1898-66-4

Basic information

• Product Name: 1,1-DIPHENYL-2-PICRYLHYDRAZYL
• Synonyms: 2,2-Diphenyl-1-picrylhydrazyl,1,1-Diphenyl-2-picrylhydrazyl radical, 2,2-Diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl, DPPH;2,2-Diphenylpicrylhydrazyl;1-diphenyl-2-picrylhydrazyl;1,1-Diphenyl-2-picrylhydrazyl (DPPH);2,2-Diphenyl-1-(2,4,6-trinitrophenyl)-hydrazyl (DPPH);2,2-Diphenyl-1-picrylhydrazyl(DPPH);2,2-Diphenyl-1-picrylhydrazyl (contains 10-20% Benzene);2,2-diphenyl-1-(2,4,6-trinitrophenyl)hydrazyl
• CAS NO: 1898-66-4
• Molecular Formula: C₁₈H₁₂N₅O₆
• Molecular Weight: 394.32
• EINECS: 217-591-8
• Product Categories: DPPH;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes
• Mol File: 1898-66-4.mol
• Article Data: 11

Chemical Properties

• Melting Point: ~135 °C (dec.)(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: green/
• Density: g/cm³
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), DMSO (Slightly), Methanol (Sligh
• Water Solubility: Soluble in dimethyl formamide, ethanol, chloroform, ether, carbon disulfinde, acetone, oils, carbon tetrachloride, glacial aceti
• Stability: Shock Sensitive
• Merck: 14,3330
• BRN: 1846081
• CAS DataBase Reference: 1,1-DIPHENYL-2-PICRYLHYDRAZYL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-DIPHENYL-2-PICRYLHYDRAZYL(1898-66-4)
• EPA Substance Registry System: 1,1-DIPHENYL-2-PICRYLHYDRAZYL(1898-66-4)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43
• Safety Statements: 22-36/37-45
• RIDADR: UN2811
• WGK Germany: 1
• RTECS: MW3250000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 1898-66-4(Hazardous Substances Data)

Usage

Chemical Properties

Solid

Uses

Different sources of media describe the Uses of 1898-66-4 differently. You can refer to the following data:
1. 2,2-Diphenyl-1-picrylhydrazyl is a stable free radical molecule most commonly used as a tool to monitor chemical reactions involving radicals, most notably in antioxidant assay.
2. 2,2-Diphenyl-1-picrylhydrazyl is used as a sensitive colorimetric free radical scavenger. It serves as a general antioxidant detector. It is utilized to monitor chemical reactions involving radicals as well as a standard of the position and intensity of electron paramagnetic resonance signals. Further, it is employed in the quantitative determination of aliphatic and aromatic thiols by indirect spectroscopy and for photometric determination of tocopherol.

General Description

2,2-diphenyl-1-picrylhydrazyl is a free radical, which shows hydrogen acceptor ability towards antioxidants. Hence, it is commonly used in DPPH assay for measuring the antioxidant activity of different natural samples such as wine, fruits, herbal tea etc.

InChI:InChI=1/C18H12N5O6/c24-21(25)15-11-16(22(26)27)18(17(12-15)23(28)29)19-20(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-12H

Synthetic route

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) → 2,2-diphenyl-1-picrylhydrazine (1707-75-1)

Conditions	Yield
With 2,5-dihydroxy-1,4-benzoquinone In tetrahydrofuran
With (+)-kunstlerone In ethanol at 20℃; for 30h;
With C16H13NO4
With 5-amino-2,3-dihydrophthalazine-1,4-dione; scutellarin; sodium hydroxide In water
With 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + C22H27N3OS (122508-33-2) → C22H28N3OS + C22H28N3OS + 2,2-diphenyl-1-picrylhydrazine (1707-75-1)

Conditions	Yield
In ethanol Kinetics; Concentration;

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + C27H34N4O2 (1239471-70-5, 1446937-86-5) → C27H35N4O2 + 2,2-diphenyl-1-picrylhydrazine (1707-75-1)

Conditions	Yield
In ethanol Kinetics; Concentration;

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + 3,5-di(tert-butyl)-4-hydroxybenzaldehyde N-(benzothiazolyl-2-thioacetyl)hydrazone → C24H30N3O2S2 + 2,2-diphenyl-1-picrylhydrazine (1707-75-1)

Conditions	Yield
In ethanol Kinetics; Concentration;

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + 2,6-di-tert-butyl-4-methyl-phenol (128-37-0) → 4-methyl-2,6-di-t-butylphenoxyl radical (24473-56-1, 6858-01-1) + 2,2-diphenyl-1-picrylhydrazine (1707-75-1)

Conditions	Yield
In ethanol Kinetics; Concentration;

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) → C18H12Cl2N5O10S2

Conditions	Yield
With chlorosulfonic acid

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + corilagin (23094-69-1) → C45H33N5O24

Conditions	Yield
In methanol at 20℃; for 24h;

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + 1,3,6-tri-O-galloyl-β-D-glucose (18483-17-5, 23140-70-7, 135029-93-5) → C45H35N5O24

