538-62-5

Usage

Uses

Used in Chemical Analysis:
DIPHENYLCARBAZONE is used as an indicator for the detection of mercury (Hg), forming a blue-colored complex when it reacts with the metal. This characteristic makes it a valuable tool in chemical analysis and laboratory settings for identifying and quantifying mercury content in various samples.
Used in Environmental Testing:
In the environmental industry, DIPHENYLCARBAZONE is used as a reagent for mercury determination. It plays a crucial role in monitoring and assessing mercury pollution levels in water, soil, and air samples, contributing to the protection of ecosystems and human health from the harmful effects of mercury contamination.
Used in Pharmaceutical and Medical Research:
DIPHENYLCARBAZONE's sensitivity to mercury also makes it useful in pharmaceutical and medical research. It can be employed as a diagnostic tool to detect mercury intoxication or to study the effects of mercury on biological systems. Additionally, its reactivity with mercury can be utilized in the development of new drugs or therapies targeting mercury-related conditions.

Purification Methods

It crystallises from EtOH (ca 5mL/g), and dry the orange-red needles at 50o. A commercial sample, nominally sym-diphenylcarbazone (m 154-156o) was a mixture of diphenylcarbazide and diphenylcarbazone. The former was removed by dissolving 5g of the crude material in 75mL of warm EtOH, then adding 25g Na2CO3 dissolved in 400mL of distilled water. The alkaline solution was cooled and extracted six times with 50mL portions of diethyl ether (discarded). Diphenylcarbazone was then precipitated by acidifying the alkaline solution with 3M HNO3 or glacial acetic acid. It was filtered off, air dried, and stored in the dark [Gerlach & Frazier Anal Chem 30 1142 1958]. Other impurities are phenylsemicarbazide and diphenylcarbodiazone. Impurities can be detected by chromatography [Willems et al. Anal Chim Acta 51 544 1970]. It is used for detection and estimation of Hg, Zn, Cd, Cr, Cu, Fe and Mo [Cheng et al. Handbook of Organic Analytical Reagents, Boca Baton 277 1982, Beilstein 16 H 24, 16 IV 17.]

InChI:InChI=1/C13H12N4O/c18-13(16-14-11-7-3-1-4-8-11)17-15-12-9-5-2-6-10-12/h1-10,14H,(H,16,18)/b17-15-

Synthetic route

1,5-diphenyl-thiocarbazone (60-10-6) → diphenylcarbazone (538-62-5)

Conditions	Yield
With Oxone for 0.333333h;	99%
With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 0.25h; Heating;	99%
With quinolinium monofluorochromate(VI) In acetonitrile for 0.5h; Heating;	97%

1,5-diphenylcarbazide (140-22-7) → diphenylcarbazone (538-62-5)

Conditions	Yield
With sodium hydrogen sulfate; silica gel; sodium nitrite In dichloromethane at 20℃;	95%
With acetic anhydride; sodium nitrite In dichloromethane at 20℃; for 0.833333h;	94%
With sulfuric acid; iron(III) chloride In acetone for 0.5h; Ambient temperature;	91%

furan-2,3,5(4H)-trione pyridine (1:1) + 1,5-diphenylcarbazide (140-22-7) + air oxygen → diphenylcarbazone (538-62-5)

1,5-diphenylcarbazide (140-22-7) + alcoholic KOH-solution + air oxygen → diphenylcarbazone (538-62-5)

potassium salt of phenylazoformic acid phenylhydrazide → diphenylcarbazone (538-62-5)

Conditions	Yield
With sulfuric acid

nickel diphenylcarbazonate + benzoin oxime (441-38-3) → nickel (α-benzoin oximate)2 + diphenylcarbazone (538-62-5)

Conditions	Yield
In chloroform CHCl3-soln. of α-benzoin oxime is added to metal diphenylcarbazonate.;

palladium diphenylcarbazonate + benzoin oxime (441-38-3) → palladium (α-benzoin oximate)2 + diphenylcarbazone (538-62-5)

Conditions	Yield
In chloroform CHCl3-soln. of α-benzoin oxime is added to metal diphenylcarbazonate.;

copper diphenylcarbazonate + benzoin oxime (441-38-3) → copper (α-benzoin oximate)2 + diphenylcarbazone (538-62-5)

Conditions	Yield
In chloroform Refluxing α-benzoin oxime and copper salt in ethanolic soln..;

cadmium diphenylcarbazonate + benzoin oxime (441-38-3) → cadmium (α-benzoin oximate)2 + diphenylcarbazone (538-62-5)

