66943-05-3

Basic information

• Product Name: Aza-15-crown-5
• Synonyms: 1,4,7,10-TETRAOXA-13-AZACYCLOPENTADECANE;1-AZA-15-CROWN-5;1-AZA-15-CROWN 5-ETHER;AZA-15-CROWN-5;Aza-15-crown-5, 99+%;1-aza-12-crown-5;1,4,7,10-Tetraoxa-15-azacyclopentadecane;1-Aza-4,7,10,13-tetraoxacyclopentadecane
• CAS NO: 66943-05-3
• Molecular Formula: C₁₀H₂₁NO₄
• Molecular Weight: 219.28
• EINECS: 266-523-3
• Product Categories: Azacrown Ethers;Crown Ethers;Macrocycles for Host-Guest Chemistry;Functional Materials
• Mol File: 66943-05-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 35-37 °C(lit.)
• Boiling Point: 90-100C
• Flash Point: >230 °F
• Appearance: light brown crystalline mass
• Density: 1.1223 (rough estimate)
• Vapor Pressure: 5.54E-05mmHg at 25°C
• Refractive Index: 1.4711
• Storage Temp.: 0-6°C
• Water Solubility: soluble
• Sensitive: Air Sensitive
• BRN: 971959
• CAS DataBase Reference: Aza-15-crown-5(CAS DataBase Reference)
• NIST Chemistry Reference: Aza-15-crown-5(66943-05-3)
• EPA Substance Registry System: Aza-15-crown-5(66943-05-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 66943-05-3(Hazardous Substances Data)

Usage

Chemical Properties

LIGHT BROWN CRYSTALLINE MASS

Uses

1-Aza-15-crown-5 is used as building block for the synthesis of bis-crown ethers, lariat ethers and other monofuctionalized macrocycles. It is also used as pharmaceutical intermediate.

InChI:InChI=1/C10H21NO4/c1-3-12-5-7-14-9-10-15-8-6-13-4-2-11-1/h11H,1-10H2/p+1

Synthetic route

1-benzyl-1-aza-15-crown-5 (71089-11-7) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal	98%
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 3102.9 Torr; for 24h;	98%
With hydrogen; palladium on activated charcoal In ethanol under 5171.5 Torr; for 6h;	89%

13-(p-Tolylsulfonyl)-1,4,7,10-tetraoxa-13-azacyclopentadecan (71089-10-6) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With lithium aluminium tetrahydride	83%
With lithium aluminium tetrahydride In tetrahydrofuran Heating;

2,2'-iminobis[ethanol] (111-42-2) + triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With sodium t-butanolate In 1,4-dioxane; tert-butyl alcohol at 40℃; for 2h;	59%
With sodium t-butanolate In 1,4-dioxane at 40℃; for 1h;	45%
With sodium In tert-butyl alcohol at 40℃;	35%
With sodium t-butanolate In 1,4-dioxane; tert-butyl alcohol at 20 - 40℃; for 3h;	25%
With sodium t-butanolate In 1,4-dioxane; tert-butyl alcohol at 40℃; for 4h;	3.19 g

triethylene glycol di(toluene-p-sulphonate) + 2,2'-iminobis[ethanol] (111-42-2) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With sodium; tert-butyl alcohol at 40℃; for 19h; Inert atmosphere; Glovebox;	28%

1,2-bis(2-chloroethoxy)ethane (112-26-5) + 2,2'-iminobis[ethanol] (111-42-2) → 2-{2-[2-(2-Vinyloxy-ethoxy)-ethoxy]-ethylamino}-ethanol + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With sodium t-butanolate In tert-butyl alcohol at 60℃; for 38h;	A n/a B 12%

1,4,7,10-Tetraoxa-13-aza-cyclopentadecane-13-carboximidic acid methyl ester (80900-29-4) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With acetic acid for 24h; Heating; Yield given;

3,6,12-trioxa-9-azatetradecane-1,14-diol (85971-96-6) → 2-[2-(2-morpholin-4-yl-ethoxy)-ethoxy]-ethanol (7037-28-7) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; for 5h; Yields of byproduct given;	A n/a B 50 % Spectr.
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 20℃; for 5h; Product distribution; variation of arenesulphonyl chloride, base and temperature;	A 10 % Spectr. B 48 % Spectr.

