Iminostilbene Chemical Properties

Melting point:

197 °C

Boiling point:

221 °C(lit.)

Density 

1.290 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.523(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

dioxane: 50 mg/mL, clear

form 

powder

pka

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

LogP

4.06

CAS DataBase Reference

256-96-2(CAS DataBase Reference)

NIST Chemistry Reference

o,o'-Iminostilbene(256-96-2)

EPA Substance Registry System

5H-Dibenz[b,f]azepine (256-96-2)

Safety Information

Hazard Codes 

C,Xi,N,Xn

Risk Statements 

34-51/53-22-36/37/38

Safety Statements 

26-36/37/39-45-61-27-24/25

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Irritant

HS Code 

29339900

MSDS

• Language:English Provider:5H-Dibenz[b,f]azepine
• Language:English Provider:SigmaAldrich

Iminostilbene Usage And Synthesis

Chemical Properties

Yellow to orange-yellow fine powder

Uses

Iminostilbene 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.

Application

Iminostilbene has good antioxidant effects. N-acetyl iminostilbene was synthesized by incubating iminostilbene (2.0020 g, 10.360 mmol) with acetic anhydride.

Preparation

iminostilbene 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.

Definition

ChEBI: 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.

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.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.

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.

Synthesis

The general procedure for the synthesis of iminostilbene from N-acetyl iminostilbene was as follows: NaOH was stirred and mixed with triethylboron under argon protection at room temperature to form a clear and clarified solution with a concentration of 1 M/L. Subsequently, 10 μmol (2 mol%) of amide substrate, 5 mmol of triethoxysilane or polymethylhydrosiloxane (PMHS) were sequentially added to the above triethylboron solution. 15 mmol of the reaction mixture with 2 mL of methyl tert-butyl ether (MTBE) was added to a 10 mL sealed tube and heated and stirred in an oil bath at 80 °C for 6 hours. Upon completion of the reaction, the reaction system was exposed to air and the amine products were subsequently isolated directly by column chromatography. According to the column chromatographic separation, the yield of the target product iminostilbene was when triethoxysilane or polymethylhydrosiloxane (PMHS) was used as the reducing agent:

References

[1] Patent: CN107337573, 2017, A. Location in patent: Paragraph 0038; 0039; 0040; 0041

Iminostilbene(256-96-2)Related Product Information

• Iminodibenzyl
• EC 2.6.1.2
• Iminodiacetonitrile
• Acetaminophen
• Iminodiacetic acid
• Dibenz[b,f]azepine-5-carbonyl chloride
• 10-Methoxy-2,2'-iminostilbene,10-METHOXY IMINOSTILBENE
• Depramine
• Amezepine
• OPIPRAMOL DIHYDROCHLORIDE
• 5-Cyano-5H-dibenz[b,f]azepine
• Iminostilbene-N-carboxamide
• N-[3-[4-(2-hydroxyethyl)piperazino]propyl]iminostilbene
• 2,2'-IMINOSTILBENE
• 10-Methoxy Iminostilbene Carbonylchloride
• Cycloheptatriene
• Bromine
• 3-Hydroxy Carbamazepine