5394-50-3

Basic information

• Product Name: 1,2-DICARBOBENZYLOXYHYDRAZINE
• Synonyms: dibenzyl hydrazine-1,2-dicarboxylate;1,2-Hydrazinedicarboxylicacid, 1,2-bis(phenylmethyl) ester
• CAS NO: 5394-50-3
• Molecular Formula: C₁₆H₁₆N₂O₄
• Molecular Weight: 300.3169
• EINECS: 611-069-7
• Mol File: 5394-50-3.mol

Chemical Properties

• Melting Point: 104-105.5 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• Boiling Point: 462.4°Cat760mmHg
• Flash Point: 233.5°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 9.9E-09mmHg at 25°C
• Refractive Index: 1.582
• PKA: 8.52±0.43(Predicted)
• CAS DataBase Reference: 1,2-DICARBOBENZYLOXYHYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-DICARBOBENZYLOXYHYDRAZINE(5394-50-3)
• EPA Substance Registry System: 1,2-DICARBOBENZYLOXYHYDRAZINE(5394-50-3)

Safety Data

• Hazardous Substances Data: 5394-50-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,2-Dicarbobenzyloxyhydrazine is used as a building block for the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new compounds with therapeutic and agricultural applications.
Used in Chemical Reactions as a Protecting Group:
In the chemical industry, 1,2-Dicarbobenzyloxyhydrazine is utilized as a protecting group for aldehydes and ketones, enabling selective and controlled transformations of functional groups, which is crucial for the synthesis of complex organic molecules.
Used in Medicinal Applications:
1,2-Dicarbobenzyloxyhydrazine is studied for its potential applications in medicine, particularly in the development of new drugs for the treatment of various diseases, highlighting its importance in pharmaceutical research and drug discovery.
Used in Research and Development:
In the field of research and development, 1,2-Dicarbobenzyloxyhydrazine is employed for exploring its properties and potential uses, including its toxicological profile and methods for safe handling and application in chemical processes.

InChI:InChI=1/C16H16N2O4/c19-15(21-11-13-7-3-1-4-8-13)17-18-16(20)22-12-14-9-5-2-6-10-14/h1-10H,11-12H2,(H,17,19)(H,18,20)

Upstream product

• 501-53-1 benzyl chloroformate 
• 7732-18-5 water 
• 7803-57-8 hydrazine hydrate 
• 2449-05-0 dibenzyl azodicarboxylate 

Downstream Products

• 78076-79-6 C₄₈H₄₄N₁₀O₈P₂ 
• 114059-50-6 tert-butyl 6-O-(tert-butyldimethylsilyl)-3-(N,N'-dicarbobenzyloxyhydrazino)-3,4-dideoxy-4-C-<(trimethylacetoxy)methyl>-α-D-arabino-hexopyranosid-2-ulose 
• 114059-47-1 C₃₃H₄₈N₂O₈Si 
• 90690-35-0 dibenzyl 5,6,7,8-tetrahydro-2,11,4,9-propane-1,3-diylidene-1,6,7,12-benzotetra-azacyclotetradecine-6,7-dicarboxylate 
• 189026-25-3 C₂₇H₃₄N₂O₉ 
• 1174758-20-3 1-allyl-1-benzyloxycarbonyl-2-benzyloxycarbonyl hydrazine 
• 186419-15-8 C₂₂H₂₄N₂O₄ 
• 1398752-13-0 3-(1,1-dimethylethyl) 1,2-bis(phenylmethyl) 1,2,3-pyrazolidinetricarboxylate 
• 58965-34-7 indazole-1-carboxylic acid benzyl ester 

Relevant articles and documents

Synthesis of α-aminocarbonyl compounds via hetero dielsalder reaction

A synthetic route to α-aminoketone derivatives via a hetero DielsAlder reaction is described. Diacylhydrazine was oxidized by tert-butyl hypochlorite in the presence of pyridine. After evaporation, the hetero DielsAlder reaction with diene was carried out without isolation of the azodicarbonyl compound. Quantitative hetero DielsAlder reaction was possible with 1 equivalent of diene when Hf(OTf)4 or AgOTf was used as the catalyst. The NN bond of the product was cleaved by SmI2-reduction in the presence of tert-BuOH in THF. Further, ozonolysis of the C=C double bond afforded the α-aminoketone derivative in excellent yield.

