13529-51-6

Basic information

• Product Name: 2,2'-hydrazonobisethanol
• Synonyms: 2,2'-hydrazonobisethanol;1,1-DIETHANOLHYDRAZINE
• CAS NO: 13529-51-6
• Molecular Formula: C₄H₁₂N₂O₂
• Molecular Weight: 120.15028
• EINECS: 236-873-1
• Mol File: 13529-51-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 224.15°C (rough estimate)
• Flash Point: 146.2°C
• Appearance: /
• Density: 1.1625 (rough estimate)
• Refractive Index: 1.4800 (estimate)
• CAS DataBase Reference: 2,2'-hydrazonobisethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-hydrazonobisethanol(13529-51-6)
• EPA Substance Registry System: 2,2'-hydrazonobisethanol(13529-51-6)

Safety Data

• Hazardous Substances Data: 13529-51-6(Hazardous Substances Data)

Usage

Physical state

colorless liquid

Odor

slight amine odor

Solubility

water-soluble

Hazard class

moderately hazardous

Uses

reagent for the synthesis of chiral ligands and catalysts, preparation of organic compounds, pharmaceuticals, and agricultural chemicals

Handling precautions

handle with caution and follow proper safety protocols in laboratory or industrial settings.

Upstream product

• 75-21-8 oxirane 
• 109-84-2 2-hydroxyethylhydrazine 
• 107-07-3 2-chloro-ethanol 
• 1116-54-7 N-nitrosodiethanolamine 
• 302-01-2 hydrazine 
• 1068-57-1 acetic acid hydrazide 

Downstream Products

• 95174-06-4 1.1-Bis-<2-hydroxy-ethyl>-4-<4-chlor-phenyl>-thiosemicarbazid 
• 96198-81-1 1.1-Bis-<2-hydroxy-ethyl>-4-<4-ethoxy-phenyl>-thiosemicarbazid 
• 110-91-8 morpholine 
• 85095-64-3 p,p'-diphenylmethanebis<4-(1,1-di-2-hydroxyethylsemicarbazide)> 
• 145887-62-3 1-phenyl-3,3-bis(β-hydroxyethyl)triazene 1-oxide 
• 145887-63-4 C₁₁H₁₅N₃O₄ 
• 145887-64-5 C₁₂H₁₅N₃O₅ 
• 1215-42-5 4,4'-dibromoazoxybenzene 
• 91338-26-0 p-nitrobenzaldehyde N,N-di(2-hydroxyethyl)hydrazone 
• 99648-05-2 2,3-di(p-nitrophenyl)-1,4-dioxa-9,10-diazadecalin 
• 107946-18-9 N,N-di(2-hydroxyethyl)-N'-(o-carboxyphenylcarbonyl)hydrazine 
• 95983-18-9 1.1-Bis-<2-hydroxy-ethyl>-4-<4-methoxy-phenyl>-thiosemicarbazid 
• 95074-26-3 1,1-Bis-<2-hydroxy-aethyl>-4-phenyl-thiosemicarbazid 
• 17173-86-3 N',N'-Bis-(2-chlor-aethyl)-N-sulfinyl-hydrazin 

Relevant articles and documents

Synthesis of multi-substituted 1,2,4-triazoles utilising the ambiphilic reactivity of hydrazones

The synthesis of N-alkyl-1H-1,2,4-triazoles from N,N-dialkylhydrazones and nitriles via formal [3+2] cycloaddition including the C-chlorination/nucleophilic addition/cyclisation/dealkylation sequence was developed. This sequential reaction utilising the in situ generation of hydrazonoyl chloride based on the ambiphilic reactivity of hydrazones afforded a variety of multi-substituted N-alkyl-triazoles in high yields. The synthetic utility of multi-substituted triazoles was also demonstrated by further transformations.

Hydrogen bonding of 2-tetrazenes, 2. Synthesis and structural studies of hydroxyalkyl-substituted 2-tetrazenes

Five hydroxyethyl-2-tetrazenes (1 - 5) and their methyl ethers (6 - 10) have been synthesized and hydrogen bonding in these compounds has been investigated by theoretical and spectroscopic (IR, 1H NMR, 15N NMR) methods. The structure of 1,1,4,4-tetrakis(2-hydroxyethyl)-2-tetrazene (4) was determined by X-ray diffraction analysis. Several conformations with intramolecular hydrogen bonds were investigated by ab initio B3LYP as well as semiempirical SCF calculations. In all cases, conformers with OH---N hydrogen bonds with azo nitrogen atoms as acceptors (conformers A, B, C) are found as most stable. In compounds with small or flexible N1- and N4- substituents R besides the hydroxyethyl group (3, 4), hydrogen bonds forming six-membered rings, with the R groups taking syn positions at the N1-N2 and N3-N4 bonds (conformer A), are preferred over those with seven-membered rings and R taking anti positions (conformer B). Steric interaction in the other compounds (1, 2, 5) leads to destabilization of conformers A and conformers B become more stable. A special case is presented by compound 4 which has only hydroxyethyl substituents on the 2-tetrazene unit. In the most stable conformer (4C) there are two OH---O and one OH---N hydrogen bonds. By IR solution measurements intra- and intermolecular hydrogen bonds could be distinguished. Association shifts Δδ measured by 1H NMR spectroscopy, indicate that the investigated compounds exhibit comparable association properties with intermolecular association clearly prevailing. 15N NMR spectra of compounds 1 - 10 in two solvents have been measured if solubility was sufficient. The data indicate that all nitrogen atoms of 1 - 5 participate in H bonding. In the crystalline state, molecules 4 adopt a conformation without intramolecular H bonds (4D) and are associated by intermolecular OH---O hydrogen bonds that form a three-dimensional network. An untypical decomposition pattern was discovered for benzyl derivatives 5 and 10.

1]: N,N-Bis-(2-chlorethyl)-hydrazine and some derivatives.

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