Description

2-(Methylthio)benzeneboronic acid (CAS: 168618-42-6) is a high-purity boronic acid derivative with the molecular formula C₇H₉BO₂S. This organoboron compound features a methylthio (-SCH₃) functional group at the ortho position of the phenyl ring, making it a versatile intermediate for Suzuki-Miyaura cross-coupling reactions, a cornerstone methodology in pharmaceutical and materials science research. The product is supplied as a white to off-white crystalline powder with ≥95% purity (HPLC), ensuring optimal performance in catalytic applications.

Key applications include its use as a ligand precursor in transition-metal catalysis, a building block for thioether-containing bioactive molecules, and a probe in chemical biology studies. The compound is packaged under inert gas to prevent boroxine formation and stored at 2-8°C for maximum stability. Available in research (1g, 5g) and bulk (25g, 100g) quantities, each batch is accompanied by comprehensive NMR, HPLC, and MS analytical data.

Synonyms: 2-Methylthiophenylboronic acid, [2-(Methylthio)phenyl]boronic acid (see full list for regulatory compliance).

Properties

• CAS Number: 168618-42-6
• Complexity: 121
• IUPAC Name: (2-methylsulfanylphenyl)boronic acid
• InChI: InChI=1S/C7H9BO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3
• InChI Key: QXBWTYBCNFKURT-UHFFFAOYSA-N
• Exact Mass: 168.0416309
• Molecular Formula: C7H9BO2S
• Molecular Weight: 168.03
• SMILES: B(C1=CC=CC=C1SC)(O)O
• Topological: 65.8
• Monoisotopic Mass: 168.0416309
• Synonyms: 2-(Methylthio)benzeneboronic Acid, 2-Methylsulfanylphenylboronic acid, 605-521-2, 2-(Methylthio)phenylboronic acid, 168618-42-6, 2-Methylthiophenylboronic acid, (2-(Methylthio)phenyl)boronic acid, (2-methylsulfanylphenyl)boronic Acid, [2-(methylsulfanyl)phenyl]boronic acid, Boronic acid, B-[2-(methylthio)phenyl]-, MFCD01318165, 168818-42-6, 2-(methylthio)benzene boronic acid, [2-(methylthio)phenyl]boronic acid, C7H9BO2S, 2-THIOANISOLEBORONIC ACID, BORONIC ACID, [2-(METHYLTHIO)PHENYL]-, 2-BORONOTHIOANISOLE, 2-Methylthiophenylboronicacid, SCHEMBL24389, 2-methylthiophenyl boronic acid, CHEMBL352894, 2-methylthiophenyldihydroxyborane, QXBWTYBCNFKURT-UHFFFAOYSA-, 2-methylthiophenyl-dihydroxyborane, DTXSID30378542, 2-(methylthio)-phenylboronic acid, 2-(methylthio)phenyl-boronic acid, 2-(methylthio) phenyl boronic acid, CS-D1039, 2-methylmercapto phenyl boronic acid, 2-(methylsulfanyl)benzeneboronic acid, BBL100654, SBB052543, STL554448, VT1354, 2-(Methylthio)phenylboronic acid (contains varying amounts of Anhydride), AKOS005255174, AB08660, AC-5351, DS-1797, (2-methylsulphanyl-phenyl)-boronic acid, SY014952, DB-005791, M1570, EN300-152979, doi:10.14272/QXBWTYBCNFKURT-UHFFFAOYSA-N.1, Z381540876, InChI=1/C7H9BO2S/c1-11-7-5-3-2-4-6(7)8(9)10/h2-5,9-10H,1H3

2-(Methylthio)benzeneboronic acid serves as a critical reagent in palladium-catalyzed cross-couplings to construct biaryl motifs for drug discovery (e.g., kinase inhibitors). Its electron-rich thioether group enables chelation-assisted C-H functionalization in medicinal chemistry. Researchers utilize this compound to develop sulfur-containing OLED materials due to its enhanced charge transport properties. In chemical biology, it acts as a protease activity sensor via boronic acid-thiol interactions.

Safety and Hazards

GHS Hazard Statements

• H302 (11.1%): 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 (77.8%): 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 (11.1%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (77.8%)

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