Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 12h; Heating; | 100% |
With hydrazine hydrate; acetic acid In ethanol at 100℃; for 21h; Inert atmosphere; | 100% |
With hydrazine hydrate In ethanol for 4h; Reflux; | 100% |
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol for 1h; Heating; | 95% |
With hydrazine hydrate In diethylene glycol for 1h; Heating; |
diazodiphenylmethane
benzophenone hydrazone
Conditions | Yield |
---|---|
With tetramethylammonium tetrafluoroborate; benzoic acid In N,N-dimethyl-formamide at 23℃; Product distribution; other proton donors, other temp.; electrolytic reduction; | 86% |
Conditions | Yield |
---|---|
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 100℃; for 4h; | 95.2% |
diazodiphenylmethane
A
benzophenone
B
Diphenylmethane
C
benzophenone hydrazone
D
benzophenone azine
E
N-benzhydrylbenzophenone hydrazone
Conditions | Yield |
---|---|
With 2,2,2-trifluoroethanol; tetrabutylammonium perchlorate In N,N-dimethyl-formamide Product distribution; Ambient temperature; electrolytic reduction; other reagents, reagent ratio, potentials; | A 0.1% B 88% C 2.5% D 0.5% E 0.4% |
diazodiphenylmethane
A
benzophenone
B
Diphenylmethane
C
benzophenone hydrazone
D
N-benzhydrylbenzophenone hydrazone
Conditions | Yield |
---|---|
With tetrabutylammonium perchlorate; diethyl malonate In N,N-dimethyl-formamide at 20 - 23℃; Pt-cathode; Further byproducts given; | A 1% B 85% C 7.6% D 3% |
A
[Ni(1,5,9-cyclododecatriene)]
B
benzophenone hydrazone
C
nickel
Conditions | Yield |
---|---|
In diethyl ether byproducts: N2; heating cautiously to 20°C; | A 89% B n/a C n/a |
benzophenone semicarbazone
benzophenone hydrazone
Conditions | Yield |
---|---|
With silica gel In dichloromethane Microwave irradiation; |
Conditions | Yield |
---|---|
With silica gel In dichloromethane Microwave irradiation; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: manganese(IV) oxide / 130 °C / Microwave irradiation 2: toluene-4-sulfonic acid; hydrazine hydrate / ethanol / 6.5 h / Reflux View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol Reflux; |
diazodiphenylmethane
A
Diphenylmethane
B
benzophenone hydrazone
C
benzophenone azine
D
N-benzhydrylbenzophenone hydrazone
Conditions | Yield |
---|---|
With tetrabutylammonium perchlorate; diethyl malonate In N,N-dimethyl-formamide at 20 - 23℃; Mechanism; interm. anion radicals, var. temp.; | A 34% B 37% C 0.3% D 2.5% |
With tetrabutylammonium perchlorate; diethyl malonate In N,N-dimethyl-formamide at 20 - 23℃; Pt-cathode; | A 34% B 37% C 0.3% D 2.5% |
diphenyldiazomethane triphenylphosphazine
A
benzophenone hydrazone
B
triphenylphosphine
C
benzophenone azine
D
diphenylphosphane
E
Benzhydrylamine
Conditions | Yield |
---|---|
With sodium In tetrahydrofuran for 45h; Mechanism; | A 5.5% B 38% C 30% D 25% E 40% |
Conditions | Yield |
---|---|
at 150℃; im Rohr; |
ethanol
benzophenone-(triethylphosphoranylidene-hydrazone)
benzophenone hydrazone
ethanol
diphenyldiazomethane triphenylphosphazine
A
benzophenone hydrazone
B
Triphenylphosphine oxide
ethanol
diazodiphenylmethane
A
Diphenylmethane
B
benzophenone hydrazone
Conditions | Yield |
---|---|
Hydrogenation; |
benzophenone hydrazone
diazodiphenylmethane
Conditions | Yield |
---|---|
With lead(IV) acetate; 1,1,3,3-tetramethylguanidine In dichloromethane at -78℃; | 100% |
With sodium sulfate; potassium hydroxide; mercury(II) oxide In diethyl ether; ethanol for 1h; | 100% |
With sodium sulfate; potassium hydroxide; mercury(II) oxide In diethyl ether; ethanol for 1h; | 100% |
benzophenone hydrazone
Conditions | Yield |
---|---|
With caesium carbonate; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In toluene at 100℃; for 4.5h; | 100% |
1-(4-bromobenzyl)-4-methanesulfonylpiperazine
benzophenone hydrazone
N-benzhydrylidene-N'-[4-(4-methanesulfonylpiperazin-1-ylmethyl)phenyl]hydrazine
Conditions | Yield |
---|---|
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene at 105℃; for 4h; | 100% |
methyl 3-(4-bromophenyl)-2,2-dimethyl-3-phenylpropanoate
benzophenone hydrazone
C31H30N2O2
Conditions | Yield |
---|---|
With caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In toluene at 95℃; for 12h; | 100% |
benzophenone hydrazone
5-Bromo-2-fluoro-benzonitrile
Conditions | Yield |
---|---|
With sodium hydroxide; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tert-Amyl alcohol at 103℃; for 12h; | 100% |
