Cyclen supplier | CasNO.294-90-6

Name
Cyclen
EINECS 202-928-3
CAS No. 294-90-6
Article Data55
CAS DataBase
Density 0.874 g/cm³
Solubility almost transparency
Melting Point 108-113 °C
Formula C₈H₂₀N₄
Boiling Point 283.8 °C at 760 mmHg
Molecular Weight 172.274
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
Hazard Symbols Xi
Synonyms 1,4,7,10-Tetrazacyclododecane;NSC 629374;Tetraaza-12-crown-4;
PSA 48.12000
LogP -0.32640

Synthetic route

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

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

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane for 0.333333h;	100%

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

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

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; bromine In water; toluene	99.23%
With hydrogenchloride; sodium hydroxide; bromine In water; toluene	99.23%
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

Conditions	Yield
With hydrogenchloride	95%
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; toluene	12 g

: C11H13NO2

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

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C32H36N4O8S4

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

Conditions

Conditions	Yield
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

Conditions	Yield
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;

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

A: 107-15-3
ethylenediamine

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

Conditions

Conditions	Yield
With ethylenediamine In water	A n/a B 56%

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

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

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 12h; Product distribution / selectivity; Heating / reflux;	50%

30%-water sodium hydroxide: 30%-water sodium hydroxide

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

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

Conditions

Conditions	Yield
In sulfuric acid; toluene	22%
In sulfuric acid; toluene	22%

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride In water at 60℃; for 6h;

: 112-24-3
triethylentetramine

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In water	100%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
In chloroform at 20℃;	100%
In chloroform	100%
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With triethylamine In chloroform Cooling; Reflux;	100%

: C14H21NO5S2

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

: C21H37N5O2S

Conditions

Conditions	Yield
In chloroform at 20℃;	100%

: N-iodoacetyl ω-aminocaproic acid methyl ester

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

: C44H80N8O12

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trimethylsilylazide In methanol; acetonitrile	100%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
In chloroform	100%

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

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

: C80H116N12O20

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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 acetonitrile	89%

: 131543-46-9
Glyoxal

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

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

Conditions

Conditions	Yield
In methanol; water at 20℃;	98%
In methanol; water at 20℃; for 2h;	95%
In water; acetonitrile	91%

: 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

Conditions	Yield
With pH 2-3	98%
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

Conditions	Yield
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 chloroform	98%

: 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

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

: C13H13ClN2O3

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

: C21H32N6O3

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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.

Product Name

Cyclen

Synthetic route

Cyclen Specification

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