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294-90-6 Usage

Uses

Different sources of media describe the Uses of 294-90-6 differently. You can refer to the following data:
1. Macrocyclic aza analogue of the crown ether 12-crown-4. Cyclen compounds are capable of selectively binding cations and are used as a ligand with chemicals used in MRI contrast (as well ass other imaging) agents.
2. Cyclen is an azamocrocycle, which can be used in the development of fluorescent nanosensors for the detection of metal ions.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 2268, 1974 DOI: 10.1021/ja00814a056

General Description

Cyclen is a microcyclic tetramine that can be used as a ligand that forms a co-ordination linkage with the surface metal cations. It can be used as a synthetic precursor. It can be prepared by S-alkylation of dithiooxamide with an excess amount of bromoethane.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 294-90-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,9 and 4 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 294-90:
(5*2)+(4*9)+(3*4)+(2*9)+(1*0)=76
76 % 10 = 6
So 294-90-6 is a valid CAS Registry Number.
InChI:InChI=1/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2/p+4

294-90-6 Well-known Company Product Price

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  • TCI America

  • (T1874)  1,4,7,10-Tetraazacyclododecane  >97.0%(GC)(T)

  • 294-90-6

  • 1g

  • 331.00CNY

  • Detail
  • TCI America

  • (T1874)  1,4,7,10-Tetraazacyclododecane  >97.0%(GC)(T)

  • 294-90-6

  • 5g

  • 986.00CNY

  • Detail
  • Aldrich

  • (339652)  Cyclen  97%

  • 294-90-6

  • 339652-250MG

  • 1,078.74CNY

  • Detail

294-90-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 1,4,7,10-tetraazacyclododecane

1.2 Other means of identification

Product number -
Other names 1,4,7,10-tetrazacyclododecane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:294-90-6 SDS

294-90-6Synthetic route

tert-butyl 1,4,7,10-tetraazacyclododecane carboxylate
916671-24-4

tert-butyl 1,4,7,10-tetraazacyclododecane carboxylate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 0.333333h;100%
cyclen-glyoxal
74199-09-0, 79236-92-3

cyclen-glyoxal

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; bromine In water; toluene99.23%
With hydrogenchloride; sodium hydroxide; bromine In water; toluene99.23%
With hydrogenchloride; bromine In water pH=6;55%
1,4,7,10-tetraazacyclododecane tetrahydrochloride
10045-25-7

1,4,7,10-tetraazacyclododecane tetrahydrochloride

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With hydrogenchloride95%
With potassium hydroxide In water at 0 - 10℃;91.3%
With potassium hydroxide
With sodium hydroxide In toluene at 40℃; for 1h; Reflux;13.77 g
With sodium hydroxide In water; toluene12 g
C11H13NO2

C11H13NO2

1,5-diamino-3-azapentane
111-40-0

1,5-diamino-3-azapentane

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen; potassium carbonate In 2-methyltetrahydrofuran at 15℃; for 4h; Reagent/catalyst; Temperature; Solvent;94.9%
2,3,4,5,6,7,8,8c-octahydro-1H-4a,6a,8a-triaza-2a-azoniacyclopent[fg]acenaphthylene bromide salt

2,3,4,5,6,7,8,8c-octahydro-1H-4a,6a,8a-triaza-2a-azoniacyclopent[fg]acenaphthylene bromide salt

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With potassium hydroxide In water at 100℃; Temperature;93.2%
With caustic In water for 0.5h; Heating;88%
With potassium hydroxide In water for 0.5h; Heating;71%
1,2-Diiodoethane
624-73-7

1,2-Diiodoethane

ethylenediamine
107-15-3

ethylenediamine

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With tetrabutylammomium bromide In ethanol at 80℃; for 8h;88.4%
cyclen tetratosylate
52667-88-6

cyclen tetratosylate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With sulfuric acid at 165℃;88%
Stage #1: cyclen tetratosylate With sulfuric acid at 100℃; for 0.05h; Microwave irradiation;
Stage #2: With hydrogenchloride In water
Stage #3: With sodium hydroxide In water
87%
With sulfuric acid at 100 - 105℃; Heating; 30-48 h;85%
1,4,7,10-tetraazatricyclo<8.2.1.14,7>tetradecane-13,14-dione