4-chloropentanoyl chloride
benzophenone hydrazone
4-Chloro-N'-(diphenylmethylene)pentane hydrazide
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 16h; | 100% |
benzophenone hydrazone
Conditions | Yield |
---|---|
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 105℃; for 16h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
at 100℃; for 0.0166667h; Microwave irradiation; Green chemistry; | 100% |
Conditions | Yield |
---|---|
at 100℃; for 0.0166667h; Microwave irradiation; Green chemistry; | 100% |
Conditions | Yield |
---|---|
at 100℃; for 0.0166667h; Microwave irradiation; Green chemistry; | 100% |
benzophenone hydrazone
Conditions | Yield |
---|---|
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.05h; Inert atmosphere; Stage #2: 2-bromo-5-(2,6-dichloro-4-nitrophenoxy)benzonitrile With caesium carbonate In toluene at 100℃; for 5h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 25 - 45℃; for 0.416667h; | 99% |
With iron(III) chloride In chloroform for 3h; Reflux; | 99% |
With iron(III) chloride In chloroform for 3h; Time; Reflux; | 99% |
benzophenone hydrazone
cyclohexanone
1-cyclohexylidene-2-(diphenylmethylene)hydrazine
Conditions | Yield |
---|---|
In ethanol for 16h; Reflux; | 99% |
Conditions | Yield |
---|---|
99% |
para-bromotoluene
benzophenone hydrazone
N-(4-methylphenyl) benzophenone hydrazone
Conditions | Yield |
---|---|
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; Arylation; | 99% |
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; | 97% |
With sodium hydroxide; 2-(dicyclohexylphosphino)-2'-methylbiphenyl; palladium diacetate In tert-Amyl alcohol at 103℃; for 3h; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; Temperatures; | 92% |
2-methylphenyl bromide
benzophenone hydrazone
N-(2-methylphenyl)benzophenone hydrazone
Conditions | Yield |
---|---|
With sodium t-butanolate; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate In toluene at 90℃; for 8h; | 99% |
With sodium hydroxide; 2-(dicyclohexylphosphino)-2'-methylbiphenyl; palladium diacetate In tert-Amyl alcohol at 103℃; | 85% |
Stage #1: 2-methylphenyl bromide With sodium hydroxide In tert-Amyl alcohol Heating; Stage #2: benzophenone hydrazone With 2-(dicyclohexylphosphino)-2'-methylbiphenyl; palladium diacetate In tert-Amyl alcohol at 103℃; | 85% |
2-chloropyridine
benzophenone hydrazone
2-[2-(diphenylmethylene)hydrazinyl]pyridine
Conditions | Yield |
---|---|
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 70℃; for 16h; | 99% |
With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; palladium diacetate In toluene at 100℃; for 16h; | 70% |
Conditions | Yield |
---|---|
With (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl di-t-butylphosphine; sodium t-butanolate; palladium diacetate In 1,2-dimethoxyethane at 70℃; for 16h; | 99% |
benzophenone hydrazone
o-cyanobromobenzene
2-(2-(diphenylmethylene)hydrazinyl)benzonitrile
Conditions | Yield |
---|---|
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.05h; Inert atmosphere; Stage #2: o-cyanobromobenzene With caesium carbonate In toluene at 20 - 100℃; for 7h; Inert atmosphere; | 99% |
Stage #1: benzophenone hydrazone With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 0.25h; Inert atmosphere; Stage #2: o-cyanobromobenzene With caesium carbonate In toluene at 100℃; for 43h; Inert atmosphere; | 74% |
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 12h; Inert atmosphere; |
benzophenone hydrazone
2,5-hexanedione
N-(diphenylmethylidene)-2,5-dimethyl-1H-pyrrol-1-amine
Conditions | Yield |
---|---|
With sulfated anatase In neat (no solvent) at 20℃; for 0.05h; Paal-Knorr Pyrrole Synthesis; Milling; Green chemistry; | 99% |
Conditions | Yield |
---|---|
In neat (no solvent) Heating; Inert atmosphere; Sealed tube; | 99% |
at 40℃; for 12h; | 98% |
at 40℃; for 12h; | 98% |
In ethanol at 40℃; for 4h; | 98% |
In ethanol at 40℃; for 4h; | 98% |
Conditions | Yield |
---|---|
In neat (no solvent) Heating; Inert atmosphere; Sealed tube; | 99% |
at 40℃; for 12h; Concentration; | 93% |
at 40℃; for 12h; | 93% |
Stage #1: 1,1-difluoroacetone; benzophenone hydrazone In ethanol at 40℃; for 3h; Stage #2: With sodium hydrogencarbonate In ethanol for 1h; | |
In ethanol at 40℃; for 3h; |
Conditions | Yield |
---|---|
With pyridine In dichloromethane | 99% |
Conditions | Yield |
