Description

2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)aniline (CAS: 1058062-64-8) is a high-purity boronic ester derivative designed for advanced synthetic applications in pharmaceutical and materials research. With the molecular formula C₁₃H₁₇BF₃NO₂, this compound features a pinacol boronate group coupled with a trifluoromethyl-substituted aniline moiety, offering exceptional reactivity in Suzuki-Miyaura cross-coupling reactions. Its robust stability under ambient conditions and compatibility with diverse reaction media make it an indispensable reagent for constructing complex aryl-aryl bonds. Ideal for medicinal chemistry, agrochemical development, and OLED material synthesis, this compound is rigorously tested to ensure >95% purity (HPLC/GC) and is supplied in moisture-resistant packaging to maintain integrity.

Properties

• CAS Number: 1058062-64-8
• Complexity: 357
• IUPAC Name: 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)aniline
• InChI: InChI=1S/C13H17BF3NO2/c1-11(2)12(3,4)20-14(19-11)9-7-8(13(15,16)17)5-6-10(9)18/h5-7H,18H2,1-4H3
• InChI Key: GFSAGCJSHFVPJZ-UHFFFAOYSA-N
• Exact Mass: 287.1304434
• Molecular Formula: C13H17BF3NO2
• Molecular Weight: 287.09
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=CC(=C2)C(F)(F)F)N
• Topological: 44.5
• Monoisotopic Mass: 287.1304434
• Synonyms: 1058062-64-8, 2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-4-(TRIFLUOROMETHYL)ANILINE, 992-308-5, 2-AMINO-5-(TRIFLUOROMETHYL)PHENYLBORONIC ACID, PINACOL ESTER, 2-(4,4,5,5-TetraMethyl-1,3,2-dioxaborolan-2-yl)-_4-(trifluoroMethyl)_benzenaMine, 4-(Trifluoromethyl)aniline-2-boronic acid pinacol ester, (2-AMINO-5-(TRIFLUOROMETHYL)PHENYL)BORONIC ACID PINACOL ESTER, 2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)aniline, MFCD16996235, SCHEMBL44941, 2-Amino-5-(trifluoromethyl)phenylboronic acid pinacol ester, AKOS017343142, PB19495, 2-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-4-trifluoromethyl-phenylamine, AS-51142, DB-103590, CS-0054880, P11979, EN300-7363765, Z2044750730, 4-(trifluoromethyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine

Application

This compound serves as a key intermediate in the synthesis of trifluoromethyl-substituted biaryl scaffolds, widely used in drug discovery and functional materials. Its boronate ester group enables efficient Pd-catalyzed cross-coupling reactions, while the electron-withdrawing CF₃ group enhances metabolic stability in bioactive molecules. Applications include the development of kinase inhibitors, PET radiotracers, and liquid crystal materials. The aniline moiety further allows derivatization via diazotization or amide formation.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• 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, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

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