283-56-7

Basic information

• Product Name: TRIETHANOLAMINE BORATE
• Synonyms: BORATRANE;2,2',2''-NITRILOTRIETHYL BORATE;2,2',2''-NITRILOTRIETHANOL BORATE;2,8,9-TRIOXA-5-AZA-1-BORABICYCLO(3.3.3)UNDECANE;TRIS(HYDROXYETHYL)AMINE BORATE;TRIETHANOLAMINE BORATE;TRIHYDROXYTRIETHYLAMINE BORATE;2,2’,2’’-nitrilotri-ethanocyclicborate
• CAS NO: 283-56-7
• Molecular Formula: C₆H₁₂BNO₃
• Molecular Weight: 156.98
• EINECS: 206-003-5
• Product Categories: B (Classes of Boron Compounds);Boric Acid Esters;Boric Acid Triesters
• Mol File: 283-56-7.mol

Chemical Properties

• Melting Point: 235-237 °C(lit.)
• Boiling Point: 149.6 °C at 760 mmHg
• Flash Point: 44.3 °C
• Appearance: white/Powder
• Density: 1.13 g/cm³
• Storage Temp.: Room Temperature, under inert atmosphere
• Solubility: slightly soluble in acetone, benzene
• PKA: 6.40±0.20(Predicted)
• BRN: 774536
• CAS DataBase Reference: TRIETHANOLAMINE BORATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRIETHANOLAMINE BORATE(283-56-7)
• EPA Substance Registry System: TRIETHANOLAMINE BORATE(283-56-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: YJ8968050
• F: 10-21
• Hazardous Substances Data: 283-56-7(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white solid

Uses

Triethanolamine Borate is an intermediate in the synthesis of Silatrane (S433000) which can be used as a reversible cholinesterase inhibitor. Silatrane and its derivatives can also be used as antitumor agents.

Preparation

triethanolamine borate synthesis: Adding trimethyl borate into the reaction bottle62.7g (0.6mol), 74.6g (0.5mol) of triethanolamine and 300g of toluene are slowly heated to reflux for 1 hour at room temperature, then distillate is distilled out under normal pressure (65-100°C) while reaction is carried out, sampling is carried out by GC detection, after the reaction is finished, reduced pressure concentration is carried out until no liquid distillation is carried out, acetonitrile is added for recrystallization, filtration and drying are carried out, 68g of white solid is obtained, HPLC (high performance liquid chromatography) is 98.8%, and the yield is 86.6%.

General Description

Triethanolamine borate can be formed from the 1:1 aqueous solution of boric acid and triethanolamine. It is used as buffer.

Safety Profile

A poison by intravenous route.When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C6H12BNO3/c1-4-9-7-10-5-2-8(1)3-6-11-7/h1-6H2

Synthetic route

triethanolamine (102-71-6) → 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7)

Conditions	Yield
With boric acid In 5,5-dimethyl-1,3-cyclohexadiene Reflux; Inert atmosphere;	89%
With boric acid
With boric acid; toluene

Trimethyl borate (121-43-7) + triethanolamine (102-71-6) → 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7)

Conditions	Yield
In toluene for 1h; Reflux; Inert atmosphere; Large scale;	87.7%

triethyl borate (150-46-9) + triethanolamine (102-71-6) → 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7)

Conditions	Yield
In toluene for 1h; Reflux;	85.9%

triethanolamine (102-71-6) + Triisopropyl borate (5419-55-6) → 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7)

Conditions	Yield
In toluene for 1h; Reflux;	82.9%

triethanolamine (102-71-6) + boric acid (11113-50-1) → 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7)

Conditions	Yield
In water at 120℃;	70%
In benzene azeotropic distn. (reflux); crystn., elem. anal.;
In toluene azeotropic distn. (reflux); crystn., elem. anal.;
In xylene byproducts: H2O; refluxing with sepn. of H2O; hot filtration, crystn., recrystn. (acetone);
In water at 120℃;

triethanolamine (102-71-6) + water (7732-18-5) + metaboric acid (13460-50-9) → 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7)

Conditions	Yield
at 10 - 30℃; Equilibrium constant;

triethoxyphenylsilane (780-69-8) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane (2097-19-0)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 80℃; for 2h;	95%

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%

2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-hydrosilatrane

Conditions	Yield
With aluminum (III) chloride; Triethoxysilane for 4h; Inert atmosphere; Reflux;	88%

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%

tetraethoxy orthosilicate (78-10-4) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-ethoxysilatrane (3463-21-6)

Conditions	Yield
With aluminum isopropoxide In xylene at 140℃; for 3h;	80%

2-furyltriethoxysilane (55811-52-4) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-furan-2-yl-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane (68011-86-9)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 140℃; for 8h;	71%

Triethoxyvinylsilane (78-08-0) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-vinylsilatrane (2097-18-9)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 140℃; for 20h;	68%

triethoxy(thiophen-2-yl)silane (17984-89-3) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 2-silatranylthiophene (41422-87-1)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 140℃; for 28h;	66%

tri-furan-2-yl-phenyl-silane (3294-64-2) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane (2097-19-0)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 80℃; for 3h;	65%

hexa-N-methyl-Si-phenyl-silanetriamine (4840-75-9) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane (2097-19-0)