Turning the Nitrogen Atoms of an Ar2P?CH2?N?N?CH2?PAr2 Motif into Uniquely Configured Stereocenters: A Novel Diphosphane Design for Asymmetric Catalysis

Hexahydropyridazines with CH2PAr2 groups at both N atoms are newly designed 1,4-diphosphanes and were synthesized for the first time. Their N atoms assume a single configuration under the influence of stereocenters at C-5 and C-6. In the solid state, these N-atoms bind the CH2PAr2 substituents axially. Combined with Pd0, N,N′-chiral diphosphanes of this kind catalyzed Tsuji–Trost type allylations of dialkyl malonates with racemic 1,3-diphenylallyl acetate efficiently and with up to 91 % ee.

Photocatalytic esterification under Mitsunobu reaction conditions mediated by flavin and visible light

The usefulness of flavin-based aerial photooxidation in esterification under Mitsunobu reaction conditions was demonstrated, providing aerial dialkyl azodicarboxylate recycling/generation from the corresponding dialkyl hydrazine dicarboxylate. Simultaneously, activation of triphenylphosphine (Ph3P) by photoinduced electron transfer from flavin allows azo-reagent-free esterification. An optimized system with 3-methylriboflavin tetraacetate (10%), oxygen (terminal oxidant), visible light (450 nm), Ph3P, and dialkyl hydrazine dicarboxylate (10%) has been shown to provide efficient and stereoselective coupling of various alcohols and acids to esters with retention of configuration.

Peptide deformylase inhibitors

The present invention relates to a compound of Formula (I): or a pharmaceutically acceptable salt thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods directed to bacterial infections and inhibition of bacterial peptide deformylase (PDF) activity.

PEPTIDE DEFORMYLASE INHIBITORS

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Asymmetric α-amination of aldehydes catalyzed by PS-diphenylprolinol silyl ethers: Remediation of catalyst deactivation for continuous flow operation

Polystyrene (PS)-supported diphenylprolinol silyl ethers have been developed as highly active catalysts for the enantioselective α-amination of aldehydes. Understanding the mechanism of catalyst deactivation has led to the development of reaction conditions notably extending catalyst life in repeated recycling (10 cycles; accumulated TON of 480) and has allowed the implementation of a continuous flow α-amination process (6 min residence time, 8 h operation). Copyright

Asymmetric α-amination of aldehydes catalyzed by PS-diphenylprolinol silyl ethers: Remediation of catalyst deactivation for continuous flow operation

Polystyrene (PS)-supported diphenylprolinol silyl ethers have been developed as highly active catalysts for the enantioselective α-amination of aldehydes. Understanding the mechanism of catalyst deactivation has led to the development of reaction conditions notably extending catalyst life in repeated recycling (10 cycles; accumulated TON of 480) and has allowed the implementation of a continuous flow α-amination process (6 min residence time, 8 h operation). Copyright

Metal-free oxyaminations of alkenes using hydroxamic acids

A radical-mediated approach to metal-free alkene oxyamination is described. This method capitalizes on the unique reactivity of the amidoxyl radical in alkene additions to furnish a general difunctionalization using simple diisopropyl azodicarboxylate (DIAD) as a radical trap. This protocol capitalizes on the intramolecular nature of the process, providing single regioisomers in all cases. Difunctionalizations of cyclic alkenes provide trans oxyamination products inaccessible using current methods with high levels of stereoselectivity, complementing cis-selective oxyamination processes.

IMPROVED PROCESS FOR THE MANUFACTURE OF 1,2-DISUBSTITUTED HEXAHYDROPYRIDAZINE-3-CARBOXYLIC ACIDS AND ESTERS THEREOF

The invention relates to an improved process for the manufacture of 1,2-disubstituted hexahydro-pyridazine-3-carboxylic acids and esters thereof by reacting N,N’-disubstituted hydrazine with 2,5-dihalogenated valeric acids and thereof by means of phase transfer catalysis. Said pyridazine carboxylic acids and esters thereof can be used as intermediates for the production of pharmaceutical products

Derivatives of octahydro-6,10-dioxo-6H-pyridazino [1,2-a] [1,2] diazepine-1-carboxylic acid, their preparation process and their use in the preparation of therapeutically active compounds

Novel intermediates of the formulae where the substituents are defined as in the specification.