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5419-55-6

5419-55-6

Identification

  • Product Name:Boricacid (H3BO3), tris(1-methylethyl) ester

  • CAS Number: 5419-55-6

  • EINECS:226-529-9

  • Molecular Weight:188.075

  • Molecular Formula: C9H21BO3

  • HS Code:2920.90 DERIVATION

  • Mol File:5419-55-6.mol

Synonyms:Boricacid (H3BO3), triisopropyl ester (8CI);Isopropyl borate (6CI,7CI);Boric acidtriisopropyl ester;Boron isopropoxide;Boron triisopropoxide;Borontriisopropylester;NSC 9779;Triisopropoxyborane;Triisopropoxyboron;Triisopropyl orthoborate;Trisisopropoxyborane;

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Safety information and MSDS view more

  • Pictogram(s):FlammableF,IrritantXi

  • Hazard Codes:F,Xi

  • Signal Word:Danger

  • Hazard Statement:H225 Highly flammable liquid and vapourH319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:Usbiological
  • Product Description:Triisopropyl borate 99+%
  • Packaging:25g
  • Price:$ 156
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:Triisopropyl borate
  • Packaging:25g
  • Price:$ 60
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Triisopropyl Borate >98.0%(T)
  • Packaging:25mL
  • Price:$ 16
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Triisopropyl Borate >98.0%(T)
  • Packaging:100mL
  • Price:$ 34
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Triisopropyl Borate >98.0%(T)
  • Packaging:500mL
  • Price:$ 89
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Tris(isopropyl) borate 99%
  • Packaging:2.5 L
  • Price:$ 176
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Tris(isopropyl) borate 99%
  • Packaging:500 mL
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:Tris(isopropyl) borate 99%
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Tri-i-propylborate, min. 98%
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  • Manufacture/Brand:Strem Chemicals
  • Product Description:Tri-i-propylborate, min. 98%
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Relevant articles and documentsAll total 19 Articles be found

Addition compounds of alkali-metal hydrides. 23. Preparation of potassium triisopropoxyborohydride in improved purity

Brown, Herbert C.,Nazer, Behrooz,Sikorski, James A.

, p. 634 - 637 (1983)

Commercial potassium triisopropoxyborohydride, K(i-PrO)3BH, or the usual material prepared at 25 °C from potassium hydride and triisopropoxyborane in tetrahydrofuran contains a significant impurity, detectable in the 11B NMR spectrum. This impurity, probably potassium tetraisopropoxyborohydride, significantly decreases the yield when the reagent is used to hydride thexylmonoalkylchloroboranes, ThxBR1Cl, for the synthesis of mixed thexyldialkylboranes. This impurity can be removed by refluxing a THF solution of the impure potassium triisopropoxyborohydride over potassium hydride. Alternatively, the reaction of triisopropoxyborane with excess KH in refluxing THF gives a product essentially free of the impurity. Storage of the solution KIPBH over a small excess of potassium hydride (~10%) maintains the product essentially free of the impurity. Use of this material permits the preparation of essentially quantitative yields of the desired mixed thexyldialkylboranes, ThxBR1R2, via the hydridation of the intermediate ThxBR1Cl in the presence of a second olefin.

Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion

Cox, Paul A.,Reid, Marc,Leach, Andrew G.,Campbell, Andrew D.,King, Edward J.,Lloyd-Jones, Guy C.

supporting information, p. 13156 - 13165 (2017/09/26)

Pioneering studies by Kuivila, published more than 50 years ago, suggested ipso protonation of the boronate as the mechanism for base-catalyzed protodeboronation of arylboronic acids. However, the study was limited to UV spectrophotometric analysis under acidic conditions, and the aqueous association constants (Ka) were estimated. By means of NMR, stopped-flow IR, and quenched-flow techniques, the kinetics of base-catalyzed protodeboronation of 30 different arylboronic acids has now been determined at pH > 13 in aqueous dioxane at 70 °C. Included in the study are all 20 isomers of C6HnF(5-n)B(OH)2 with half-lives spanning 9 orders of magnitude: a and Sδ values, kinetic isotope effects (2H, 10B, 13C), linear free-energy relationships, and density functional theory calculations, we have identified a mechanistic regime involving unimolecular heterolysis of the boronate competing with concerted ipso protonation/C-B cleavage. The relative Lewis acidities of arylboronic acids do not correlate with their protodeboronation rates, especially when ortho substituents are present. Notably, 3,5-dinitrophenylboronic acid is orders of magnitude more stable than tetra-and pentafluorophenylboronic acids but has a similar pKa.

Synthesis of 3-(5-methylthiophen-2-yl)coumarins and their photochromic dihetarylethene derivatives

Bochkov, Andrei Y.,Krayushkin, Mikhail M.,Yarovenko, Vladimir N.,Barachevsky, Valery A.,Beletskaya, Irina P.,Traven, Valery F.

