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150-46-9 Usage

Chemical Properties

Triethyl borate is a Colorless liquid; mild odor. Hydrolyzes rapidly depositing boric acid in finely divided crystalline form.

Uses

Different sources of media describe the Uses of 150-46-9 differently. You can refer to the following data:
1. Triethyl borate is used as a solvent in resins, paints, varnishes, adhesives and sealant chemicals. It is used as a catalyst of synthetic waxes and resins. It is an active component of flame retardants in the textile industry and in welding fluxes. It is used to prepare m-tolyl-acetic acid ethyl ester by reacting with 1-bromomethyl-3-methyl-benzene and carbon monoxide using as1,5-hexadiene?dium chloride as a catalyst. Further, it is used in pyrotechnics.
2. Triethyl borate may be used as boron source to synthesize lithium borophosphates, alumina borosilicate ceramic nanofibres and boron-doped single wall carbon nanotubes.
3. Antiseptics, disinfectants, antiknock agent. Triethyl borate is used as a solvent in resins, paints, varnishes, adhesives and sealant chemicals. It is used as a catalyst of synthetic waxes and resins. It is an active component of flame retardants in the textile industry and in welding fluxes. It is used to prepare m-tolyl-acetic acid ethyl ester by reacting with 1-bromomethyl-3-methyl-benzene and carbon monoxide using as 1,5-hexadiene dium chloride as a catalyst. Further, it is used in pyrotechnics. Triethyl borate may be used as boron source to synthesize lithium borophosphates, alumina borosilicate ceramic nanofibres and boron-doped single wall carbon nanotubes.CVD precursor for boron modified SiO2 in microelectronics Intermediate for organic-modified borosiloxanes.

Preparation

Triethyl borate can be prepared by adding anhydrous ethanol with boric acid or boron trioxide. Can be purified via distillation.

Definition

ChEBI: A member of the class of borate esters obtained by the formal condensation of three equivalents of ethanol with boric acid.

Hazard

Flammable, dangerous fire risk.

Safety Profile

Moderately toxic by ingestion. Aneye irritant. A very dangerous fire hazard when exposed toheat or flame. When heated to decomposition it emitsacrid smoke and irritating fumes.

Purification Methods

Dry it over sodium, then distil it. Also fractionate it through a gauze packed column. [Charnlet et al. J Chem Soc 2288 1952, as for tributyl borate Johnson & Tompkins Org Synth Coll Vol II 106 1943, Beilstein 1 III 1339, 1 IV 1365.]

Check Digit Verification of cas no

The CAS Registry Mumber 150-46-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 0 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 150-46:
(5*1)+(4*5)+(3*0)+(2*4)+(1*6)=39
39 % 10 = 9
So 150-46-9 is a valid CAS Registry Number.
InChI:InChI=1/C17H20N2O2S.B/c1-3-20-15-9-5-13(6-10-15)18-17(22)19-14-7-11-16(12-8-14)21-4-2;/h5-12H,3-4H2,1-2H3,(H2,18,19,22);/q;+3

150-46-9 Well-known Company Product Price

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  • Alfa Aesar

  • (A18728)  Triethyl borate, 97%   

  • 150-46-9

  • 100ml

  • 605.0CNY

  • Detail
  • Alfa Aesar

  • (A18728)  Triethyl borate, 97%   

  • 150-46-9

  • 500ml

  • 2025.0CNY

  • Detail
  • Alfa Aesar

  • (A18728)  Triethyl borate, 97%   

  • 150-46-9

  • 2500ml

  • 4824.0CNY

  • Detail
  • Sigma-Aldrich

  • (T59307)  Triethylborate  99%

  • 150-46-9

  • T59307-100ML

  • 786.24CNY

  • Detail
  • Sigma-Aldrich

  • (T59307)  Triethylborate  99%

  • 150-46-9

  • T59307-500ML

  • 2,508.48CNY

  • Detail

150-46-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name triethyl borate

1.2 Other means of identification

Product number -
Other names BORON ETHOXIDE

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:150-46-9 SDS

150-46-9Synthetic route

bis(3,5-dimethyl-4-methoxyphenyl)phosphane-borane(1:1)

bis(3,5-dimethyl-4-methoxyphenyl)phosphane-borane(1:1)

ethanol
64-17-5

ethanol

A

triethyl borate
150-46-9

triethyl borate

B

bis(4-methoxy-3,5-dimethylphenyl)-phosphine
122708-97-8

bis(4-methoxy-3,5-dimethylphenyl)-phosphine

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 73%
ethyl trimethylsilyl ether
1825-62-3

