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346225

Sigma-Aldrich

(2-Methylpropyl)boronic acid

≥95.0%

Synonym(s):

Isobutaneboronic acid

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About This Item

Linear Formula:
(CH3)2CHCH2B(OH)2
CAS Number:
84110-40-7
Molecular Weight:
101.94
MDL number:
MFCD00134156
UNSPSC Code:
12352103
PubChem Substance ID:
24861382
NACRES:
NA.22

Assay

≥95.0%

form

solid

mp

108-111 °C (lit.)

SMILES string

CC(C)CB(O)O

InChI

1S/C4H11BO2/c1-4(2)3-5(6)7/h4,6-7H,3H2,1-2H3

InChI key

ZAZPDOYUCVFPOI-UHFFFAOYSA-N

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Application

(2-Methylpropyl)boronic acid can be used as:   
  • A reactant in the preparation of 4-isobutylisoquinoline from 4-bromoisoquinoline by Suzuki-Miyaura type couple reaction.
  •  A catalyst along with aluminum hydroxide, boric acid in the polymerization of styrene.

It can also be used as a reactant in:    
  • Copper catalyzed cross-coupling reactions.      
  • The synthesis of polyborylalkanes by Ir-catalyzed C-H borylation reaction.        
  • The preparation of heterosubstituted diazaboroles and borinines.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Study of Rate-accelerating of Aluminum Hydroxide, Boric Acid, and (2-Methylpropyl) Boronic Acid for Atom Transfer Radical Polymerization of Styrene
Luo Yu-tai, et al.
Journal of Xiamen University (Natural Science), 47(1), 63-63 (2008)
Steven A Rossi et al.
Organic letters, 15(9), 2314-2317 (2013-04-25)
For the first time, a general catalytic procedure for the cross-coupling of primary amides and alkylboronic acids is demonstrated. The key to the success of this reaction was the identification of a mild base (NaOSiMe3) and oxidant (di-tert-butyl peroxide) to
Takeshi Yamamoto et al.
Organic letters, 21(16), 6235-6240 (2019-08-07)
Pyrazolylaniline serves as a temporary directing group attached to the boron atom of alkylboronic acids in Ir-catalyzed C(sp3)-H borylation. The reaction takes place at α-, β-, and γ-C-H bonds, giving polyborylated products including di-, tri-, tetra-, and even pentaborylalkanes. α-C-H
Solution-state 15N NMR and solid-state single-crystal XRD study of heterosubstituted diazaboroles and borinines prepared via an effective and simple microwave-assisted solvent-free synthesis
Slabber CA, et al.
Journal of Organometallic Chemistry, 723, 122-128 (2013)
Benjamin M Reeves et al.
Angewandte Chemie (International ed. in English), 58(44), 15697-15701 (2019-09-06)
A transition-metal-free reductive hydroxymethylation reaction has been developed, enabling the preparation of tetrahydroisoquinolines bearing C4-quaternary centers from the corresponding isoquinolines. Deuterium labelling studies and control experiments enable a potential mechanism to be elucidated which features a key Cannizzaro-type reduction followed
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