Description

3-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester (CAS No. 909391-56-6) is a highly versatile boronic acid derivative with the molecular formula C₁₅H₂₄BNO₂. This compound features a pinacol ester-protected boronic acid group, enhancing its stability and handling properties under ambient conditions. The presence of a dimethylaminomethyl substituent on the phenyl ring introduces additional reactivity, making it a valuable intermediate in Suzuki-Miyaura cross-coupling reactions and other palladium-catalyzed transformations. With a purity of ≥95%, this reagent is ideal for pharmaceutical research, material science, and organic synthesis applications. Its robust structure ensures compatibility with a wide range of reaction conditions, while its high solubility in common organic solvents facilitates easy integration into synthetic workflows. Packaged under inert gas to ensure longevity, this product is a must-have for researchers seeking reliable and efficient boronic acid derivatives.

Properties

• CAS Number: 909391-56-6
• Complexity: 301
• IUPAC Name: N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine
• InChI: InChI=1S/C15H24BNO2/c1-14(2)15(3,4)19-16(18-14)13-9-7-8-12(10-13)11-17(5)6/h7-10H,11H2,1-6H3
• InChI Key: LBUOWYCATLFSRN-UHFFFAOYSA-N
• Exact Mass: 261.1900092
• Molecular Formula: C15H24BNO2
• Molecular Weight: 261.17
• SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=CC=C2)CN(C)C
• Topological: 21.7
• Monoisotopic Mass: 261.1900092
• Synonyms: 3-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester, 804-824-9, 909391-56-6, N,N-Dimethyl-1-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine, N,N-dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine, Dimethyl-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-amine, dimethyl({[3-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl})amine, 3-(n,n-dimethylaminomethyl)phenylboronic acid pinacol ester, MFCD08669568, SCHEMBL2587679, DTXSID00396657, LBUOWYCATLFSRN-UHFFFAOYSA-N, ALBB-030560, JLB39156, AKOS015995522, AS-2740, SB14577, dimethyl({[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl})amine, N,N-dimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanamine, DB-008576, CS-0153843, C77095, EN300-1706249, Z1336748329, 3-(N,N-dimethylaminomethy)phenylboronic acid pinacol ester, dimethyl-[3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzyl]amine, dimethyl{[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}amine, N,N-Dimethyl-1-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methylamine

Application

3-(N,N-Dimethylaminomethyl)phenylboronic acid, pinacol ester is widely used as a key intermediate in Suzuki-Miyaura cross-coupling reactions for the synthesis of biaryl compounds. Its stability and reactivity make it suitable for constructing complex organic molecules in pharmaceutical and agrochemical research. Additionally, this compound serves as a valuable building block in the development of boron-containing materials for optoelectronic applications.

Safety and Hazards

GHS Hazard Statements

• H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H318 (50%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
• H319 (50%): 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, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (50%)
• Skin Irrit. 2 (100%)
• Eye Dam. 1 (50%)
• STOT SE 3 (100%)

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