3027-05-2

Basic information

• Product Name: N,N'-DIACETYLGLYCINE ANHYDRIDE
• Synonyms: N,N'-DIACETYLGLYCINE ANHYDRIDE;1,4-DIACETYL-PIPERAZINE-2,5-DIONE;1,4-DIACETYLTETRAHYDRO-2,5-PYRAZINEDIONE;1,4-DIACETYL-2,5-DIKETOPIPERAZINE;1,4-DIACETYL-2,5-DIOXOPIPERAZINE;1,4-DIACETYL-2,5-PIPERAZINEDIONE;1,4-Diacetyl-2,5-diketopiperazine 1,4-Diacetyl-2,5-dioxopiperazine 1,4-Diacetyl-2,5-piperazinedione;N,N′-Diacetyl-2,5-dioxopiperazine
• CAS NO: 3027-05-2
• Molecular Formula: C₈H₁₀N₂O₄
• Molecular Weight: 198.18
• Mol File: 3027-05-2.mol

Chemical Properties

• Melting Point: 99-100°C
• Boiling Point: 424.4 °C at 760 mmHg
• Flash Point: 216.6 °C
• Appearance: /
• Density: 1.375 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -1.74±0.20(Predicted)
• BRN: 188115
• CAS DataBase Reference: N,N'-DIACETYLGLYCINE ANHYDRIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIACETYLGLYCINE ANHYDRIDE(3027-05-2)
• EPA Substance Registry System: N,N'-DIACETYLGLYCINE ANHYDRIDE(3027-05-2)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-43-36/38-22
• Safety Statements: 26-36/37/39-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 3027-05-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Diacetylglycine anhydride is used as an acetylation reagent for the production of pharmaceuticals and other organic compounds. It aids in the synthesis of various drugs by acetylating functional groups, enhancing their stability and bioavailability.
Used in Organic Synthesis:
N,N'-Diacetylglycine anhydride is used as a building block in the synthesis of complex organic molecules. Its versatile reactivity allows for the formation of various chemical structures, contributing to the development of new compounds with potential applications in various fields.
Used in Peptide Reagent Preparation:
N,N'-Diacetylglycine anhydride is utilized in the preparation of peptide reagents. It serves as a key component in the synthesis of peptides, which are essential in biological research and drug development.
It is important to handle N,N'-Diacetylglycine anhydride with care and follow proper safety precautions when working with it in the laboratory to ensure the safety of researchers and the integrity of the experiments.

Upstream product

• 106-57-0 Glycine anhydride 
• 108-24-7 acetic anhydride 
• 5535-48-8 PVS 
• 153074-39-6 1,4-Diacetyl-3-bromopiperazine-2,5-dione 
• 107-13-1 acrylonitrile 
• 109-92-2 ethyl vinyl ether 
• 292638-85-8 acrylic acid methyl ester 
• 75-36-5 acetyl chloride 

Downstream Products

• 68691-68-9 1-acetyl-3-((Z)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethylene)-piperazine-2,5-dione 
• 68738-17-0 (5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8c'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione 
• 68691-66-7 (5S)-4c-(4-bromo-benzoyloxy)-3c-hydroxy-3t-methyl-12-methylene-(5rN,5r'O,8t'O)-1,9-dioxa-6,13-diaza-dispiro[4.2.4.2]tetradecane-7,14-dione 
• 117563-34-5 1-acetyl-3-(3-oxophthalylidene)piperazine-2,5-dione 
• 117563-35-6 3,6-di(3-oxophthalylidene)piperazine-2,5-dione 
• 137043-30-2 (3Z,6Z)-3,6-Bis-<(2,4,5-trimethoxy-3-methylphenyl)methylene>piperazinedione 
• 113296-74-5 (Z)-1-acetyl-3-(2,4,5-trimethoxy-3-methylphenylmethylene)-2,5-piperazinedione 
• 94807-44-0 1-acetyl-3-(3-benzyloxypropylidene)-2,5-piperazinedione 
• 127103-51-9 1-Acetyl-3-[1-(5-benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-meth-(Z)-ylidene]-piperazine-2,5-dione 
• 100592-97-0 (Z)-1-acetyl-3-(4-methylbenzylidene)-2,5-piperazinedione 
• 100592-97-0 1-Acetyl-3-[1-p-tolyl-meth-(E)-ylidene]-piperazine-2,5-dione 
• 117563-31-2 3,6-di(4-carboxybenzylidene)piperazine-2,5-dione 
• 117563-32-3 4-phenylenebis(ylidenepiperazine-2,5-dione) 
• 41808-13-3 1-Acetyl-3-[1-(4-nitro-phenyl)-meth-(E)-ylidene]-piperazine-2,5-dione 

Relevant articles and documents

A highly substituted pyrazinophane generated from a quinoidal system: Via a cascade reaction

The generation of a highly-substituted [2.2](2,5)pyrazinophane via a cascade reaction is presented. The pyrazinophane product is formed via the dimerization of a member of the para-azaquinodimethane (p-AQM) family of conjugated quinoidal compounds - reactivity that sheds light on the nature of stability in p-AQMs. Additionally, the electronic and structural nature of this highly-strained ring system are characterized.

