8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one (CAS 50892-62-1): Specialized Pharmaceutical Intermediate — Full Analysis of Molecular Structure, Clozapine Synthesis, Heterocyclic Chemistry and Pharmaceutical Applications

1、 Product Overview

8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one (CAS 50892-62-1) is a specialized chlorinated dibenzodiazepinone compound featuring a rigid fused aromatic heterocyclic framework, two nitrogen atoms, and a lactam carbonyl group. With a molecular formula of C₁₃H₉ClN₂O and a molecular weight of 244.68 g/mol, it serves as a valuable building block and advanced intermediate in pharmaceutical and medicinal chemistry.

Its greatest value lies in its pre-formed dibenzo[b,e][1,4]diazepin-11-one scaffold, which can be further modified to construct structurally diverse nitrogen-containing compounds. The chlorine substituent provides an additional functional handle for synthetic diversification, while the rigid heterocyclic framework is particularly relevant to Clozapine-related synthesis, pharmaceutical intermediate development, heterocyclic chemistry, medicinal chemistry, and structure–activity relationship (SAR) research. The compound can also be used in analytical and pharmaceutical research as a specialized reference material or impurity-related standard.

2. Basic Product Information

1. Product Name: 8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one

2. Synonyms: 6-chloro-2,9-diazatricyclo[9.4.0.0,3,8]pentadeca-1(15),3,5,7,11,13-hexaen-10-one;Clozapineimpurity1/ClozapineEPImpurityA/ClozapineimpurityC(USP)/8-chloro-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one;8-CHLORO-11-OXO-10,11-DIHYDRO-5H-DIBENZO-1,4-DIAZEPINE;8-CHLORO-5,Chemicalbook10-DIHYDRO-11H-DIBENZO[B,E][1,4]-DIAZEPIN-11-ONE;8-CHLORO-5,10-DIHYDRODEBENZO[B,E][1,4]DIAZEPIN-11-ONE;8-chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one;8-CHLORO-10,11-DIHYDRO-5H-DIBENZO[B,E][1,4]DIAZEPIN-11-ONE;8-Chloro-11-oxo-10,11-dihydro-5h-debenzo-1,4-diazepine

3. CAS NO.: 50892-62-1

4. Molecular Formula: C13H9ClN2O

5. Molecular Weight: 244.68

6. Structural Formula:

6. Purity: ≥ 98%

7. Appearance: Grey to dark grey solid powder

8. Functional Groups: One lactam carbonyl group, two nitrogen atoms, one chlorine substituent, and a fused dibenzo[b,e][1,4]diazepine heterocyclic framework

9. Chemical Classification: Chlorinated dibenzodiazepinone; nitrogen-containing heterocyclic compound; pharmaceutical intermediate; specialty chemical building block

10. Main Applications: Clozapine-related synthesis; pharmaceutical intermediate development; medicinal chemistry; heterocyclic synthesis; structure–activity relationship (SAR) research; pharmaceutical process development; analytical and reference-standard research

11. Storage Conditions: Store in a cool, dry and dark environment at room temperature. Keep the container tightly closed and protect from moisture, excessive heat, and prolonged exposure to direct light.

12. Product Manager Email: selina@coreychem.com

3、 Frequently Asked Questions (FAQ)

Question 1: What are the basic physical properties of 8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one (CAS NO.: 50892-62-1)?

This product is a chlorinated dibenzodiazepinone derivative containing a fused aromatic ring system and a diazepinone moiety. It is generally handled as a specialty organic intermediate and is typically supplied as a solid. Its molecular formula is C₁₃H₉ClN₂O, with a molecular weight of 244.68 g/mol. The product should be stored in a tightly closed container in a cool, dry place, protected from excessive heat, moisture, and direct light.

Question 2: What are the common synthesis methods for this compound?

1. Cyclization of appropriately substituted benzophenone or aniline intermediates:


A common synthetic strategy involves preparing an appropriately substituted aromatic precursor containing the required chloro, amino, and carbonyl functionalities, followed by intramolecular cyclization to construct the seven-membered diazepinone ring system.

2. Condensation and intramolecular ring-closing synthesis:


Another approach involves condensation between suitably functionalized aromatic amines and carbonyl-containing intermediates, followed by controlled cyclization to form the dibenzo[b,e][1,4]diazepin-11-one skeleton. Reaction conditions need to be carefully controlled to minimize regioisomeric and over-reaction impurities.

For commercial production, the synthetic route should be optimized according to the required purity, batch size, reaction yield, and impurity profile.