, p. 891 - 898 (2013/08/23)

Novel unsymmetrical di(thienyl)maleic acid anhydride, including coumarin moiety, has been designed and synthesized. Its photochromism study and fatigue resistance estimation are reported. Microwave-assisted procedure has been successfully used for synthesis of 3-(5-methylthiophen-2-yl)coumarins.

A new method for the chemoselective reduction of aldehydes and ketones using boron tri-isopropoxide, B(OiPr)3: Comparison with boron tri-ethoxide, B(OEt)3

Uysal, Burcu,Oksal, Birsen S.

body text, p. 681 - 685 (2012/06/18)

A chemoselective Meerwein-Ponndorf-Verley reduction process of various aliphatic and allylic α,β-unsaturated aldehydes and ketones is described. This chemoselective reduction is catalysed by boron triisopropoxide B(Oi Pr)3. Kinetics of reduction of aldehydes and ketones to corresponding alcohols were also examined and rate constant of each carbonyl compounds were measured. Rate constant and reduction yield of each carbonyl compounds in the presence of B(Oi Pr)3 were compared with those in the presence of B(OEt)3. The alcohols that are the reduction product were analysed by GC-MS. The rate constants and alcohol yields were found to be higher with B(OEt)3 than with B(Oi Pr) 3. The mechanism proposed involves a six-membered transition state in which both the alcohol and the carbonyl are coordinated to the same boron centre of a boron alkoxide catalyst. Indian Academy of Sciences.

In vitro antibacterial and antifungal activities of some sulfur-nitrogen-oxygen and oxygen-nitrogen-oxygen donor bifunctional tridentate schiff bases and their boron(III) complexes

Yadav, Sunita,Swami, Monika,Singh

experimental part, p. 394 - 401 (2010/07/03)

Antimicrobial properties of sulfur, nitrogen, and oxygen bonded organoboron (III) complexes with biologically potent ligands viz., 2-hydroxy-N-phenyl benzamide hydrazine carboxamide(HO∩N∩OH), 2-hydroxy-N-phenyl benzamide hydrazine carbothioamide (HO∩N∩∩SH), and 2-hydroxy-N-phenyl benzamide hydrazine carbodithioic acid (HO∩N∩SH), have been studied. The unimolar and bimolar reactions of triisopropoxy borane with dibasic tridentate ligands resulted in the formation of colored solids, which have been characterized by elemental analysis, molecular weight determinations, and conductance measurements. The UV, IR, and NMR (1H, 13C, and 11B) spectral studies indicate a tetra-coordinated geometry for the resulting complexes. The ligands and their complexes have been screened for their fungicidal and bactericidal activities, and the results indicate that they exhibit significant antimicrobial properties. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Effect of the secondary reduction on the enantioselectivity and function of additives in the chiral oxazaborolidine-catalyzed asymmetric borane reduction of ketones

Liu, Han,Du, Da-Ming,Xu, Jiaxi

, p. 1067 - 1074 (2007/10/03)

The secondary reduction in the direct and oxazaborolidine-catalyzed asymmetric borane reduction of ketones was investigated by the use of GC/MS tracing titration and control experiments. The results indicate that the secondary reduction affects the enantioselectivity only in noncoordinated solvents at low temperature and not under the usual catalytic reduction conditions because the intermediate alkoxyborane is unstable and quickly converts to borane and dialkoxyborane. The function of an alcohol additive in the asymmetric borane reduction of ketones is to consume excess borane in the reduction system thus inhibiting noncatalytic reduction, which leads to increased enantioselectivity in the catalytic reduction.

Process route upstream and downstream products

Process route

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

Hexamethyldisiloxane
107-46-0

Hexamethyldisiloxane

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

(C<sub>3</sub>H<sub>7</sub>O)2BOSi(CH<sub>3</sub>)3

(C3H7O)2BOSi(CH3)3

C<sub>3</sub>H<sub>7</sub>OB(OSi(CH<sub>3</sub>)3)2

C3H7OB(OSi(CH3)3)2

Triisopropyl borate
5419-55-6

Triisopropyl borate

tris(trimethylsilyl)borate
4325-85-3

tris(trimethylsilyl)borate

Conditions
Conditions Yield
In neat (no solvent); Me3SiCl, Me3SiOSiMe3 and 2-propanol stirred for 30 min, boric acid added and stirred for 3 h; soln. filtered and concd., mixt. analysed by using combined gas chromatograph-mass spectroscopy;
isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
Conditions Yield
With calcium hydride; In neat (no solvent); byproducts: H2; react. under N2, slow addn. of the alcohol via syringe to B(OH)3 (ratio 3:1) and CaH2, cooling in a water bath, slow heating to 80 - 90°C for 12 h after abating the H2 gas evolution; distn. of the volatile products under reduced pressure (distn. pot temp. <= 120°C);
87%
With calcium hydride; at 90 ℃; Inert atmosphere; Schlenk technique;
66%
In benzene; for 18h; Heating;
48%
isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
Conditions Yield
With boric acid; benzene; unter Entfernen des entstehenden Wassers;
With boron trioxide; at 130 ℃;
With boron trioxide; toluene;
With sodium borate; acetic acid;
With boron trioxide;
With boron trioxide; benzene;
With dimethylsulfide borane complex;
With boric acid; In benzene;
With borane-THF;
U(BH<sub>4</sub>)3(OCH(CH<sub>3</sub>)2)(C<sub>4</sub>H<sub>8</sub>O)2

