Basic information
- Standard SMILES
C1=Cc2ccccc2Nc2ccccc21- InChIKey
LCGTWRLJTMHIQZ-UHFFFAOYSA-N- Molecular formula
- C14H11N
- Average molar mass
- 193.24 g/mol
- Monoisotopic mass
- 193.08914935
Overview
5H-dibenzo[b,f]azepine is a mancude organic heterotricyclic parent that consists of a seven-membered nitrogen hetrocycle fused with two benzene rings. It has a role as a marine xenobiotic metabolite. It is a mancude organic heterotricyclic parent and a dibenzoazepine.
Names & identifiers
- Preferred name
- Dibenz(b,f)azepine
- IUPAC
- 11H-benzo[b][1]benzazepine
- English name
- Iminostilbene
- Molecular formula
- C14H11N
- Molecular weight
- 193.24
Names & synonyms
Iminostilbene256-96-2Dibenz(b,f)azepine2,2'-Iminostilbene2,3,6,7-DibenzazepineStilbene, 2,2'-imino-Dibenz[b,f]azepine5-AZADIBENZO(A,E)CYCLOHEPTATRIENENSC-123458J411KQJ8C25-Azadibenzo[a,e]cycloheptatrieneDTXSID90871625
Show more names
5H-Dibenz[b,f]azepineCarbaMazepine Related CoMpound BIminostilben5H-Dibenz[b,f]azepin5H-Dibenzo(b,f)azepineR-FMOCRP 9989IminostiLNSC 123458
RefChem:132797DTXCID4020458DTXCID60819276205-970-0(2S)-2-((2-(3,5-difluorophenyl)acetyl)amino)-N-((7S)-5-methyl-6-oxo-7H-benzo(d)(1)benzazepin-7-yl)propanamideDibenzazepineDTXSID60404585H-Dibenzo[b,f]azepine
Database identifiers
- CAS
256-96-2- PubChem CID
- 9212
- DTXSID
DTXSID90871625- ChEMBL
CHEMBL243596- ChEBI
CHEBI:47802- UNII
- J411KQJ8C2
- EC Number
- 205-970-0
- Nikkaji
- J24.602F
Properties
Computed structural properties
- XLogP
- 4
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 222
Experimental & physicochemical properties
Chemical ClassesPharmaceutical
DrugsPharmaceuticals -> Metabolite of Carbamazepine
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 197 °C · 197 °C
- Boiling point
- 221 °C · 221 °C(lit.)
- Density
- 1.29 g/mL · 1.290 g/mL at 20 °C(lit.)
- refractive index
- 20 · n20/D 1.523(lit.)
- Flash point
- 230 °F · >230 °F
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 50 mg/mL, · dioxane: 50 mg/mL, clear
- form
- powder
- pka
- 1.71 · 1.71±0.20(Predicted)
- color
- yellow to orange
- Water Solubility
- Soluble in ethyl acetate (25 mg/ml), water (partly), dioxane, chloroform, and DMSO.
- BRN
- 1343358 · 1343358
- InChI
- 1S/C14H11N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-10,15H
- InChIKey
- LCGTWRLJTMHIQZ-UHFFFAOYSA-N
- SMILES
- N1c2ccccc2C=Cc3ccccc13
- LogP
- 4.06 · 4.06
- CAS DataBase Reference
- 256 · 256-96-2(CAS DataBase Reference)
- FDA UNII
- 411 KQJ8C2 · J411KQJ8C2
- NIST Chemistry Reference
- o,o'-Iminostilbene(256-96-2)
- EPA Substance Registry System
- 5 H-Dibenz[b,f]azepine · 5H-Dibenz[b,f]azepine (256-96-2)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H411
- Precautionary statements
- 273 · P273-P301+P312+P330
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- C,Xi,N,Xn
- Risk Statements
- 34 · 34-51/53-22-36/37/38
- Safety Statements
- 26 · 26-36/37/39-45-61-27-24/25
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- F
- 10 · 10-21
- Hazard Note
- Irritant
- HS Code
- 29339900 · 29339900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (78.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P272, P273, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 55 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 28-01-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/13753
Hazard Classes and CategoriesAcute Tox. 4 (78.2%)
Toxicology
USGS Health-Based Screening Levels for Evaluating Water-Quality
Iminostilbene
Pharmaceutical
Smith, C.D. and Nowell, L.H., 2024. Health-Based Screening Levels for evaluating water-quality data (3rd ed.). DOI:10.5066/F71C1TWP
Safety data
- F
- 10-21
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- UN 3265 8/PG 2
- hs_code
- 29339900
- risk_code
- 34-51/53-22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS09
- hazard_code
- C,Xi,N,Xn
- hazard_note
- Irritant
- safety_code
- 26-36/37/39-45-61-27-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H411
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2
- Precautionary statements
- P273-P301+P312+P330
Chemistry & industry
Pharmacology
ATC CodeN03AF01
MeSH Pharmacological Classification
Agents that suppress GAMMA-SECRETASE by inhibiting or modulating its activities. Targeted enzymatic activities include its involvement in accumulation of toxic AMYLOID BETA-PEPTIDES (e.g., Aβ42) in ALZHEIMER DISEASE and activation of NOTCH RECEPTOR mediated SIGNAL PATHWAYS in certain cancer types.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Uses & manufacturing
Use ClassificationPharmaceuticals -> Nervous System -> Antiepileptics -> Carboxamide derivatives -> Transformation products
Applications
UsesIminostilbene is mainly used as a pharmaceutical intermediate for the production of carbamazepine, Oxcarbazepine, and rhodium catalyst ligand. It is a metabolite of of carbamazepine which is used primarily in the treatment of epilepsy and neuropathic pain.
General Description5H-Dibenz[b,f]azepine, a tricyclic amine with a seven-membered ring, is commonly known as iminostilbene. It is used as an intermediate or a starting material in the synthesis of many anticonvulsant drugs.It is also used as a starting material to prepare pharmacologically important dibenzoazepine-pyridazine derivatives and synthesize olefinic multidentate ligand, which is used to prepare Rh(I) complexes.
Preparation methods
Preparationiminostilbene synthesis: 10,11-Dihydro-5-dibenz(b,f)azepine [Iminodibenzyl, 494-19-9] as raw material was acylated by triphosgene, after bromination by bromine and dehydrobromination, reacted with sodium hydroxide in isopropanol to give Iminostilbene.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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Additional notes
DefinitionChEBI: Iminostilbene is a mancude organic heterotricyclic parent that consists of a seven-membered nitrogen hetrocycle fused with two benzene rings. It has a role as a marine xenobiotic metabolite. It is a mancude organic heterotricyclic parent and a dibenzoazepine.
Related reactions
42 records
Linked notes
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