azid;
Multi-step reaction with 3 steps 1: 33percent HBr / acetic acid / 1 h / 20 °C 2: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 3: aq. NaHCO3 / 4 h / 20 °C View Scheme

6-(6-aminohexanamido)hexanoic acid (2014-58-6) + chloroformic acid ethyl ester (541-41-3) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With tributyl-amine

6-(6-Amino-hexanoylamino)-hexanoyl azide; hydrobromide → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With sodium hydrogencarbonate at 20℃; for 4h; Yield given;

6-(6-amino-hexanoylamino)-hexanoic acid-(4-nitro-phenyl ester); hydrobromide (109565-05-1) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With pyridine In N,N-dimethyl-formamide at 60℃; for 4h; Yield given;

6-(6-Amino-hexanoylamino)-hexanoic acid 4-nitro-phenyl ester; compound with trifluoro-acetic acid → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Yield given;

6-<6-amino-hexanoylamino>-hexanoic acid <2,4-dinitro-phenyl ester>-hydrobromide → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With tributyl-amine; N,N-dimethyl-formamide

6-<6-amino-hexanoylamino>-hexanoic acid <4-nitro-phenyl ester>-hydrobromide → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide

6-<6-amino-hexanoylamino>-hexanoyl chloride-hydrochloride → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
With triethylamine; N,N-dimethyl-formamide

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 4 steps 1: 95 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 2: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 3: 0.25 h / 50 °C 4: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 5 steps 1: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 2: 95 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 3: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 4: 0.25 h / 50 °C 5: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

6-(benzyloxycarbonylamino)hexanoic acid (1947-00-8) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: DCC / dioxane / 24 h / 0 °C 2: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 3: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 4: 33percent HBr / acetic acid / 2 h / 20 °C 5: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 7 steps 1: DCC / dioxane / 24 h / 0 °C 2: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 3: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 4: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 5: 33percent HBr / acetic acid / 1 h / 20 °C 6: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 7: aq. NaHCO3 / 4 h / 20 °C View Scheme

13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid (49701-55-5) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 2: 33percent HBr / acetic acid / 2 h / 20 °C 3: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 5 steps 1: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 2: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 3: 33percent HBr / acetic acid / 1 h / 20 °C 4: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 5: aq. NaHCO3 / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine; chlorocarbonic acid ethyl ester; THF / anschliessend Behandeln mit N2H4+H2O in H2O 2: ueber 6-<6-Amino-hexanoylamino>-hexansaeure-hydrazid-hydrobromid und das entsprechende Azid View Scheme

methyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate (25580-88-5) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 2: 33percent HBr / acetic acid / 1 h / 20 °C 3: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 4: aq. NaHCO3 / 4 h / 20 °C View Scheme

p-nitrophenyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate (121759-91-9) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 33percent HBr / acetic acid / 2 h / 20 °C 2: pyridine / dimethylformamide / 4 h / 60 °C View Scheme

N-hydroxysuccinimide ester of 6-{[(benzyloxy)carbonyl]amino}hexanoic acid (53733-98-5) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 2: 90 percent / DCC / dimethylformamide / 3 h / 0 - 20 °C 3: 33percent HBr / acetic acid / 2 h / 20 °C 4: pyridine / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1: aq. NaHCO3 / 1,2-dimethoxy-ethane / 5 h / 20 °C 2: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 3: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 4: 33percent HBr / acetic acid / 1 h / 20 °C 5: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 6: aq. NaHCO3 / 4 h / 20 °C View Scheme

13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoic acid (14254-45-6) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 2: 0.25 h / 50 °C 3: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

benzyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate (144366-96-1) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / H2, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr 2: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 3: 0.25 h / 50 °C 4: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

6-Amino-hexanoic acid (5-hydrazinocarbonyl-pentyl)-amide; hydrobromide → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 2: aq. NaHCO3 / 4 h / 20 °C View Scheme

p-nitrophenyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate (144366-97-2) → 1,8-diazacyclotetradecane-2,9-dione (56403-09-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.25 h / 50 °C 2: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

