1,5,9-Triazacyclododecane supplier

Name
1,5,9-Triazacyclododecane
EINECS
CAS No. 294-80-4
Article Data17
CAS DataBase
Density 0.852 g/cm³
Solubility
Melting Point 32-35 °C
Formula C₉H₂₁N₃
Boiling Point 225.8 °C at 760 mmHg
Molecular Weight 171.286
Flash Point 124.9 °C
Transport Information
Appearance
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols
Synonyms 1,5,9-Triaza-cyclododecane;
PSA 36.09000
LogP 0.92550

Synthetic route

: 127623-71-6
1,5,9-triazacyclododecane-2,4-dione

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With borane-THF In tetrahydrofuran for 24h; Heating;	99%

: 67705-41-3
1,5,9-triazatricyclo[7.3.1.05,13 ]tridecane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With sulfuric acid for 9.5h; Heating;	94%
With hydrogenchloride for 22h; Heating;	89%
With sulfuric acid In water for 5h; Reflux;	89%
Stage #1: 1,5,9-triazatricyclo[7.3.1.05,13 ]tridecane With ethylene dibromide In acetonitrile Heating; Stage #2: With trifluorormethanesulfonic acid for 18h; Heating; Further stages.;

: 340970-56-1
N,N',N''-tris(β-trimethylsilylethanesulfonyl)-1,5,9-triazacyclododecane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 95℃; for 24h;	81%

: 35980-67-7
1,5,9-tritosyl-1,5,9-triazacyclododecane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With sulfuric acid at 100 - 105℃; Heating; 50-70 h;	63%
With hydrogen bromide; acetic acid; phenol at 50℃; for 14h;	63%
With sulfuric acid at 100℃; for 39h;	63%

: 35980-62-2
1,5,9-triazacyclododecane trihydrobromide

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With potassium hydroxide In methanol

: 1,5,9-triazacyclododecane tritosylate

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With sulfuric acid at 120℃; for 30h; Yield given;

: 1,5,9-Tris-trifluoromethanesulfonyl-1,5,9-triaza-cyclododecane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With ammonia; lithium Yield given;

: 56-18-8
bis(3-aminopropyl)amine

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / sodium hydroxide / H2O / 1.) 1 hr., 5 deg C, 2.) r.t., 3 hrs. 2: 90 percent / tetrabutylammonium iodide, sodium hydroxide (50 percent) / toluene; H2O / 9 h / Heating 3: 63 percent / sulfuric acid, (conc.) / 39 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1.1: 90 percent / aq. NaOH / CH2Cl2 / 3 h / 20 °C 2.1: NaH / dimethylformamide / 1 h / 80 - 100 °C 2.2: 50 percent / dimethylformamide / 12 h / 100 °C 3.1: 55 percent / H2SO4 / 54 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 22 percent / sodium methoxide / ethanol / 168 h / Heating 2: 99 percent / BH3.THF / tetrahydrofuran / 24 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 63 percent / Et3N / dimethylformamide / 1.5 h / 0 °C 2: 73 percent / Cs2CO3 / dimethylformamide / 48 h / 20 °C 3: 81 percent / CsF / dimethylformamide / 24 h / 95 °C View Scheme

: 35980-64-4
1,5,9-Tritosyl-1,5,9-triazanonane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / tetrabutylammonium iodide, sodium hydroxide (50 percent) / toluene; H2O / 9 h / Heating 2: 63 percent / sulfuric acid, (conc.) / 39 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: NaH / dimethylformamide / 1 h / 80 - 100 °C 1.2: 50 percent / dimethylformamide / 12 h / 100 °C 2.1: 55 percent / H2SO4 / 54 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / Bu4NI, 50 percent aq. NaOH / toluene / 10 h / Heating 2: 63 percent / phenol, 30 percent HBr, acetic acid / 14 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 66 percent / 5percent NaOH / tetrabutylammonium iodide / H2O; toluene / Heating; 8-10 h 2: 63 percent / conc. H2SO4 / 100 - 105 °C / Heating; 50-70 h View Scheme

: 340970-54-9
N,N',N''-tris(β-trimethylsilylethanesulfonyl)-1,5,9-triazanonane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / Cs2CO3 / dimethylformamide / 48 h / 20 °C 2: 81 percent / CsF / dimethylformamide / 24 h / 95 °C View Scheme

: 5807-14-7
1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / KOH, KBr, NaBH4 / toluene / 42.5 h / Ambient temperature 2: 94 percent / aq. H2SO4 / 9.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: -20 - 20 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C 3: sulfuric acid / water / 5 h / Reflux View Scheme

