Benzophenone hydrazone

Base Information

• Chemical Name: Benzophenone hydrazone
• CAS No.: 5350-57-2
• Molecular Formula: C13H12N2
• Molecular Weight: 196.252
• Hs Code.: 2928.00 DERIVATION
• European Community (EC) Number: 226-321-8
• NSC Number: 43
• UNII: S2WWI81YAL
• DSSTox Substance ID: DTXSID6063806
• Nikkaji Number: J1.834A
• ChEMBL ID: CHEMBL1881268
• Mol file: 5350-57-2.mol

Synonyms:Benzophenone hydrazone;5350-57-2;(diphenylmethylene)hydrazine;Methanone, diphenyl-, hydrazone;Diphenylmethanone hydrazone;Benzophenonehydrazone;benzhydrylidenehydrazine;Benzophenone, hydrazone;Diphenyl ketone hydrazone;(diphenylmethylidene)hydrazine;Diphenyldiazomethane precursor;NSC 43;benzhydrylidene-hydrazine;EINECS 226-321-8;S2WWI81YAL;Diphenylmethylidenehydrazine;AI3-52536;NSC-43;Diphenylhydrazon;Methanone, hydrazone;MFCD00007624;Diphenylketone hydrazone;UNII-S2WWI81YAL;BENZOPHENONHYDRAZONE;Benzophenoneimine N-amino-;Methanone diphenyl hydrazone;Benzophenonehydrazone (BPH);NSC43;Benzophenone hydrazone, 96%;CBDivE_000311;di(phenyl)methylidenehydrazine;Diphenylmethanone hydrazone #;MLS001181010;1-(diphenylmethylene)hydrazine;SCHEMBL1141828;CHEMBL1881268;DTXSID6063806;QYCSNMDOZNUZIT-UHFFFAOYSA-;HMS1577E15;HMS2776F08;STK328083;N-(DIPHENYLMETHYLENE)HYDRAZINE;AKOS000119692;CS-W010590;AS-11962;Benzophenone, hydrazone (6CI,7CI,8CI);LS-91250;SMR000475984;B1163;FT-0622721;EN300-19840;E82988;AB00374770-05;AE-848/30735021;W-105728;F9995-0250

Chemical Property of Benzophenone hydrazone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Melting Point: 95-98 °C(lit.)
• Refractive Index: 1.677
• Boiling Point: 328 °C at 760 mmHg
• PKA: 1.44±0.70(Predicted)
• Flash Point: 152.1 °C
• PSA: 38.38000
• Density: 1.05 g/cm³
• LogP: 3.09800
• Storage Temp.: 0-6°C
• Solubility.: Soluble in ether, benzene, chloroform and other organic solvents
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 196.100048391
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

99.5% ^*data from raw suppliers

Benzophenone hydrazone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-20/21/22
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: C1=CC=C(C=C1)C(=NN)C2=CC=CC=C2
• Uses: An important compound in organic photochemistry and perfumery as well as in organic synthesis. Used in the antibiotics synthesis of 6-APA and 7-ACA of the carboxyl protecting groups and other organic compounds. Used as organic pigment and medical intermediate. It is used as a photoinitiator of UV-curing applications in inks, adhesive, coatings and optical fiber.

Technology Process of Benzophenone hydrazone

There total 19 articles about Benzophenone hydrazone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzophenone (119-61-9) → benzophenone hydrazone (5350-57-2)

Guidance literature:

With hydrazine hydrate; In ethanol; for 12h; Heating;

DOI:10.1080/00397910600977574

Reference yield: 95.2%

benzophenone (119-61-9) + hydrazine hydrate (7803-57-8,79785-97-0) → benzophenone hydrazone (5350-57-2)

Guidance literature:

With 1-butyl-3-methylimidazolium Tetrafluoroborate; at 100 ℃; for 4h;

DOI:10.1080/00397911.2010.517612

Reference yield: 95.0%

Benzophenone oxime (574-66-3) → benzophenone hydrazone (5350-57-2)

Guidance literature:

With hydrazine hydrate; In ethanol; for 1h; Heating;

DOI:10.1081/SCC-200034750

upstream raw materials:

benzophenone

ethanol

diphenyldiazomethane triphenylphosphazine

benzophenone-(triethylphosphoranylidene-hydrazone)

Downstream raw materials:

Diphenylmethane

2,6-dibromo-[1,4]benzoquinone-4-benzhydrylidenehydrazone

N-phenyl benzoyl amide

benzophenone azine

Refernces

Hypervalent-iodine(iii) oxidation of hydrazones to diazo compounds and one-pot nickel(ii)-catalyzed cyclopropanation

10.1039/c5nj02378e

The study presents a novel one-pot method for the catalytic cyclopropanation of various alkenes with unsubstituted hydrazones. The process utilizes iodosobenzene as an oxidant to convert hydrazones into diazo compounds, which are then cyclopropanated in the presence of a nickel(II) catalyst, Ni(OH)2. This method allows for the efficient generation of cyclopropane products under mild conditions (80°C) within a short time frame (5 minutes to 4 hours) and with moderate to good yields (42–91%). The protocol is applicable to a wide range of substrates, including aryl alkenes with different electronic effects, aliphatic alkenes with halogen functional groups, and alkyl acrylates. The study also explores the reaction mechanism and provides a promising approach to synthesizing cyclopropane compounds, which are prevalent in natural products and have significant value in pharmaceutical chemistry.

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