Conditions	Yield
In chloroform CHCl3-soln. of α-benzoin oxime is added to metal diphenylcarbazonate.;

cobalt diphenylcarbazonate + benzoin oxime (441-38-3) → cobalt (α-benzoin oximate)2 + diphenylcarbazone (538-62-5)

Conditions	Yield
In chloroform CHCl3-soln. of α-benzoin oxime is added to metal diphenylcarbazonate.;

phenylmercury(II) chloride (100-56-1) + diphenylcarbazone (538-62-5) → C6H5Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	85%

4-Bromphenylquecksilberchlorid (28969-28-0) + diphenylcarbazone (538-62-5) → C6H4(Br)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	85%

4-chlorophenylmercury chloride (1802-38-6) + diphenylcarbazone (538-62-5) → C6H4(Cl)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	85%

2-Methoxyphenylmercuric chloride (10366-02-6) + diphenylcarbazone (538-62-5) → C6H4(OCH3)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	80%

Di-tert-butyl acetylenedicarboxylate (66086-33-7) + triphenylphosphine (603-35-0) + diphenylcarbazone (538-62-5) → C43H45N4O5P

Conditions	Yield
In acetone at -10 - 20℃;	79.5%

p-anisylmercuric chloride (3009-79-8) + diphenylcarbazone (538-62-5) → C6H4(OCH3)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	78%

4-hydroxymethyl-phenylmercury (1+); chloride (23000-61-5) + diphenylcarbazone (538-62-5) → C6H4(CH2OH)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	78%

chloro(2-hydroxymethylphenyl)mercury (91713-41-6) + diphenylcarbazone (538-62-5) → C6H4(CH2OH)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	76%

dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) + diphenylcarbazone (538-62-5) → C37H33N4O5P

Conditions	Yield
In acetone at -10 - 20℃;	75.4%

4-hydroxyphenyl mercury(II) chloride (623-07-4) + diphenylcarbazone (538-62-5) → C6H4(OH)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	75%

(2-hydroxyphenyl)mercury chloride (90-03-9) + diphenylcarbazone (538-62-5) → C6H4(OH)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	72%

p-chloromercuribenzoic acid (59-85-8) + diphenylcarbazone (538-62-5) → C6H4(COOH)Hg[C6H5NNCONNHC6H5]

Conditions	Yield
With perchlorate buffer In tetrachloromethane; water a soln. of the arylmercuric chloride in perchlorate buffer (pH 7) is shaken with a soln. of diphenylcarbazone in CCl4 for 20 min; the organic layer is separated, the solvent is evapd. under reduced pressure, the residue is washed, elem. anal.;	70%

germaniumtetrachloride (10038-98-9) + diphenylcarbazone (538-62-5) → [Ge(C6H5NHNCONNC6H5)2Cl2]

Conditions	Yield
In benzene byproducts: diphenylcarbazone hydrochloride; Ge : ligand molar ratio of 1 : 2, stirring for 10 min at room temp.; filtration, evapn., crystn., washing with pentane, drying in vac.; elem. anal.;	60%

praseodymium(III) nitrate hydrate + diphenylcarbazone (538-62-5) → [Pr(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

56%

samarium(III) nitrate hydrate + diphenylcarbazone (538-62-5) → [Sm(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

52%

cerium(III) nitrate hydrate + diphenylcarbazone (538-62-5) → [Ce(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

51%

neodymium(III) nitrate hydrate + diphenylcarbazone (538-62-5) → [Nd(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

50%

lanthanum(III) nitrate hydrated + diphenylcarbazone (538-62-5) → [La(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

48%

dysprosium(III) nitrate hydrate + diphenylcarbazone (538-62-5) → [Dy(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

45%

holmium(III) nitrate hydrate + diphenylcarbazone (538-62-5) → [Ho(diphenylcarbazone)2(NO3)2]NO3*2H2O

Conditions

Yield

With aq. ammonia In ethanol; water byproducts: H2O; a soln. of ligand (0.01 mol) in abs. alcohol was added gradually to a soln. of lanthanide(III) nitrate (0.005 mol) in a min. amt. of double distd. H2O; room temp.; the mixt. was stirred for 4 h; dil. aq. ammonia wasadded (pH ca. 6); the complex was filtered by suction, washed with water and dried under vac. at room temp.; purifn. by the Soxhlet method; elem. anal.;

42%

tetrabutylammonium octamolybdate + diphenylcarbazone (538-62-5) → {n-Bu4N}{MoO2(PhNNC(O)NHNPh)(PhNNC(O)NNPh)}