1,4,7,10-tetraazatricyclo<8.2.1.14,7>tetradecane-13,14-dione

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With hydrazine hydrate In methanol at 20℃; for 20.5h; Solvent; Temperature; Reflux;87.21%
1-bromo-2-iodoethane
590-16-9

1-bromo-2-iodoethane

ethylenediamine
107-15-3

ethylenediamine

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With tetrabutylammomium bromide In ethanol at 80℃; for 8h;86%
ethylenediamine
107-15-3

ethylenediamine

ethylene dibromide
106-93-4

ethylene dibromide

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide In ethanol at 80℃; for 8h; Reagent/catalyst; Solvent; Temperature;85%
ethylenediamine
107-15-3

ethylenediamine

1-Bromo-2-chloroethane
107-04-0

1-Bromo-2-chloroethane

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With tetrabutylammomium bromide In ethanol at 80℃; for 8h;76.7%
ethylenediamine
107-15-3

ethylenediamine

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With tetrabutylammomium bromide In ethanol at 80℃; for 8h;74.4%
C32H36N4O8S4

C32H36N4O8S4

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With sulfuric acid at 90℃; for 60h; Large scale;73%
2,3,5,6,8,9-hexahydrodiimidazo[1,2-a:2′,1′-c]pyrazine

2,3,5,6,8,9-hexahydrodiimidazo[1,2-a:2′,1′-c]pyrazine

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran; toluene at 0 - 130℃; for 1h;70%
With diisobutylaluminium hydride In toluene for 16h; Cooling with ice; Reflux; Inert atmosphere;58%
With diisobutylaluminium hydride; sodium fluoride 1) toluene, reflux, 15 h; 2) toluene, water, 0 deg C --> rt; Yield given. Multistep reaction;
cyclen-glyoxal
74199-09-0, 79236-92-3

cyclen-glyoxal

A

ethylenediamine
107-15-3

ethylenediamine

B

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With ethylenediamine In waterA n/a
B 56%
8b-methyldecahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene

8b-methyldecahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With hydrogenchloride In water at 80℃; for 12h; Product distribution / selectivity; Heating / reflux;50%
30%-water sodium hydroxide

30%-water sodium hydroxide

cyclen-glyoxal
74199-09-0, 79236-92-3

cyclen-glyoxal

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
In sulfuric acid; toluene22%
In sulfuric acid; toluene22%
7-<2-(1,3-Dioxolan-2-yl)ethyl>-1,4,7,10-tetraazacyclododecane-1-carbaldehyde
137145-78-9

7-<2-(1,3-Dioxolan-2-yl)ethyl>-1,4,7,10-tetraazacyclododecane-1-carbaldehyde

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With water for 0.0833333h; Ambient temperature; pH 1; dealkylating reaction;
cis-octahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene-3,4-dione
368864-09-9

cis-octahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene-3,4-dione

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 48h; Hydrolysis; Heating;
trans-decahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene
261921-97-5

trans-decahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
Stage #1: trans-decahydro-2a,4a,6a,8a-tetraazacyclopenta[fg]acenaphthylene With hydrogenchloride; bromine In water at 20℃; Oxidation;
Stage #2: With sodium hydroxide In water for 36h; Hydrolysis; Heating;
1.121 g
C14H24N4

C14H24N4

A

cyclohexane-1,2-dione
765-87-7

cyclohexane-1,2-dione

B

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With hydrogenchloride In water at 60℃; for 6h;
triethylentetramine
112-24-3

triethylentetramine

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / ethanol / 3 h / 0 °C
2: 50 percent / cesium carbonate / acetonitrile / 96 h / 40 °C
3: hydrochloric acid / H2O / 6 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 90 percent / ethanol / 3 h / 0 °C
2: 90 percent / cesium carbonate / acetonitrile / 120 h / 40 °C
3: hydrochloric acid / H2O / 6 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: 97 percent / Et3N / acetonitrile / 5 h / 20 °C
2: 78 percent / K2CO3 / dimethylformamide / 30 h / 100 °C
3: 33 percent / conc. H2SO4 / 28 h / 115 °C
View Scheme
C12H22N4

