70384-51-9

Basic information

• Product Name: Tris(2-(2-methoxyethoxy)ethyl)amine
• Synonyms: Tris(3,6-dioxaheptane-1-yl)amine;Tris(dioxa-3,6-heptyl)amine,95%;Tris(3,6-dioxaheptyl)amine ,95%;Tris(dioxa-3,6-heptyl)aMine, 95% 100ML;Tris(dioxa-3,6-heptyl)aMine, 95% 25ML;Tris(3,6-dioxaheptyl)amine TDA-1;TRIS[2-(2-METHOXYETHOXY)ETHYL]AMINE FOR;Tris(3,6-dioxaheptyl
• CAS NO: 70384-51-9
• Molecular Formula: C₁₅H₃₃NO₆
• Molecular Weight: 323.43
• EINECS: 274-590-5
• Product Categories: Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 70384-51-9.mol

Chemical Properties

• Melting Point: <-100°C
• Boiling Point: 330 °C
• Flash Point: >230 °F
• Appearance: Clear pale yellow to brown/Liquid
• Density: 1.011 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.78E-06mmHg at 25°C
• Refractive Index: n20/D 1.4486(lit.)
• Storage Temp.: Store below +30°C.
• PKA: 6.92±0.50(Predicted)
• Water Solubility: miscible
• Sensitive: Air Sensitive & Hygroscopic
• BRN: 2369296
• CAS DataBase Reference: Tris(2-(2-methoxyethoxy)ethyl)amine(CAS DataBase Reference)
• NIST Chemistry Reference: Tris(2-(2-methoxyethoxy)ethyl)amine(70384-51-9)
• EPA Substance Registry System: Tris(2-(2-methoxyethoxy)ethyl)amine(70384-51-9)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• F: 3-9-23
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 70384-51-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Tris(2-(2-methoxyethoxy)ethyl)amine is used as a phase-transfer catalyst for the oxidation of arylmethanols under phase-transfer conditions. This application is crucial in the synthesis of various organic compounds, where the selective oxidation of arylmethanols is required.
Used in Cryptand Chemistry:
In the field of cryptand chemistry, Tris(2-(2-methoxyethoxy)ethyl)amine serves as a cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidine. Cryptands are multidentate ligands that can encapsulate metal ions, and their use in this context highlights the versatility of Tris(2-(2-methoxyethoxy)ethyl)amine in facilitating specific chemical reactions.
Used in Pharmaceutical Synthesis:
Tris(2-(2-methoxyethoxy)ethyl)amine is used as a phase-transfer catalyst in the synthesis of 1,3-dideaza-2′-deoxyadenosine and related benzimidazole 2′-deoxyribonucleosides. These compounds are of significant interest in the pharmaceutical industry due to their potential applications as therapeutic agents.
Used in Chemical Research:
In the broader field of chemical research, Tris(2-(2-methoxyethoxy)ethyl)amine is utilized for its phase-transfer catalytic properties, enabling the development of new synthetic pathways and the discovery of novel compounds with potential applications in various industries.

InChI:InChI=1/C15H33NO6/c1-17-10-13-20-7-4-16(5-8-21-14-11-18-2)6-9-22-15-12-19-3/h4-15H2,1-3H3

Synthetic route

2-Bromoethyl methyl ether (6482-24-2) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
With tetrabutyl-ammonium chloride; sodium hydroxide In sulfolane at 60 - 120℃; Reagent/catalyst;	92.7%

2-chloroethyl methyl ether (627-42-9) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
With tetrabutylammomium bromide; potassium hydroxide In dimethyl sulfoxide at 60 - 120℃; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Autoclave; Large scale;	86.3%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) + 2-(2-methoxyethoxy)ethanamine (31576-51-9) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
With sodium carbonate at 110℃; for 24h; Temperature;	85.48%

1-chloro-2-(2-methoxyethoxy)ethane (52808-36-3) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
With ammonia In methanol