Conditions	Yield
In dichloromethane excess of diphenylcarbazone, refluxed; addn. of diethyl ether, standing at room temp. for three days;	30%

tetrakis(tetrabutylammonium) octamolybdate + diphenylcarbazone (538-62-5) → {(n-Bu)4N}{MoOCl3(C6H5NNC(O)NNC6H5)} * CH2Cl2

Conditions	Yield
With concd. HCl In methanol addn. of concd. HCl to soln. of Mo-complex and org. compound in MeOH, stirring (12 h); evapn., dissolution (CH2Cl2), addn. of anhyd. ether, standing (8 d), collection; elem. anal.;	22%

tetrakis(tetrabutylammonium) octamolybdate + diphenylcarbazone (538-62-5) → {(n-Bu)4N}{MoO2(C6H5NNC(O)NNC6H5)(C6H5(H)NNC(O)NNC6H5)}

Conditions	Yield
In dichloromethane dissolution of Mo-complex in warm CH2Cl2, cooling to room temp., addn. of org. compound, stirring overnight, concn., addn. of anhyd. ether, pptn. on standing (2 weeks); filtration, washing (ether), air drying (room temp.); elem. anal.;	15%

diphenylcarbazone (538-62-5) → 2,3-diphenyl-1,2,3,4-tetrazolium-5-olate (6888-71-7)

Conditions	Yield
With ethanol; silver(I) acetate
With ammonia; water unter Zusatz von CuSO4;

9,9'-oxydi(9-boraxanthene) (95925-64-7) + diphenylcarbazone (538-62-5) → 1-phenoxaborin-10-yl-1,5-diphenyl-carbazone (106952-49-2)

Conditions	Yield
In acetic acid

pyridine (110-86-1) + diphenylcarbazone (538-62-5) → C13H12N4O*C5H5N*Zn(2+)

Conditions	Yield
With zinc(II) cation

Upstream product

• 441-38-3 benzoin oxime 
• 140-22-7 1,5-diphenylcarbazide 
• 60-10-6 1,5-diphenyl-thiocarbazone 

Downstream Products

• 108171-31-9 Fe(III)-tris-diphenylcarbazonate 
• 441-38-3 benzoin oxime 

Relevant academic research and scientific papers

Rhodamine B degradation and reactive oxygen species generation by a ZnSe-graphene/TiO2 sonocatalyst

Nanostructured ZnSe-graphene/TiO2 was synthesized by a hydrothermal-assisted approach. ZnSe-graphene/TiO2 exhibited favorable adsorption of rhodamine B, a wide wavelength absorption range, and efficient charge separation. Reactive oxygen species were generated by the oxidation of 1,5-diphenyl carbazide to 1,5-diphenyl carbazone. The sonocatalytic reaction mechanism was proposed. These findings potentially broaden the applications of sonocatalytic technologies.

Spectroscopic analyses on ROS generation catalyzed by TiO2, CeO2/TiO2 and Fe2O3/TiO2 under ultrasonic and visible-light irradiation

In this work, the TiO2, CeO2/TiO2 and Fe2O3/TiO2 powders were irradiated, respectively, by ultrasound and visible-light, and the generation of reactive oxygen species (ROS) were estimated by the method of Oxidation-Extraction Photometry (OEP). That is, the 1,5-diphenyl carbazide (DPCI) can be oxidized by generated ROS into 1,5-diphenyl carbazone (DPCO), which can be extracted by mixed solvent of benzene and carbon tetrachloride. The DPCO extract liquor displays an obvious absorbance at 563 nm wavelength. In addition, some influencing factors, such as (ultrasonic or visible-light) irradiation time, catalyst addition amount and DPCI concentration, on the generation of ROS were also reviewed. The results indicated that the quantities of generated ROS increase with the increase of (ultrasonic or visible-light) irradiation time and catalyst addition amount. Moreover, the displayed quantities of ROS are also related with DPCI concentration. And then, several radical scavengers were used to determine the kinds of the generated ROS. At last, the researches on the sonocatalytic and photocatalytic degradation of several organic dyes have also been performed. It is wished that this paper might offer some important subjects for broadening the applications of sonocatalytic and photocatalytic technologies in future environment treatment.

Solid state selective synthesis of diaryl carbazone

The selective synthesis of diaryl carbazone using K3Fe(CN)6 as oxidant under alkaline condition in solid state is reported for the first time. Eight diaryl carbazone have been synthesized in excellent yields, and this method only needs cheap reagents, and simple procedure under mild condition.