C12H22N4

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 50 percent / cesium carbonate / acetonitrile / 96 h / 40 °C
2: hydrochloric acid / H2O / 6 h / 60 °C
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / cesium carbonate / acetonitrile / 120 h / 40 °C
2: hydrochloric acid / H2O / 6 h / 60 °C
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / K2CO3 / dimethylformamide / 30 h / 100 °C
2: 33 percent / conc. H2SO4 / 28 h / 115 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.) NaOEt / 1.) EtOH, reflux, 30 min, 2.) DMF, 110 deg C, 24 h
2: 54 percent / 96percent aq. H2SO4 / 72 h / 110 °C
View Scheme
Multi-step reaction with 2 steps
1: Bu4NI, 50 percent aq. NaOH / toluene / 10 h / Heating
2: 70 percent / phenol, 30 percent HBr, acetic acid / 14 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: 86 percent / 5percent NaOH / tetrabutylammonium iodide / H2O; toluene / Heating; 8-10 h
2: 85 percent / conc. H2SO4 / 100 - 105 °C / Heating; 30-48 h
View Scheme
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 35 °C
2: sulfuric acid / water / 24 h / 80 °C
3: sodium hydroxide / water; toluene
View Scheme

A

B

(OMe)2CHCH2-halide

(OMe)2CHCH2-halide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / ethanol / 15 h
2: BH3*SMe2 / tetrahydrofuran / 48 h / Heating
View Scheme
1,4,7,10-Tetrazacyclodecane tetrahydrochloride

1,4,7,10-Tetrazacyclodecane tetrahydrochloride

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
In chloroform
oxirane
75-21-8

oxirane

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetrakis-(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane
67896-40-6

1,4,7,10-tetrakis-(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
In water100%
In ethanol at 5℃;69%
In water at 0℃; for 2h;
N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetraazatricyclo[5.5.1.04,13]tridecane
67705-42-4

1,4,7,10-tetraazatricyclo[5.5.1.04,13]tridecane

Conditions
ConditionsYield
In toluene at 120℃; Cyclization;100%
at 120℃;95%
In toluene
In toluene at 90 - 100℃; for 1h;
1,2-epoxytetradecane
3234-28-4

1,2-epoxytetradecane

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1-(2-hydroxytetradecyl)-1,4,7-10-tetraazacyclododecane

1-(2-hydroxytetradecyl)-1,4,7-10-tetraazacyclododecane

Conditions
ConditionsYield
In ethanol for 120h;100%
In ethanol
tert-butyl 2,5-dioxopyrrolidin-1-yl carbonate
13139-12-3

tert-butyl 2,5-dioxopyrrolidin-1-yl carbonate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

di-tert-butyl-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate
913542-69-5

di-tert-butyl-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate

Conditions
ConditionsYield
In chloroform at 20℃;100%
In chloroform100%
In chloroform at 20℃; for 31h;100%
N-(Benzyloxycarbonyloxy)succinimide
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester
162148-45-0

1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester

Conditions
ConditionsYield
In chloroform at 20℃; for 48h;100%
In chloroform at 20℃; for 0.5h; Inert atmosphere;100%
In chloroform at 20℃; for 48h;
benzyl chloroformate
501-53-1

benzyl chloroformate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

4,10-bis((benzyloxy)carbonyl)-4,10-diaza-1,7-diazoniacyclododecane-1,7-diium chloride

4,10-bis((benzyloxy)carbonyl)-4,10-diaza-1,7-diazoniacyclododecane-1,7-diium chloride

Conditions
ConditionsYield
In chloroform at 20℃; for 24h; Cooling with ice;100%
Stage #1: benzyl chloroformate; 1,4,7,10-tetraazacyclododecan In chloroform Cooling with ice;
Stage #2: In chloroform at 20℃; for 24h;
100%
In chloroform Cooling with ice;100%
In chloroform at 0 - 20℃; for 10h;99%
1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

2-chloro-N-[1-(1-naphthyl)ethyl]acetamide

2-chloro-N-[1-(1-naphthyl)ethyl]acetamide

N-[1-(1-naphthyl)ethyl]-1,4,7,10-tetraazacyclododecane-1-acetamide
1512804-14-6

N-[1-(1-naphthyl)ethyl]-1,4,7,10-tetraazacyclododecane-1-acetamide

Conditions
ConditionsYield
With triethylamine In chloroform Cooling; Reflux;100%
C14H21NO5S2

