Product Name

  • Name

    1,8-Diazacyclotetradecane-2,9-dione

  • EINECS
  • CAS No. 56403-09-9
  • Article Data7
  • CAS DataBase
  • Density 0.97 g/cm3
  • Solubility
  • Melting Point 341 °C
  • Formula C12H22N2O2
  • Boiling Point 497.766 °C at 760 mmHg
  • Molecular Weight 226.319
  • Flash Point 204.11 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 56403-09-9 (1,8-Diazacyclotetradecane-2,9-dione)
  • Hazard Symbols
  • Synonyms 1,8-Diaza-2,9-dioxocyclotetradecane;2H-Azepin-2-one, hexahydro-, cyclic dimer;6-Aminohexanoate cyclic dimer;Caprolactam cyclic dimer;Caprolactam dimer;Cyclic dimer of e-caprolactam;Hexanoic acid,6-amino-, bimol. cyclic lactam;e-Aminocaproic acid cyclic dimer;e-Caprolactam cyclic dimer;
  • PSA 65.18000
  • LogP 1.90500

Synthetic route

13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid hydrazide
112507-71-8

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

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-(6-aminohexanamido)hexanoic acid

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
With tributyl-amine
6-(6-Amino-hexanoylamino)-hexanoyl azide; hydrobromide

6-(6-Amino-hexanoylamino)-hexanoyl azide; hydrobromide

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
With sodium hydrogencarbonate at 20℃; for 4h; Yield given;
6-(6-amino-hexanoylamino)-hexanoic acid-(4-nitro-phenyl ester); hydrobromide
109565-05-1

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

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-(6-Amino-hexanoylamino)-hexanoic acid 4-nitro-phenyl ester; compound with trifluoro-acetic acid

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-<6-amino-hexanoylamino>-hexanoic acid <2,4-dinitro-phenyl ester>-hydrobromide

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
With tributyl-amine; N,N-dimethyl-formamide
6-<6-amino-hexanoylamino>-hexanoic acid <4-nitro-phenyl ester>-hydrobromide

6-<6-amino-hexanoylamino>-hexanoic acid <4-nitro-phenyl ester>-hydrobromide

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
With triethylamine; N,N-dimethyl-formamide
6-<6-amino-hexanoylamino>-hexanoyl chloride-hydrochloride

6-<6-amino-hexanoylamino>-hexanoyl chloride-hydrochloride

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
With triethylamine; N,N-dimethyl-formamide
N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester
51513-80-5

N-Boc-6-aminohexanoic acid N-hydroxysuccinimide ester

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-(tert-butoxycarbonylamino)hexanoic acid

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-(benzyloxycarbonylamino)hexanoic acid

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

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

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

methyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

p-nitrophenyl 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoate

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

N-hydroxysuccinimide ester of 6-{[(benzyloxy)carbonyl]amino}hexanoic acid

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoic acid

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

benzyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-Amino-hexanoic acid (5-hydrazinocarbonyl-pentyl)-amide; hydrobromide

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

p-nitrophenyl 13-tert-butyloxycarbonylamino-8-oxo-7-azatridecanoate

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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

6-aminohexanoic acid

1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

Conditions
ConditionsYield
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-2,9-dione

1,8-diazacyclotetradecane
295-29-4

1,8-diazacyclotetradecane

Conditions
ConditionsYield
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

1,8-diazacyclotetradecane-2,9-dione

aqueous H2SO4 (3 n)

aqueous H2SO4 (3 n)

6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

Conditions
ConditionsYield
at 78℃; Rate constant; und 100grad.Hydrolysis;
1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

aqueous HCl (7.7 n)

aqueous HCl (7.7 n)

6-aminohexanoic acid
60-32-2

6-aminohexanoic acid

Conditions
ConditionsYield
at 110℃; Rate constant; Hydrolysis;
1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

1,8-dinitroso-1,8-diaza-cyclotetradecane
108880-79-1

1,8-dinitroso-1,8-diaza-cyclotetradecane

Conditions
ConditionsYield
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-diazacyclotetradecane-2,9-dione

1,8-diacetyl-1,8-diaza-cyclotetradecane
109452-16-6

1,8-diacetyl-1,8-diaza-cyclotetradecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4
View Scheme
1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

1,8-dibenzyl-1,8-diaza-cyclotetradecane
119276-12-9

1,8-dibenzyl-1,8-diaza-cyclotetradecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4
2: ethanolic KOH
View Scheme
1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

1,8-dibenzoyl-1,8-diaza-cyclotetradecane
121972-55-2

1,8-dibenzoyl-1,8-diaza-cyclotetradecane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4
2: aqueous KOH; THF
View Scheme
1,8-diazacyclotetradecane-2,9-dione
56403-09-9

1,8-diazacyclotetradecane-2,9-dione

1-(2,4-dinitro-phenyl)-1,8-diaza-cyclotetradecane
109600-31-9

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

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

1,8-Diazacyclotetradecane-2,9-dione Specification

The 1,8-Diazacyclotetradecane-2,9-dione, with the CAS registry number 56403-09-9, is also known as 7,14-Diazacyclotetradecane-1,8-dione. This chemical's molecular formula is C12H22N2O2 and molecular weight is 226.32. What's more, its IUPAC name is the same with its product name.

Physical properties about 1,8-Diazacyclotetradecane-2,9-dione are: (1)ACD/LogP: -0.079; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.08; (4)ACD/LogD (pH 7.4): -0.08; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 21.59; (8)ACD/KOC (pH 7.4): 21.59; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 58.2 Å2; (13)Index of Refraction: 1.446; (14)Molar Refractivity: 62.298 cm3; (15)Molar Volume: 233.421 cm3; (16)Polarizability: 24.697×10-24cm3; (17)Surface Tension: 30.377 dyne/cm; (18)Density: 0.97 g/cm3; (19)Flash Point: 204.11 °C; (20)Enthalpy of Vaporization: 76.581 kJ/mol; (21)Boiling Point: 497.766 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1NCCCCCC(=O)NCCCCC1
(2) InChI: InChI=1S/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)
(3) InChIKey: HERSSAVMHCMYSQ-UHFFFAOYSA-N

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