16297-94-2

Basic information

• Product Name: 3-Methyl-3H-diazirine-3-propanol
• Synonyms: 3-Methyl-3H-diazirine-3-propanol;3-(3-Methyl-3H-diazirin-3-yl)propan-1-ol;3-(3-Methyl-3H-diaziren-3-yl)propan-1-ol
• CAS NO: 16297-94-2
• Molecular Formula: C₅H₁₀N₂O
• Molecular Weight: 114.1457
• Mol File: 16297-94-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 155.9±32.0℃ (760 Torr)
• Flash Point: 69.8±14.4℃
• Appearance: /
• Density: 1.19±0.1 g/cm3 (20 ºC 760 Torr)
• PKA: 15.04±0.10(Predicted)
• CAS DataBase Reference: 3-Methyl-3H-diazirine-3-propanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-3H-diazirine-3-propanol(16297-94-2)
• EPA Substance Registry System: 3-Methyl-3H-diazirine-3-propanol(16297-94-2)

Safety Data

• Hazardous Substances Data: 16297-94-2(Hazardous Substances Data)

Usage

Description

3-Methyl-3H-diazirine-3-propanol is a chemical compound characterized by a diazirine ring with a methyl group and a propanol functional group. It is recognized for its photolytic properties, which enable the formation of reactive carbene intermediates upon exposure to ultraviolet light. These unique characteristics make it a valuable asset in the field of chemical biology for studying molecular interactions.

Uses

Used in Chemical Biology Research:
3-Methyl-3H-diazirine-3-propanol is utilized as a photoaffinity labeling agent for crosslinking experiments. Its application is crucial for investigating protein-protein interactions, ligand-receptor binding, and other molecular interactions within biological systems. The ability of this compound to undergo photolysis and form reactive carbene intermediates allows researchers to probe and analyze the structure and function of biomolecules with precision.
Used in the Synthesis of Photoactive Probes:
In the development of molecular tools for studying biological systems, 3-Methyl-3H-diazirine-3-propanol serves as a key component in the synthesis of various photoactive probes. These probes are essential for illuminating the mechanisms of biological processes and for the advancement of chemical biology techniques, providing researchers with innovative ways to explore and understand complex biological phenomena.

Upstream product

• 1071-73-4 5-Hydroxy-2-pentanone 

Downstream Products

• 1337883-32-5 C₁₂H₂₃N₅O₃ 
• 129451-62-3 3-(3-methyl-3H-diazirin-3-yl)propyl 4-methylbenzenesulfonate 
• 25055-86-1 3-(3-methyl-3H-diazirine-3-yl)propionic acid 
• 821-09-0 n-Pent-4-enyl alcohol 
• 764-38-5 (3Z)-pent-3-en-1-ol 
• 764-37-4 (E)-3-penten-1-ol 
• 6077-72-1 2-methylcyclopropanemethanol 

Relevant articles and documents

Diazirine-based DNA photo-cross-linking probes for the study of protein-DNA interactions

(Figure Presented) Small modification, large effect: Diazirine can be installed quickly and simply in the major or minor groove of DNA for efficient photo-cross-linking to proteins (see picture). This method should be suitable for mapping out protein-DNA interactions, in particular those that may be sensitive to steric hindrance.

Photoaffinity palladium reagents for capture of protein-protein interactions

Protein-protein interactions (PPIs) are indispensable in almost all cellular processes. Probing of complex PPIs provides new insights into the biological system of interest and paves the way for the development of therapeutics. Herein, we report a strategy for the capture of protein-protein interactions using photoaffinity palladium reagents. First, the palladium-mediated reagent site specifically transferred a photoaffinity modified aryl group to the designated cysteine residue. Next, the photoaffinity group was activated by UV radiation to trap the proximal protein residue for the formation of a crosslink. This strategy was used to capture the PYL-ABA-PP2C interaction, which is at the core of the abscisic acid (ABA) signalling pathway. Our results indicated that this palladium-mediated strategy can serve as an alternative for incorporating an increasing number of diverse substrates for protein crosslinking through cysteine modifications and can be explored for use in mapping protein-peptide or protein-protein interaction surfaces and in trapping potential interacting partners.

The Thermal Decomposition of Diazirines: 3-(3-Methyldiazirin-3-yl)propan-1-ol and 3-(3-Methyldiazirin-3-yl)propanoic Acid

The thermolyses of 3-(3-methyldiazirin-3-yl)propan-1-ol (1) and 3-(3-methyldiazirin-3-yl)propanoic acid (2) have been studied in solution over the temperature range 96-125 deg C.The reactions are unimolecular and fit linear Arrhenius plots with k(1)=1013.85+/-0.69exp-1/RT>s-1 and k(2)=1012.38+/-0.43exp-1/RT>s-1.The major products are the alkenes derived from the corresponding carbenes MeC2.CH2CH2CH2OH (3) and MeC2.CH2CH2CO2H (4).The new rate data, taken together with previous work, tend to confirm that diazirine thermolysis involves ring opening to a "complex" followed either by nitrogen loss or by isomerization to a diazo compound.Whereas (1) gives no product of closure onto oxygen, the acid (2) affords about 5percent γ-valerolactone.