84110-40-7

Basic information

• Product Name: Isobutaneboronic acid
• Synonyms: RARECHEM AH PB 0258;2-METHYL-1-PROPYLBORONIC ACID;2-METHYL-1-PROPANEBORONIC ACID;(2-METHYLPROPYL)BORONIC ACID;1-ISOBUTANEBORONIC ACID;ISOBUTYLBORONIC ACID;2-Methylprop-1-ylboronic acid;Isobutylboronic
• CAS NO: 84110-40-7
• Molecular Formula: C₄H₁₁BO₂
• Molecular Weight: 101.94
• EINECS: 1312995-182-4
• Product Categories: Boron, Nitrile, Thio,& TM-Cpds;Boronic acids;Organoborons;Alkyl;B (Classes of Boron Compounds);CHIRAL CHEMICALS
• Mol File: 84110-40-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 108-111 °C(lit.)
• Boiling Point: 180 °C at 760 mmHg
• Flash Point: 62.7 °C
• Appearance: White to cream/Crystalline Powder or Flakes
• Density: 0.91 g/cm³
• Vapor Pressure: 0.27mmHg at 25°C
• Refractive Index: 1.398
• Storage Temp.: 0-6°C
• Solubility: Acetonitrile (Slightly), DMSO, Methanol (Slightly)
• PKA: 10.49±0.43(Predicted)
• CAS DataBase Reference: Isobutaneboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Isobutaneboronic acid(84110-40-7)
• EPA Substance Registry System: Isobutaneboronic acid(84110-40-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 84110-40-7(Hazardous Substances Data)

Usage

Description

Isobutaneboronic acid is also known as isobutylboronic acid. Isobutaneboronic acid has been used to synthesize potent and selective dipeptidyl boronic acid proteasome inhibitors, which are promising therapeutics to treat cancer and inflammatory diseases.1

Reference

J. Adams, M. Behnke, S. Chen, A. A. Cruickshank, L. R. Dick, L. Grenier, J. M. Klunder, Y. Ma, L. Plamondon, R. L. Stein, Potent and selective inhibitors of the proteasome: Dipeptidyl boronic acids, Bioorganic & Medicinal Chemistry Letters, 1998, vol. 8, pp. 333-338

Uses

Different sources of media describe the Uses of 84110-40-7 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Methylpropylboronic Acid is used in the preparation of isocoumarin analogs as inhibitors of γ-secretase cleavage. Also used in the preparation of peptide boronc acid.
3. (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.

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

Synthetic route

trifluoro(isobutyl)- λ4-borane potassium salt → Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
With water; silica gel at 20℃; for 1h; Inert atmosphere;	73%

triisobutylborane (1116-39-8) → Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
With sodium hydroxide; air
With H2O

isobutyl-bis-isobutylperoxy-borane (109511-11-7) → Dihydroxy-isobutyl-boran (84110-40-7)

isobutylboric acid dibutyl ester (22980-59-2) → Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
With water

Me2(CH2)2NHOB-C4H9-iso (112980-86-6) → 4-amino-4-methylpentan-2-ol (4404-98-2) + 2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine (26939-18-4) + Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
With sulfuric acid; acetonitrile In n-heptane at 0℃; for 5h; Title compound not separated from byproducts;

Me2(CH2)2NHOB-C4H9-iso (112980-86-6) + benzil (134-81-6) → 4-amino-4-methylpentan-2-ol (4404-98-2) + 2,4,4,6-tetramethyl-5,6-dihydro-4H-1,3-oxazine (26939-18-4) + Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
With sulfuric acid In n-heptane at 0℃; for 5h; Title compound not separated from byproducts;

triisobutylborane (1116-39-8) + 1-methyl-4-nitrosobenzene (623-11-0) + air → Dihydroxy-isobutyl-boran (84110-40-7)

boric acid trialkyl ester + isobutyl magnesium halide → Dihydroxy-isobutyl-boran (84110-40-7)

sec-butyldiisopropoxyborane (86595-33-7) → Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
With sulfuric acid

Trimethyl borate (121-43-7) + isobutylmagnesium bromide (926-62-5) → Dihydroxy-isobutyl-boran (84110-40-7)

Conditions	Yield
In diethyl ether
In diethyl ether

Dihydroxy-isobutyl-boran (84110-40-7) + 8-chloro-2,4-dimethyl-5,6-dihydrobenzo[c] acridine (1420651-23-5) → 8-isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridine (1420651-26-8)

Conditions	Yield
Stage #1: Dihydroxy-isobutyl-boran; 8-chloro-2,4-dimethyl-5,6-dihydrobenzo[c] acridine With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); tris(triphenylphosphine)ruthenium(II) chloride; potassium phosphate monohydrate In toluene for 0.333333h; Suzuki Coupling; Reflux; Stage #2: Reflux;	99.6%

Dihydroxy-isobutyl-boran (84110-40-7) + 2-hydroxymethyl-1,3-propanediol (4704-94-3) → 2-isobutyl[1,3,2]dioxaborinan-5-yl-methanol (1186624-74-7)

Conditions	Yield
In diethyl ether at 20℃;	99%
In diethyl ether byproducts: H2O;

Dihydroxy-isobutyl-boran (84110-40-7) + 1,1'-bicyclohexane-1,1'-diol (2888-11-1) → 14-isobutyl-13,15-dioxa-14-boradispiro[5.0.5.3]pentadecane (1186624-77-0)

Conditions	Yield
In diethyl ether at 20℃;	99%
In diethyl ether byproducts: H2O;

Dihydroxy-isobutyl-boran (84110-40-7) + 1-bromo-2-fluoro-4-nitrobenzene (185331-69-5) → 2-fluoro-1-isobutyl-4-nitrobenzene