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → 8-aza-2,5,11,14-tetraoxa-pentadecane (5732-47-8) + Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
With ammonia; hydrogen; nickel at 185℃; 1.) 3h, 2.) 2h;	A 3241 % B 15125 g
With ammonia; hydrogen; nickel at 185℃; 1.) 3h, 2.) 2h;	A 3241 g B 15125 g

2-(2-methoxyethoxy)ethyl alcohol (111-77-3) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2, Py 2: NH3 / methanol View Scheme
aluminum nickel
Multi-step reaction with 2 steps 1: thionyl chloride / N,N-dimethyl-formamide / 3 h / 28 - 60 °C 2: sodium carbonate / 24 h / 110 °C View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / N,N-dimethyl-formamide / 3 h / 28 - 60 °C 2: ammonia / 6 h / 130 °C / 11251.1 Torr / Autoclave 3: sodium carbonate / 24 h / 110 °C View Scheme

triethanolamine (102-71-6) → Tris(3,6-dioxaheptyl)amine (70384-51-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 1 h / Reflux; Inert atmosphere; Large scale 2: potassium hydroxide; tetrabutylammomium bromide / dimethyl sulfoxide / 60 - 120 °C / Inert atmosphere; Autoclave; Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 1 h / Reflux 2: potassium hydroxide; tetrabutylammomium bromide / dimethyl sulfoxide / 60 - 120 °C / Inert atmosphere; Autoclave; Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 1 h / Reflux 2: potassium hydroxide; tetrabutylammomium bromide / dimethyl sulfoxide / 60 - 120 °C / Inert atmosphere; Autoclave; Large scale View Scheme
Multi-step reaction with 2 steps 1: toluene / 1 h / Reflux; Inert atmosphere; Large scale 2: sodium hydroxide; tetrabutyl-ammonium chloride / sulfolane / 60 - 120 °C View Scheme
Multi-step reaction with 2 steps 1: toluene / 1 h / Reflux 2: sodium hydroxide; tetrabutyl-ammonium chloride / sulfolane / 60 - 120 °C View Scheme

α-ketoglutaric acid (328-50-7) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → AKG-diTMEEA

Conditions	Yield
In acetone at 35 - 45℃;	100%

2-acrylamido-2-methylpropanesulfonic acid (15214-89-8) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → tris-[2-(2-methoxy-ethoxy)-ethyl]-amine; compound with 2-acryloylamino-2-methyl-propane-1-sulfonic acid

Conditions	Yield
at 25℃; for 8h;	99%

3-Acryloyloxypropane-1-sulfonic acid (39121-78-3) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → C15H33NO6*C6H10O5S (1509627-70-6)

Conditions	Yield
In water at 20℃; for 10h; Inert atmosphere; Schlenk technique;	99%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + (2-hydroxyphenyl)acetic acid disodium salt (117571-22-9) + potassium 2-iodo-5-methylbenzoate (117571-21-8) → 2-<2-(carboxymethyl)phenoxy>-5-methylbenzoic acid (117571-23-0)

Conditions	Yield
With hydrogenchloride; copper(l) chloride In 1,4-dioxane; sodium hydroxide	91%

3,3-Dibutyl-2,3-dihydro-5H-7-fluoro-1,5-benzothiazepine-4-one + para-iodoanisole (696-62-8) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → 3,3-dibutyl-2,3-dihydro-7-fluoro-5-(4'-methoxyphenyl)-1,5-benzothiazepine-4-one

Conditions	Yield
With CuI; potassium carbonate	90%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + N,N-dimethylethylenediamine (108-00-9) + ortho-nitrofluorobenzene (1493-27-2) → N1,N1-dimethyl-N2-(2-nitrophenyl)ethane-1,2-diamine (25238-55-5)

Conditions	Yield
With potassium carbonate	90%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + toluene-4-sulfonic acid (104-15-4) → 8-amino-8-(2-(2-methoxyethoxy)ethyl)-2,5,11,14-tetraoxa-8-azapentadecan-8-ium4-methylbenzenesulfonate

Conditions	Yield
With iodosylbenzene; ammonium carbamate In acetonitrile at 25℃; for 2h;	89%

