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143650

Sigma-Aldrich

5H-Dibenz[b,f]azepine

97%

Synonym(s):

Iminostilbene

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About This Item

Empirical Formula (Hill Notation):
C14H11N
CAS Number:
256-96-2
Molecular Weight:
193.24
Beilstein:
1343358
EC Number:
205-970-0
MDL number:
MFCD00005071
UNSPSC Code:
12352100
PubChem Substance ID:
24848600
NACRES:
NA.22

Assay

97%

mp

196-199 °C (lit.)

solubility

ethyl acetate: soluble 25 mg/mL, clear, yellow to orange

SMILES string

N1c2ccccc2C=Cc3ccccc13

InChI

1S/C14H11N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-10,15H

InChI key

LCGTWRLJTMHIQZ-UHFFFAOYSA-N

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General description

5H-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.

Application

5H-Dibenz[b,f]azepine can be used:
  • As a starting material to prepare pharmacologically important dibenzoazepine-pyridazine derivatives.
  • To synthesize 3-chloro-1-(5H-dibenz[b,f]azepine-5yl)propan-1-one, a key intermediate used to prepare aminophenol derivatives.
  • In the synthesis of dibenzazepine derivatives.
  • As a starting material to synthesize olefinic multidentate ligand, which is used to prepare Rh(I) complexes.

Biochem/physiol Actions

2-(Bromomethyl)naphthalene is a fluorescent alkyl bromide. It causes the esterification of free carboxyl groups formed at the surface of polyethylene terephthalate by enzyme hydrolysis. It acts as organic electrophile in the P4S10/acyloin reaction.

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H302,H411

Precautionary Statements

P273 - P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and Calorimetry of Some Derivatives of Dibenzazepine
Analytical Calorimetry (1970)
Kuppuswamy Arumugam et al.
Inorganic chemistry, 46(8), 3283-3288 (2007-03-16)
The reaction of P4S10 with acyloins, RC(O)CH(OH)R, in refluxing dioxane, followed by the addition of alkylating agents, forms dithiolene thiophosphoryl thiolate compounds, (R2C2S2)P(S)(SR'), which are readily isolated and purified. The compounds that have been prepared and identified spectroscopically are those
Synthesis of N-substituted dibenzoazepine--pyridazine derivatives as potential neurologically active drugs
Erdougan M and Dacstan A
Synthetic Communications, 50(24), 1-9 (2020)
Synthesis and antioxidant properties of some novel 5H-dibenz [b, f] azepine derivatives in different in vitro model systems
Kumar HV and Naik N
European Journal of Medicinal Chemistry, 45(1), 2-10 (2010)
Rh (I) Complex with a Tridentate Pyridine-Amino--Olefin Actor Ligand-Metal-Ligand Cooperative Activation of CO2 and Phenylisocyanate under C-C and Rh-E (E=O, N) Bond Formation
Heuermann I, et al.
Organometallics, 38(8), 1787-1799 (2019)
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