66143-67-7

Basic information

• Product Name: Hexadecane, 1-azido-
• CAS NO: 66143-67-7
• Molecular Formula: C16H33N3
• Molecular Weight: 267.458
• Mol File: 66143-67-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Hexadecane, 1-azido-(CAS DataBase Reference)
• NIST Chemistry Reference: Hexadecane, 1-azido-(66143-67-7)
• EPA Substance Registry System: Hexadecane, 1-azido-(66143-67-7)

Safety Data

• Hazardous Substances Data: 66143-67-7(Hazardous Substances Data)

Upstream product

• 36653-82-4 1-Hexadecanol 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 1093682-80-4 1-n-hexadecylaziridine-2-(N-phenyl)carboxamide 
• 1093682-81-5 1-n-hexadecylaziridine-2-(N-cyclohexyl)carboxamide 
• 1379671-48-3 1-hexadecyl-4,5-diphenyl-1H-1,2,3-triazole 
• 38528-34-6 2-hexadecylamino-1,4-naphthoquinone 
• 1456899-73-2 tert-butyl ((3S,4R,5S)-4-(benzyloxy)-5-(((1-hexadecyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)tetrahydrofuran-3-yl)carbamate 
• 1456899-62-9 tert-butyl ((3S,4S,5S)-4-(benzyloxy)-5-(((1-hexadecyl-1H-1,2,3-triazol-4-yl)methoxy)methyl)tetrahydrofuran-3-yl)carbamate 
• 1421926-65-9 C₃₃H₄₃BrN₅O₃Re 
• 1432662-70-8 C-(2-benzyloxy)ethyl-C'-[1-hexadecyl-(1H-1,2,3-triazol-4-yl)]-o-carborane 
• 1009089-53-5 1-hexadecyl-4-phenyl-1H-1,2,3-triazole 

Relevant articles and documents

Regioselective and Stereospecific Azidation of 1,2- and 1,3-Diols by Azidotrimethylsilane via a Mitsunobu Reaction

A one-pot regio- and stereospecific azidation reaction of 1,2- and 1,3-diols with azidotrimethylsilane (MB3SiN3) via a Mitsunobu reaction has been achieved. With 1,2- and 1,3-diols, the reaction of triphenylphosphine, diisopropyl azodicarboxylate, and Me3SiN3 in dichloromethane gave regioselective azidation at C-2 and C-3, respectively, in good yield (74-90% combined yield of 1a + 1b or of 2a + 2b). However, application of the same reaction conditions to a 1,4-diol led to the exclusive formation of the cyclic ether. The regioselectivity of this one-pot reaction is influenced by the solvent, the degree of steric bulk at C-2 of the 1,2-diol or at C-3 of the 1,3-diol, and the presence of electron-donating and electron-withdrawing groups near the secondary carbinol carbon. This selectivity is discussed in terms of the mechanistic model proposed by Mathieu-Pelta and Evans (Mathieu-Pelta, I.; Evans, S. A., Jr. J. Org. Chem. 1992, 57, 3409-3413), which involves reaction of the dioxaphospholane intermediate with Me3SiN3 to form oxyphosphonium ions 4 and 5.