5625-52-5

Basic information

• Product Name: 1 - Methylpiperazine - 2,5 - dione
• Synonyms: 1 - Methylpiperazine - 2,5 - dione;1-methyl-2,5-Piperazinedione
• CAS NO: 5625-52-5
• Molecular Formula: C₅H₈N₂O₂
• Molecular Weight: 128.12922
• Mol File: 5625-52-5.mol

Chemical Properties

• Melting Point: 141-143 °C
• Boiling Point: 427°Cat760mmHg
• Flash Point: 212.1°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 1.69E-07mmHg at 25°C
• Refractive Index: 1.481
• PKA: 13.04±0.20(Predicted)
• CAS DataBase Reference: 1 - Methylpiperazine - 2,5 - dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1 - Methylpiperazine - 2,5 - dione(5625-52-5)
• EPA Substance Registry System: 1 - Methylpiperazine - 2,5 - dione(5625-52-5)

Safety Data

• Hazardous Substances Data: 5625-52-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Methylpiperazine-2,5-dione is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs due to its chemical properties and reactivity.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Methylpiperazine-2,5-dione serves as an intermediate, playing a crucial role in the production of various agrochemicals that are essential for agricultural applications.
Used in Medicinal Chemistry:
1-Methylpiperazine-2,5-dione is employed as a building block in medicinal chemistry for the creation of organic compounds with potential therapeutic applications, highlighting its importance in drug discovery and development.

InChI:InChI=1/C5H8N2O2/c1-7-3-4(8)6-2-5(7)9/h2-3H2,1H3,(H,6,8)

Upstream product

• 29816-01-1 Glycylsarcosine 
• 38082-72-3 sarcosine-glycine 
• 24515-53-5 [(2-chloroacetyl)(methyl)amino]acetic acid ethyl ester 
• 5076-82-4 sarcosine anhydride 
• 174311-10-5 methyl N'-(tert-butoxycarbonyl)glycylsarcosinate 
• 145590-97-2 N-tert-butoxycarbonylglycylsarcosine ethyl ester 
• 65332-01-6 methyl N-(2-chloroacetyl)glycine 

Downstream Products

• 109-01-3 1-methyl-piperazine 
• 59136-05-9 1-benzyl-4-methylpiperazine-2,5-dione 
• 79247-68-0 1-Methoxymethyl-4-methyl-piperazine-2,5-dione 
• 170376-79-1 1-Acetyl-4-methylpiperazine-2,5-dione 
• 562814-60-2 3,6-dihydro-1-methyl-5-methylthiopyrazin-2(1H)-one 
• 562814-58-8 1-methylpiperazin-2,5-dithione 
• 562814-59-9 1-methyl-5-thioxopiperazin-2-one 
• 67-99-2 dl-Gliotoxin 
• 1668-07-1 dl-dehydrogliotoxin 
• 79247-63-5 (1R,5R)-6-(2-Hydroxymethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione 
• 565433-79-6 2-(2,5-Bis-acetylsulfanyl-4-methyl-3,6-dioxo-piperazin-1-yl)-3-methoxy-benzoic acid methyl ester 
• 79247-64-6 C₂₁H₂₀N₂O₄S₂ 
• 50627-34-4 3-methoxy-2-[3ξ-(4-methoxy-phenyl)-8-methyl-7,9-dioxo-2,4-dithia-6,8-diaza-bicyclo[3.2.2]non-6-yl]-benzoic acid methyl ester 
• 79247-65-7 (1S,3R,5S)-1-Benzyloxymethyl-6-(2-chloromethyl-6-methoxy-phenyl)-3-(4-methoxy-phenyl)-8-methyl-2,4-dithia-6,8-diaza-bicyclo[3.2.2]nonane-7,9-dione 

Relevant articles and documents

N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE

The invention relates to compounds of formula (I), or a salt thereof wherein R1, A, L, and R2 and n are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are ανβ1 integrin inhibitors that are useful for treating tissue specific fibrosis.

