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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/REAXYS Number:
1343358
EC Number:
205-970-0
MDL number:
MFCD00005071
UNSPSC Code:
12352100
PubChem Substance ID:
24848600
NACRES:
NA.22

Quality Level

200

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

signalword

Warning

hcodes

H302,H411

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 2

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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9-Methylacridine United States Pharmacopeia (USP) Reference Standard

USP

1424084

9-Methylacridine

Sigma-Aldrich

Sigma-Aldrich

SML0649

Deshydroxy LY-411575

(S)-(+)-N-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl)-dibenzo[b,f]azepine ≥95% (elemental analysis)

Sigma-Aldrich

744646

(S)-(+)-N-(3,5-Dioxa-4-phosphacyclohepta[2,1-a;3,4-a′]dinaphthalen-4-yl)-dibenzo[b,f]azepine

Acridine ≥96.5% (HPLC)

Sigma-Aldrich

A23609

Acridine

Phenothiazine ≥98%

Sigma-Aldrich

P14831

Phenothiazine

Phenothiazine purum, ≥98.0% (GC)

Sigma-Aldrich

88580

Phenothiazine

Synthesis and Calorimetry of Some Derivatives of Dibenzazepine
Analytical Calorimetry (1970)
Synthesis and Calorimetry of Some Derivatives of Dibenzazepine.
Gipstein E, et al.
Analytical Calorimetry, 127-134 (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
S M Furst et al.
Biochemical pharmacology, 45(6), 1267-1275 (1993-03-24)
Carbamazepine is an anticonvulsant which is associated with a significant incidence of hypersensitivity reactions including agranulocytosis. We have postulated that many drug hypersensitivity reactions, especially agranulocytosis and lupus, are due to reactive metabolites generated by the myeloperoxidase (MPO) (EC 1.11.1.7)
A Varenne et al.
Journal of immunological methods, 186(2), 195-204 (1995-10-26)
As part of our ongoing work to extend the range of applications of the non-isotopic carbonyl metalloimmunoassay (CMIA), previously developed in our laboratory, we describe here the first CMIA study of carbamazepine. The CMIA method uses a metal carbonyl complex
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