ethyl trimethylsilyl ether

benzenediazonium tetrafluoroborate
369-57-3

benzenediazonium tetrafluoroborate

A

triethyl borate
150-46-9

triethyl borate

B

trimethylsilyl fluoride
420-56-4

trimethylsilyl fluoride

C

Phenetole
103-73-1

Phenetole

Conditions
ConditionsYield
In 1,1,2-Trichloro-1,2,2-trifluoroethane 1.) 0 to 55 deg C very slowly, 2.) sonication, reflux, 16-17 h;A 63%
B n/a
C 54%
nido-decaborane
17702-41-9

nido-decaborane

ethyl nitrite
109-95-5

ethyl nitrite

A

nido-NB9H12
58985-53-8

nido-NB9H12

B

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
In tetrahydrofuran byproducts: H2, NO, NO2; addn. of ethylnitrite soln. to borane soln., -78°C; heating to room temp.; stirring, 3h; evapn.; extn. (hexane); evapn.; sublimation, 25°C, 0.001 Torr;A 52%
B n/a
ethanol
64-17-5

ethanol

(2-biphenyl)dicyclohexylphosphane-borane(1:1)
1186392-99-3

(2-biphenyl)dicyclohexylphosphane-borane(1:1)

A

triethyl borate
150-46-9

triethyl borate

B

CyJohnPhos
247940-06-3

CyJohnPhos

Conditions
ConditionsYield
Inert atmosphere; Reflux;A n/a
B 52%
boric acid
11113-50-1

boric acid

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
With ethanol In benzene a mixt. of ethanol, benzene, orthoboric acid, and anhydrous CuSO4 is boiled on a Dean-Stark apparatus with driving off water (40-50 h);; repeated fractional distn.;;35%
With ethanol
With ethanol In ethanol at room temp.;
With ethanol In ethanol at room temp.;
With C2H5OH
Trimethyl borate
121-43-7

Trimethyl borate

ethanol
64-17-5

ethanol

triethyl borate
150-46-9

triethyl borate

boric acid tributyl ester
688-74-4

boric acid tributyl ester

ethanol
64-17-5

ethanol

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
With sulfuric acid
ethanol
64-17-5

ethanol

diethyl boronate
23561-28-6

diethyl boronate

triethyl borate
150-46-9

triethyl borate

ethanol
64-17-5

ethanol

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
With boron trichloride
With sodium borate; acetic acid
With boron trichloride at -60℃; im Hochvakuum;
bis(ethoxy)chloroborane
20905-32-2

bis(ethoxy)chloroborane

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
With sodium
With zinc
acetic anhydride
108-24-7

acetic anhydride

triethyl borate
150-46-9

triethyl borate

Conditions
ConditionsYield
With tert-butyl-N-methyl-N-isopropylamine-borane In tetrahydrofuran at 20℃; for 24h; Reduction;
tetraethoxy orthosilicate
78-10-4

tetraethoxy orthosilicate

boron bromide

boron bromide

A

triethyl borate
150-46-9

triethyl borate

B

tribromo-ethoxy-silane
18076-81-8

tribromo-ethoxy-silane

ethanol
64-17-5

ethanol

acetic boric anhydride

acetic boric anhydride

triethyl borate
150-46-9

triethyl borate

ethanol
64-17-5

ethanol

boranyl disulfate

boranyl disulfate

triethyl borate
150-46-9

triethyl borate

triethyl borate
150-46-9

triethyl borate

carbon monoxide
201230-82-2

carbon monoxide

1-bromomethyl-3-methyl-benzene
620-13-3

1-bromomethyl-3-methyl-benzene

ethyl m-methylphenylacetate
40061-55-0

ethyl m-methylphenylacetate

Conditions
ConditionsYield
1,5-hexadienerhodium(I)-chloride dimer at 75℃; under 760 Torr; Heating; overnight; other solvent;100%
triethyl borate
150-46-9

triethyl borate

2-Methoxybenzyl chloride
7035-02-1

2-Methoxybenzyl chloride

carbon monoxide

carbon monoxide

ethyl (2-methoxyphenyl)acetate
6056-23-1

ethyl (2-methoxyphenyl)acetate

Conditions
ConditionsYield
With potassium iodide; <1,5-HDRhCl>2100%
triethyl borate
150-46-9

