329281-02-9

Basic information

• Product Name: N-(4-BROMO-2-HYDROXYMETHYL-PHENYL)-4-METHYL-BENZENESULFONAMIDE
• Synonyms: N-(4-BROMO-2-HYDROXYMETHYL-PHENYL)-4-METHYL-BENZENESULFONAMIDE
• CAS NO: 329281-02-9
• Molecular Formula: C₁₄H₁₄BrNO₃S
• Molecular Weight: 356.23
• Mol File: 329281-02-9.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(4-BROMO-2-HYDROXYMETHYL-PHENYL)-4-METHYL-BENZENESULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-BROMO-2-HYDROXYMETHYL-PHENYL)-4-METHYL-BENZENESULFONAMIDE(329281-02-9)
• EPA Substance Registry System: N-(4-BROMO-2-HYDROXYMETHYL-PHENYL)-4-METHYL-BENZENESULFONAMIDE(329281-02-9)

Safety Data

• Hazardous Substances Data: 329281-02-9(Hazardous Substances Data)

Upstream product

• 5794-88-7 5-Bromo-2-aminobenzoic acid 
• 20357-20-4 5-bromo-2-nitrobenzaldehyde 
• 1241894-37-0 5-bromo-2-nitrobenzylic alcohol 
• 31100-21-7 5-bromo-2-[(4-methylphenyl)sulfonamido]benzoic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 20712-12-3 (2-amino-5-bromophenyl)methanol 

Downstream Products

• 1210801-66-3 C₁₈H₁₈BrNO₄S 
• 34159-05-2 N-(4-bromo-2-formylphenyl)-4-methylbenzenesulfonamide 
• 1448808-96-5 1-(5-bromo-2-(tosylamino)phenyl)prop-2-yn-1-ol 
• 1448809-05-9 5-bromo-2-(iodomethylene)-1-tosylindolin-3-one 
• 1426677-85-1 N-(4-bromo-2-formylphenyl)-4-methyl-N-(2-oxo-2-phenylethyl)benzenesulfonamide 
• 1426678-18-3 (R)-6-bromo-3-hydroxy-3-phenyl-1-tosyl-2,3-dihydroquinolin-4(1H)-one 
• 1426678-02-5 C₂₂H₂₀BrNO₄S 
• 1439384-18-5 N-(4-bromo-2-formylphenyl)-4-methyl-N-(prop-2-yn-1-yl)benzenesulfonamide 

Relevant articles and documents

A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triazepines

The base-induced formal [4+3] cycloaddition reaction of C,N-cyclic azomethine imines with aza-ortho-quinone methides, generated in situ, is reported. This protocol provided an efficient method for the synthesis of biologically important 1,2,4-triazepine derivatives, with a wide substrate scope and excellent functional-group tolerance, and it gives moderate to excellent yields under mild conditions. Several of the derivatives exhibited in vitro antitumor activities against the A2780 cell line in a screening of the cancer cell lines HCT-116, H2228, and A2780 by an MTT assay.

Ynamide Smiles Rearrangement Triggered by Visible-Light-Mediated Regioselective Ketyl-Ynamide Coupling: Rapid Access to Functionalized Indoles and Isoquinolines

In the past decades, significant advances have been made on radical Smiles rearrangement. However, the eventually formed radical intermediates in these reactions are limited to the amidyl radical, except for the few examples initiated by a N-centered radical. Here, a novel and practical radical Smiles rearrangement triggered by photoredox-catalyzed regioselective ketyl-ynamide coupling is reported, which represents the first radical Smiles rearrangement of ynamides. This method enables facile access to a variety of valuable 2-benzhydrylindoles with broad substrate scope in generally good yields under mild reaction conditions. In addition, this chemistry can also be extended to the divergent synthesis of versatile 3-benzhydrylisoquinolines through a similar ketyl-ynamide coupling and radical Smiles rearrangement, followed by dehydrogenative oxidation. Moreover, such an ynamide Smiles rearrangement initiated by intermolecular photoredox catalysis via addition of external radical sources is also achieved. By control experiments, the reaction was shown to proceed via key ketyl radical and α-imino carbon radical intermediates.

Palladium-Catalyzed Regioselective Syn-Chloropalladation-Olefin Insertion-Oxidative Chlorination Cascade: Synthesis of Dichlorinated Tetrahydroquinolines

A palladium catalyzed cascade process involving syn-chloropalladation, intramolecular olefin insertion, and oxidative C-Cl bond formation reactions was demonstrated for the synthesis of dichlorinated tetrahydroquinolines in high yields (up to 93%). The N-propargyl arylamines having a tethered α,β-unsaturated carbonyl moiety underwent a regioselective syn-chloropalladation followed by a Heck-type reaction to deliver the tetrahydroquinoline scaffold. The rare insertion of the second chlorine atom was rationalized comprising a PdII/IV catalytic cycle and oxidative cleavage of the C-PdII bond.