C14H21NO5S2

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C21H37N5O2S

C21H37N5O2S

Conditions
ConditionsYield
In chloroform at 20℃;100%
N-iodoacetyl ω-aminocaproic acid methyl ester

N-iodoacetyl ω-aminocaproic acid methyl ester

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C44H80N8O12

C44H80N8O12

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; for 18h;100%
N-iodoacetyl 3-amino-3-methylbutyric acid methyl ester

N-iodoacetyl 3-amino-3-methylbutyric acid methyl ester

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C40H72N8O12

C40H72N8O12

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; for 18h;100%
N-iodoacetyl p-aminomethylbenzoic acid methyl ester

N-iodoacetyl p-aminomethylbenzoic acid methyl ester

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C52H64N8O12

C52H64N8O12

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 60℃; for 18h;100%
formaldehyd
50-00-0

formaldehyd

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

β-cyanoethylisocyanide

β-cyanoethylisocyanide

3,3',3'',3'''-((1,4,7,10-tetrakis((1H-tetrazol-5-yl)methyl)-1,4,7,10-tetraazacyclododecane(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrakis(methylene))tetrakis(1H-tetrazole-5,1-diyl))tetrapropanenitrile

3,3',3'',3'''-((1,4,7,10-tetrakis((1H-tetrazol-5-yl)methyl)-1,4,7,10-tetraazacyclododecane(1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrayl)tetrakis(methylene))tetrakis(1H-tetrazole-5,1-diyl))tetrapropanenitrile

Conditions
ConditionsYield
With trimethylsilylazide In methanol; acetonitrile100%
1-(3-bromopropyl)-3-carbamoylpyridin-1-ium bromide

1-(3-bromopropyl)-3-carbamoylpyridin-1-ium bromide

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1-(3-(1,4,7,10-tetraazacyclododecan-1-yl)propyl)-3-carbamoylpyridin-1-ium bromide

1-(3-(1,4,7,10-tetraazacyclododecan-1-yl)propyl)-3-carbamoylpyridin-1-ium bromide

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Sonication;100%
N-(tert-butoxycarbonyl)-succinimide
41839-96-7

N-(tert-butoxycarbonyl)-succinimide

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

di-tert-butyl-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate
913542-69-5

di-tert-butyl-1,4,7,10-tetraazacyclododecane-1,7-dicarboxylate

Conditions
ConditionsYield
In chloroform100%
N-iodoacetyl-Gly-Tyr(t-Bu)-OMe

N-iodoacetyl-Gly-Tyr(t-Bu)-OMe

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C80H116N12O20

C80H116N12O20

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 70℃; for 24h;99%
N-iodoacetyl-Lys(Boc)-OMe

N-iodoacetyl-Lys(Boc)-OMe

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C64H116N12O20

C64H116N12O20

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; for 18h;99%
N-iodoacetyl-Gly-L-Tyr(O-propargyl)-OMe

N-iodoacetyl-Gly-L-Tyr(O-propargyl)-OMe

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C72H84N12O20

C72H84N12O20

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 70℃; for 18h;99%
glyoxal trimer dihydrate
4405-13-4

glyoxal trimer dihydrate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

cyclen-glyoxal
74199-09-0, 79236-92-3

cyclen-glyoxal

Conditions
ConditionsYield
In methanol at 0℃; for 3h;99%
In methanol at 0 - 20℃; for 2.5h;94%
In methanol; water at 20℃; for 3h;82%
1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

7-(4-bromobutyloxy)-4-methyl-2H-chromen-2-one
70846-42-3

7-(4-bromobutyloxy)-4-methyl-2H-chromen-2-one

1,4,7,10-(7-(4-bromobutoxy)-4-methyl-coumarin) cyclen

1,4,7,10-(7-(4-bromobutoxy)-4-methyl-coumarin) cyclen

Conditions
ConditionsYield
With potassium carbonate In acetonitrile Reflux;98.8%
benzyl bromide
100-39-0

benzyl bromide

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1-benzyl-1,4,7,10-tetraazacyclododecane
112193-83-6

1-benzyl-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
Stage #1: 1,4,7,10-tetraazacyclododecan With tris(dimethylamino)borane; sodium hydride In toluene for 4h; Heating;
Stage #2: benzyl bromide In toluene at 110℃; for 1h;
98%
In acetonitrile for 1h; Heating;89%
With sodium carbonate In acetonitrile89%
Glyoxal
131543-46-9