: C,C,C-Trifluoro-N,N-bis-(3-trifluoromethanesulfonylamino-propyl)-methanesulfonamide

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / dimethylformamide / 4 h / 100 °C 2: Li, NH3 View Scheme

: 3518-88-5
3,3'-imino-di-propionic acid diethyl ester

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) HO-, 2.) H3O+ 2: BH3*S(CH3)2 3: pyridine / acetonitrile 4: KH / dimethylformamide 5: HBr 6: KOH / methanol View Scheme

: 5446-58-2
3,3'-(tosylazanediyl)dipropionic acid

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: BH3*S(CH3)2 2: pyridine / acetonitrile 3: KH / dimethylformamide 4: HBr 5: KOH / methanol View Scheme

: 75321-10-7
3-propyl tosylate

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KH / dimethylformamide 2: HBr 3: KOH / methanol View Scheme

: 56187-12-3
N-tosyl-bis(3-hydroxypropyl)amine

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / acetonitrile 2: KH / dimethylformamide 3: HBr 4: KOH / methanol View Scheme

: C10H18N3(1+)*F6P(1-)

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / -78 - 20 °C 2: sulfuric acid / water / 5 h / Reflux View Scheme

: 56-18-8
bis(3-aminopropyl)amine

: 109-64-8
1,3-dibromo-propane

: 294-80-4
1,5,9-triazacyclododecane

Conditions

Conditions	Yield
Stage #1: bis(3-aminopropyl)amine; 1,3-dibromo-propane With Phthalic acid dibutyl ester; potassium carbonate; p-toluenesulfonyl chloride Stage #2: With sulfuric acid at 90℃; for 48h; Further stages;

: 294-80-4
1,5,9-triazacyclododecane

: nickel(II) nitrate

: C9H21N3*Ni(2+)*2NO3(1-)

Conditions

Conditions	Yield
In methanol Inert atmosphere;	100%

: 294-80-4
1,5,9-triazacyclododecane

: 62051-24-5
hexahydro-3a,6a,9a-triaza-9b-phospha-phenalene

Conditions

Conditions	Yield
With Hexamethylphosphorous triamide at 120℃; for 96h;	96%
With Hexamethylphosphorous triamide
With Hexamethylphosphorous triamide
With Hexamethylphosphorous triamide

: 112-54-9
Dodecanal

: 294-80-4
1,5,9-triazacyclododecane

: 1,5,9-tridodecyl-1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With sodium cyanoborohydride In water; acetonitrile at 20℃; pH=4 - 5;	96%

: 294-80-4
1,5,9-triazacyclododecane

: 86-52-2
1-Chloromethylnaphthalene

: 1-Naphthalen-2-ylmethyl-5,9-bis-naphthalen-1-ylmethyl-1,5,9-triaza-cyclododecane

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran	95%

: 5-(2-bromo-ethyl)-phenanthridinium bromide

: 294-80-4
1,5,9-triazacyclododecane

: AP4-55

Conditions

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 48h;	93%

: 5-(2-bromo-ethyl)-phenanthridinium bromide

: 121-44-8
triethylamine

: 294-80-4
1,5,9-triazacyclododecane

A: AP4-55

B: 636-70-4
triethylamine hydrobromide

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20℃; for 48h;	A 93% B n/a

...Expand

: C8H15ClN2O2

: 294-80-4
1,5,9-triazacyclododecane

: C32H61N9O6

Conditions

Conditions	Yield
Stage #1: 1,5,9-triazacyclododecane With potassium carbonate In methanol for 0.5h; Stage #2: C8H15ClN2O2 In methanol for 1h;	92%

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 294-80-4
1,5,9-triazacyclododecane

: 67705-41-3
1,5,9-triazatricyclo[7.3.1.05,13 ]tridecane

Conditions

Conditions	Yield
at 120℃;	90%
at 85℃; for 3h;	90%
In neat (no solvent) Heating;	36%

: 18871-66-4
N,N-dimethylacetamide dimethyl acetal

: 294-80-4
1,5,9-triazacyclododecane

: 81115-31-3, 111264-50-7, 126188-50-9
9b-Methyl-hexahydro-3a,6a,9a-triaza-phenalene