Synthesis and unusual ring transformation of 1-acyl-3- (ferrocenylmethylidene)-piperazine-2,5-diones

The reaction of 1,4-diacyl-piperazine-2,5-diones with ferrocenecarbaldehyde in the presence of tBuOK in tBuOH-DMF at room temperature afforded 1-acyl-3-(ferrocenylmethylidene)-piperazine-2,5-diones in 69-79% yields. The attempted N(4)-acylation of these compounds with carboxylic acids (2 equiv.) in the presence of N,N′-diisopropylcarbodiimide (2 equiv.) and 4-(dimethylamino)pyridine (3 equiv.) in dichloromethane at room temperature showed that the expected 1,4-diacylated products are initially formed, but undergo further transformations leading to compounds featuring conjugated ferrocenylmethylidene, azlactone (oxazolone) and oxazole units. As shown on the basis of one example, the azlactone ring in these compounds is opened in a room-temperature reaction with hydrazine, thus yielding the corresponding acyl hydrazide. The crystal structure of the starting material and the product of this reaction were confirmed by X-ray diffraction.

Phenotype-Guided Natural Products Discovery Using Cytological Profiling

Phenotype-guided natural products discovery is emerging as a useful new discovery tool that addresses challenges in early, unbiased natural product biological annotation. These high-content approaches yield screening results that report directly on the im

Radical addition of simple piperazine-2,5-diones

The polar character of a simple piperazine-2,5-dione was investigated under intermolecular radical addition conditions. The results indicate that captodative radical of this kind neither show extreme nucleophilic nor electrophilic tendencies.

Chiral 1,2,3-Triazolium Salt Catalyzed Asymmetric Mono- and Dialkylation of 2,5-Diketopiperazines with the Construction of Tetrasubstituted Carbon Centers

Novel asymmetric mono- and dialkylation reactions of α-substituted 2,5-diketopiperazines catalyzed by new chiral spirocyclic-amide-derived triazolium organocatalysts have been developed, resulting in a range of enantioenriched 2,5-diketopiperazine derivatives containing one or two tetrasubstituted carbon stereocenters. The reactions feature high yields (up to 98%), and excellent cis-diastereo- and enantioselectivities (up to >20:1 dr, >99 % ee), and they provide a new asymmetric synthetic approach to important functionalized 2,5-diketopiperazine skeletons. Furthermore, a possible reaction mechanism was proposed based on both control experiments and extensive DFT calculations.

Histamine H3 receptor antagonists with peptidomimetic (keto)piperazine structures to inhibit Aβ oligomerisation

Alzheime?s disease (AD) is the most prominent neurodegenerative disorder with high medical need. Protein-protein-interactions (PPI) interactions have a critical role in AD where β-amyloid structures (Aβ) build toxic oligomers. Design of disease modifying multi target directed ligand (MTDL) has been performed, which disable PPI on the one hand and on the other hand, act as procognitive antagonists at the histamine H3 receptor (H3R). The synthetized compounds are structurally based on peptidomimetic amino acid-like structures mainly as keto, diketo-, or acyl variations of a piperazine moiety connected to an H3R pharmacophore. Most of them showed low nanomolar affinities at H3R and some with promising affinity to Aβ-monomers. The structure–activity relationships (SAR) described offer new possibilities for MTDL with an optimized profile combining symptomatic and potential causal therapeutic approaches in AD.

One pot synthesis of N-monoalkylated plinabulin derivatives via multicomponent protocol and their application as anticancer agents

A chemical library of seventeen N-monoalkylated plinabulin derivatives was designed and synthesized in one pot with high atom economy, good yield and operational simplicity in site selective manner with Z-configuration at 3,6-positions (3Z,6Z) which have

Enantioselective Synthesis of Chiral Substituted 2,4-Diketoimidazolidines and 2,5-Diketopiperazines via Asymmetric Hydrogenation

An enantioselective hydrogenation of 5-alkylidene-2,4-diketoimidazolidines (hydantoins) and 3-alkylidene-2,5-ketopiperazines catalyzed by the Rh/f-spiroPhos complex under mild conditions has been developed, which provides an efficient approach to the highly enantioselective synthesis of chiral hydantoins and 2,5-ketopiperazine derivatives with high enantioselectivities up to 99.9% ee.

The synthesis and biological activity of the 3-ferrocenylpropenamides derived from 5(4H)-oxazolones

We described a synthesis of new 3-ferrocenylpropenamides prepared by oxazolone-ring opening reaction with various primary and secondary amines. The antiproliferative activities of the obtained compounds were screened on human tumor cell lines (HCT116, SW6

DL-neopentyl glycine intermediate and preparation method thereof and preparation method of derivative based on intermediate

The invention relates to the field of amino acid preparation, in particular to a DL-neopentyl glycine intermediate and a preparation method thereof and a preparation method of a derivative based on the intermediate. The preparation method of the DL-neopentyl glycine intermediate comprises an acetylation reaction, a condensation reaction, a hydrolysis reaction, an oximation reaction and a reductionreaction, and then a corresponding derivative is obtained through the acetylation reaction and resolution. According to the preparation method, the reaction time is shortened, the reaction is more thorough and the DL-neopentyl glycine can be obtained; two methods for preparing the derivative D-neopentyl glycine and the derivative L-neopentyl glycine are obtained at the same time, the prepared product is high in purity, secondary refining is not needed, the production cost is reduced, and industrial large-scale production is facilitated.