Conditions	Yield
In methanol at 20℃; for 24h;

2,2-diphenyl-1-picrylhydrazyl (1898-66-4) + 3′,5′‑dichloro‑2′‑hydroxyacetophenone‑3‑methoxybenzoylhydrazone → (E)-N'-(1-(3,5-dichloro-2-hydroxyphenyl)ethylidene)-3-methoxybenzohydrazide radical + 2,2-diphenyl-1-picrylhydrazine (1707-75-1)

Conditions	Yield
In methanol; dimethyl sulfoxide at 37℃; for 0.5h; Reagent/catalyst;

Upstream product

• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 2700-36-9 Tetra-tert-butylindophenoxyl 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 943-39-5 4-nitroperbenzoic acid 
• 75-91-2 tert.-butylhydroperoxide 
• 22937-64-0 3.4-Epoxyhexahydroperbenzoesaeure-tert-butylester 
• 2388-12-7 peroxylaurinoic acid 
• 35120-40-2 Dimethylaminomethyl-tert.butylperoxid 
• 13653-03-7 tert-butyl pervalerate 
• 80-15-9 Cumene hydroperoxide 
• 57272-44-3 methyl α-hydroperoxy-α,α-diphenylacetate 
• 19910-09-9 peroxyphenylacetic acid 
• 5233-67-0 α-hydroperoxy-α,α-diphenylacetonitrile 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 91-20-3 naphthalene 
• 30807-69-3 N-hydroxy-N',N'-diphenyl-N-picryl-hydrazine 
• 4293-22-5 2-(p-bromophenyl)-2-phenyl-1-picrylhydrazine 
• 2700-36-9 Tetra-tert-butylindophenoxyl 
• 1707-75-1 2,2-diphenyl-1-picrylhydrazine 
• 79628-37-8 1-<2,6-dinitro-4-(1,2,3,4-tetrahydro-4-phenyl-1-naphthyl)-phenyl>-2,2-diphenylhydrazine 
• 29946-26-7 2-(p-nitrophenyl)-2-phenyl-1-(2,4,6-trinitrophenyl)hydrazine 
• 67-64-1 acetone 
• 75-65-0 tert-butyl alcohol 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 489-98-5 picramide 
• 122-39-4 diphenylamine 
• 3018-20-0 1-phenyl-1,2,3,4-tetrahydronaphthalene 
• 16606-46-5 1-phenyl-1,2-dihydronaphtalene 

Relevant articles and documents

Synthesis and spectral comparison of electronic and molecular properties of some hydrazines and hydrazyl free radicals

Continuing our work on hydrazyl free radicals, five triphenylhydrazine derivatives, one a new compound, were synthesized to compare the electronic and molecular properties of these compounds, study the influence of substituents on the phenyl rings, and compare their properties with the parent hydrazines and corresponding anions. These hydrazines demonstrate both acid-base and redox properties. The hydrazine proton can be removed by base, yielding the corresponding anion and both the hydrazines and their anions can be oxidized to the corresponding hydrazyl free radicals. ESR spectra confirmed their formation and X-ray crystallography of one compound confirmed their structures.

Manganese-porphyrins and -azaporphyrins as catalysts in alkene epoxidations with peracetic acid. Part 2. Kinetics and mechanism

cis-Stilbene (cSt) and 1,1-diphenyl-2-picrylhydrazine (DPPH) were used as substrates for kinetic investigations of the catalytic system based on MnIII-porphyrins and peracetic acid in CH3CN. Catalysts employed were tetra-(2,6-dichlorophenyl)-porphyrinatomanganese chloride (TDCPPMnCl) 5, octanitrophthalocyaninatomanganese chloride (NO2PcMnCl) 6 and tetra(tert-butyl)-tetraazaporphyrinatomanganese chloride (TAPMnCl) 7. It was found that for all these catalysts the first step of the reaction mechanism is the formation of an adduct 'A' between the catalyst and AcOOH in a reversible way (k1/k-1), followed by an irreversible stage (k2) for the formation of Mnv-oxo species. The oxidative capability of the adduct 'A' was found to be dependent on the electronic structure of the catalyst, while the reactivity of Mn-oxo species is only slightly influenced by catalyst structure. The formation of the high-valent Mn-oxo species is the rate-determining step of alkene epoxidations as demonstrated by the same k2 value obtained with catalyst 6 in the epoxidation of cSt and trans-stilbene (tSt). Catalyst stability was found to be dependent on solvent polarity, CH3CN being the best reaction medium.

Preparation of 2,2-diaryl-1-picrylhydrazyls using potassium permanganate

Potessium permanganate is used as a reagent for the oxidation of various 2,2-diaryl-1-picrylhydrazines to their corresponding hydrazyls.Thin-layer chromatography indicates complete oxidation of the hydrazine to free radical, unlike the case with PbO2 (the most widely used oxidant for this purpose).Several other advantages over previous oxidants used to produce the hydrazyls are offered.