86499-23-2

Basic information

• Product Name: 3-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one
• Synonyms: 3-chloro-1,3,4,5-tetrahydro-2h-1-benzazepin-2-one;3-Chlorine-2,3,4,5-tetrahydro-2H-1-benzazepin-2-one;3-CHLORO-2,3,4,5-TETRAHYDRO-2H-1-BENZAZEPIN-2-ONE;3-chloro-2,3,4,5-tetrahydro-2H-1-benzazepine-2-one;3-CHLORO-1,3,4,5--TETRAHYDRO-1H-1-BENZAZEPIN-2-ONE;IHT-PI CBC;3-chloro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one;3-Chloro-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one
• CAS NO: 86499-23-2
• Molecular Formula: C₁₀H₁₀ClNO
• Molecular Weight: 195.65
• Mol File: 86499-23-2.mol

Chemical Properties

• Melting Point: 164-167 °C
• Boiling Point: 379.5 °C at 760 mmHg
• Flash Point: 183.3 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 5.84E-06mmHg at 25°C
• Refractive Index: 1.589
• PKA: 13.59±0.40(Predicted)
• CAS DataBase Reference: 3-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one(86499-23-2)
• EPA Substance Registry System: 3-Chloro-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one(86499-23-2)

Safety Data

• Hazardous Substances Data: 86499-23-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10ClNO/c11-8-6-5-7-3-1-2-4-9(7)12-10(8)13/h1-4,8H,5-6H2,(H,12,13)

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 4424-80-0 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one 
• 86499-22-1 3,3-dichloro-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one 

Downstream Products

• 1093980-71-2 (R)-3-{4-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-1,2,3-triazol-1-yl}-1,3,4,5-tetrahydro-1-benzazepin-2-one 
• 1093975-42-8 (S)-3-{4-[3-methoxy-4-(4-methylimidazol-1-yl)phenyl]-1,2,3-triazol-1-yl}-1,3,4,5-tetrahydro-1-benzazepin-2-one 
• 86499-52-7 (S)-3-amino-1-ethoxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one 
• 86541-77-7 (3S)-1-(carboxymethyl)-<<(1S)-1-(ethoxycarbonyl)-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one hydrochloride 
• 86541-78-8 (3S)-1-(carboxymethyl)-<<(1S)-1-carboxy-3-phenylpropyl>amino>-2,3,4,5-tetrahydro-1H-<1>benzazepin-2-one 
• 86541-74-4 benazepril hydrochloride 
• 239097-60-0 3-carboxy-1-N-(3-(N'-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 239097-83-7 1-N-(3-(N'-(3-isopropylureido))benzyl)-3-(methoxycarbonyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 239097-82-6 3-(aminomethyl)-1-N-(3-(N'-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 239097-84-8 3-(hydroxymethyl)-1-N-(3-(N'-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 239097-58-6 3-cyano-1-N-(3-(N'-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 239097-81-5 3-(phenylcarbamoyloxy)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 211761-80-7 3-chloro-1-N-(3-(N'-(3-isopropylureido))benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 97278-68-7 3-azido-2,3,4,5-tetrahydro-2-oxo-1 H-1-benzazepine 

Relevant articles and documents

Discovery of novel triazolobenzazepinones as γ-secretase modulators with central Aβ42 lowering in rodents and rhesus monkeys

Abstract Synthesis and SAR studies of novel triazolobenzazepinones as gamma secretase modulators (GSMs) are presented in this communication. Starting from our azepinone leads, optimization studies toward improving central lowering of Aβ42 led to the discovery of novel benzo-fused azepinones. Several benzazepinones were profiled in vivo and found to lower brain Aβ42 levels in Sprague Dawley rats and transgenic APP-YAC mice in a dose-dependent manner after a single oral dose. Compound 34 was further progressed into a pilot study in our cisterna-magna-ported rhesus monkey model, where we observed robust lowering of CSF Aβ42 levels.

The heterogeneous enantioselective hydrodehalogenation of α,α-dichlorobenzazepinone-2: A unique case of substrate specificity

The enantioselective hydrodehalogenation of α,α-dichlorobenzazepinone-2 with cinchona modified Pd- and Pt-catalysts was investigated using a random screening approach. The effect of important reaction parameters was determined and optimized. The best optical yields (50% ee) were obtained with a 5% Pd/BaSO4 catalyst modified with cinchonine in THF NBu3 as HCl acceptor. Very high modifier and catalyst concentrations were necessary to get good optical yields and reasonable rates because the modifier decreases the catalyst activity. The absolute configuration of α-chlorobenzazepinone-2 was determined. Attempts to extend this enantioselective dehalogenation reaction to other α,α-dihalogen substituted acid derivatives were unsuccessful.

3-Amino-[1]-benzazepin-2-one-1-alkanoic acids

Variously substituted 1-carboxymethyl-3-(carboxymethylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-ones and functional derivatives are angiotensin converting enzyme inhibitors and are useful as antihypertensive agents. Synthesis of, compositions and methods of treatment utilizing such compounds are included.

Synthesis and biological properties of (carboxyalkyl)amino-substituted bicyclic lactam inhibitors of angiotensin converting enzyme

Syntheses of the potent angiotensin converting enzyme inhibitor (3S)-1-(carboxymethyl)-3-[[(1S)-1-carboxy-3-phenylpropyl]amino]-2,3,4,5 -tetrahydro-1H-[1]benzazepin-2-one (CGS 14831) and the related monoester prodrug (17a; CGS 14824A) are described together with preparative details for six- and eight-membered ring analogues. Inhibitory potencies and in vivo biological activity of the compounds are discussed. The data indicate that 17a has a biological profile comparable to that of enalapril.

3-Amino-[1]-benzazepin-2-one-1-alkanoic acids

Variously substituted 1-carboxymethyl-3-(carboxymethylamino)-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-ones and functional derivatives are angiotension converting enzyme inhibitors and are useful as antihypertensive agents. Synthesis of, compositions and methods of treatment utilizing such compounds are included.