4329-75-3

Basic information

• Product Name: 1,2-Bis(4-pyridylcarbonyl)hydrazine
• Synonyms: 1,2-Bis(4-pyridinylcarbonyl)hydrazine;1,2-Bis(4-pyridylcarbonyl)hydrazine;1,2-Diisonicotinoylhydrazine;4-Pyridinecarboxylic acid 2-(4-pyridinylcarbonyl) hydrazide;Bis(4-pyridoyl)hydrazine;N,N'-Bis[isonicotinic acid]hydrazide;N,N'-Diisonicotinoylhydrazine
• CAS NO: 4329-75-3
• Molecular Formula: C₁₂H₁₀N₄O₂
• Molecular Weight: 242.23
• Mol File: 4329-75-3.mol

Chemical Properties

• Melting Point: 250 °C
• Boiling Point: 551.5 °C at 760 mmHg
• Flash Point: 287.3 °C
• Appearance: /
• Density: 1.313g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.757
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 8.92±0.23(Predicted)
• CAS DataBase Reference: 1,2-Bis(4-pyridylcarbonyl)hydrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Bis(4-pyridylcarbonyl)hydrazine(4329-75-3)
• EPA Substance Registry System: 1,2-Bis(4-pyridylcarbonyl)hydrazine(4329-75-3)

Safety Data

• Hazardous Substances Data: 4329-75-3(Hazardous Substances Data)

Usage

Uses

1,2-Diisonicotinoylhydrazine is an iron chelator.

Purification Methods

Crystallise it from water, aqueous EtOH or propan-1-ol. [Albert & Rees Biochem J 61 128 1955, Beilstein 22 III/IV 663.]

InChI:InChI=1/C38H20Cl6O8S6/c39-21-7-3-1-5-17(21)25-13-27(55-53-25)37(35(49)19-9-11-23(33(43)31(19)41)51-15-29(45)46)57-58-38(28-14-26(54-56-28)18-6-2-4-8-22(18)40)36(50)20-10-12-24(34(44)32(20)42)52-16-30(47)48/h1-14H,15-16H2,(H,45,46)(H,47,48)/b37-27+,38-28+

Upstream product

• 14254-57-0 4-(chlorocarbonyl)pyridine 
• 54-85-3 isoniazid 
• 64-17-5 ethanol 
• 15017-12-6 (E)-N'-(4-oxopentan-2-ylidene)isonicotinohydrazide 
• 39178-35-3 isonicotinoyl chloride hydrochloride 
• 3811-46-9 3-isonicotinoylhydrazono-butyric acid ethyl ester 
• 27991-08-8 N-acetoacetylphenylhydroxyloamine 
• 898-22-6 triethyl 1,3,5-triazine-2,4,6-tricarboxylate 
• 7732-18-5 water 
• 141-97-9 ethyl acetoacetate 
• 7705-08-0 iron(III) chloride 
• 7758-99-8 copper(II) sulfate 
• 55-22-1 pyridine-4-carboxylic acid 
• 302-01-2 hydrazine 

Downstream Products

• 15420-02-7 2,5-bis(4-pyridyl)-1,3,4-oxadiazole 
• 15311-09-8 2,5-bis(4-pyridyl)-1,3,4-thiadiazole 
• 586-95-8 pyridine-4-methanol 

Relevant articles and documents

Synthesis, computational studies, antimycobacterial and antibacterial properties of pyrazinoic acid-isoniazid hybrid conjugates

Benzotriazole and microwave mediated syntheses led to a new set of hybrid conjugates of pyrazinoic acid with isoniazid via amino acid linkers in excellent yields with retention of chirality. Microbiological screening of the synthesized conjugates revealed an exceptionally high activity against some of the pathogenic bacterial strains at low concentrations. Promising antimycobacterial properties were observed against tuberculous and non-tuberculous mycobacteria. Robust molecular models (2D-QSAR and 3D-pharmacophore) support the observed biological properties. Safety profile of the synthesized conjugates against human normal cell (RPE1) was evaluated by MTT technique.

A convenient and simple transformation of acid hydrazides to N,N′-diacylhydrazines with Hg(OAc)2 under solid state conditions

A highly efficient and practical methodology for the transformation of acid hydrazides 1 to N,N′-diacylhydrazines 2 is described under solid state conditions at RT utilizing inexpensive and easily available reagent Hg(OAc) 2. The products are obtained in good yields with high purity.

Synthesis of novel 5-amino-1-aroylpyrazoles

A series of 5-amino-1-aroylpyrazoles 3 are synthesized directly by the reaction of β-aminocrotononitrile 1 with some structures containing the hydrazine moiety (X-NHNH2) 2 by refluxing ethanol in presence of sodium acetate. When semicarbazide 3i was used (X = CONH2), the reaction afforded the unexpected 7-aminopyrazolo[1,5-a]pyrimidine 4.

An Efficient Oxidation of Acid Hydrazides to N,N′-Diacylhydrazines Using Copper(II) Acetate in Solvent-Free Conditions Under Microwave Irradiation

A simple and efficient method for solvent free "dry" state transformation of acid hydrazides 1 to corresponding N,N′ -diacylhydrazines 2 using copper(II) acetate under microwave irradiation has been described. The products are obtained in good yields and excellent purities.

Migration of an acyl group in the pyrazole system: Synthesis of 1-acyl-3-hydroxy-1H-pyrazoles and related derivatives. A new preparation of N,N′-diacylhydrazines

A new general method for the synthesis of 1-acyl-3-hydroxy-1H-pyrazoles 5a-f and related derivatives 5g-i starting from 4-ethoxymethylene-2-phenyloxazol-5(4H)-one (1) and hydrazides, 4-phenylsemicarbazide, 4-phenylthiosemicarbazide and benzyl carbazate in boiling dioxane is described. The method includes a migration of an acyl or related unit. The X-ray study and NMR spectroscopic examination confirmed the structure of the products. A one-pot synthesis of N,N′-diacylhydrazines from hydrazides by the assistance of oxazolone 1 is also presented.

Hypervalent iodine oxidation of acid hydrazides: A new synthesis of N,N'-diacylhydrazines

Hypervalent iodine oxidation of p-substituted benzohydrazides (1a-h), phenylacetohydrazide (1i) and heterocyclic acid hydrazides (1j-l) using one equivalent of iodobenzene diacetate in dry dichloromethane or acetonitrile leads to dimerization thereby providing a new and facile method for the synthesis of N,N-diacylhydrazines 2.

sym-TRIAZINE DERIVATIVES. 6. CONVERSION OF 2,4,6-TRIETHOXYCARBONYL-1,3,5-TRIAZINE WITH ACYLHYDRAZINES INTO 3,5-DIETHOXYCARBONYL-1,2,4-TRIAZOLE

The reaction of 2,4,6-triethoxycarbonyl-1,3,5-triazine with acylhydrazines leads to fragmentation with the formation of 3,5-diethoxycarbonyl-1,2,4-triazole, 1-acylethoxycarbonylformamidrazones N,N'-diacylhydrazines, and the amines of the corresponding carboxylic acids.