Synthesis and biological activities of a pH-dependently activated water-soluble prodrug of a novel hexacyclic camptothecin analog

CH0793076 (1) is a novel hexacyclic camptothecin analog showing potent antitumor activity in various human caner xenograft models. To improve the water solubility of 1, water-soluble prodrugs were designed to generate an active drug 1 nonenzymatically, th

[11C]Glycylsarcosine: Synthesis and in vivo evaluation as a PET tracer of PepT2 transporter function in kidney of PepT2 null and wild-type mice

[11C]Glycylsarcosine (Gly-Sar) was synthesized as a potential radiotracer to investigate the localization and in vivo function of the peptide transporter PepT2 in mouse kidney. Its C-11 labeled diketopiperazine derivative, [11C]cyclo(Gly-Sar) [1-methylpiperazine-2,5-dione], was also evaluated as a potential tracer. [11C]Gly-Sar exhibited rapid initial uptake into kidneys with slow clearance from the medulla, consistent with uptake and retention of the radiotracer through the actions of PepT2. In contrast, the corresponding cyclized dipeptide [11C]cyclo(Gly-Sar) showed rapid clearance and accumulation only in the renal pelvis region. Involvement of PepT2 in reabsorption and delayed clearance of [ 11C]Gly-Sar was confirmed using the PepT2 knockout mouse, where rapid renal elimination of [11C]Gly-Sar and the absence of radioactivity in medulla were observed. This study demonstrates using in vivo imaging technique that PepT2 is primarily responsible for renal tubular active reabsorption of Gly-Sar, and provides a new tool for studying tubular peptide reabsorption and clearance.

Solvent-free, efficient synthesis of 2,5-piperazinediones from Boc-protected dipeptide esters under microwave irradiation

Microwave irradiation allows the efficient, solvent-free transformation of N-Boc dipeptide esters into 2,5-piperazinediones. The microwave-assisted conditions were found to be much better than traditional heating in terms of reaction time, yield and stere

Active esters of N-substituted piperazine acetic acids, including isotopically enriched versions thereof

In some embodiments, this invention pertains to active esters of N-substituted piperazine acetic acid, including isotopically enriched versions thereof. In some embodiments, this invention pertains to methods for the preparation of active esters of N-subs

Isotopically enriched N-substituted piperazines and methods for the preparation thereof

In some embodiments, this invention pertains to isotopically enriched N-substituted piperazines. In some embodiments, this invention pertains to methods for the preparation of isotopically enriched N-substituted piperazines.

Isotopically enriched N-substituted piperazine acetic acids and methods for the preparation thereof

In some embodiments, this invention pertains to isotopically enriched N-substituted piperazine acetic acids. In some embodiments, this invention pertains to methods for the preparation of isotopically enriched N-substituted piperazine acetic acids.

Microwave-assisted synthesis of 2,5-piperazinediones under solvent-free conditions

A general, efficient and environmentally friendly procedure for the synthesis of 2,5-piperazinediones is described, involving the microwave irradiation of N-Boc dipeptide esters. Georg Thieme Verlag Stuttgart.

Dihydropiperazine neonicotinoid compounds. Synthesis and insecticidal activity

Syntheses of various isomeric dihydropiperazines can be approached successfully by taking advantage of the regioselective monothionation of their respective diones. Preparation of the precursor unsymmetrical N-substituted piperazinediones from readily available diamines is key to this selectivity. The dihydropiperazine ring system, as exemplified in 1-[(6-chloropyridin-3-yl)methyl]-4-methyl-3-oxopiperazin-2-ylidenecyanamide (4) and 1-[(2-chloro-1,3-thiazol-5-yl)methyl]-4-methyl-3-oxopiperazin-2- ylidenecyanamide (25), has been shown to be a suitable bioisosteric replacement for the imidazolidine ring system contained in neonicotinoid compounds. However, placement of the cyanoimino electron-withdrawing group further removed from the pyridine ring, as in 4-[(6-chloropyridin-3-yl)methyl]-3-oxopiperazin-2-ylidenecyanamide (3a), or relocation of the carbonyl group, as in 1-[(6-chloropyridin-3-yl)methyl]-4-methyl-5-oxopiperazin-2-ylidenecyanamide (5), results in significantly decreased bioisosterism. The dihydropiperazine ring system of 4 and 25 also lends a degree of rigidity to the molecule that is not offered by the inactive acyclic counterpart 2-[(6-chloropyridin-3-yl)-methyl-(methyl)amino]-2-(cyanoimino)-N, N-dimethylacetamide (6). A pharmacophore model is proposed that qualitatively explains the results on the basis of good overlap of the key pharmacophore elements of 4 and imidacloprid (1); the less active regioisomers of 4 (3a, 5, and 6) feature a smaller degree of overlap.

