1422986-77-3

Basic information

• Product Name: N,N-bis(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• Synonyms: N,N-bis(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS NO: 1422986-77-3
• Molecular Weight: 344.089
• Mol File: 1422986-77-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N,N-bis(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-bis(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(1422986-77-3)
• EPA Substance Registry System: N,N-bis(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline(1422986-77-3)

Safety Data

• Hazardous Substances Data: 1422986-77-3(Hazardous Substances Data)

Upstream product

• 106-40-1 4-bromo-aniline 
• 1422986-76-2 2,2'-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)azanediyl)bis(ethan-1-ol) 
• 13165-33-8 1-bromo-4-benzene 
• 1422986-54-6 2,2′-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylazanediyl)bis(ethane-2,1-diyl) dimethanesulfonate 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 553-27-5 aniline mustard 
• 1422986-68-2 4-(bis(2-chloroethyl)amino)phenylboronic acid 

Relevant articles and documents

Reactive oxygen species (ROS) inducible DNA cross-linking agents and their effect on cancer cells and normal lymphocytes

Reducing host toxicity is one of the main challenges of cancer chemotherapy. Many tumor cells contain high levels of ROS that make them distinctively different from normal cells. We report a series of ROS-activated aromatic nitrogen mustards that selectively kill chronic lymphocytic leukemia (CLL) over normal lymphocytes. These agents showed powerful DNA cross-linking abilities when coupled with H2O2, one of the most common ROS in cancer cells, whereas little DNA cross-linking was detected without H2O2. Consistent with chemistry observation, in vitro cytotoxicity assay demonstrated that these agents induced 40-80% apoptosis in primary leukemic lymphocytes isolated from CLL patients but less than 25% cell death to normal lymphocytes from healthy donors. The IC50 for the most potent compound (2) was ～5 μM in CLL cells, while the IC 50 was not achieved in normal lymphocytes. Collectively, these data provide utility and selectivity of these agents that will inspire further and effective applications.