Protein damage and reactive oxygen species generation induced by the synergistic effects of ultrasound and methylene blue

The sonodynamic damage to protein in the presence of methylene blue (MB) and the various influencing factors including ultrasonic irradiation time and MB concentration on the damage of protein were studied by fluorescence and absorption spectra. In addition, the mechanisms of the synergistic effects of ultrasound and MB were studied by oxidation-extraction photometry with several reactive oxygen species (ROS) scavengers. The results indicated that the damage of protein induced by the synergistic effects of ultrasound and MB were more serious than those that ultrasound or MB alone was applied. The damage of protein could be mainly due to the generation of ROS. The damage degree of protein increased with the increase of ultrasonic irradiation time and MB concentration because of the increased quantities of ROS generation. Both 1O2 and OH were the important mediators of the ultrasound-inducing protein damage in the presence of MB.

Rapid synthesis of diaryl carbazone by N-bromosuccinimide and pyridine as the oxidation system

A new and rapid synthetic method of diaryl carbazone (ArN=NCONHNHAr) from aryl substituted carbazide is reported for the first time. Eight of the compounds were prepared by oxidation of aryl substituted carbazide using N- Bromosuccinimide and pyridine as the oxidation system in good yield under mild condition. This method only need simple instrument and short reaction time. A possible mechanism is suggested.

An efficient and convenient procedure for preparation of diaryl carbazone from aryl substituted carbazide

A new facile method for the synthesis of diaryl carbazone (ArN=NCONHNHAr) from aryl substituted carbazide is described. Eight of the compounds were preparated by oxidation of aryl substituted carbazide with ferric chloride in acid medium at room temperature in good yield.

A facile preparation of graphene-based MxSy visible light driven photocatalyst and study of photochemically generating of oxygen species

The as-synthesized graphene-MxSy (Sb2S3, MnS2, SnS) composites via a facile hydrothermal method efficiently catalyzed the photodegradation of methylene orange (MO) with high concentration in aqueous solutions under visible light irradiation. The generation of reactive oxygen species were detected through the oxidation reaction from 1,5-diphenyl carbazide (DPCI) to 1,5-diphenyl carbazone (DPCO). Based on the high photocatalytic activity, the graphene-SnS composite can be expected to be a practical visible light photocatalyst.

Bubble template synthesis of CdLa2S4 hollow spheres/reduced graphene oxide nanocomposites as efficient and sustainable visible-light driven photocatalysts

A hollow sphere CdLa2S4/reduced graphene oxide (rGO) composite was successfully synthesized for the first time via a simple microwave assisted hydrothermal approach using bubbles generated from the decomposition of NH3H2O and Na2S2O3 in a domestic microwave oven within several minutes. The large number of catalytic active sites together with the advantages of the hollow structure makes the as-synthesized CdLa2S4/rGO composite an efficient catalyst for the degradation of rhodamine B (RhB) and industrial dyes such as Texbrite BA-L (TBA) at high concentration in aqueous solutions. The oxidation reaction of 1,5-diphenyl carbazide (DPCI) by a generated reactive oxygen species (ROS) that has very strong oxidizing power could be attributed to the excellent photoinduced charge separation abilities and observed red shift in these hybrid semiconductor materials. Moreover, the synthesized catalyst can be easily recovered and reused for at least four cycles due to its good stability. The results confirm that as-synthesized CdLa2S4/rGO composites are promising potential candidates for high-performance visible light driven photocatalyst materials.

Efficient and convenient deprotection of thiocarbonyl to carbonyl compounds using 3-carboxypyridinium and 2,2′-bipyridinium chlorochromates in solution, dry media, and under microwave irradiation

A synthetic utility of 3-carboxypyridinium (CPCC) and 2,2′- bipyridinium (BPCC) chlorochromates in deprotection reactions is reported. Different types of thioamides, thioureas, thiono esters, and thioketones are deprotected to their corresponding carbonyl compounds with these reagents in good to excellent yields. The reactions were carried out in solution, under solvent-free conditions, and under microwave irradiation. The results show that with both reagents the rates of the reactions and the yields are usually highest under microwave irradiation. Springer-Verlag 2003.

A convenient and inexpensive method for conversion of thiocarbonyl compounds to their oxo derivatives using oxone under solvent-free conditions

A series of thioamides, thioureas and thioesters are transformed to their corresponding carbonyl compounds in good to excellent yields with oxone under solid phase conditions, while thioketones remained unchanged under these conditions.