---|---|
Stage #1: benzophenone hydrazone With chloro-trimethyl-silane; sodium iodide In acetonitrile at 20℃; Stage #2: With water In acetonitrile for 0.0833333h; | 98% |
With copper(II) sulfate In tetrahydrofuran; methanol; water for 3.5h; Heating; | 90% |
With dinitrogen tetraoxide In acetonitrile at -40℃; for 0.166667h; | 85% |
bromochlorobenzene
benzophenone hydrazone
N-benzhydrylidene-N'-(4-chlorophenyl)-hydrazine
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 80℃; for 1.5h; Arylation; | 98% |
With sodium hydroxide; 2-(dicyclohexylphosphino)-2'-methylbiphenyl; palladium diacetate In tert-Amyl alcohol at 103℃; | 97% |
Stage #1: bromochlorobenzene With sodium hydroxide In tert-Amyl alcohol Heating; Stage #2: benzophenone hydrazone With 2-(dicyclohexylphosphino)-2'-methylbiphenyl; palladium diacetate In tert-Amyl alcohol at 103℃; | 97% |
3-methoxyphenyl bromide
benzophenone hydrazone
N-(3-methoxyphenyl) benzophenone hydrazone
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 80℃; for 6h; Arylation; | 98% |
With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene at 100℃; | 95% |
With bis(triphenylphosphine)nickel(II) chloride; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 50℃; for 5h; Inert atmosphere; | 59% |
benzophenone hydrazone
cyclohexa-1,3-diene
1-(cyclohex-2-enyl)-2-(diphenylmethylene)hydrazine
Conditions | Yield |
---|---|
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(η3-allyl-μ-chloropalladium(II)) In dichloromethane at 23℃; for 24h; | 98% |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; water; hydrazine hydrate In ethanol at 100℃; Reagent/catalyst; | 97% |
With potassium hydroxide for 0.5h; Reduction; Wolff-Kishner reduction; microwave irradiation; | 95% |
With castor soap at 240℃; for 4h; | 50% |
With potassium hydroxide In diethylene glycol for 3.5h; Wolff-Kishner reduction; Heating; | |
With potassium hydroxide In ethylene glycol at 200℃; Wolff-Kishner Reduction; |
1.4-dibromobenzene
benzophenone hydrazone
N-benzhydrylidene-N'-(4-bromophenyl)-hydrazine
Conditions | Yield |
---|---|
With palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 80℃; for 4h; Arylation; | 97% |
With bis(triphenylphosphine)nickel(II) chloride; sodium t-butanolate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 1,4-dioxane at 50℃; for 5h; Inert atmosphere; | 50% |
The Benzophenone Hydrazone is an organic compound with the formula C13H12N2. The IUPAC name of this chemical is benzhydrylidenehydrazine. With the CAS registry number 5350-57-2, it is also named as (Diphenylmethylene)hydrazine. The product's categories are Pharmaceutical Intermediates; Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes; Phenylhydrazine; Heterocyclic Compounds. Besides, it is a white to light yellow crystal powder, which should be stored in a dark cool and closed place. It can be used for intermediates of organic pigments and pharmaceutical.
Physical properties about Benzophenone Hydrazone are: (1)ACD/LogP: 2.79; (2)ACD/LogD (pH 5.5): 2.79; (3)ACD/LogD (pH 7.4): 2.79; (4)ACD/BCF (pH 5.5): 77.69; (5)ACD/BCF (pH 7.4): 77.7; (6)ACD/KOC (pH 5.5): 784.71; (7)ACD/KOC (pH 7.4): 784.8; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 15.6 Å2; (12)Index of Refraction: 1.583; (13)Molar Refractivity: 62.32 cm3; (14)Molar Volume: 186.3 cm3; (15)Polarizability: 24.7×10-24cm3; (16)Surface Tension: 41.7 dyne/cm; (17)Density: 1.05 g/cm3; (18)Flash Point: 152.1 °C; (19)Enthalpy of Vaporization: 57.03 kJ/mol; (20)Boiling Point: 328 °C at 760 mmHg; (21)Vapour Pressure: 0.000196 mmHg at 25°C.
Preparation: this chemical can be prepared by benzophenone. This reaction will need reagent anhydrous ethanol and hydrazine.
Uses of Benzophenone Hydrazone: it can be used to produce diazo-diphenyl-methane at ambient temperature. It will need reagent methanol and CH2Cl2.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: N(/N)=C(/c1ccccc1)c2ccccc2
(2)InChI: InChI=1/C13H12N2/c14-15-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,14H2
(3)InChIKey: QYCSNMDOZNUZIT-UHFFFAOYAR
(4)Std. InChI: InChI=1S/C13H12N2/c14-15-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,14H2
(5)Std. InChIKey: QYCSNMDOZNUZIT-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 134mg/kg (134mg/kg) | Pharmaceutical Chemistry Journal Vol. 27, Pg. 58, 1993. |
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