1401307-49-0

Basic information

• Product Name: C₁₇H₂₁⁽²⁾H₅Si
• Synonyms: C₁₇H₂₁⁽²⁾H₅Si
• CAS NO: 1401307-49-0
• Molecular Weight: 263.439
• Mol File: 1401307-49-0.mol

Chemical Properties

• CAS DataBase Reference: C₁₇H₂₁⁽²⁾H₅Si(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₇H₂₁⁽²⁾H₅Si(1401307-49-0)
• EPA Substance Registry System: C₁₇H₂₁⁽²⁾H₅Si(1401307-49-0)

Safety Data

• Hazardous Substances Data: 1401307-49-0(Hazardous Substances Data)

Upstream product

• 4165-57-5 bromobenzene-d5 
• 89343-06-6 tris-iso-propylsilyl acetylene 

Downstream Products

• 25837-46-1 ethynylbenzene-D5 
• 1401307-47-8 5-deutero-1,4-diphenyl-D₁₀-1H-1,2,3-triazole 
• 1401307-46-7 5′-O-(t-butyldimethylsilyl)-3′-deoxy-3′-(5-deutero-4-(phenyl-D₅)-1H-1,2,3-triazol-1-yl)thymidine 

Relevant articles and documents

Synthesis of deuterated 1,2,3-triazoles

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl 2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D + ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.

METHODS FOR PREPARING DEUTERATED 1,2,3-TRIAZOLES

This disclosure relates to a method that involves reacting an azide with an alkyne in the presence of deuterated water and a copper-containing catalyst, thereby forming a deuterated 1,2,3-triazole.

Synthesis of deuterated 1,2,3-triazoles

The copper-catalyzed azide-alkyne cycloaddition (CuAAC) is a highly effective method for the selective incorporation of deuterium atom into the C-5 position of the 1,2,3-triazole structure. Reactions of alkynes and azides can be conveniently carried out in a biphasic medium of CH2Cl 2/D2O, using the CuSO4/Na ascorbate system. The mildness of the method renders it applicable to substrates of relatively high complexity, such as nucleosides. Good yields and high levels of deuterium incorporation were observed. A reaction conducted in equimolar H2O and D2O showed 2.7 times greater incorporation of hydrogen atom as compared to deuterium. This is consistent with the H+ and D + ion concentrations in H2O and D2O, respectively. With appropriately deuterated precursors, partially to fully deuterated triazoles were assembled where the final deuterium atom was incorporated in the triazole-forming step.