U(BH4)3(OCH(CH3)2)(C4H8O)2

Triisopropyl borate
5419-55-6

Triisopropyl borate

U(BH<sub>4</sub>)2(OCH(CH<sub>3</sub>)2)2(C<sub>4</sub>H<sub>8</sub>O)2

U(BH4)2(OCH(CH3)2)2(C4H8O)2

Conditions
Conditions Yield
With acetone; In tetrahydrofuran; addn. of acetone via microsyringe to U complex soln.; standing at room temp., 1h; reducing volume; addn. of pentane; cooling to -78°C; pptn.; rapid filtration, drying (vac.); evapn. of mother liquor, extn. in pentane: B compd.;
81%
triisopropoxyboroxin
10298-87-0

triisopropoxyboroxin

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
Conditions Yield
With calcium hydride; In cyclohexane; byproducts: H2; react. under N2, slow addn. of the alcohol to the trialkoxyboroxine and CaH2 in cyclohexane, cooling in a water bath, rapid gas evolution, stirring for 1 h at room temp., heating to 80-90°C overnight; distn. of the product under reduced pressure;
88%
boron trioxide

boron trioxide

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

Conditions
Conditions Yield
at 100-120 °C;
With catalyst: Zeokar 2; In solid; prepd. from predried reagents by mechanochemical activation in planetarycentrifuge mill at rotation frequency of 10-17 s**-1 for 1-30 min; equi librium reaction; analyzed by (1)H NMR spectroscopy and XRD; Kinetics;
With catalyst: zeolite NaA; In solid; prepd. from predried reagents by mechanochemical activation in planetarycentrifuge mill at rotation frequency of 10-17 s**-1 for 1-30 min; equi librium reaction; analyzed by (1)H NMR spectroscopy and XRD; Kinetics;
With catalyst: zeolite NaX; In solid; prepd. from predried reagents by mechanochemical activation in planetarycentrifuge mill at rotation frequency of 10-17 s**-1 for 1-30 min; equi librium reaction; analyzed by (1)H NMR spectroscopy and XRD; Kinetics;
at 100-120 °C;
hafnium borohydride

hafnium borohydride

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

hafnium(IV) isopropoxide isopropanolate

hafnium(IV) isopropoxide isopropanolate

Conditions
Conditions Yield
In pentane; byproducts: H2; (Ar (N2) or vac.); dropwise addn. of excess of i-PrOH to Hf-complex in pentane with stirring (60 min, room temp.); concn., filtration, drying (vac.); elem. anal.;
88%
zirconium(IV) borohydride

zirconium(IV) borohydride

isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

zirconium isopropoxide

zirconium isopropoxide

Conditions
Conditions Yield
In pentane; byproducts: H2; (Ar (N2) or vac.); dropwise addn. of excess of i-PrOH to Zr-complex in pentane with stirring (60 min, room temp.); concn., sepn. by filtration, a) pptn. drying (vac.), b) distn. of filtrate gives B compd.; elem. anal.;
90%
75%
isopropyl alcohol
67-63-0,8013-70-5

isopropyl alcohol

Triisopropyl borate
5419-55-6

Triisopropyl borate

diisopropyl allylboronate
51851-79-7

diisopropyl allylboronate

Conditions
Conditions Yield
In benzene; byproducts: H2O; under Ar, soln. of allylboronic acid in C6H6 treated with 2-propanol (2 equiv), heated to reflux until evolution of H2O completed (Dean-Stark trap); fractionally distd. (bp 62-64°C, 40 mmHg);
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

(E)-1-hexenyldiisopropoxyborane
91083-27-1

(E)-1-hexenyldiisopropoxyborane

Triisopropyl borate
5419-55-6

Triisopropyl borate

ethyl-1-hexenylisopropoxyborane
148058-18-8

ethyl-1-hexenylisopropoxyborane

Conditions
Conditions Yield
With acetyl chloride; In diethyl ether; dropwise addn. of EtMgBr (1-2.5 equiv.) to soln. of C6H11B(OCH(CH3)2)2 (2.5 mmol) in ether at -78°C via syringe; stirring at -78°C for 3 h; addn. of CH3COCl at -78°C; warming slowly to room temp.; stirring (room temp.);; not isolated; product distribution is determined by 11B-NMR;;

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