Peptide Peroxyl Radicals: Base-Induced O2*- Elimination versus Bimolecular Decay. A Pulse Radiolysis and Product Study

Radiolytically generated OH radicals react with the cyclic dipeptides glycine anhydride (1) and alanine anhydride (2), forming a single type of peptide radical in each case by abstracting a carbon-bound H atom at the ring.In the case of sarcosine anhydride (3), besides the C(3) or C(6) atoms (78percent), the H atoms at the N-methyl groups are also targets of the OH radical attack (22percent).In N2O/O2 (4:1 v/v) saturated solutions these peptide radicals add oxygen (k ca. 2*109 dm3 mol-1 s-1) to form the corresponding peroxyl radicals 6 (from 1), 7 (from 2), and 12 and 13 (from 3).The kinetics of O2*- elimination from the radicals 6 and 7 has been monitored by pulse radiolysis techniques.The pKa values of the peroxyl radicals 6 and 7 have been determined to be 10.8 and 11.2, respectively.The anions of these peroxyl radicals (6a and 7a) rapidly eliminate O2*- with the rate constants 1.6*105 and 3.7*106 s-1, respectively.In contrast, the spontaneous HO2* elimination reactions of the peroxyl radicals 6 and 7 are very slow, with rate constants of -1 as estimated from product analysis.The overall bimolecular decay rate constants of the cyclic dipeptide peroxyl radicals have been determined by pulse radiolysis measurements (2k(6) = 8.6*108 dm3 mol-1 s-1; 2k (7) = 1.6*108 dm3 mol-1 s-1; 2k(12/13) = 4.0*108 dm3 mol-1 s-1).The main products (G values) in the γ radiolysis of glycine anhydride in N2O/O2-saturated solution at pH 6 are 3-hydroxy-2,5-dioxopiperazine (14) (3.5*10-7 mol J-1), 2,3,5-trioxopiperazine (17) (1.6*10-7 mol J-1), and 2,5-dioxo-2,3,4,5-tetrahydropyrazine (8) (0.4*10-7 mol J-1).The product 8 is in equilibrium with its hydrate 14, which is again in equilibrium with its ring-opened form N-glyoxylyl glycinamide (16).In acidic solutions radical 6 decays essentially bimolecularly, giving equal amounts of 14 (present in an equilibrium mixture of 8, 14, and 16) and 17.In basic solution 14 becomes the single main product as the OH(-) -induced O2*- elimination reaction becomes much faster than the bimolecular decay.This is in good agreement with the yield of O2*- formation as monitored by its reaction with tetranitromethane under various pH conditions.With alanine anhydride (2), the main reaction under γ radiolysis conditions even at pH 6 is still the OH(-) -induced O2*- elimination reaction with 3-hydroxy-2,5-dioxo-3,6-dimethylpiperazine (15) as the single main product (G(15) = 4.7*10-7 mol J-1.The major peroxyl radical in sarcosine anhydride system (12) only decays bimolecularly either by self-termination or by cross-termination with the minor peroxy radical (13) (products at pH 6 in γ radiolysis: 2,3,5-trioxo-1,4-dimethylpiperazine (20), G = 4.0*10-7 mol J-1; 3-hydroxy-2,5-dioxo-1,4-dimethylpiperazine (21), G = 0.4*10-7 mol J-1; 1-formyl-2,5-dioxo-4-methylpiperazine (22), G = 0.6*10-7 mol J-1; and 2,5-dioxo-1-methylpiperazine (24), G = 0.6...