Glyoxal

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

cyclen-glyoxal
74199-09-0, 79236-92-3

cyclen-glyoxal

Conditions
ConditionsYield
In methanol; water at 20℃;98%
In methanol; water at 20℃; for 2h;95%
In water; acetonitrile91%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,7-bis(ethoxycarbonyl)-1,4,7,10-tetraazacyclododecane
162148-43-8

1,7-bis(ethoxycarbonyl)-1,4,7,10-tetraazacyclododecane

Conditions
ConditionsYield
With pH 2-398%
With hydrogenchloride for 24h;40%
pH=2.5; Acylation;
Stage #1: chloroformic acid ethyl ester; 1,4,7,10-tetraazacyclododecan pH=2 - 3;
Stage #2: With sodium hydroxide In water
benzyl chloroformate
501-53-1

benzyl chloroformate

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester
162148-45-0

1,4,7,10-tetraaza-cyclododecane-1,7-dicarboxylic acid dibenzyl ester

Conditions
ConditionsYield
In ethanol for 24h;98%
Stage #1: benzyl chloroformate; 1,4,7,10-tetraazacyclododecan In chloroform; water at 0 - 20℃; for 10h;
Stage #2: With sodium hydroxide In chloroform
98%
In chloroform98%
1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

2,4-bis(bromomethyl)-1,3,5-triethyl benzene
190779-61-4

2,4-bis(bromomethyl)-1,3,5-triethyl benzene

1,1′-((2,4,6-triethyl-1,3-phenylene)bis(methylene))bis(1,4,7,10-tetraazacyclo-dodecane)

1,1′-((2,4,6-triethyl-1,3-phenylene)bis(methylene))bis(1,4,7,10-tetraazacyclo-dodecane)

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 121.5h; Inert atmosphere;98%
C13H13ClN2O3

C13H13ClN2O3

1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

C21H32N6O3

C21H32N6O3

Conditions
ConditionsYield
In chloroform; N,N-dimethyl-formamide at 20℃;97%
With potassium carbonate In chloroform; N,N-dimethyl-formamide at 20℃; for 24h;320 mg
1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

1,4,7,10-Tetraazabicyclo[8.2.2]tetradecane-11,12-dione
260410-34-2

1,4,7,10-Tetraazabicyclo[8.2.2]tetradecane-11,12-dione

Conditions
ConditionsYield
In ethanol for 48h; Acylation;96%
In ethanol at 20℃; for 72h;93%
In ethanol
In ethanol for 24h; Reflux;
1,4,7,10-tetraazacyclododecan
294-90-6

1,4,7,10-tetraazacyclododecan

[4-(2-chloro-acetylamino)-butyl]-carbamic acid tert-butyl ester
133264-58-1

[4-(2-chloro-acetylamino)-butyl]-carbamic acid tert-butyl ester

[4-(2-{4,7,10-tris-[(4-tert-butoxycarbonylamino-butylcarbamoyl)-methyl]-1,4,7,10-tetraaza-cyclododec-1-yl}-acetylamino)-butyl]-carbamic acid tert-butyl ester
913972-24-4

[4-(2-{4,7,10-tris-[(4-tert-butoxycarbonylamino-butylcarbamoyl)-methyl]-1,4,7,10-tetraaza-cyclododec-1-yl}-acetylamino)-butyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With caesium carbonate; potassium iodide In acetonitrile for 120h; Heating;96%

294-90-6Relevant articles and documents

Preparation and animal biodistribution of 166Ho labeled DOTA for possible use in intravascular radiation therapy (IVRT)

Das, Tapas,Chakraborty, Sudipta,Banerjeel, Sharmila,Samuel, Grace,Sarma,Venkatesh, Meera,Pillai

, p. 197 - 209 (2003)