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; toluene for 1h; Heating;	99%

Dihydroxy-isobutyl-boran (84110-40-7) + ethyl (R)-3-benzamido-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate → (R)-N-(2-hydroxy-5-oxo-1,2-oxaborolan-3-yl)benzamide

Conditions	Yield
With hydrogenchloride In methanol; water; pentane for 1h; Glovebox; Inert atmosphere;	98%

Dihydroxy-isobutyl-boran (84110-40-7) + (+)-pinanediol (57022-61-4, 57022-63-6) → 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole (84110-34-9)

Conditions	Yield
In diethyl ether at 20℃; for 23h;	97.2%
With sodium sulfate In diethyl ether	95%

Dihydroxy-isobutyl-boran (84110-40-7) + pinanediol (18680-27-8) → 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole (84110-34-9)

Conditions	Yield
In diethyl ether	97%
In diethyl ether at 40℃; for 8h;	95%
With magnesium sulfate In diethyl ether	94.8%

Dihydroxy-isobutyl-boran (84110-40-7) + ortho-bromobenzaldehyde (6630-33-7) → 2-isopentylbenzaldehyde (1268267-77-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In toluene for 2h; Inert atmosphere; Reflux;	97%

Dihydroxy-isobutyl-boran (84110-40-7) + 2,4,6-trimethylphenyl bromide (576-83-0) → 2-isobutyl-1,3,5-trimethylbenzene

Conditions	Yield
With potassium phosphate monohydrate; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; C20H34O3P2 In toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere;	96%

dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane (657408-07-6) + Dihydroxy-isobutyl-boran (84110-40-7) + 5,7-dichloro isoquinoline (73075-58-8) → 5,7-diisobutylisoquinoline (1443013-08-8)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0) In hexane; water; toluene	95%

Dihydroxy-isobutyl-boran (84110-40-7) + 4-amino-3,5-dichlorobenzonitrile (78473-00-4) → 4-amino-3,5-diisobutylbenzonitrile

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 130℃; for 12h; Inert atmosphere;	95%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; bis(dibenzylideneacetone)-palladium(0) In toluene at 130℃; for 12h; Inert atmosphere;	95%
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In toluene at 130℃; for 8h; Inert atmosphere;	87%

Dihydroxy-isobutyl-boran (84110-40-7) + 4-chloro-2-(3,5-dimethylphenyl)quinoline → 2-(3,5-dimethylphenyl)-4-isobutylquinoline

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In water; toluene Inert atmosphere; Reflux;	95%

Dihydroxy-isobutyl-boran (84110-40-7) + (+)-α-pinanediol (20536-51-0) → 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole

Conditions	Yield
In diethyl ether at 20℃; for 24h;	94%

Dihydroxy-isobutyl-boran (84110-40-7) + ethyl 5-bromo-3-(3-ethoxy-3-oxopropyl)-7-nitro-1H-indole-2-carboxylate → ethyl 3-(3-ethoxy-3-oxopropyl)-5-isobutyl-7-nitro-1H-indole-2-carboxylate

Conditions	Yield
With potassium phosphate; palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate In water; toluene at 90℃; for 4h; Buchwald-Hartwig Coupling; Inert atmosphere;	94%
With potassium phosphate; tri-tert-butylphosphonium tetrafluoroborate; palladium diacetate In water; toluene at 90℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	94%

Dihydroxy-isobutyl-boran (84110-40-7) + C17H18ClNO → C21H27NO

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); potassium phosphate monohydrate In toluene Inert atmosphere; Reflux;	93%

Upstream product

• 86595-33-7 sec-butyldiisopropoxyborane 
• 121-43-7 Trimethyl borate 
• 926-62-5 isobutylmagnesium bromide 
• 1116-39-8 triisobutylborane 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 112980-86-6 Me₂(CH₂)2NHOB-C₄H₉-iso 
• 134-81-6 benzil 
• 22980-59-2 isobutylboric acid dibutyl ester 
• 109511-11-7 isobutyl-bis-isobutylperoxy-borane 

Downstream Products

• 7439-47-6 Triisobutyl-boroxin 
• 676137-86-3 2-Fluoro-5-isobutyl-benzonitrile 
• 1312175-74-8 1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene (2-methylpropyl)borane complex 
• 288251-96-7 2-(2-methylpropyl)-5-nitrobenzonitrile 
• 1034689-19-4 methyl 3-cyano-4-(2-methylpropyl)benzoate 
• 1262870-03-0 (+)-2-isobutyl-3-methoxy-N-(benzyloxycarbonyl)morphinan 
• 1130345-25-3 Methyl 2-isobutyl-6-(4-methylphenyl)-4-(trifluoromethyl)nicotinate 
• 1130345-24-2 Methyl 6-(4-chlorophenyl)-2-isobutyl-4-(trifluoromethyl)nicotinate 
• 1198613-97-6 C₁₅H₂₁N₃ 
• 84110-34-9 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole 
• 957205-77-5 3-Isobutyl-4-trifluoromethylbenzoic acid methyl ester 
• 957206-17-6 4-isobutyl-3-trifluoromethylbenzoic acid methyl ester 
• 957206-37-0 4-isobutyl-3-trifluoromethoxybenzoic acid methyl ester 
• 957206-25-6 4-isobutyl-3-methoxybenzoic acid ethyl ester 

Relevant articles and documents

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P1 Phenethyl peptide boronic acid inhibitors of HCV NS3 protease

A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin.

ALPHA-AMINOBORONIC ACID DERIVATIVES

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