1,2-bis(2-chloroethoxy)ethane (112-26-5) + 2,2'-iminobis[ethanol] (111-42-2) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With sodium t-butanolate In tert-butyl alcohol at 60℃; Yield given;

3,6,9-trioxa-12-azatetradecane-1,14-diol (85971-95-5) → 2-{2-[2-(2-Aziridin-1-yl-ethoxy)-ethoxy]-ethoxy}-ethanol (85971-99-9) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; for 5h; Yields of byproduct given;	A n/a B 59 % Spectr.

13-(4-nitrosophenyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane (66750-07-0) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
With hydrogen sulfite In ethanol at 60 - 70℃; for 0.333333h; Yield given;

C25H42NO5*Na(1+) → 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + C25H43NO5*Na(1+) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
In acetonitrile at 25℃; Kinetics;

C25H42NO5*Ca(2+) → 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + C25H43NO5*Ca(2+) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
In acetonitrile at 25℃; Kinetics;

C25H42NO5*Mg(2+) → 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + C25H43NO5*Mg(2+) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
In acetonitrile at 25℃; Kinetics;

C25H42NO5*Sr(2+) → 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + C25H43NO5*Sr(2+) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
In acetonitrile at 25℃; Kinetics;

C25H42NO5*C16H36N(1+) → 3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + C25H43NO5*C16H36N(1+) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
In acetonitrile at 25℃; Kinetics;

2,2'-[1,2-ethanediylbis(oxy)]bisethanol (112-27-6) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / aq. KOH / tetrahydrofuran / 10 h / 0 - 20 °C 2: 25 percent / sodium tert-butoxide / 2-methyl-propan-2-ol; dioxane / 3 h / 20 - 40 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride / dichloromethane; water / 6.5 h 2.1: sodium hydroxide; tetrabutylammomium bromide / water; benzene / 10 h / 70 °C 3.1: hydrogen; palladium 10% on activated carbon; acetic acid / methanol / 4 - 5 h 3.2: pH 9 - 10 View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / tetrahydrofuran; water / 18 h / 0 - 20 °C / Inert atmosphere; Glovebox 2: tert-butyl alcohol; sodium / 19 h / 40 °C / Inert atmosphere; Glovebox View Scheme
Multi-step reaction with 3 steps 1.1: dmap / dichloromethane / Inert atmosphere 1.2: 12 h / 0 - 20 °C / Inert atmosphere 2.1: sodium hydroxide; tetrabutylammomium bromide / water; toluene / 10 h / 70 °C / Inert atmosphere 3.1: acetic acid; palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C / 7500.75 Torr / Autoclave; Inert atmosphere View Scheme

penta(ethylene glycol) bis(p-toluenesulfonate) (41024-91-3) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / Na2CO3 / toluene / 3 h / Heating 2: 89 percent / H2 / Pd/C / ethanol / 6 h / 5171.5 Torr View Scheme
Multi-step reaction with 3 steps 1: 12 percent / NaH, NaBr / dimethylsulfoxide / 2 h / 40 °C 2: 95 percent / KCN / 20 h / Heating 3: aqueous AcOH / 24 h / Heating View Scheme

triethylene glycol di-(p-toluenesulfonate) (19249-03-7) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 46 percent / NaH / tetrahydrofuran 2: 98 percent / H2, trace HCl / Pd-C View Scheme
Multi-step reaction with 2 steps 1: 52 percent / 80 percent NaH / tetrahydrofuran / Heating 2: 83 percent / LiAlH4 View Scheme
Multi-step reaction with 2 steps 1: (i) NaH, THF, (ii) /BRN= 632509/ 2: LiAlH4 / tetrahydrofuran / Heating View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydroxide; tetrabutylammomium bromide / water; benzene / 10 h / 70 °C 2.1: hydrogen; palladium 10% on activated carbon; acetic acid / methanol / 4 - 5 h 2.2: pH 9 - 10 View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; tetrabutylammomium bromide / water; toluene / 10 h / 70 °C / Inert atmosphere 2: acetic acid; palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C / 7500.75 Torr / Autoclave; Inert atmosphere View Scheme

1,14-diiodo-3,6,9,12-tetraoxatetradecane (76871-59-5) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: Na2CO3 / acetonitrile / Heating 2: 88 percent / H2 / Pd/C / ethanol View Scheme

2-(2-(2-(2-chloroethoxy)ethoxy)ethoxy)ethanol (5197-66-0) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 64 percent / Na2CO3 / 24 h / 120 °C 2: 59 percent Spectr. / p-toluenesulphonyl chloride, NaOH / dioxane / 5 h / 60 °C View Scheme

