Description

tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (CAS No. 159624-15-4) is a high-purity boronic ester derivative widely utilized in organic synthesis and pharmaceutical research. With the molecular formula C₁₇H₂₆BNO₄, this compound features a pinacol-protected boronic ester group and a tert-butyl carbamate (Boc) moiety, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions and peptide coupling strategies. Its stable crystalline form ensures excellent handling and storage properties. Ideal for researchers in medicinal chemistry, this reagent is rigorously tested for quality, ensuring consistent performance in complex synthetic pathways. Available in various quantities to suit lab-scale and industrial applications.

Properties

• CAS Number: 159624-15-4
• Complexity: 428
• IUPAC Name: tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate
• InChI: InChI=1S/C17H26BNO4/c1-15(2,3)21-14(20)19-13-11-9-8-10-12(13)18-22-16(4,5)17(6,7)23-18/h8-11H,1-7H3,(H,19,20)
• InChI Key: LVHGGVGVAUJQBB-UHFFFAOYSA-N
• Exact Mass: 319.1954885
• Molecular Formula: C17H26BNO4
• Molecular Weight: 319.2
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2NC(=O)OC(C)(C)C
• Topological: 56.8
• Monoisotopic Mass: 319.1954885
• Synonyms: 159624-15-4, tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate, 2-(Boc-amino)phenylboronic Acid Pinacol Ester, Tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate, (2-boc-aminophenyl)boronic acid, pinacol ester, 2-boc-aminophenylboronic acid, pinacol ester, 2-(boc-amino)benzeneboronic acid pinacol ester, MFCD03411943, 2-(N-Boc-amino)phenylboronic acid pinacol ester, tert-Butyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-carbamate, Carbamic acid, N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-, 1,1-dimethylethyl ester, tert-butyl [2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate, LVHGGVGVAUJQBB-UHFFFAOYSA-N, tert-Butyl-N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate, SCHEMBL14560, DTXSID20378293, STR09002, (2-((TERT-BUTOXYCARBONYL)AMINO)PHENYL)BORONIC ACID PINACOL ESTER, AKOS015960066, AB14302, SY023463, 2-(Boc-amino)phenylboronicAcidPinacolEster, 2-BOC-aminophenylboronic acid pinacol ester, CS-0112317, O10021, 2-(N-Boc-amino)phenylboronic acid pinacol ester, 97%, 2-(tert-Butoxycarbonylamino)phenylboronic acid pinacol ester, tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate, [2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid tert-butyl ester, tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylcarbamate, Carbamic acid,N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-,1,1-dimethylethylester

Application

This compound is primarily employed as a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of biaryl structures prevalent in drug discovery. The Boc-protected amine enhances stability during synthetic transformations, while the pinacol boronic ester group facilitates efficient palladium-catalyzed couplings. It is also used in the preparation of protease inhibitors and other bioactive molecules requiring boronate functionalization.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.