triethyl borate

tert-butyl-dimethyl-(4-bromo-2-ethyl-5-methoxy-benzyloxy)-silane
511277-96-6

tert-butyl-dimethyl-(4-bromo-2-ethyl-5-methoxy-benzyloxy)-silane

tert-butyl-dimethyl-(4-boronic acid-2-ethyl-5-methoxy-benzyloxy)-silane
511277-98-8

tert-butyl-dimethyl-(4-boronic acid-2-ethyl-5-methoxy-benzyloxy)-silane

Conditions
ConditionsYield
Stage #1: tert-butyl-dimethyl-(4-bromo-2-ethyl-5-methoxy-benzyloxy)-silane With n-butyllithium In tetrahydrofuran at -78 - -70℃; for 1h;
Stage #2: triethyl borate In tetrahydrofuran at -30 - 23℃; for 2h;
100%
With n-butyllithium In tetrahydrofuran9.0 g (100%)
triethyl borate
150-46-9

triethyl borate

2-(4'-aminophenyl)ethyl alcohol
104-10-9

2-(4'-aminophenyl)ethyl alcohol

B(OCH2CH2C6H4NH2)3
76644-60-5

B(OCH2CH2C6H4NH2)3

Conditions
ConditionsYield
In benzene byproducts: ethanol; molar ratio B(OEt)3:alcohol=1:3, refluxing; distn. (reduced pressure); elem. anal.;100%
triethyl borate
150-46-9

triethyl borate

2-(4-bromo-2,5-dimethoxy-phenyl)-[1,3]dioxolane
681171-32-4

2-(4-bromo-2,5-dimethoxy-phenyl)-[1,3]dioxolane

2-(4-boronic acid-2,5-dimethoxy-phenyl)-[1,3]dioxolane
681171-33-5

2-(4-boronic acid-2,5-dimethoxy-phenyl)-[1,3]dioxolane

Conditions
ConditionsYield
Stage #1: 2-(4-bromo-2,5-dimethoxy-phenyl)-[1,3]dioxolane With n-butyllithium In tetrahydrofuran at -78 - -70℃; for 0.5h;
Stage #2: triethyl borate In tetrahydrofuran at -30 - 23℃; for 2h;
100%
triethyl borate
150-46-9

triethyl borate

[2-(4-Bromo-2-ethyl-5-methoxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane
681171-47-1

[2-(4-Bromo-2-ethyl-5-methoxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane

[2-(4-boronic acid-2-ethyl-5-methoxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane
681171-48-2

[2-(4-boronic acid-2-ethyl-5-methoxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane

Conditions
ConditionsYield
Stage #1: [2-(4-Bromo-2-ethyl-5-methoxy-phenyl)-ethoxy]-tert-butyl-dimethyl-silane With n-butyllithium In tetrahydrofuran at -78 - -70℃; for 1h;
Stage #2: triethyl borate In tetrahydrofuran at -30 - 23℃; for 2h;
100%
triethyl borate
150-46-9

triethyl borate

1-bromo-3,5-diphenylbenzene
103068-20-8

1-bromo-3,5-diphenylbenzene

3,5-diphenylphenylboronic acid
128388-54-5

3,5-diphenylphenylboronic acid

Conditions
ConditionsYield
Stage #1: 1-bromo-3,5-diphenylbenzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;
Stage #2: triethyl borate In tetrahydrofuran at -78℃; for 24h; Inert atmosphere;
97%
triethyl borate
150-46-9

triethyl borate

trimethyl(pentafluoroethyl)silane
124898-13-1

trimethyl(pentafluoroethyl)silane

potassium (pentafluoroethyl)triethoxyborate

potassium (pentafluoroethyl)triethoxyborate

Conditions
ConditionsYield
With potassium fluoride In tetrahydrofuran at 20 - 50℃; for 8h;96%
salicylaldazine

salicylaldazine

triethyl borate
150-46-9

triethyl borate

ethoxyboron(salicylaldehydeazinate)
75777-73-0

ethoxyboron(salicylaldehydeazinate)