1,14-dichloro-3,6,9,12-tetraoxatetradecane (5197-65-9) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 34 percent / NaH, NaBr / dimethylsulfoxide / 2 h / 40 °C 2: 95 percent / KCN / 20 h / Heating 3: aqueous AcOH / 24 h / Heating View Scheme

N-cyano monoaza 15-crown-5 (80900-27-2) → 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / KCN / 20 h / Heating 2: aqueous AcOH / 24 h / Heating View Scheme

carbon disulfide (75-15-0) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → sodium (aza-15-crown-5) dithiocarbamate (128093-17-4)

Conditions	Yield
With sodium hydroxide In ethanol at 0 - 5℃; for 2 - 3h;	100%
With sodium hydroxide In water at 0℃; for 6h;	68%

13-(6-Chloro-3-nitro-pyridin-2-yl)-1,4,7,10-tetraoxa-13-aza-cyclopentadecane + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C25H42N4O10

Conditions	Yield
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h;	100%

4,8-dibromo-2,6-dioctylpyrrolo[3,4-f]isoindole-1,3,5,7(2H,6H)-tetraone + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C36H54BrN3O8

Conditions	Yield
In N,N-dimethyl acetamide at 120℃; for 18h; Inert atmosphere;	100%

2,7-bis(bromomethyl)naphthalene (38309-89-6) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C32H50N2O8 (74776-82-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Heating;	99%

2-chlorothiazole (3034-52-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-(thiazol-2-yl)-1,4,7,10-tetraoxa-13-azacyclopentadecane

Conditions	Yield
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 120h;	99%

2-chloro-1,3-benzoxazole (615-18-9) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-(benzoxazol-2-yl)-1,4,7,10-tetraoxa-13-azacyclopentadecane

Conditions	Yield
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h;	99%

2-chlorobenzo[d][1,3]thiazole (615-20-3) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-(benzothiazol-2-yl)-1,4,7,10-tetraoxa-13-azacyclopentadecane

Conditions	Yield
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h;	99%

silver hexafluoroantimonate + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → (C10O4NH21)2Ag(1+)*SbF6(1-)=(C10O4NH21)2AgSbF6 (238739-12-3)

Conditions	Yield
In not given	99%

tantalum(V) oxide + hydrogen fluoride (7664-39-3) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → [azonia-15-crown-5]2[(TaF5)2O]

Conditions	Yield
In water Ta2O5 reacted with 40% aq. HF; treated with aza-15-crown-5; crystals obtained; elem. anal.;	99%

1-(Dicyanomethylene)-2,3-dichloroindene + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1-dicyanomethylene-2-chloro-3-(4,7,10,13-tetraoxa-1-azacyclopentadec-1-yl)indene (1215228-33-3)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	99%

7-isothiocyanato-4-methyl-2H-chromen-2-one (74802-03-2) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C21H28N2O6S (1234108-17-8)

Conditions	Yield
In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	99%

meta-hydroxybenzaldehyde (100-83-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → m-(aza-15-crown-5)methylphenol

Conditions	Yield
Stage #1: meta-hydroxybenzaldehyde; 1,4,7,10-tetraoxa-15-azacyclopentadecane In tetrahydrofuran for 1h; Schlenk technique; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran Schlenk technique;	98.8%

methanol (67-56-1) + formaldehyd (50-00-0) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → N-Methoxymethylmonoaza-15-crown-5 ether (91043-70-8)

Conditions	Yield
at 20℃; for 12h;	98%
for 0.5h;

1-isothiocyanato-2-[2-(isothiocyanato)ethoxy]ethane (103144-36-1) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C26H50N4O9S2 (111039-22-6)

Conditions	Yield
In methanol at 40 - 45℃; for 0.25h;	98%

1,15-dithioxo-5,8,11-trioxa-2,14-diazapentadecane (103144-38-3) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C30H58N4O11S2 (111039-23-7)

Conditions	Yield
In methanol at 40 - 45℃; for 0.25h;	98%

1,18-dithioxo-5,8,11,14-tetraoxa-2,17-diazaoctadecane (103144-39-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C32H62N4O12S2 (111039-24-8)

Conditions	Yield
In methanol at 40 - 45℃; for 0.25h;	98%

ferrocenoyl chloride (1293-79-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1,4,7,10-tetraoxa-13-azacyclopentadec-13-ylcarbonylferrocene (130586-20-8)

Conditions	Yield
With triethylamine In benzene soln. of chlorocarbonylferrocene added slowly to a soln. of aza-15-crown-5 and NEt3; stirring (1 h); filtration, evapn. (reduced pressure), column chromy. (neutral Al2O3; CH2Cl2, then CH2Cl2/MeOH);	98%

