Description

2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CAS No. 627526-56-1) is a high-purity boronic ester compound with the molecular formula C₁₅H₂₁BO₂. This organoboron reagent is widely utilized in Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology in modern synthetic organic chemistry. The compound features a cyclopropylphenyl moiety tethered to a pinacol boronate ester group, offering enhanced stability and reactivity compared to boronic acids. With a molecular weight of 244.14 g/mol, this white to off-white crystalline solid is meticulously synthesized and purified to meet the stringent requirements of pharmaceutical research, materials science, and advanced chemical synthesis. Suitable for use under inert atmospheres, it is packaged in amber glass vials to ensure long-term stability. Purity is typically ≥95% by HPLC analysis.

Properties

• CAS Number: 627526-56-1
• Complexity: 306
• IUPAC Name: 2-(3-cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• InChI: InChI=1S/C15H21BO2/c1-14(2)15(3,4)18-16(17-14)13-7-5-6-12(10-13)11-8-9-11/h5-7,10-11H,8-9H2,1-4H3
• InChI Key: VHNQNDFTCALSPV-UHFFFAOYSA-N
• Exact Mass: 244.1634601
• Molecular Formula: C15H21BO2
• Molecular Weight: 244.14
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)C3CC3
• Topological: 18.5
• Monoisotopic Mass: 244.1634601
• Synonyms: 627526-56-1, 2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, DTXSID20623715, DTXCID10574469, 961-441-0, 2-(3-CYCLOPROPYLPHENYL)-4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLANE, MFCD08061969, 1,3,2-Dioxaborolane, 2-(3-cyclopropylphenyl)-4,4,5,5-tetramethyl-, (3-CYCLOPROPYLPHENYL)BORONIC ACID PINACOL ESTER, SCHEMBL1821378, VHNQNDFTCALSPV-UHFFFAOYSA-N, CAB52656, AKOS005259000, AB43369, DS-18286, SY105604, DB-073186, CS-0153844, 3-Cyclopropylphenylboronic Acid Pinacol Ester, Cyclopropylphenyl-3-boronic acid pinacol ester, EN300-705479, N10508, 3-(Cyclopropyl) phenyl boronic acid pinacol ester, Z2044776603, 2-(3-cyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Application

This boronic ester is principally employed as a key intermediate in palladium-catalyzed cross-coupling reactions for constructing biaryl systems prevalent in drug discovery. Its cyclopropyl group confers unique steric and electronic properties to resultant compounds, making it valuable for developing bioactive molecules. Researchers utilize it in synthesizing advanced materials with tailored optoelectronic characteristics. The compound’s stability allows for convenient handling in multi-step synthetic sequences.

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. 2A (100%)
• STOT SE 3 (100%)

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