6276-48-8

Basic information

• Product Name: 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one
• Synonyms: 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one;4-Methyl-1H-1,5-benzodiazepine-2(3H)-one
• CAS NO: 6276-48-8
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.1992
• EINECS: 228-473-0
• Mol File: 6276-48-8.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 355.3°C at 760 mmHg
• Flash Point: 168.7°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 3.15E-05mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one(6276-48-8)
• EPA Substance Registry System: 1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one(6276-48-8)

Safety Data

• Hazardous Substances Data: 6276-48-8(Hazardous Substances Data)

Usage

Description

1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is a chemical compound that serves as a key intermediate in the synthesis of benzodiazepine pharmacophores, which are of significant medicinal interest. It is also an impurity found in Filbanserin (F336750), a drug used to treat hypoactive sexual desire disorder in females.

Uses

Used in Pharmaceutical Industry:
1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is used as a precursor in the preparation of benzodiazepine pharmacophores, including s-triazine derivatives, which exhibit medicinal properties and potential therapeutic applications.
Used in the Development of Filbanserin:
1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is an impurity in Filbanserin, a drug that acts as an agonist of the serotonin-5HT1A receptor and an antagonist of the 5-HT2A receptor. It is utilized in the treatment of hypoactive sexual desire disorder in females.
Used in Neurotransmitter Receptor Research:
1,3-dihydro-4-methyl-2H-1,5-benzodiazepin-2-one is also used in the study of its binding affinity to dopamine receptors, with Ki values ranging from 4-24 nM, which can provide insights into its potential role in modulating neurotransmitter activity and related disorders.

InChI:InChI=1/C10H10N2O/c1-7-6-10(13)12-9-5-3-2-4-8(9)11-7/h2-5H,6H2,1H3,(H,12,13)

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 95-54-5 1,2-diamino-benzene 
• 71-43-2 benzene 
• 90915-86-9 N-(2-nitrophenyl)-3-oxobutanamide 
• 141-97-9 ethyl acetoacetate 
• 127782-85-8 4-[2-[(E)-2-Amino-phenylimino]-prop-(E)-ylidene]-1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one 
• 137-07-5 2-amino-benzenethiol 
• 98-01-1 furfural 
• 487-89-8 Indole-3-carboxaldehyde 
• 120-57-0 piperonal 
• 104-88-1 4-chlorobenzaldehyde 
• 100-52-7 benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 3967-01-9 4-methyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one 
• 80948-05-6 4a-methyl-2,3-diphenyl-4a,6,7,11b-tetrahydro-1H,5H-1,3-oxazino<3,2-a>-1,5-benzodiazepin-1,6-dion 
• 122773-86-8 acetoacetic acid N-(2-acetamidophenyl)amide 
• 115847-05-7 4-[(E)-2-(3-Nitro-phenyl)-vinyl]-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 83773-11-9 1H-3-p-nitrobenzylidene-2,3-dihydro-4-methyl-1,5-benzodiazepin-2-one 
• 115847-04-6 4-(p-nitrostyryl)-2,3-dihydro-1H-1,5-benzodiazepin-2-one 
• 127535-63-1 3a-Methyl-1-phenyl-3a,4-dihydro-6H-3-oxa-2,6,10b-triaza-benzo[e]azulen-5-one 
• 83773-14-2 3-[1-(4-Dimethylamino-phenyl)-meth-(E)-ylidene]-4-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 106366-68-1 3a-Methyl-5-oxo-1,3-diphenyl-3a,4,5,6-tetrahydro-3H-<1,2,4>triazolo<4,3-a><1,5>benzodiazepine 
• 52099-72-6 1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one 
• 167871-11-6 4-Methyl-3-[1-p-tolyl-meth-(E)-ylidene]-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 167871-09-2 3-[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-4-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 167871-08-1 3-[1-(2-Chloro-phenyl)-meth-(E)-ylidene]-4-methyl-1,3-dihydro-benzo[b][1,4]diazepin-2-one 
• 167871-07-0 4-Methyl-3-[1-phenyl-meth-(E)-ylidene]-1,3-dihydro-benzo[b][1,4]diazepin-2-one 

Relevant articles and documents

Asymmetric Ir-catalyzed hydrogenation of 1,5-benzodiazepinones using mixtures of ligands

The catalytic hydrogenation of benzodiazepinones using metal complexes with phosphite and phosphoramidite ligands was carried out for the first time. The mixed-ligand catalytic systems containing a chiral phosphoramidite or phosphite in combination with an achiral phosphine were shown to exhibit a higher enantioselectivity compared to catalysts containing homocombinations of chiral ligands.

Synthesis of highly regioselective bifunctional tricyclic tetrazole-1 H -benzo[ b ][1,4]diazepins

A new approach for the synthesis of arrays of bifunctional tricyclic tetrazole-1H-benzo[b][1,4]diazepines has been investigated. It includes a sequential two-step isocyanide-based condensation reaction of diamines or 2-nitroanilines, ethyl 3-oxobutanoate or 2,2,6-trimethyl-4H-1,3-dioxin-4-one, isocyanides and trimethylsilyl azide in good yields. Georg Thieme Verlag Stuttgart · New York.

A facile and efficient synthesis of arylsulfonamido-substituted 1,5-benzodiazepines and N-[2-(3-benzoylthioureido)aryl]-3-oxobutanamide derivatives

A facile and efficient synthesis of 1,5-benzodiazepines with an arylsulfonamido substituent at C(3) is described. 1,5-Benzodiazepine, derived from the condensation of benzene-1,2-diamine and diketene, reacts with an arylsulfonyl isocyanate via an enamine intermediate to produce the title compounds of potential synthetic and pharmacological interest in good yields (Scheme 1). In addition, reaction of benzene-1,2-diamine and diketene in the presence of benzoyl isothiocyanate leads to N-[2-(3-benzoylthioureido)aryl]-3- oxobutanamide derivatives (Scheme 2). This reaction proceeds via an imine intermediate and ring opening of diazepine. The structures were corroborated spectroscopically (IR, 1Hand 13C-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this type of cyclization is proposed (Scheme 3).