Conditions	Yield
With aluminum isopropoxide In xylene at 140℃; for 10h;	60%

5-Methoxy-1-tetralone (33892-75-0) + ethyl iodide (75-03-6) + chromium(0) hexacarbonyl (199620-14-9, 13007-92-6) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) + lithium diisopropyl amide (4111-54-0) → Cr(CO)3(C13H18O2)

Conditions	Yield
In not given sequential treatment of 5-methoxy-1-tetralone with Cr(CO)6, LiN(i-Pr)2,B(OC2H4)3N, EtI and LiAlH4; further educt: LiAlH4;	51%

Methyltriethoxysilan (2031-67-6) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-methylsilatrane (2288-13-3)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 140℃; for 22h;	50%

2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → silatrane (283-60-3)

Conditions	Yield
With aluminum (III) chloride; Triethoxysilane In 5,5-dimethyl-1,3-cyclohexadiene Inert atmosphere;	24%
With aluminum (III) chloride; Triethoxysilane In 5,5-dimethyl-1,3-cyclohexadiene for 4h; Reflux;	10.80 g

sodium (7440-23-5) + chlorobenzene (108-90-7) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → triethanolamine phenylborate sodium

Conditions	Yield
Stage #1: sodium; chlorobenzene In hexane at 30℃; for 0.5h; Stage #2: 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane In tetrahydrofuran; hexane at 0℃; for 0.166667h;	14%

(4-Nitrophenyl)acetylene (937-31-5) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-[2-(4-nitrophenyl)ethenyl]silatrane + 1-[1-(4-nitrophenyl)ethenyl]silatrane

Conditions	Yield
Stage #1: (4-Nitrophenyl)acetylene With trimethoxysilane; dihydrogen hexachloroplatinate In isopropyl alcohol; toluene hydrosilylation; Heating; Stage #2: 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane With aluminium trichloride In xylene for 24h; Esterification; transesterification; Heating;	A 9% B 13%

chloromethyltriethoxysilane (15267-95-5) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → 1-(chloromethyl)silatrane (42003-39-4)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at 140℃; for 75h;	10%

2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → perfluorodiethyl ether (358-21-4) + Perfluoro-N,N-dimethylaminoacetyl fluoride (382-27-4) + 2,2,3,3,5,5,6,6-Octafluoro-4-trifluoromethyl-morpholine (382-28-5) + 2,2-difluoro-2-(2,2,3,3,5,5,6,6-octafluoromorpholin-4-yl)acetyl fluoride (130279-34-4)

Conditions	Yield
With hydrogen fluoride at 7 - 8℃; for 10.3h; Fluorination; Cyclization; Electrochemical reaction; Further byproducts given;	A 7.5% B 5% C 8.8% D 3.9%

water (7732-18-5) + 2,8,9-trioxa-5-aza-1-borabicyclo[3.3.3]undecane (283-56-7) → metaboric acid (13460-50-9) + tris-<2-hydroxy-ethylamine>

Conditions	Yield
at 10 - 30℃; Equilibrium constant;

Upstream product

• 102-71-6 triethanolamine 
• 7732-18-5 water 
• 13460-50-9 metaboric acid 
• 11113-50-1 boric acid 
• 121-43-7 Trimethyl borate 
• 150-46-9 triethyl borate 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 41422-87-1 2-thienylsilatrane 
• 3463-21-6 1-ethoxysilatrane 
• 68011-86-9 1-furan-2-yl-2,8,9-trioxa-5-aza-1-sila-bicyclo[3.3.3]undecane 
• 2097-19-0 1-phenyl-2,8,9-trioxa-5-aza-1-silabicyclo{3.3.3}undecane 
• 2288-13-3 1-methylsilatrane 
• 2097-18-9 1-vinylsilatrane 
• 42003-39-4 1-(chloromethyl)silatrane 
• 358-21-4 perfluorodiethyl ether 
• 382-27-4 Perfluoro-N,N-dimethylaminoacetyl fluoride 
• 382-28-5 2,2,3,3,5,5,6,6-Octafluoro-4-trifluoromethyl-morpholine 
• 130279-34-4 2,2-difluoro-2-(2,2,3,3,5,5,6,6-octafluoromorpholin-4-yl)acetyl fluoride 
• 13460-50-9 metaboric acid 
• 70384-51-9 Tris(3,6-dioxaheptyl)amine 
• 283-60-3 silatrane 

Relevant articles and documents

Synthesis method of tri(3, 6-dioxyheteroheptyl)amine

The invention discloses a synthesis method of tri(3, 6- dioxyheteroheptyl)amine and belongs to the technical field of organic synthesis. The method includes: exchanging triethanolamine and triborate to form ester, and reacting with 2-haloethyl methyl ether in a condition with alkali and a phase transfer catalyst to obtain tri(3, 6-dioxyheteroheptyl)amine. The method can be completed in a same reaction kettle, so that high efficiency of reaction operation is realized, a product obtained by reaction is high in purity and easy to purify, and reference is provided for industrial amplification.

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