Description

4,4,5,5-Tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane (CAS No. 190788-59-1) is a high-purity boronic ester compound widely used in organic synthesis, pharmaceutical research, and material science. With the molecular formula C₁₂H₁₆BNO₄, this compound features a stable pinacol boronate ester group, making it an excellent precursor for Suzuki-Miyaura cross-coupling reactions. The 2-nitrophenyl substituent enhances its reactivity in palladium-catalyzed transformations, enabling the construction of complex aromatic frameworks. This product is supplied as a crystalline solid with >95% purity (HPLC), ensuring optimal performance in sensitive applications. It is stored under inert conditions to maintain stability and shelf life.

Applications include drug discovery, agrochemical development, and advanced polymer synthesis. Its compatibility with a wide range of reaction conditions makes it a versatile building block for researchers. Each batch undergoes rigorous QC testing (NMR, LC-MS) to guarantee consistency. Available in scalable quantities from milligrams to kilograms.

Properties

• CAS Number: 190788-59-1
• Complexity: 323
• IUPAC Name: 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane
• InChI: InChI=1S/C12H16BNO4/c1-11(2)12(3,4)18-13(17-11)9-7-5-6-8-10(9)14(15)16/h5-8H,1-4H3
• InChI Key: VLJYUDGCEKORNG-UHFFFAOYSA-N
• Exact Mass: 249.1172382
• Molecular Formula: C12H16BNO4
• Molecular Weight: 249.07
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2[N+](=O)[O-]
• Topological: 64.3
• Monoisotopic Mass: 249.1172382
• Synonyms: 190788-59-1, 4,4,5,5-tetramethyl-2-(2-nitrophenyl)-1,3,2-dioxaborolane, DTXSID70395213, DTXCID60346072, 681-615-7, 2-Nitrobenzeneboronic acid pinacol ester, 2-Nitrophenylboronic acid pinacol ester, 1,3,2-DIOXABOROLANE, 4,4,5,5-TETRAMETHYL-2-(2-NITROPHENYL)-, 2-NITROPHENYLBORONIC ACID, PINACOL ESTER, MFCD02179447, (2-Nitrophenyl)boronic acid pinacol ester, SCHEMBL7690779, VLJYUDGCEKORNG-UHFFFAOYSA-N, AKOS015951144, AB11147, AS-2981, CS-W000891, SY108998, (2-Nitrophenyl)boronic acid, pinacol ester, DB-015862, N1006, EN300-267736, Z2044805156, 1-Nitro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene

This compound is primarily used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl structures in pharmaceuticals and OLED materials. It enables efficient C-C bond formation under mild conditions. Researchers also employ it in PROTAC development and as a boron source for isotopic labeling. Suitable for both solution-phase and solid-phase synthesis workflows.

Safety and Hazards

GHS Hazard Statements

• H302 (30%): Harmful if swallowed [Warning Acute toxicity, oral]
• H312 (20%): Harmful in contact with skin [Warning Acute toxicity, dermal]
• H315 (80%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (80%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H332 (20%): Harmful if inhaled [Warning Acute toxicity, inhalation]
• H335 (60%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (30%)
• Acute Tox. 4 (20%)
• Skin Irrit. 2 (80%)
• Eye Irrit. 2A (80%)
• Acute Tox. 4 (20%)
• STOT SE 3 (60%)

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