Description

4,4,5,5-Tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane (CAS No. 171364-83-3) is a high-purity boronic ester compound with the molecular formula C₁₂H₁₆BNO₄. This organoboron reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology in modern synthetic organic chemistry. The compound features a stable dioxaborolane ring system with tetramethyl substitution, enhancing its shelf stability while maintaining reactivity. The para-nitro phenyl group serves as an excellent electrophilic handle for subsequent transformations. Supplied as a crystalline solid, this reagent is rigorously tested by HPLC, NMR, and elemental analysis to ensure >95% purity, making it suitable for demanding synthetic applications. Proper storage under inert atmosphere at 2-8°C is recommended to maintain optimal performance.

Properties

• CAS Number: 171364-83-3
• Complexity: 315
• IUPAC Name: 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-5-7-10(8-6-9)14(15)16/h5-8H,1-4H3
• InChI Key: LUWACRUAJXZANC-UHFFFAOYSA-N
• Exact Mass: 249.1172382
• Molecular Formula: C12H16BNO4
• Molecular Weight: 249.07
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)[N+](=O)[O-]
• Topological: 64.3
• Monoisotopic Mass: 249.1172382
• Synonyms: 171364-83-3, 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-1,3,2-dioxaborolane, DTXSID60378550, DTXCID10329577, 664-253-4, 4-Nitrophenylboronic acid pinacol ester, 4-Nitrophenylboronic acid, pinacol ester, 1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-, MFCD02179437, 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nitrobenzene, (4-NITROPHENYL)BORONIC ACID, PINACOL ESTER, LUWACRUAJXZANC-UHFFFAOYSA-N, SCHEMBL56104, CHEMBL2024454, BCP15090, CS-M0976, RB3074, AKOS015920324, GS-6751, PB41224, AC-22594, SY033603, DB-015877, T3710, EN300-211493, Z2037318348, 4,4,5,5-tetramethyl-2-(4-nitrophenyl)-[1,3,2]dioxaborolane, 4,4,5,5-tetramethyl-2-(4-nitro-phenyl)-[1,3,2]dioxaborolane

Application

This boronic ester is primarily employed as a key intermediate in palladium-catalyzed cross-coupling reactions for biaryl synthesis. The electron-withdrawing nitro group activates the phenyl ring for efficient transmetalation in Suzuki reactions. Researchers utilize it for constructing complex molecular architectures in pharmaceutical intermediates and material science applications. Its stability makes it particularly valuable for multi-step synthetic sequences requiring air-tolerant handling.

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 (97.7%): 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. 2A (100%)
• STOT SE 3 (97.7%)

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