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

Conditions	Yield
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 View Scheme
Multi-step reaction with 8 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: 92 percent / p-TsOH / CH2Cl2 / 15 h / Heating 5: 93 percent / 85percent N2H4*H2O / methanol / 24 h / 20 °C 6: 33percent HBr / acetic acid / 1 h / 20 °C 7: 1 M HCl, aq. NaNO2 / 0.25 h / 0 °C 8: aq. NaHCO3 / 4 h / 20 °C View Scheme
Multi-step reaction with 7 steps 1: 96 percent / MgO, H2O / dioxane / 26 h / 50 °C 2: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 3: 94 percent / 1,2-dimethoxy-ethane / 3 h 4: 100 percent / H2, AcOH / 10percent Pd/C / methanol / 1 h / 760 Torr 5: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 6: 0.25 h / 50 °C 7: Et3N / dimethylformamide / 4 h / 60 °C View Scheme
Multi-step reaction with 6 steps 1: 96 percent / MgO, H2O / dioxane / 26 h / 50 °C 2: 55 percent / DCC / 1,2-dimethoxy-ethane / 20 h / 0 °C 3: 95 percent / aq. NaHCO3 / 1,2-dimethoxy-ethane / 3 h / Ambient temperature 4: 90 percent / DCC / ethyl acetate / 3 h / 0 - 20 °C 5: 0.25 h / 50 °C 6: Et3N / dimethylformamide / 4 h / 60 °C View Scheme

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) → 1,8-diazacyclotetradecane (295-29-4)

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran for 4h; Heating;	64%
With lithium aluminium tetrahydride

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) + aqueous H2SO4 (3 n) → 6-aminohexanoic acid (60-32-2)

Conditions	Yield
at 78℃; Rate constant; und 100grad.Hydrolysis;

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) + aqueous HCl (7.7 n) → 6-aminohexanoic acid (60-32-2)

Conditions	Yield
at 110℃; Rate constant; Hydrolysis;

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) → 1,8-dinitroso-1,8-diaza-cyclotetradecane (108880-79-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: aqueous HCl; NaNO2 View Scheme

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) → 1,8-diacetyl-1,8-diaza-cyclotetradecane (109452-16-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 View Scheme

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) → 1,8-dibenzyl-1,8-diaza-cyclotetradecane (119276-12-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: ethanolic KOH View Scheme

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) → 1,8-dibenzoyl-1,8-diaza-cyclotetradecane (121972-55-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: aqueous KOH; THF View Scheme

1,8-diazacyclotetradecane-2,9-dione (56403-09-9) → 1-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane (109600-31-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: LiAlH4 2: DMF; H2O / 140 °C View Scheme

Upstream product

• 121759-91-9 p-nitrophenyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate 
• 60-32-2 6-aminohexanoic acid 
• 2014-58-6 6-(6-aminohexanamido)hexanoic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 112507-71-8 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid hydrazide 
• 144366-97-2 p-nitrophenyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate 
• 144366-96-1 benzyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate 
• 14254-45-6 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoic acid 
• 53733-98-5 N-hydroxysuccinimide ester of 6-{[(benzyloxy)carbonyl]amino}hexanoic acid 
• 25580-88-5 methyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate 
• 49701-55-5 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid 
• 1947-00-8 6-(benzyloxycarbonylamino)hexanoic acid 
• 6404-29-1 6-(tert-butoxycarbonylamino)hexanoic acid 
• 51513-80-5 N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester 

Downstream Products

• 2014-58-6 6-(6-aminohexanamido)hexanoic acid 
• 105-60-2 caprolactam 
• 124135-61-1 1,8-bis-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane 
• 117372-87-9 1,8-bis-(3-oxo-3-phenyl-propyl)-1,8-diaza-cyclotetradecane 
• 109600-31-9 1-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane 
• 121972-55-2 1,8-dibenzoyl-1,8-diaza-cyclotetradecane 
• 119276-12-9 1,8-dibenzyl-1,8-diaza-cyclotetradecane 
• 60-32-2 6-aminohexanoic acid 

Relevant articles and documents

SYNTHESIS OF AZA-CROWN COMPOUNDS BY INTRAMOLECULAR CYCLIZATION OF ω-AMINO ACIDS

A method for the synthesis of aza-crown compounds by the intramolecular cyclization of ω-amino acids with subsequent reduction of the lactam to a macrocyclic amine was developed. 1,8-Diazacyclotetradecane and 1,8-dioxa-4,11-diazacyclotetradecane was synthesized in preparative yields.The structural assignments were made using the IR, 1H and 13C NMR, and mass spectra.