Product Name	2-(4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid
CAS Number	1255945-85-7
Molecular Formula	C₁₄H₁₈BFO₄
Molecular Weight	280.1
SMILES Code	O=C(O)CC1=CC=C(F)C(B2OC(C)(C)C(C)(C)O2)=C1
MDL No.	MFCD18383451
Pubchem ID	68657588
InChI Key	DYFNQNVMHCQXDI-UHFFFAOYSA-N

Synthetic Route

Synthesis：1255945-85-7

	+		→
N/A		73183-34-3		1255945-85-7

Yield	Synthesis conditions	Experimental steps
43%	Stage #1: With potassium acetate In 1,4-dioxane at 90℃; for 24 h; Inert atmosphere Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water; Ethyl acetate Stage #3: With hydrogenchloride In water	Example 3 N-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-2-(3-{6-[1-(2,6-difluoro-phenyl)-ureido]-pyridin-2-yl}-4-fluoro-phenyl)-acetamide a. A suspension of [4-fluoro-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid (3-bromo-4-fluorophenyl)-acetic acid (1 g, 4.29 mmol), bis(pinacolato)diboron (1.3 g, 5.15 mmol) and KOAc (1.28 g, 13 mmol) in dioxane (15 mL) was purged with argon and treated with dichlorobis(diphenylphosphino)palladium. The reaction mixture was heated at 90°C for 24 h, diluted with EtOAc and extracted with saturated aqueous NaHCO₃. NaHCO₃ solution. The aqueous layer was acidified with concentrated HCl. The HCl was extracted with HCl and twice with EtOAc. The combined organic layers were dried (Na₂SO₄), concentrated in vacuo, and purified by chromatography (0 to 100% EtOAc in cyclohexane with 1% acetic acid) to afford the title compound as a white solid (520 mg, 43%). LCMS (Method 3): Rt 2.66 min, m/z 281 [MH⁺]. ℓ NMR (300 MHz, CDCl₃): 7.61 (1H, dd, J 5.5, 2.5), 7.35 (1H, ddd, J 8.5, 5.2, 2.5), 7.00 (1H, t, J 8.7), 3.62 (2H, s), 1.35 (12H, s).

Chemical Properties

This compound is an arylboronic acid pinacol ester coupled with a phenylacetic acid group.The pinacol ester protects the boronic acid,granting superior stability against protodeboronation and hydrolysis compared to the free acid,allowing storage at 0-8°C under inert gas.The carboxylic acid(predicted pKa~4.3)provides aqueous solubility at basic pH.It dissolves well in DMF,DMSO,and moderately in less polar organics.

Description

2-[4-Fluoro-3-(pinacolboronyl)phenyl]acetic acid is a dual-functional linchpin molecule for sequential and orthogonal synthesis.It features a protected boronic acid for Suzuki-Miyaura cross-coupling and a carboxylic acid for amide/ester formation,separated by a methylene spacer.The meta-relationship of the boron and fluorine on the ring is a less common but valuable substitution pattern that can be used to influence the electronics and dipole of the resulting biaryl products.

Uses

1.Pharmaceutical Synthesis

Extensively used in the synthesis of fluorinated biphenylacetic acid derivatives,which are analogs of important NSAIDs(e.g.,derivatives of flurbiprofen).The boronic ester allows introduction of diverse aryl groups,creating libraries to optimize COX-1/COX-2 selectivity and anti-inflammatory activity.

2.Agrochemical R&D

Applied in creating new aryloxyacetic acid herbicide analogs(mimicking 2,4-D family).The boronic ester enables facile variation of the aromatic moiety to find compounds with improved selectivity between crops and weeds,while the fluorine atom can fine-tune metabolism and environmental fate.

3.Functional Material Synthesis

Serves as a monomer for constructing conjugated polymers with pendant carboxylic acid groups.Suzuki polymerization using the boronic ester can create the main chain,while the acid groups on the side chains allow for post-polymerization functionalization,solubility tuning,or attachment to surfaces/inorganic components in hybrid materials.

4.Organic Synthesis Building Block

A classic example of a substrate for one-pot tandem reactions:the carboxylic acid can be activated for amide formation,and in the same pot,the boronic ester can undergo Suzuki coupling,enabling rapid assembly of complex molecules in a convergent manner.It's a workhorse for parallel synthesis of biaryl-acetic acid derivatives.

2-(4-Fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic Acid

Synthetic Route

Chemical Properties

Description

Uses