Isopropylboronic acid

Base Information

• Chemical Name: Isopropylboronic acid
• CAS No.: 80041-89-0
• Molecular Formula: C3H9BO2
• Molecular Weight: 87.9143
• Hs Code.: 29163990
• European Community (EC) Number: 676-846-5
• DSSTox Substance ID: DTXSID90370481
• Nikkaji Number: J2.235.033A
• Wikidata: Q72485789
• Mol file: 80041-89-0.mol

Synonyms:Isopropylboronic acid;80041-89-0;propan-2-ylboronic acid;(Propan-2-yl)boronic acid;2-Propaneboronic acid;Boronic acid, (1-methylethyl)-;MFCD01319021;(1-Methylethyl)boronic acid;Isopropylboronicacid;isopropylboric acid;DTXSID90370481;BCP21922;Boronic acid, B-(1-methylethyl)-;AM1192;AKOS005146521;AB08847;CS-W004088;GS-6619;SY006229;FT-0647396;I0787;EN300-74363;A839820

Chemical Property of Isopropylboronic acid

Chemical Property:

• Appearance/Colour: white flakes
• Vapor Pressure: 0.833mmHg at 25°C
• Melting Point: 95-100 °C(lit.)
• Refractive Index: 1.385
• Boiling Point: 160.4 °C at 760 mmHg
• PKA: 10.49±0.43(Predicted)
• Flash Point: 50.8 °C
• PSA: 40.46000
• Density: 0.921 g/cm³
• LogP: -0.13080
• Storage Temp.: Refrigerator (+4°C)
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 88.0695597
• Heavy Atom Count: 6
• Complexity: 35.8

Purity/Quality:

99% ^*data from raw suppliers

Isopropylboronic Acid (contains varying amounts of Anhydride) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 37/39-26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C(C)C)(O)O
• Uses: Isopropylboronic acid as a reagent is involved in copper-promoted cross-coupling, Domino Heck-Suzuki reactions, Suzuki-Miyaura type couple reactions and alkylation-hydride reduction sequence.

Technology Process of Isopropylboronic acid

There total 6 articles about Isopropylboronic acid 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:

triethyl borate (150-46-9) + isopropylmagnesium chloride (1068-55-9) → isopropylboronic acid (80041-89-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran;

Reference yield:

water (7732-18-5) + 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (76347-13-2) → isopropylboronic acid (80041-89-0)

Guidance literature:

water; 2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; With sodium periodate; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere; Sealed tube;

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 18h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.orglett.0c00471

Reference yield:

diethyl ether (60-29-7,927820-24-4) + triethyl borate (150-46-9) + isopropylmagnesium chloride (1068-55-9) → isopropylboronic acid (80041-89-0)

Guidance literature:

upstream raw materials:

boric acid tributyl ester

isopropylmagnesium bromide

diethyl ether

triethyl borate

Downstream raw materials:

tri(isopropyl)boroxine

3,5-dimethoxy-4-(1-methylethyl)benzaldehyde

2-methylisopropylbenzene

1-ethyl-2-isopropylbenzene

Refernces

• 1、 Lennox, Alastair J. J.,Lloyd-Jones, Guy C.. "Organotrifluoroborate hydrolysis: Boronic acid release mechanism and an acid-base paradox in cross-coupling". . p. 7431 - 7441. Retrieved 2012/06/16.
• 2、 -. "1-pyrimidinylacetamide compounds which are inhibitors of human leukocyte elastase". . . Retrieved 2008/06/13.