Question 3: What is the main feature of this product in terms of application?

Its main application feature is its rigid fused aromatic diazepinone structure combined with a chloro substituent. The molecule contains both nitrogen atoms and a lactam carbonyl group, providing a useful functional framework for further chemical modification.

It can be used primarily as a specialty pharmaceutical or medicinal-chemistry intermediate, particularly for the synthesis and structural modification of heterocyclic compounds and biologically active molecules. The chlorinated aromatic position can also provide a potential site for subsequent functionalization in multistep synthetic routes.

Question 4: What are the solubility and stability characteristics of this product? Can it be used in aqueous systems?

Because the molecule contains a rigid aromatic system with relatively limited polar functionality, it is expected to have limited solubility in water and may show better solubility in selected polar organic solvents, depending on solvent type and temperature.

The product should generally be handled under controlled conditions and protected from prolonged exposure to strong acids, strong bases, excessive heat, and moisture. For pharmaceutical or medicinal-chemistry applications, actual solubility and chemical stability should be evaluated in the specific solvent system and formulation conditions required by the downstream process.

Question 5:Is this product suitable as a pharmaceutical or medicinal-chemistry intermediate? What are the considerations?

Yes. 8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one can serve as a useful heterocyclic building block or intermediate in pharmaceutical and medicinal-chemistry research.

When used as a synthetic intermediate, important considerations include chemical purity, positional-isomer content, residual solvents, moisture content, inorganic impurities, and batch-to-batch consistency. Depending on the downstream synthesis, control of trace impurities is particularly important because they may affect subsequent reactions and the quality of the final active or lead compound.

For research and scale-up applications, high-purity material with a consistent impurity profile and reliable analytical documentation is generally preferred.

4、 Application Cases

Application 1:What is the role of 8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one (CAS NO.: 50892-62-1) in pharmaceutical and medicinal chemistry research?

8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one is a chlorinated dibenzodiazepinone derivative featuring a rigid fused aromatic ring system and a lactam-containing diazepine framework. Its defined heterocyclic structure makes it a useful specialized building block for pharmaceutical and medicinal chemistry research. It can be employed as a synthetic intermediate for the preparation of structurally related heterocyclic compounds and for exploring structure-activity relationships (SAR) in drug discovery programs.

Application 2:What is the role of the product in the field of heterocyclic synthesis?

The dibenzo[b,e][1,4]diazepin-11-one skeleton provides a valuable framework for the synthesis of nitrogen-containing heterocyclic compounds. The lactam functionality and aromatic ring system offer opportunities for further chemical transformations and structural modification. 8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one can therefore be used as an intermediate in the development of diversified benzodiazepine-related and fused nitrogen-containing heterocycles, supporting research into new molecular architectures and functional compounds.

Application 3:What is the role of the product in medicinal chemistry and structure-activity relationship studies?

The chloro substituent and heterocyclic lactam framework provide useful structural features for medicinal chemistry optimization. Researchers can investigate subsequent functionalization or substitution reactions to introduce different chemical groups and generate compound libraries. Such derivatives can be evaluated in structure-activity relationship (SAR) studies, where changes to the aromatic substituent or heterocyclic framework are correlated with biological properties. This makes the compound potentially valuable as a research intermediate in early-stage drug discovery.

Application 4:What is the role of the product in the development of advanced pharmaceutical intermediates?

The combination of a fused aromatic system, two nitrogen atoms, a carbonyl group, and a chlorine substituent provides multiple structural characteristics that can be incorporated into more complex pharmaceutical molecules. The compound can serve as a specialty intermediate for multi-step organic synthesis, allowing researchers to construct more elaborate heterocyclic structures through subsequent functionalization, coupling, reduction, oxidation, or other synthetic transformations. Its well-defined molecular structure can be particularly useful when developing reproducible synthetic routes from laboratory scale toward process development.

Application 5:What is the role of the product in chemical and pharmaceutical research?

8-Chloro-5,10-dihydrodibenzo[b,e][1,4]diazepin-11-one is a specialized heterocyclic research building block that can support the synthesis of structurally diverse nitrogen-containing compounds. Its rigid aromatic framework and lactam functionality provide a defined platform for chemical modification, while the chloro substituent offers an additional handle for synthetic diversification. It can therefore be used in organic synthesis, medicinal chemistry, pharmaceutical intermediate development, compound-library synthesis, and structure-activity relationship research. High-purity material is generally preferred for reproducible synthetic reactions, impurity control, and subsequent analytical evaluation.