Conditions
ConditionsYield
In benzene addn. of ligand to boron ethoxide in dry benzene, refluxing over a fractionating column; removal of solvent, drying under reduced pressure, elem. anal.;96%
triethyl borate
150-46-9

triethyl borate

(trifluoromethyl)trimethylsilane
81290-20-2

(trifluoromethyl)trimethylsilane

potassium (trifluoromethyl)triethoxyborate

potassium (trifluoromethyl)triethoxyborate

Conditions
ConditionsYield
With potassium fluoride In tetrahydrofuran at 20℃; for 24h;95%
With potassium fluoride In 1,2-dimethoxyethane at 20℃;
triethyl borate
150-46-9

triethyl borate

2-Anilinoethanol
122-98-5

2-Anilinoethanol

Borsaeure-tris-(β-anilino-ethylester)
22394-30-5

Borsaeure-tris-(β-anilino-ethylester)

Conditions
ConditionsYield
In benzene byproducts: ethanol; molar ratio B(OEt)3:alcohol=1:3, refluxing; distn. (reduced pressure); elem. anal.;95%
bis-{2-hydroxy-1-naphthyl-methylene} hydrazine

bis-{2-hydroxy-1-naphthyl-methylene} hydrazine

triethyl borate
150-46-9

triethyl borate

ethoxyboron(2-hydroxy-1-naphthaldehydeazinate)

ethoxyboron(2-hydroxy-1-naphthaldehydeazinate)

Conditions
ConditionsYield
In benzene addn. of ligand to boron ethoxide in dry benzene, refluxing over a fractionating column; removal of solvent, drying under reduced pressure, elem. anal.;95%
triethylsilane
617-86-7

triethylsilane

triethyl borate
150-46-9

triethyl borate

tris-(triethylsilyl)-borate
18546-66-2

tris-(triethylsilyl)-borate

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In benzene at 85℃; for 3h;95%
triethyl borate
150-46-9

triethyl borate

2-[(1,1-dimethylethyl)amino]-ethanol
4620-70-6

2-[(1,1-dimethylethyl)amino]-ethanol

B(OCH2CH2NHC(CH3)3)3
76644-57-0

B(OCH2CH2NHC(CH3)3)3

Conditions
ConditionsYield
In benzene byproducts: ethanol; molar ratio B(OEt)3:alcohol=1:3, refluxing; distn. (reduced pressure); elem. anal.;94%
triethyl borate
150-46-9

triethyl borate

C10H12N4O3(2-)*2Na(1+)

C10H12N4O3(2-)*2Na(1+)

C10H11BN4O3
1188369-98-3

C10H11BN4O3

Conditions
ConditionsYield
Stage #1: C10H12N4O3(2-)*2Na(1+) With sulfuric acid In 1,4-dioxane; acetonitrile at 0℃;
Stage #2: triethyl borate In 1,4-dioxane; acetonitrile at 50℃;
94%
triethyl borate
150-46-9

triethyl borate

N,N'-di-tert-butoxycarbonyl-2,2'-bipyrrole

N,N'-di-tert-butoxycarbonyl-2,2'-bipyrrole

(N,N'-di-tert-butoxycarbonyl-2,2'-bipyrrol-5-yl)boronic acid

(N,N'-di-tert-butoxycarbonyl-2,2'-bipyrrol-5-yl)boronic acid

Conditions
ConditionsYield
Stage #1: N,N'-di-tert-butoxycarbonyl-2,2'-bipyrrole With 2,2,6,6-tetramethyl-piperidine; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 3h; Inert atmosphere;
Stage #2: triethyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 18.5h; Inert atmosphere;
94%
triethyl borate
150-46-9

triethyl borate

1-chloromethyl-4-fluorobenzene
352-11-4

1-chloromethyl-4-fluorobenzene

carbon monoxide

carbon monoxide

ethyl 2-(4-fluorophenyl)acetate
587-88-2

ethyl 2-(4-fluorophenyl)acetate

Conditions
ConditionsYield
With potassium iodide; <1,5-HDRhCl>293%
triethyl borate
150-46-9

triethyl borate

2,2,3,5,5,6,6-Heptafluoro(5,6-dihydro-2H-1,4-oxazine)
4777-13-3

2,2,3,5,5,6,6-Heptafluoro(5,6-dihydro-2H-1,4-oxazine)

5-ethoxy-2,2,3,3,6,6-hexafluoro-3,6-dihydro-2H-1,4-oxazine

5-ethoxy-2,2,3,3,6,6-hexafluoro-3,6-dihydro-2H-1,4-oxazine

Conditions
ConditionsYield
With tert-amyl peroxy-2-ethylhexanoate at 75 - 90℃; Sealed tube; Cooling with acetone-dry ice;92.4%

150-46-9Relevant articles and documents

Beachell,Schar

, p. 2943 (1958)

Urs

, p. 29 (1957)

-

Lehmann et al.

