Triisopropyl borate

Base Information

• Chemical Name: Triisopropyl borate
• CAS No.: 5419-55-6
• Molecular Formula: C9H21BO3
• Molecular Weight: 188.075
• Hs Code.: 2920.90 DERIVATION
• European Community (EC) Number: 226-529-9
• NSC Number: 9779
• UN Number: 2616
• UNII: YWV817MXF3
• DSSTox Substance ID: DTXSID7027598
• Nikkaji Number: J35.126A
• Wikidata: Q2319620
• ChEMBL ID: CHEMBL1902909
• Mol file: 5419-55-6.mol

Synonyms:TRIISOPROPYL BORATE;5419-55-6;Isopropyl borate;Triisopropoxyborane;Triisopropoxyboron;Boron isopropoxide;Triisopropyl orthoborate;Boric acid triisopropyl ester;tripropan-2-yl borate;tri-i-Propylborate;Trisisopropoxyborane;Triisopropoxy borane;Boric acid (H3BO3), triisopropyl ester;Boron triisopropoxide;triisopropylborate;Boric acid (H3BO3), tris(1-methylethyl) ester;Triisopropoxy boron;tris(propan-2-yl) borate;Isopropyl borate, ((C3H7O)3B);Boric acid, triisopropyl ester;Boric acid, tris(1-methylethyl) ester;NSC 9779;tri(isopropyl)borate;Boric acid triisopropyl;EINECS 226-529-9;UN2616;Tris(1-methylethyl) borate;BRN 1701469;YWV817MXF3;AI3-61082;DTXSID7027598;NSC-9779;Boric acid, (H3BO3), triisopropyl ester;EC 226-529-9;4-01-00-01488 (Beilstein Handbook Reference);DTXCID607598;CAS-5419-55-6;MFCD00008872;triisopropyborate;triisopropyl borat;triisoproyl-borate;triisopropyl-borate;Tri-isopropylborate;triisopropoxylborane;tri isopropyl borate;tri-iso-propylborate;Tri-isopropyl borate;tri-isopropoxy borane;tris(isopropyl)borate;tris-iso-propylborate;tri(iso-propyl)borate;tri(isopropyl) borate;tri-iso-propyl borate;tri (i-propyl) borate;tri(iso-propyl) borate;(iPrO)3B;B(OiPr)3;Tris(propan-2-yl)borate;tris(1-methylethyl)borate;(i-PrO)3B;B(O-iPr)3;B(Oi-Pr)3;UNII-YWV817MXF3;B(O-i-Pr)3;SCHEMBL38188;Triisopropyl borate, >=98%;BORICACIDTRIISOPROPYLESTER;CHEMBL1902909;NSC9779;AMY11087;STR03840;Tox21_201514;Tox21_303129;NA2616;AKOS005259716;AT24467;OL10118;UN 2616;ISOPROPYL BORATE ((C3H7O)3B);WLN: 1Y1&OBOY1&1&OY1&1;NCGC00164082-01;NCGC00164082-02;NCGC00256934-01;NCGC00259064-01;BP-30231;LS-45053;B0521;FT-0657054;EN300-29557;A830025;Triisopropyl borate [UN2616] [Flammable liquid];J-525098;Q2319620;Triisopropyl borate [UN2616] [Flammable liquid];F0001-1425

Chemical Property of Triisopropyl borate

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 76 mm Hg ( 75 °C)
• Melting Point: -59 °C
• Refractive Index: 1.3760
• Boiling Point: 140 °C at 760 mmHg
• Flash Point: 10 °C
• PSA: 27.69000
• Density: 0.814 g/cm³
• LogP: 2.24630
• Storage Temp.: Flammables area
• Sensitive.: Moisture Sensitive
• Solubility.: Miscible with ether, ethanol, isopropanol and benzene.
• Water Solubility.: decomposes
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 188.1583747
• Heavy Atom Count: 13
• Complexity: 102
• Transport DOT Label: Flammable Liquid

Purity/Quality:

99% ^*data from raw suppliers

Triisopropyl borate 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11
• Safety Statements: 7-16-23-24/25-33-9

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Metals -> Metalloid Compounds (Boron)
• Canonical SMILES: B(OC(C)C)(OC(C)C)OC(C)C
• Uses: Triisopropyl borate is used as reagent in Pd-catalyzed coupling reaction with aryl halides such as Suzuki reaction. It is used as a reagent for the preparation of the boronic acids and esters; as a Lewis acid catalyst and involved in the ortho-borylation of 1-substituted naphthalenes. Furthermore, it plays an important role as a catalyst for the production of resins, waxes, paints and varnishes.

Technology Process of Triisopropyl borate

There total 32 articles about Triisopropyl borate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

zirconium(IV) borohydride + isopropyl alcohol (67-63-0,8013-70-5) → Triisopropyl borate (5419-55-6) + zirconium isopropoxide

Guidance literature:

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.;

Reference yield: 88.0%

triisopropoxyboroxin (10298-87-0) + isopropyl alcohol (67-63-0,8013-70-5) → Triisopropyl borate (5419-55-6)

Guidance literature:

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;

Reference yield: 88.0%

hafnium borohydride + isopropyl alcohol (67-63-0,8013-70-5) → Triisopropyl borate (5419-55-6) + hafnium(IV) isopropoxide isopropanolate

Guidance literature:

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.;

upstream raw materials:

Trimethyl borate

isopropyl alcohol

acetone

di-isopropyl ether

Downstream raw materials:

Trimethyl borate

(i-C₃H₇O)2B(O-C₆H₃-2.6-(t-C₄H₉)2)

2,6-Di-t-butyl-p-kresyl-diisopropylborat

(i-C₃H₇O)2B(OC₆H₂(C₄H₉)2C(CH₃)3)

Refernces

• 1、 Cox, Paul A.,Reid, Marc,Leach, Andrew G.,Campbell, Andrew D.,King, Edward J.,Lloyd-Jones, Guy C.. "Base-Catalyzed Aryl-B(OH)2 Protodeboronation Revisited: From Concerted Proton Transfer to Liberation of a Transient Aryl Anion". supporting information. p. 13156 - 13165. Retrieved 2017/09/26.
• 2、 Uysal, Burcu,Oksal, Birsen S.. "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". body text. p. 681 - 685. Retrieved 2012/06/18.