3-formyl-10-methylphenothiazine (4997-36-8) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → (E)-3-(10-methyl-10H-phenothiazin-3-yl)acrylaldehyde (1374005-27-2)

Conditions	Yield
With (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide; potassium carbonate In dichloromethane for 20h; Reflux;	88.6%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + ethyl iodide (75-03-6) → N-ethyl-2-(2-methoxyethoxy)-N,N-bis(2-(2-methoxyethoxy)ethyl)ethan-1-aminium iodide

Conditions	Yield
In acetonitrile at 50℃; Inert atmosphere;	88%

butyldimethylsilyl chloride (1000-50-6) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → tetramethyldibutyldisilane

Conditions	Yield
With sodium iodide	85%

3,4-Dinitrotoluene (610-39-9) + Tris(3,6-dioxaheptyl)amine (70384-51-9) + N,N-dimethylethylenediamine (108-00-9) → N,N-Dimethyl-2-(5-methyl-2-nitroanilino)ethanamine (138423-04-8) + N,N,N-Trimethyl-2-(5-methyl-2-nitroanilino)ethanaminium Iodide (144674-99-7)

Conditions	Yield
In dimethyl sulfoxide	A 80% B n/a

Tris(3,6-dioxaheptyl)amine (70384-51-9) → N,N-bis(2-(2-methoxyethoxy)ethyl)formamide

Conditions	Yield
With pyridine; copper(l) chloride In acetonitrile at 100℃; under 7500.75 - 22502.3 Torr; for 24h; Autoclave; regioselective reaction;	75%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + aniline (62-53-3) → N-(2-(2-methoxyethoxy)ethyl)aniline (189077-66-5)

Conditions	Yield
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) In tert-Amyl alcohol at 150℃; for 24h; Inert atmosphere;	74%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + ethylmagnesium bromide (925-90-6) → C15H33NO6*2C2H5BrMg

Conditions	Yield
In diethyl ether; cyclohexane for 1h;	72%

2,4-imidazolidinedione (461-72-3) + Benzyloxymethyl chloride (3587-60-8) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → 3-benzyloxymethyl-imidazolidine-2,4-dione (151918-26-2)

Conditions	Yield
With potassium hydroxide In water; 4-methyl-2-pentanone	70%

2,4-Difluoronitrobenzene (446-35-5) + Tris(3,6-dioxaheptyl)amine (70384-51-9) + N,N-dimethylethylenediamine (108-00-9) → N,N,N-Trimethyl-2-(5-β-hydroxyethoxy-2-nitroanilino)ethanaminium Iodide (144674-98-6)

Conditions	Yield
With potassium carbonate In N-methyl-acetamide; ethylene glycol; dimethyl sulfoxide	70%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + potassium hexamethylsilazane (40949-94-8) → C21H51KN2O6Si2

Conditions	Yield
In hexane Inert atmosphere; Schlenk technique;	69%

1-(6-bromohexyl)-2,3-dihydroxybenzene + 1-(6-bromohexyl)-2,3-dimethoxybenzene (123014-42-6) + 1-hexyl-4-methyl-benzene (1595-01-3) + Tris(3,6-dioxaheptyl)amine (70384-51-9) + benzyl bromide (100-39-0) → 1,2-bis-(phenylmethoxy)-3-(6-bromohexyl)benzene (134472-49-4)

Conditions	Yield
With hydrogenchloride; boron tribromide; potassium carbonate In dichloromethane; water; toluene	67%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + vinyl magnesium bromide (1826-67-1) → C15H33NO6*2C2H3BrMg

Conditions	Yield
In tetrahydrofuran; cyclohexane for 1h;	64%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + 3-butyl-7-chloro-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one → 3-butyl-7-chloro-5-(4-fluorophenyl)-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

Conditions	Yield
With potassium carbonate	64%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + [4-(4-bromobutoxy)phenyl][4-(hexyloxy)phenyl]diazene → C37H62N3O8(1+)*Br(1-)

