2-Bromo-N,N-dimethylacetamide

• CAS: 5468-77-9
• Catalog Number: ACM5468779
• Category: Main Products
• Molecular Weight: 166.01642
• Molecular Formula: C₄H₈BrNO
• Synonyms: 2-Bromo-N,N-dimethylacetamide;2-bromo-N,N-dimethyl-ethanamide;N,N-dimethyl-bromoacetamide
• IUPAC Name: 2-bromo-N,N-dimethylacetamide
• SMILES: CN(C)C(=O)CBr
• InChI Key: QPIOVNJLOVNTMW-UHFFFAOYSA-N
• Boiling Point: 196.3ºC at 760 mmHg
• Flash Point: 72.5ºC
• Density: 1.395g/cm³
• Exact Mass: 164.97900

Case Study

2-Bromo-N,N-Dimethylacetamide Enabling Simultaneous Quantification of Reduced/Oxidized Aminothiols via Double Derivatization LC-MS

Wang, Mindan, et al. Journal of Chromatography A 1740 (2025): 465557.

The reduced and oxidized thiol forms are critical for clinical diagnostics and redox biology research. This study demonstrated the pivotal role of 2-Bromo-N,N-dimethylacetamide (Br-DMA) in a novel double derivatization strategy for comprehensive analysis of biological aminothiols (BATs). This work developed and validated a dual-labeling LC-MS platform using Br-DMA as the thiol-specific derivatization agent for parallel detection of reduced/oxidized BATs in complex biological matrices.
Methodology: Br-DMA first selectively alkylated thiol groups of reduced BATs, followed by isotope-coded [d0]/[d3]-DMMIC labeling of amino groups on all BATs; detection leveraged Br-DMA's diagnostic fragment (C4H8NOS+) and DMMIC fragments for LC-MS quantification, with rigorous validation of linearity, accuracy, precision, recovery, and matrix effects.
Key Findings
· Br-DMA enabled exclusive derivatization of reduced BAT thiols, generating a characteristic fragment (m/z 118) that facilitated sensitive detection (linearity R2>0.99, accuracy 85-120%, precision RSD 5-19%).
· The method successfully quantified BAT redox dynamics in A549 cells under anticancer drug treatment and discriminated BAT levels in lung adenocarcinoma versus paracarcinoma tissues.

2-Bromo-N,N-dimethylacetamide Used in the Photoredox Synthesis of Phenanthridines

Yu, Yulan, et al. The Journal of Organic Chemistry 82.15 (2017): 8148-8156.

A novel cascade reaction combining radical addition, nitrile insertion, and homolytic aromatic substitution (HAS) was established for the synthesis of 6-quaternary alkylated phenanthridines. This process involves the addition of active methylene radicals derived from 2-bromoacetonitrile, ethyl 2-bromoacetate, 2-bromo-N,N-dimethylacetamide, or 2-bromo-1-phenylethan-1-one to the carbon-carbon double bonds of N-arylacrylamides. The subsequent cyclization, facilitated by cyano group participation, yields various phenanthridines in moderate to good yields through photoredox catalysis.
Synthesis Procedure Using 2-Bromo-N,N-dimethylacetamide:
· N-Arylacrylamide (0.2 mmol), 2-Bromo-N,N-dimethylacetamide (99.6 mg, 0.6 mmol), fac-Ir(ppy)3 (2 mol%), and Na2CO3 (0.4 mmol) were dissolved in a 2 mL mixture of DMSO and acetonitrile (1:1). The reaction was stirred under an argon atmosphere and illuminated with a 5W blue LED for 32 hours. The crude product was extracted with EtOAc, dried using MgSO4, concentrated, and purified by silica gel chromatography (hexane/EtOAc 5:1).
· Reaction Scope: The cascade reaction demonstrated good reactivity with various N-arylacrylamides, featuring both electron-donating and electron-withdrawing groups, resulting in phenanthridine derivatives with moderate to good yields (72%-80% for products 4f-4i).