1,3-bis(bromomethyl)-2-nitrobenzene (55324-01-1) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → C28H47N3O10 (74782-93-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Heating;	97%

25,27-bis(methoxycarboxylic, acid)-26,28-dihydroxy-4-tert-butylcalix-[4]arene (121633-88-3, 147513-53-9) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 2,2'-[5,11,17,23-tetra-tert-butyl-26,28-dihydroxycalix[4]arene-25,27-diylbis(oxy)]bis[1-(1,4,7,10-tetraoxa-13-azacyclopentadec-13-yl)ethanone] (1448219-80-4)

Conditions	Yield
Stage #1: 25,27-bis(methoxycarboxylic, acid)-26,28-dihydroxy-4-tert-butylcalix-[4]arene With benzotriazol-1-ol; dicyclohexyl-carbodiimide In chloroform at 0 - 20℃; Stage #2: 1,4,7,10-tetraoxa-15-azacyclopentadecane In chloroform for 12h;	97%
Stage #1: 25,27-bis(methoxycarboxylic, acid)-26,28-dihydroxy-4-tert-butylcalix-[4]arene With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran; dichloromethane at 0℃; for 1h; Stage #2: 1,4,7,10-tetraoxa-15-azacyclopentadecane In tetrahydrofuran; dichloromethane at 0℃;	96.7%

4-(oxiran-2-ylmethyl)morpholine (6270-19-5) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-/2-hydroxy-3-(morpholino)propyl/-1,4,7,10-tetraoxa-13-azacyclopentadecane (116136-95-9)

Conditions	Yield
at 80℃; for 9h;	96%

2-nitrobenzyl chloride (612-23-7) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → N-(2-nitrobenzyl)monoaza-15-crown-5 (88548-59-8)

Conditions	Yield
With sodium carbonate In acetonitrile Heating;	96%
With sodium carbonate In acetonitrile for 24h; Heating;	96%
With sodium carbonate In acetonitrile for 24h; Heating;	35%

3,6-dichlorpyridazine (141-30-0) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-(6-chloropyridazin-3-yl)-1,4,7,10-tetraoxa-13-azacyclopentadecane

Conditions	Yield
With triethylamine In tetrahydrofuran at 100℃; under 6000480 Torr; for 96h;	96%

ruthenocenecarbonyl chloride (120471-09-2) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1,4,7,10-tetraoxa-13-azacyclopentadec-13-ylcarbonylruthenocene (198883-26-0)

Conditions	Yield
With triethylamine In benzene soln. of Ru-complex added dropwise to soln. of aza-15-crown-5 and NEt3; stirring (1 h); filtration, evapn. (reduced pressure), column chromy. (neutral Al2O3; CH2Cl2, then CH2Cl2/MeOH);	96%

1-fluoro-2-methoxy-4-nitrobenzene (454-16-0) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-(2-methoxy-4-nitrophenyl)-1,4,7,10-tetraoxa-13-cyclopentadecane

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide for 10h; Reflux;	96%

N-(Hydroxymethyl)-aziridine (20276-43-1) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → N-(Aziridinomethyl)-aza-15-crown-5 (91043-71-9)

Conditions	Yield
In benzene at 20℃; for 3h;	95%

1-chloro-2,4-dinitro-benzene (97-00-7) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1-(2,4-dinitrophenyl)-1-aza-4,7,10,13-tetraoxapentadecane (191226-78-5)

Conditions	Yield
With tetrabutylammonium acetate In diethyl ether for 24h; Substitution; Heating;	95%

3,5-dibromobenzyl bromide (56908-88-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 13-(3,5-dibromobenzyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane (1313610-71-7)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	95%

1,3,5-Tris(bromomethyl)benzene (18226-42-1) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1,3,5-tris[(1'-aza-4',7',10',13'-tetraoxapentadec-1'-yl)methyl]benzene (1415606-93-7)

Conditions	Yield
With sodium carbonate In acetonitrile at 20℃; for 24h; Inert atmosphere; Reflux;	95%

1,3,5-tris(bromomethyl)-2,4,6-trimethylbenzene (21988-87-4) + 1,4,7,10-tetraoxa-15-azacyclopentadecane (66943-05-3) → 1,3,5-tris[(1'-aza-4',7',10',13'-tetraoxapentadec-1'-yl)methyl]-2,4,6-trimethylbenzene (1415606-94-8)