Conditions

Conditions	Yield
Heating;	89%

: zinc perchlorate

: 294-80-4
1,5,9-triazacyclododecane

: [Zn(1,5,9-triazacyclododecane)](ClO4)2*H2O

Conditions

Conditions	Yield
In ethanol azamacrocycle in ethanol was heated and stirred at 65°C, Zn-salt in ethanol was slowly added at 65°C dropwise, stirred at 65°C for 2 h; cooled, filtered, washed with cold ethanol (3x), ppt. was dried under vac. over two days at ambient temp.; elem. anal.;	89%

: 4292-19-7
1-Iodododecane

: 294-80-4
1,5,9-triazacyclododecane

: 1,5-didodecyl-1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl acetamide at 80℃;	88%

: 75-21-8
oxirane

: 294-80-4
1,5,9-triazacyclododecane

: 1,5,9-tris(2-hydroxyethyl)-1,5,9-triazacyclododecane

Conditions

Conditions	Yield
In ethanol at 0℃;	88%

: 294-80-4
1,5,9-triazacyclododecane

: 13939-06-5, 199620-15-0
molybdenum hexacarbonyl

: 97703-29-2
Mo(CO)3(NHC3H6NHC3H6NHC3H6)

Conditions

Conditions	Yield
In decalin byproducts: CO; heated to 150°C for 10 min under Ar; filtn., ppt. is washed (benzene, ether), air-dried, elem. anal.;	85%

: 17616-43-2
3-iodo-2-(iodomethyl)-1-propene

: 294-80-4
1,5,9-triazacyclododecane

: 11-methylene-1,5,9-triazabicyclo<7.3.3>pentadecane

Conditions

Conditions	Yield
With potassium carbonate In isopropyl alcohol Heating;	83%

: 129018-26-4
thioacetic acid S-(4-chlorocarbonyl-phenyl) ester

: 294-80-4
1,5,9-triazacyclododecane

: 146070-03-3
1,5,9-tris(4-acetylthiobenzoyl)-1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With triethylamine In dichloromethane Ambient temperature;	83%

: potassium hexacyanoruthenate(II)

: 7732-18-5
water

: 6018-89-9
nickel(II) acetate tetrahydrate

: 294-80-4
1,5,9-triazacyclododecane

: [Ni(1,5,9-triazocyclododecane)(H2O)]2[hexacyanoruthenate(II)]*8H2O

Conditions

Conditions	Yield
In water aq. soln. of ligand (0.24 mmol) and Ru compd. (0.24 mmol) added slowly to aq. soln. of Ni salt (0.24 mmol), filtered; crystd. at room temp. in darkness, filtered off, washed (methanol, Et2O), dried in air, elem. anal.;	83%

...Expand

: 294-80-4
1,5,9-triazacyclododecane

: 224557-85-1
O-Benzyl-2-bromo-N-methylacetohydroxamic acid

: 1,5,9-Triazacyclododecane-N,N',N''-tris(O-benzyl-N-methylacetohydroxamic acid)

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 90-100 deg C, 2 h, 2.) r.t., 18 h;	82%

: 1199-01-5
2-phenylazlactone

: 294-80-4
1,5,9-triazacyclododecane

: 174783-34-7
1,5,9-tris<(benzoylamino)acetyl>-1,5,9-triazacyclododecane

Conditions

Conditions	Yield
In acetonitrile for 20h; Ambient temperature;	82%

: 557-34-6
zinc diacetate

: 143-66-8
sodium tetraphenyl borate

: 294-80-4
1,5,9-triazacyclododecane

: 162024-82-0
(η(3)-1,5,9-triazacyclododecane)zinc(II) acetate tetraphenylborate

Conditions

Conditions	Yield
In ethanol inert atmosphere; dropwise addn. of NaBPh4 (in THF) to mixt. of Zn-saltand ligand (in EtOH), stirring overnight; filtering, concn., addn. of Et2O (pptn.), filtering off, washing (Et2O), drying (vac.);	80%

...Expand

: H4(ruthenium)4(carbonyl)12

: 294-80-4
1,5,9-triazacyclododecane

: H(CH2)9(NH)3(1+)*H3Ru4(1-)*12CO=[H(CH2)9(NH)3][H3Ru4(CO)12]

Conditions

Conditions	Yield
In hexane N2-atmosphere; addn. of equimolar amt. of dodecane derivative to Ru-complex soln. at reflux, stirring (70°C, 2 h); cooling to room temp., filtration, extn. into hexane, drying (vac.); elem. anal.;	78.5%

