IdentificationPhysical DataSpectraRoute of Synthesis (ROS)Safety and HazardsOther Data
Identification
Product Name5-Chloro-2-(methylamino)benzophenoneIUPAC Name-phenylmethanone Molecular StructureCAS Registry Number 1022-13-5EINECS Number213-822-1MDL NumberMFCD00008284Synonyms1022-13-55-Chloro-2-(methylamino)benzophenone5-Chloro-2-methylaminobenzophenone(5-Chloro-2-(methylamino)phenyl)(phenyl)methanone2-Methylamino-5-chlorobenzophenoneMethanone, phenyl--phenylmethanoneBENZOPHENONE, 5-CHLORO-2-(METHYLAMINO)-2-benzoyl-4-chloro-N-methylanilineMFCD00008284(5-Chloro-2-(methylamino)phenyl)phenylmethanoneMethanone, (5-chloro-2-(methylamino)phenyl)phenyl-D4GD5770PIphenylmethanone-phenylmethanone (5-Chloro-2-(methylamino)benzophenone)BRN 0882187EINECS 213-822-1UNII-D4GD5770PI2-(Methylamino)-5-chlorobenzophenoneOprea1_680102BIDD:GT0238SCHEMBL333291DTXSID40614162-Methylamino-5-chlorbenzophenon2-Methylamino-5-chlorbenzophenoneAC1105Benzophenone, 2-acetamido-5-chloro-AKOS000120857CS-W012707HY-W0119912-(N-methylamino)-5-chlorobenzophenoneAC-10169AS-11966DIAZEPAM IMPURITY D PD163859SY037878TEMAZEPAM IMPURITY A DB-014567RO-5-43655-Chloro-2-(methylamino)benzophenone, 99%C2281CHLORO-2-METHYLAMINOBENZOPHENONE, 5-NS00023126EN300-20890A800545SR-01000395967Q-200536SR-01000395967-1-phenyl-methanoneQ27276093Z104484472Molecular FormulaC14H12ClNOMolecular Weight245.7InChIInChI=1S/C14H12ClNO/c1-16-13-8-7-11(15)9-12(13)14(17)10-5-3-2-4-6-10/h2-9,16H,1H3InChI KeyWPNMLCMTDCANOZ-UHFFFAOYSA-NIsomeric SMILESCNC1=C(C=C(C=C1)Cl)C(=O)C2=CC=CC=C2
Patent InformationPatent IDTitlePublication DateCN117229206Preparation method for synthesizing polysubstituted 2-quinolinone compound through base catalysis2023US6407111Phenyl substituted pyridine and benzene derivatives2002
Physical Data
AppearanceYellow crystalline powder
Melting Point, °C 89 - 9193 - 9494.2 - 95.494.3 - 95.494.3 - 95.294.2 - 95.394.2 - 95.1
Density, g·cm-31.385
Spectra
Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Frequency (NMR Spectroscopy), MHzChemical shifts, Spectrum1Hchloroform-d1600Chemical shifts, Spectrum13Cchloroform-d1150DEPT (Distorsionless Enhancement by Polarisation Transfer), Spectrum13Cchloroform-d1150Chemical shifts, Spectrum13Cchloroform-d1100Chemical shifts, Spectrum1Hchloroform-d1400Chemical shifts1Hchloroform-d1400Chemical shifts13Cchloroform-d1101
Description (IR Spectroscopy)Solvent (IR Spectroscopy)ATR (attenuated total reflectance), BandsBandsneat (no solvent, solid phase), sodium chlorideIntensity of IR bands, Bandspotassium bromideBandsBandspotassium bromideBandsKBr
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1Oscillator strength, Band assignment, Spectrumethanol406ethanol532Absorption maximamethanol235, 40020300, 6410Spectrumacetonitrile210 - 470 nmAbsorption maximaacetonitrile23619800Absorption maxima4126950
Route of Synthesis (ROS)
Route of Synthesis (ROS) of 5-Chloro-2-(methylamino)benzophenone CAS 1022-13-5
ConditionsYieldWith hydrazine hydrate; zinc(II) chloride In water at 20 - 30℃; for 4h; Temperature;Experimental Procedure3 Example 3:Add to the reaction bottleAqueous solution of N-methyl-3-phenyl-5-chloro-2,1-benzisoxazole methyl quaternary ammonium salt 500g(containing N-methyl-3-phenyl-5-chloro-2,1-benzisoxazole methyl quaternary ammonium salt 200g),3 g of zinc chloride and 90 g of an aqueous solution of hydrazine hydrate.The reaction was carried out at 20 to 30 ° C for 3 hours. Cool down, filter,Wash the filter cake with 200g of purified water and dry it.2-methylamino-5-chlorobenzophenone 135g,The yield was 97.7%, the melting point was 94.3 to 95.2 ° C, and the HPLC purity was 99.2%.97.7%With hydrazine hydrate; methylamine In water at 25 - 30℃; for 5h; Temperature;Experimental Procedure3 Example 3:500 g of an aqueous solution of N-methyl-3-phenyl-5-chloro-2,1-benzisoxazole methyl quaternary ammonium salt was added to the reaction flask (containingN-methyl-3-phenyl-5-chloro-2,1-benzisoxazole methyl quaternary ammonium salt 200 g), 2.4 g of monomethylamine aqueous solution and 60 g of aqueous hydrazine hydrate solution. The reaction was carried out at 25 to 30 ° C for 5 hours. The mixture was cooled, filtered, and washed with 200 g of purified water, and dried to obtain 135 g of 2-methylamino-5-chlorobenzophenone, the yield was 97.7%, the melting point was 94.3 to 95.1 ° C, and the HPLC purity was 99.3%.97.7%With Saccharomyces cerevisiae bakers' yeast In methanol at 20℃; for 8h; pH=7; aq. phosphate buffer; Microbiological reaction; shaking;92%With aluminium trichloride; zinc In tetrahydrofuran for 8h; Ambient temperature;62%
Safety and Hazards
Pictogram(s)SignalWarningGHS Hazard StatementsH315 (97.8%): Causes skin irritation H319 (97.8%): Causes serious eye irritation H335 (95.6%): May cause respiratory irritation Precautionary Statement CodesP261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501(The corresponding statement to each P-code can be found at the GHS Classification page.)
Other Data
DruglikenessLipinski rules componentMolecular Weight245.708logP4.273HBA2HBD1Matching Lipinski Rules4Veber rules componentPolar Surface Area (PSA)29.1Rotatable Bond (RotB)3Matching Veber Rules2
Use Pattern2-Methylamino-5-chlorobenzophenone is an essential intermediate primarily used in synthesizing diazepam and medazepam. These medications are widely used for their anxiolytic, sedative, and anticonvulsant properties. The structural characteristics of 2-Methylamino-5-chlorobenzophenone make it a valuable precursor for synthesizing various pharmacologically active compounds, especially in the benzodiazepine drug class.In diazepam synthesis, 2-Methylamino-5-chlorobenzophenone plays a crucial role by providing the necessary amino and chloroaromatic groups required for the cyclization process, forming the core structure of the medication. Medazepam, another benzodiazepine derivative, has similar sedative effects and is structurally related to diazepam. https://www.chemwhat.com/5-chloro-2-methylaminobenzophenone-cas-1022-13-5/
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