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
• Article Data: 13

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

Tris[2-(2-methoxyethoxy)ethyl]amine was used:in oxidation of arylmethanols under phase-transfer conditionsas cryptand during phase-transfer glycosylation of 2-amino-4-methoxy-7H-pyrrolo[2,3-d]pyrimidineas phase-transfer catalyst in synthesis of 1,3-dideaza-2′-deoxyadenosine and related benzimidazole 2′-deoxyribonucleosides

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

• 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 
• 90213-74-4 2-Amino-4-chloro-7-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)-7H-pyrrolo[2,3-d]-pyrimidine 
• 443642-36-2 4-chloro-7-[3,5-bis-O-(2,4-dichlorophenylmethyl)-2-C-ethyl-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidine 
• 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 
• 117571-23-0 2-<2-(carboxymethyl)phenoxy>-5-methylbenzoic acid 
• 22483-40-5 4-(2-methoxy-ethoxy)-1-nitrobenzene 
• 162140-51-4 2-Cyclohexylamino-4-cyclopentoxy-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 
• 186456-55-3 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 

Relevant articles and documents

Novel method for preparing tris (3,6 -dioxo-heptyl) amine

The invention relates to a new method for preparing tris(3,6-dioxaheptyl)amine. The new method is characterized in that ammonia water, diethylene glycol monomethyl ether and thionyl chloride are takenas raw materials, and the tris(3,6-dioxaheptyl)amine is synthesized through three steps. The new method provided by the invention has the following advantages that reaction conditions are mild, the operation is safe, and the danger of using high-risk chemicals such as hydrogen and Raney nickel is avoided; the reaction conversion rate is high, and the product yield is high; only products, sodium chloride and a very small amount of pre-distillation fractions are produced in the process, excess materials can be recycled after treatment, three wastes are very few, and the production process is green and environmentally friendly.

Photocurable resin composition, dry film thereof, pattern forming method, and electrical/electronic part protective film

A photocurable composition includes: (A) an epoxy group-containing polymer compound having repeating units represented by the following formula (1), where R1 to R4 are each a hydrocarbon group, m is an integer of 1 to 100, a, b, c and d are each 0 or a positive number, such that 0 (c+d)/(a+b+c+d) ≤ 1.0, and X and Y are each the formula (2) or (3), provided that at least one group of the formula (3) is present, (B) a photoacid generator represented by the formula (8) and (C) a solvent.

POSITIVE RESIST COMPOSITION AND PATTERNING PROCESS

A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid and (B) an acid generator. The resin (A) is a polymer comprising recurring units containing a non-leaving hydroxyl group represented by formula (1) wherein R1 is H, methyl or trifluoromethyl, X is a single bond or methylene, m is 1 or 2, and the hydroxyl group attaches to a secondary carbon atom. The composition is improved in resolution when processed by lithography.