: 10136-57-9
5-(chloromethyl)quinolin-8-ol

: 294-80-4
1,5,9-triazacyclododecane

: C39H42N6O3

Conditions

Conditions	Yield
With potassium carbonate In water; acetone for 3h; Reflux;	78%

: 24424-99-5
di-tert-butyl dicarbonate

: 294-80-4
1,5,9-triazacyclododecane

: 174192-40-6
bis(1,1-dimethylethyl) 1,5,9-triazacyclododecane-1,5-dicarboxylate

Conditions

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;	72%
With triethylamine In chloroform for 24h;

: 67217-55-4
mono-6-deoxy-6-(p-tolylsulphonyl)-β-cyclodextrin

: 294-80-4
1,5,9-triazacyclododecane

: mono-6-deoxy-6-(1,5,9-triazacyclododecanyl)-β-cyclodextrin

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 5h; amynation;	72%

: 557-42-6
zinc(II) thiocyanate

: 294-80-4
1,5,9-triazacyclododecane

: (1,5,9-triazacyclododecane)Zn(II)(NCS)2

Conditions

Conditions	Yield
In ethanol mixing at 50°C; recrystallized from 50% MeOH; elem. anal.;	72%

: 4053-45-6
5-chloromethyl-8-hydroxyquinoline hydrochloride

: 294-80-4
1,5,9-triazacyclododecane

: C39H42N6O3

Conditions

Conditions	Yield
With potassium carbonate In water; acetone for 3h; Reflux;	72%

: 17616-43-2
3-iodo-2-(iodomethyl)-1-propene

: 294-80-4
1,5,9-triazacyclododecane

: 104875-18-5
11-Methylene-1,5,9-triazabicyclo[7.3.3] pentadecane

Conditions

Conditions	Yield
With potassium carbonate In isopropyl alcohol for 6h; Heating;	70%
With potassium carbonate In isopropyl alcohol	60%

: 98-59-9
p-toluenesulfonyl chloride

: 294-80-4
1,5,9-triazacyclododecane

: 164913-31-9
N1,N5-ditosyl-1,5,9-triazacyclododecane

Conditions

Conditions	Yield
With sodium hydroxide In diethyl ether; water at 0℃; for 1h;	68%

1,5,9-Triazacyclododecane Specification

The 1,5,9-Triazacyclododecane, with the CAS registry number 294-80-4, is also known as 1,5,9-Triaza-cyclododecane. It belongs to the product categories of Amine Monomers; Chelation/Complexation Compounds; Crown Ethers Monomers; Secondary Amines; Synthetic Reagents. This chemical's molecular formula is C₉H₂₁N₃ and molecular weight is 171.28. What's more, its systematic name is called 1,5,9-Triazacyclododecane.

Physical properties about 1,5,9-Triazacyclododecane are: (1)ACD/LogP: 0.31; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.79; (4)ACD/LogD (pH 7.4): -4.66; (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: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 9.72 Å²; (13)Index of Refraction: 1.426; (14)Molar Refractivity: 51.54 cm³; (15)Molar Volume: 200.9 cm³; (16)Surface Tension: 27.1 dyne/cm; (17)Density: 0.852 g/cm³; (18)Flash Point: 124.9 °C; (19)Enthalpy of Vaporization: 46.23 kJ/mol; (20)Boiling Point: 225.8 °C at 760 mmHg; (21)Vapour Pressure: 0.0847 mmHg at 25 °C; (22)Melting Point: 32-35 °C.

Preparation of 1,5,9-Triazacyclododecane: this chemical can be prepared by Hexahydro-3α,6α,9α-triaza-phenalene. The reaction occurs with reagent 3 M aq. HCl and other condition of heating for 22 hours. The yield is 89 %.

1,5,9-Triazacyclododecane can be prepared by Hexahydro-3α,6α,9α-triaza-phenalene

Uses of 1,5,9-Triazacyclododecane: it is used to produce other chemicals. For example, it is used to produce Hexahydro-3α,6α,9α-triaza-phenalene. This reaction needs solvent Neat and other condition of heating. The yield is 36 %.

1,5,9-Triazacyclododecane is used to produce Hexahydro-3α,6α,9α-triaza-phenalene

When you are dealing with this chemical, you should be very careful. This chemical may destroy living tissue on contacting. What's more, it could cause burns. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. In case of contacting with eyes, you should rinse immediately with plenty of water. And in case of other accidents or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1) SMILES: N1CCCNCCCNCCC1
(2) InChI: InChI=1/C9H21N3/c1-4-10-6-2-8-12-9-3-7-11-5-1/h10-12H,1-9H2
(3) InChIKey: VQFZKDXSJZVGDA-UHFFFAOYAY

Product Name

1,5,9-Triazacyclododecane

Synthetic route

1,5,9-Triazacyclododecane Specification

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