, p. 1226,1227,1228 (1959)

-

Denson, C. L.,Crowell, T. I.

, p. 5656 - 5658 (1957)

Lalancette,Beauregard

, p. 5169 (1967)

Bains,Arthur jr.

, p. 365,368 (1971)

Methyl camouflage in the ten-vertex: Closo -dicarbaborane(10) series. Isolation of closo -1,6-R2C2B8Me8 (R = H and Me) and their monosubstituted analogues

Bakardjiev, Mario,Tok, Oleg L.,R??i?ka, Ale?,R??i?ková, Zdeňka,Holub, Josef,Hnyk, Drahomír,?palt, Zbyněk,Fanfrlík, Jind?ich,?tíbr, Bohumil

, p. 11070 - 11076 (2018)

Reported are procedures leading to the first types of methyl camouflaged dicarbadecaboranes with fewer than eleven vertices. The compounds contain the closo-1,6-C2B8 scaffolding inside the egg-shaped hepta-decamethyl sheath, which im

Beachell,Meeker

, p. 1796 (1956)

Low-Temperature Hypergolic Ignition of 1-Octene with Low Ignition Delay Time

Sheng, Haoqiang,Huang, Xiaobin,Chen, Zhijia,Zhao, Zhengchuang,Liu, Hong

, p. 423 - 434 (2021/02/05)

The attainment of the efficient ignition of traditional liquid hydrocarbons of scramjet combustors at low flight Mach numbers is a challenging task. In this study, a novel chemical strategy to improve the reliable ignition and efficient combustion of hydrocarbon fuels was proposed. A directional hydroboration reaction was used to convert hydrocarbon fuel into highly active alkylborane, thereby leading to changes in the combustion reaction pathway of hydrocarbon fuel. A directional reaction to achieve the hypergolic ignition of 1-octene was designed and developed by using Gaussian simulation. Borane dimethyl sulfide (BDMS), a high-energy additive, was allowed to react spontaneously with 1-octene to achieve the hypergolic ignition of liquid hydrocarbon fuel at -15 °C. Compared with the ignition delay time of pure 1-octene (565 °C), the ignition delay time of 1-octene/BDMS (9:1.2) decreased by 3850% at 50 °C. Fourier transform infrared spectroscopy and gas chromatography-mass spectrometry confirmed the directional reaction of the hypergolic ignition reaction pathway of 1-octene and BDMS. Moreover, optical measurements showed the development trend of hydroxyl radicals (OH·) in the lower temperature hypergolic ignition and combustion of 1-octene. Finally, this study indicates that the enhancement of the low-temperature ignition performance of 1-octene by hydroboration in the presence of BDMS is feasible and promising for jet propellant design with tremendous future applications.

Rehydrogenation of aminoboranes to amine-boranes using H2O: Reaction scope and mechanism

Leitao, Erin M.,Manners, Ian

, p. 2199 - 2205 (2015/05/13)

Water has been successfully employed as a reagent with which to rehydrogenate aminoboranes (e.g., iPr2N=BH2, 2,2,6,6-Me4C5H6N=BH2, and also transient Me2N=BH2 derived from 1/2[Me2N-BH2]2) to amine-boranes (e.g., iPr2NH·BH3, 2,2,6,6-Me4C5H6NH·BH3, Me2NH·BH3) in approximately 30 yield. The conversion to amine-boranes from the corresponding aminoboranes using this method represents an example of a metal-free, single-step route for the hydrogenation of the B=N bond. Deuterium labeling studies indicated that the protic hydrogen (N-H) on the rehydrogenated amine-borane was derived from H2O, whereas the third hydridic hydrogen (B-H) on the amine-borane was generated from the formation of a postulated hydride-bridged intermediate H2B(μ-H)(μ-NR2)B(OH)H (R2 = Me2, iPr2, 2,2,6,6-Me4C5H6), which requires a second equivalent of the starting aminoborane, thus explaining the low yield. Formation of insoluble borates (BxOyHz) provides a driving force for the reaction. Significantly, the yield can be increased by adding a sacrificial source of BH3 (e.g., to ca. 53% for BH3·THF) or by adding a separate source of H- (e.g., to ca. 95% for LiBH4) to complement the H+ (from H2O) in a more atom-efficient reaction.

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