Conditions	Yield
In acetonitrile for 96h; Reflux;	62%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + 2,4-dibromo-N-(1-((4-fluorophenyl)amino)hexan-2-yl)-5-methoxybenzenesulfonamide → 7-bromo-3-butyl-5-(4-fluorophenyl)-8-methoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine 1,1-dioxide

Conditions	Yield
With potassium carbonate	55%

cesium bis(trimethylsilyl)amide + Tris(3,6-dioxaheptyl)amine (70384-51-9) → tris{2-(2-methoxyethoxy)ethyl}amine*cesium bis(trimethylsilyl)amide

Conditions	Yield
In hexane for 0.166667h; Schlenk technique; Inert atmosphere;	49%

tris[2-(2-methoxyethoxy]amine + Tris(3,6-dioxaheptyl)amine (70384-51-9) + potassium 2-chlorobenzoate (16463-38-0) + sodium 2-allyl-4-methylphenolate (118537-94-3) → 2-(2-allyl-4-methylphenoxy)benzoic acid (117571-24-1)

Conditions	Yield
copper(l) chloride In methoxybenzene	47%

6-(bromomethyl)-1,3,8-trimethoxyanthracene-9,10-dione (60699-01-6) + Tris(3,6-dioxaheptyl)amine (70384-51-9) → 2-(2-methoxyethoxy)-N-(2-(2-methoxyethoxy)ethyl)-N-((4,5,7-trimethoxy-9,10-anthraquinone-2-yl)methyl)ethanaminium bromide

Conditions	Yield
for 24h; Reflux;	31.4%

Tris(3,6-dioxaheptyl)amine (70384-51-9) + C22H29BrN2O2 → C37H62N3O8(1+)*Br(1-)

Conditions	Yield
In acetonitrile for 72h; Reflux;	25%

Upstream product

• 52808-36-3 1-chloro-2-(2-methoxyethoxy)ethane 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 
• 6482-24-2 2-Bromoethyl methyl ether 
• 283-56-7 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane 
• 102-71-6 triethanolamine 
• 627-42-9 2-chloroethyl methyl ether 
• 31576-51-9 2-(2-methoxyethoxy)ethanamine 

Downstream Products

• 117571-24-1 2-(2-allyl-4-methylphenoxy)benzoic acid 
• 150779-46-7 N-(2-cyclohexyloxy-5-nitrophenyl)methanesulfonamide 
• 151918-26-2 3-benzyloxymethyl-imidazolidine-2,4-dione 
• 22483-40-5 4-(2-methoxy-ethoxy)-1-nitrobenzene 
• 186456-97-3 4-N-phenylamino-5-phenyl-7-(2',3'-O-isopropylidene-β-D-erythro-furanosyl)pyrrolo[2,3-d]pyrimidine 
• 143804-53-9 4-benzyl-2-(methoxymethyl)morpholine 
• 186456-68-8 4-N-phenylamino-5-phenyl-7-(5'-deoxy-2',3'-O-isopropylidene-4'-C-methyl-β-D-ribo-furanosyl)pyrrolo[2,3-d]pyrimidine 
• 186456-55-3 4-N-phenylamino-5-phenyl-7-(4-C-[(phenylmethyl)oxy]methyl-2,3,5-tri-O-(phenylmethyl)-β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 99840-22-9 4-chloro-1-[(4-chlorobutyl)thiomethyl]benzene 
• 25238-55-5 N¹,N¹-dimethyl-N²-(2-nitrophenyl)ethane-1,2-diamine 
• 144674-98-6 N,N,N-Trimethyl-2-(5-β-hydroxyethoxy-2-nitroanilino)ethanaminium Iodide 
• 138423-04-8 N,N-Dimethyl-2-(5-methyl-2-nitroanilino)ethanamine 
• 144674-99-7 N,N,N-Trimethyl-2-(5-methyl-2-nitroanilino)ethanaminium Iodide 
• 80054-80-4 1-chloro-4-(2,2,2-trifluoroethoxy)benzene 

Relevant articles and documents

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