Conditions	Yield
With sodium carbonate In acetonitrile at 20℃; for 35h; Inert atmosphere; Reflux;	95%

Upstream product

• 85971-96-6 3,6,12-trioxa-9-azatetradecane-1,14-diol 
• 85971-95-5 3,6,9-trioxa-12-azatetradecane-1,14-diol 
• 111-42-2 2,2'-iminobis[ethanol] 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 41024-91-3 penta(ethylene glycol) bis(p-toluenesulfonate) 
• 5197-66-0 2-(2-(2-(2-chloroethoxy)ethoxy)ethoxy)ethanol 
• 76871-59-5 1,14-diiodo-3,6,9,12-tetraoxatetradecane 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 66750-07-0 13-(4-nitrosophenyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 112-26-5 1,2-bis(2-chloroethoxy)ethane 
• 80900-29-4 1,4,7,10-Tetraoxa-13-aza-cyclopentadecane-13-carboximidic acid methyl ester 
• 71089-11-7 1-benzyl-1-aza-15-crown-5 
• 71089-10-6 13-(p-Tolylsulfonyl)-1,4,7,10-tetraoxa-13-azacyclopentadecan 
• 5197-65-9 1,14-dichloro-3,6,9,12-tetraoxatetradecane 

Downstream Products

• 71089-11-7 1-benzyl-1-aza-15-crown-5 
• 69978-46-7 13-methyl-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 113336-95-1 N-Phenyl-2-(1,4,7,10-tetraoxa-13-aza-cyclopentadecane-13-carbonyl)-benzamide 
• 80530-83-2 4,4'-bis-(1,4,7,10-tetraoxa-13-azacyclopenta-dec-13-ylcarbonyl)azobenzene 
• 357396-83-9 5-(1,4,7,10-tetraoxa-13-aza-cyclopentadec-13-yl)-benzene-1,3-diol 
• 222020-15-7 13-<2-(N-ethyl-N-phenyl-amino)ethyl>-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 222020-14-6 13-<2-(N-methyl-N-phenyl-amino)ethyl>-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 222020-16-8 13-<3-(N-ethyl-N-phenyl-amino)propyl>-1,4,7,10-tetraoxa-13-azacyclopentadecane 
• 222833-20-7 1-amino-2-<4-(aza-15-crown-5-ethermethyl)benzoylamino>anthraquinone 
• 245125-18-2 13-(4-nitrophenyl)-1,4,7,10-tetraoxa-13-azacyclopentadecane 

Relevant articles and documents

Synthesis of new N-pivot lariat crown ethers containing a propylene linkage in the side arm

A series of new 15- and 18-membered N-pivot lariat aza-crown ethers having a propylene linkage in the side arm was prepared starting from functionalized diethanolamines and functionalized lariat aza-crown ethers containing the easily modified benzotriazole moiety. Addition reactions of such derivatives to electron-rich vinyl ethers or vinylamides followed by displacement of the benzotriazolyl group in the addition products by hydrogen (by reduction with LiAlH4) gives a variety of N-(3-oxo-3-substituted)- and N-(3-aza-3-substituted)propylene side-armed derivatives of aza-crown ethers. Stability constants for the complexes of several synthesized lariats with metal cations are discussed.

Tridentate phosphine ligands bearing aza-crown ether lariats

Crown ethers are useful macrocycles that act as size-selective binding sites for alkali metals. These frameworks have been incorporated into a number of macromolecular assemblies that use simple cations as reporters and/or activity triggers. Incorporating crown ethers into secondary coordination sphere ligand frameworks for transition metal chemistry will lead to new potential methods for controlling bond formation steps, and routes that couple traditional ligand frameworks with these moieties are highly desirable. Herein we report the syntheses of a family of tridentate phosphine complexes bearing tethered aza-crown ethers (lariats) designed to modularize the variation of aza-crown size, lariat length, and distal phosphine substituents, followed by the synthesis and solid-state structures of Mo(III) complexes bearing cations in the pendent crown ethers.

Synthesis of N-(bisphosphonomethyl)-aza-15-Crown-5 and N- (bisphosphonomethyl)-aza-18-crown-6 ethers as artificial ion channels: An approach to channel-type molecular structures

We report the synthesis and characterization of 2 new N- (bisphosphonomethyl)-aza-15-crown-5 1a and N-(bisphosphonomethyl)-aza-18-Crown-6 ethers 1b designed to further investigate the supramolecular assemblies based on exocyclic functional groups of crown ethers. Copyright Taylor & Francis LLC.