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Cyclen

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Name

Cyclen

EINECS 202-928-3
CAS No. 294-90-6 Density 0.874 g/cm3
PSA 48.12000 LogP -0.32640
Solubility almost transparency Melting Point 108-113 °C
Formula C8H20N4 Boiling Point 283.8 °C at 760 mmHg
Molecular Weight 172.27 Flash Point 129.5 °C
Transport Information Appearance off- white to slightly yellow crystalline powder
Safety 26-36 Risk Codes 36/38-36/37/38
Molecular Structure Molecular Structure of 294-90-6 (Cyclen) Hazard Symbols IrritantXi
Synonyms

1,4,7,10-Tetrazacyclododecane;NSC 629374;Tetraaza-12-crown-4;

 

Cyclen Synthetic route

916671-24-4

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

294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane for 0.333333h;100%
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%
10045-25-7

1,4,7,10-tetraazacyclododecane tetrahydrochloride

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

111-40-0

1,5-diamino-3-azapentane

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

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%
624-73-7

1,2-Diiodoethane

107-15-3

ethylenediamine

294-90-6

1,4,7,10-tetraazacyclododecan

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

cyclen tetratosylate

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

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%
590-16-9

1-bromo-2-iodoethane

107-15-3

ethylenediamine

294-90-6

1,4,7,10-tetraazacyclododecan

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

ethylenediamine

106-93-4

ethylene dibromide

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%
107-15-3

ethylenediamine

107-04-0

1-Bromo-2-chloroethane

294-90-6

1,4,7,10-tetraazacyclododecan

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

ethylenediamine

107-06-2

1,2-dichloro-ethane

294-90-6

1,4,7,10-tetraazacyclododecan

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

C32H36N4O8S4

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

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;

A

107-15-3

ethylenediamine

B

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

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

294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
In sulfuric acid; toluene22%
In sulfuric acid; toluene22%
137145-78-9

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

294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With water for 0.0833333h; Ambient temperature; pH 1; dealkylating reaction;
368864-09-9

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

294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
With dimethylsulfide borane complex In tetrahydrofuran for 48h; Hydrolysis; Heating;
261921-97-5

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

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

A

765-87-7

cyclohexane-1,2-dione

B

294-90-6

1,4,7,10-tetraazacyclododecan

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

triethylentetramine

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

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

294-90-6

1,4,7,10-tetraazacyclododecan

Conditions
ConditionsYield
In chloroform
75-21-8

oxirane

294-90-6

1,4,7,10-tetraazacyclododecan

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;
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

294-90-6

1,4,7,10-tetraazacyclododecan

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;
3234-28-4

1,2-epoxytetradecane

294-90-6

1,4,7,10-tetraazacyclododecan

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

Conditions
ConditionsYield
In ethanol for 120h;100%
In ethanol
13139-12-3

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

294-90-6

1,4,7,10-tetraazacyclododecan

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%
13139-17-8

N-(Benzyloxycarbonyloxy)succinimide

294-90-6

1,4,7,10-tetraazacyclododecan

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;
501-53-1

benzyl chloroformate

294-90-6

1,4,7,10-tetraazacyclododecan

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%
294-90-6

1,4,7,10-tetraazacyclododecan

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

294-90-6

1,4,7,10-tetraazacyclododecan

C21H37N5O2S

Conditions
ConditionsYield
In chloroform at 20℃;100%

N-iodoacetyl ω-aminocaproic acid methyl ester

294-90-6

1,4,7,10-tetraazacyclododecan

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

294-90-6

1,4,7,10-tetraazacyclododecan

C40H72N8O12

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

N-iodoacetyl p-aminomethylbenzoic acid methyl ester

294-90-6

1,4,7,10-tetraazacyclododecan

C52H64N8O12

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

formaldehyd

294-90-6

1,4,7,10-tetraazacyclododecan

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

Conditions
ConditionsYield
With trimethylsilylazide In methanol; acetonitrile100%

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

294-90-6

1,4,7,10-tetraazacyclododecan

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%
41839-96-7

N-(tert-butoxycarbonyl)-succinimide

294-90-6

1,4,7,10-tetraazacyclododecan

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

294-90-6

1,4,7,10-tetraazacyclododecan

C80H116N12O20

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 70℃; for 24h;99%

N-iodoacetyl-Lys(Boc)-OMe

294-90-6

1,4,7,10-tetraazacyclododecan

C64H116N12O20

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 50℃; for 18h;99%

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

294-90-6

1,4,7,10-tetraazacyclododecan

C72H84N12O20

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

glyoxal trimer dihydrate

294-90-6

1,4,7,10-tetraazacyclododecan

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%
294-90-6

1,4,7,10-tetraazacyclododecan

70846-42-3

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

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

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

benzyl bromide

294-90-6

1,4,7,10-tetraazacyclododecan

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%
294-90-6

1,4,7,10-tetraazacyclododecan

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

chloroformic acid ethyl ester

294-90-6

1,4,7,10-tetraazacyclododecan

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
501-53-1

benzyl chloroformate

294-90-6

1,4,7,10-tetraazacyclododecan

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%
294-90-6

1,4,7,10-tetraazacyclododecan

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)

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

C13H13ClN2O3

294-90-6

1,4,7,10-tetraazacyclododecan

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
294-90-6

1,4,7,10-tetraazacyclododecan

95-92-1

oxalic acid diethyl ester

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;
294-90-6

1,4,7,10-tetraazacyclododecan

133264-58-1

[4-(2-chloro-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%

Cyclen Specification

The Cyclen with cas registry number of 294-90-6 is also called 1,4,7,10-Tetraazacyclododecane which is also its systematic name and IUPAC name. Its EINECS registry number is 202-928-3. This chemical, with appearance of almost white to slightly yellow crystalline powder, belongs to the classes of Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry; Ring Systems.

Physical properties about this chemical are: (1)ACD/LogP: -2.34; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -6.44; (4)ACD/LogD (pH 7.4): -6.43; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.96 Å2; (13)Index of Refraction: 1.424; (14)Molar Refractivity: 50.28 cm3; (15)Molar Volume: 197 cm3; (16)Surface Tension: 27.6 dyne/cm; (17)Density: 0.874 g/cm3; (18)Flash Point: 129.5 °C ; (19)Enthalpy of Vaporization: 52.28 kJ/mol ; (20)Boiling Point: 283.8 °C at 760 mmHg ; (21)Vapour Pressure: 0.00309 mmHg at 25°C.

Uses of Cyclen: it can react with formaldehyde to give 1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane at pressure 760.0002 using reagent formic acid, solvent water, and other conditions like heating. The reaction time is about 30 hours. The yield is 55%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Wear suitable protective clothing when you are using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. This chemical should be stored in refrigerator.

You can still convert the following datas into molecular structure:
(1)SMILES: N1CCNCCNCCNCC1;
(2)InChI: InChI=1/C8H20N4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h9-12H,1-8H2;
(3)InChIKey: QBPPRVHXOZRESW-UHFFFAOYAQ

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 435mg/kg (435mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 19, Pg. 425, 1984.
rat LD50 intravenous 388mg/kg (388mg/kg)   Naturwissenschaften. Vol. 70, Pg. 201, 1983.

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