97135-07-4

Basic information

• Product Name: 2,5-HEXANEDIONE-D10
• Synonyms: 2,5-HEXANEDIONE-D10;2,5-HEXANEDIONE-D;Hexanedione-d10
• CAS NO: 97135-07-4
• Molecular Formula: C6D10O2
• Molecular Weight: 124.2
• Mol File: 97135-07-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Soluble), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 2,5-HEXANEDIONE-D10(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-HEXANEDIONE-D10(97135-07-4)
• EPA Substance Registry System: 2,5-HEXANEDIONE-D10(97135-07-4)

Safety Data

• Hazardous Substances Data: 97135-07-4(Hazardous Substances Data)

Usage

Uses

Used in Scientific Research:
2,5-Hexanedione-D10 is used as a stable isotope-labeled compound for [application reason] in scientific research. The deuterium labeling allows for enhanced detection and analysis of the compound in complex biological samples, providing valuable insights into its metabolism, distribution, and potential toxicological effects.
Used in Metabolite Analysis:
2,5-Hexanedione-D10 is used as an internal standard or tracer in metabolite analysis for [application reason] to improve the accuracy and precision of quantitative measurements. The presence of deuterium atoms in the compound enables its differentiation from endogenous 2,5-hexanedione, facilitating the study of its metabolic pathways and potential neurotoxic effects.
Used in Toxicological Studies:
2,5-Hexanedione-D10 is used as a research tool in toxicological studies for [application reason] to investigate the mechanisms of n-hexane-induced neurotoxicity. The deuterium-labeled compound can help elucidate the role of specific metabolic pathways in the development of neurotoxic effects and identify potential biomarkers for exposure and toxicity.
Used in Pharmaceutical Development:
2,5-Hexanedione-D10 is used as a compound in pharmaceutical development for [application reason] to design and test new drugs or interventions targeting the metabolic pathways involved in n-hexane neurotoxicity. The deuterium-labeled compound can provide valuable information on the structure-activity relationships and potential therapeutic effects of new drug candidates.
Used in Environmental Monitoring:
2,5-Hexanedione-D10 is used as a tracer compound in environmental monitoring for [application reason] to assess the presence and levels of n-hexane and its metabolites in various environmental samples. The deuterium labeling allows for the accurate measurement of these compounds, contributing to the understanding of their environmental distribution and potential health risks.

Upstream product

• 110-13-4 2,5-hexanedione 
• 666-52-4 [⁽²⁾H₆]acetone 

Relevant articles and documents

Intermediates in the Paal-Knorr Synthesis of Pyrroles

The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored.In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m).This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step.The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:0.3:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.

Molecular Recognition and Stereoselectivity: Geometrical Requirements for the Multiple Hydrogen-Bonding Interaction of Diols with a Multidentate Polyhydroxy Macrocycle

Resorcinol-dodecanal cyclotetramer 1 in CDCl3 forms hydrogen-bonded, 1/1 complexes with cyclohexanediols as well as with 2,4-pentane- and 2,5-hexanediol as their open-chain analogues and cyclohexanol and cis- and trans-4-tert-butylcyclohexanol.The affinities to 1 of cyclic diols (K=(1.1-10) * 102 M-1 at 25 deg C) are significantly larger than those of open-chain diols (36-43 M-1) and monools (8-11 M-1).Those of regio- and stereoisomers of cyclohexanediol depend on the configuration (axial-equatorial > diequatorial) and relative positions (1,4 >> 1,2 > 1,3) of the two OH groups involved and decrease in the order cis-1,4 (K=1.04 * 103) > cis-1,2 (2.64 * 102) > trans-1,3 (1.81 * 102) > trans-1,4 (1.29 * 102) > cis-1,3 (1.24 * 102) > trans-1,2 (1.06 * 102 M-1); the stereoselectivities are thus cis-1,4/trans-1,4 = 8.0, cis-1,2/trans-1,2 = 2.5, and trans-1,3/cis-1,3 = 1.5.The selectivities in the diol binding are discussed in terms of multiple hydrogen bonding of diol and 1.The relatively large binding constant (K) for cis-1,4-diol with one axial and one equatorial OH group is attributed to an effective and simultaneous two-point hydrogen bonding of the two OH groups with two adjacent binding sites of 1 as a multidentate host.