Owing to its favorable decay characteristics (T1/2 = 27 h, Eβ(max) = 1.85 MeV, Eγ = 81 keV) and its availability with a specific activity of 3.74.4GBq/mg from a moderate flux reactor, 166Ho can be considered as a potential radionuclide for intravascular radiation therapy (IVRT) using liquid-filled balloons. In the present work, studies on the use of 166Ho labeled 1,4,7,10- tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) as a possible agent for IVRT for the prevention of restenosis has been initiated. 166Ho was obtained by irradiating natural Ho2O3 powder and DOTA was synthesized by a multistep procedure. The optimum protocol of radiolabeling of DOTA with 166Ho was achieved by varying different reaction parameters. The complex was found to retain its stability for 7 days at room temperature. Bioevaluation studies carried out in Wistar rats showed that >95% of the injected activity was excreted within 3 h p.i. with almost no retention in any major organ. Both radiochemical and biological studies showed that 166Ho labeled DOTA can be further explored as a potential agent for IVRT. Copyright

Isomerization kinetics of lanthanide(III) complexes with the pendant-arm macrocyclic ligand 1,4,7,10-tetrakis(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane

Pittet, Pierre-Andre,Frueh, Dominique,Tissieres, Veronique,Buenzli, Jean-Claude G.

, p. 895 - 900 (1997)

The 13C and 1H NMR spectra of the complexes of LaIII, EuIII and LuIII with 1,4,7,10-tetrakis(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane (L1) in acetonitrile or methanol indicated the presence of two enantiomers the interconversion of which proceeds through both a ring inversion and a rearrangement of the pendant arms. The following kinetic parameters were extracted from temperature-dependent 13C NMR spectra for the ring inversion in [LaL1]3+, [EuL1]3+, [LuL1]3+ in CD3OD and [EuL1]3+ in CD3CN:k(298 K) = 1396, 1055, 1288 and 880 s-1; ΔH? = 37.6, 41.1, 48.2 and 47.7 kJ mol-1; ΔS? = -58.5, -49.2, -23.8 and -28.4 J K-1 mol-1, respectively. The lanthanide(III) substitution induces a continuous variation of the kinetic parameters, implying the same pathway for the enantiomerization. The behaviour of [LnL1]3+ in solution is compared with that of complexes with similar 12-membered tetraaza macrocycles bearing pendant arms.

-

Kossai,R. et al.

, p. 1059 - 1062 (1979)

-

A microcalorimetric determination of the enthalpies of formation in solution of nickel(II) complexes with tetraaza macrocyclic ligands of varying size

Fabbrizzi, Luigi,Micheloni, Mauro,Paoletti, Piero

, p. 535 - 538 (1980)

The enthalpies of formation of nickel complexes with tetraaza macrocyclic ligands of varying ring size, from 12 to 15 members, have been determined by destroying the complexes in aqueous solution with alkaline cyanide. The octahedral-square-planar equilibria have been investigated, and the results are presented as ΔH° for both octahedral, blue and, when possible, square-planar, yellow species. Like the Cu(II) system, the blue, octahedral series exhibits a maximum in ΔH° with [14]aneN4. This is discussed in terms of the relative size of the ligand and the metal ion. The unexpected reversal of ΔH° for the two square-planar complexes is rationalized in terms of expected ligand transformations.

DINUCLEATING LIGAND OR DINUCLEAR METAL COMPLEX

-

Paragraph 0058-0059, (2021/03/19)

To provide a metal complex that has high cancer cell toxicity and has DNA target and cyclen.SOLUTION: The present disclosure provides a dinuclear metal complex represented by the following formula (IV).SELECTED DRAWING: None

Preparation method of cyclen

-

Paragraph 0061; 0062; 0063, (2020/02/14)

The invention provides a preparation method of cyclen. The method comprises the following step: taking triethylenetetramine (TETA) as a raw material to carry out refining, then carrying out a reactionon the refined triethylenetetramine with methylglyoxal to obtain an intermediate 2, carrying out cyclization on the intermediate 2 with glyoxal, carrying out reducing with sodium borohydride to obtain a cyclized intermediate 3, finally carrying out ring opening through acid hydrolysis, and then adjusting the pH value by using an alkali solution to free out the cyclen.

Preparation method of high-purity cycleanine

-

Paragraph 0028-0031, (2020/04/06)

The invention discloses a preparation method of high-purity cycleanine. Diethylenetriamine and N-benzyl diacetaldehyde amine are used as main raw materials, a drying agent is added, generated water isabsorbed, the generation of imine is promoted, meanwhile, hydrogen is introduced to rapidly reduce the imine, the decomposition of imine is avoided, and the reaction is more thorough. The method is simple in step, low in cost, high in yield, low in equipment requirement, environmentally friendly and suitable for industrial production.

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