90137-14-7

Basic information

• Product Name: tert-butylaldehyde-d₉
• Synonyms: tert-butylaldehyde-d₉
• CAS NO: 90137-14-7
• Molecular Weight: 95.0623
• Mol File: 90137-14-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butylaldehyde-d₉(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butylaldehyde-d₉(90137-14-7)
• EPA Substance Registry System: tert-butylaldehyde-d₉(90137-14-7)

Safety Data

• Hazardous Substances Data: 90137-14-7(Hazardous Substances Data)

Usage

Description

tert-butylaldehyde-d₉ is a deuterated organic compound, specifically a derivative of tert-butylaldehyde with nine deuterium atoms incorporated into its structure. This stable isotope labeling provides unique properties for various applications in chemical and pharmaceutical research.

Uses

Used in Pharmaceutical Industry:
tert-butylaldehyde-d₉ is used as a synthetic intermediate for the preparation of deuterated analogs of pharmaceutical compounds. Its incorporation into drug molecules can enhance their stability, solubility, and metabolic profile, leading to improved therapeutic efficacy and reduced side effects.
Used in Chemical Research:
In the field of chemical research, tert-butylaldehyde-d₉ serves as a valuable tool for studying reaction mechanisms and kinetics. The presence of deuterium atoms can provide insights into the behavior of molecules and the influence of isotopic substitution on reaction pathways.
Used in the Synthesis of Deuterated Protease Inhibitors:
Specifically, tert-butylaldehyde-d₉ is utilized in the synthesis of deuterated analogs of the hepatitis C virus protease inhibitor, boceprevir. This application highlights its importance in the development of novel antiviral therapies with enhanced pharmacological properties.

Upstream product

• 918-20-7 tert-butyl chloride-d9 
• 68-12-2 N,N-dimethyl-formamide 
• 507-20-0 tertiary butyl chloride 

Downstream Products

• 1092540-45-8 (R)-2-((S)-1-cyano-2,2-d9-dimethylpropylamino)-2-phenylacetamide 
• 1158083-37-4 C₁₁H₁₂⁽²⁾H₉NO₄ 
• 1092540-48-1 C₆H₄⁽²⁾H₉NO₂*ClH 
• 1092540-47-0 C₆H₅⁽²⁾H₉N₂O 
• 1158083-48-7 C₂₀H₁₇⁽²⁾H₁₈N₃O₄ 
• 1158083-54-5 C₂₀H₁₁⁽²⁾H₂₄N₃O₄ 
• 1256751-25-3 C₂₇H₁₂⁽²⁾H₃₃N₅O₅ 
• 1158083-57-8 C₂₇H₂₁⁽²⁾H₂₄N₅O₅ 
• 1158083-51-2 C₂₇H₂₇⁽²⁾H₁₈N₅O₅ 
• 1092540-46-9 (S)-2-((R)-2-amino-2-oxo-1-phenylethylamino)-3,3-d9-dimethylbutanamide 
• 1158083-49-8 (1R,2S,5S)-6,6-dimethyl-3-((S)-4,4,4-trideutero-2-(3-(1,1,1,3,3,3-hexadeutero-2-(trideuteromethyl)propan-2-yl)ureido)-3,3-bis(trideuteromethyl)butanoyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 
• 1158083-55-6 (1R,2S,5S)-3-((S)-4,4,4-trideutero-2-(3-(1,1,1,3,3,3-hexadeutero-2-(trideuteromethyl)propan-2-yl)ureido)-3,3-bis(trideuteromethyl)butanoyl)-6,6-bis(trideuteromethyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid 
• 1158083-46-5 methyl (1R,2S,5S)-3-((S)-2-((tert-butoxycarbonyl)amino)-4,4,4-trideutero-3,3-bis(trideuteromethyl)butanoyl)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate 
• 1158083-52-3 methyl (1R,2S,5S)-3-((S)-2-((tert-butoxycarbonyl)amino)-4,4,4-trideutero-3,3-bis(trideuteromethyl)butanoyl)-6,6-bis(trideuteromethyl)-3-azabicyclo[3.1.0]hexane-2-carboxylate 

Relevant articles and documents

Design and synthesis of deuterated boceprevir analogs with enhanced pharmacokinetic properties

As part of an ongoing effort to apply the Deuterated Chemical Entity Platform (DCE Platforma) to clinically validated drugs, the synthesis of deuterated analogs of the hepatitis C virus protease inhibitor boceprevir was carried out. The devised synthetic routes allowed for site-selective deuterium incorporation with high levels of isotopic purity. Application of the DCE Platforma to boceprevir enabled the identification of several deuterated analogs that display marked levels of in vitro metabolic stabilization. Most notably, analog 1g exhibits a near doubling of in vitro half-life in human liver microsomal assays. The details of the convergent synthetic route to the boceprevir isotopologs and the results of the metabolic stability assays are described herein.

Microwave Spectrum, Molecular Structure and Dipole Moment of Pivalaldehyde

The microwave spectra of eight isotopic species of pivalaldehyde have been studied in the frequency region 9-40 GHz.The zero-point average skeletal structure has been derived to be: r = 1.206(6) Angstroem, r = 1.130(5) Angstroem, r = 1.516(7) Angstroem, r = r = 1.537(2) Angstroem, C(1)C(2)C(3) = 110.5(4) deg, C(1)C(2)C(4),(5) = 107.4(3) deg, proj.C(4),(5)C(2)C(1) = 120.78(4) deg, CCO = 126.0(5) deg and CCH(1) = 113.0(3) deg.The tert-butyl group is found to be tilted 2 deg away from the C=O bond.Accurate Stark effect measurements have been performed on the main species, (CH3)3CCDO and (CD3)3CCHO.The ground-state dipole moment of (CH3)3CCHO was determined as μs = 2.618(5) D and μb = 0.728(2) D giving μtotal = 2.717(5) D at an angle of 13.6 deg to the C=O bond.