Iminodibenzyl Chemical Properties

Melting point:

105-108 °C (lit.)

Boiling point:

321.94°C (rough estimate)

Density 

1.0778 (rough estimate)

refractive index 

1.6353 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)

form 

Crystalline Powder

pka

0.83±0.20(Predicted)

color 

Yellow to beige

BRN 

152732

InChI

InChI=1S/C14H13N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-8,15H,9-10H2

InChIKey

ZSMRRZONCYIFNB-UHFFFAOYSA-N

SMILES

N1C2=CC=CC=C2CCC2=CC=CC=C12

LogP

4.27

CAS DataBase Reference

494-19-9(CAS DataBase Reference)

NIST Chemistry Reference

5H-Dibenz[b,f]azepine, 10,11-dihydro-(494-19-9)

EPA Substance Registry System

5H-Dibenz[b,f]azepine, 10,11-dihydro- (494-19-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36-36/37/38

Safety Statements 

22-24/25-39-26-36/37/39-27

WGK Germany 

3

RTECS 

HN8950000

TSCA 

TSCA listed

HazardClass 

IRRITANT

HS Code 

29339930

MSDS

• Language:English Provider:10,11-Dihydro-5H-dibenz[b,f]azepine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Iminodibenzyl Usage And Synthesis

Description

Iminodibenzyl was not a new drug. It had been discovered in 1898 and used briefly as an intermediate, in the preparation of Sky Blue, a dye stuff. Iminodibenzyl, however, had a tricyclic ring structure, similar in appearance to the phenothiazines. Iminodibenzyl is an important drug intermediate, which can be used for the medicine synthesis as a tristimania and epilepsia.

Chemical Properties

YELLOWISH TO BEIGE CRYSTALLINE POWDER

Uses

10,11-Dihydro-5H-dibenzo[b,f]azepine is a metabolite of the tricyclic antidepressant, Imipramine (I465980). 10,11-Dihydro-5H-dibenzo[b,f]azepine can be used as a chromogenic probe for the quantification of hydrogen peroxide and glucose.

Uses

These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Preparation

Iminodibenzyl is obtained from o-nitrotoluene by condensation, reduction and cyclization.

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Synthesis

The general procedure for the synthesis of iminodibenzylidene from 1-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethanone is as follows: NaOH and triethylboron were stirred and mixed under argon protection at room temperature to form a clear, clarified solution with a concentration of 1 M/L. Subsequently, 10 μmol (2 mol%) of catalyst, 5 mmol of amide substrate, and 15 mmol of triethoxysilane or polymethylhydrosiloxane (PMHS) were sequentially added to the above triethylboron solution. The reaction mixture was added to a 10 mL sealed tube along with 2 mL of methyl tert-butyl ether (MTBE) and placed in an 80 °C oil bath with heating and stirring 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 iminodibenzyl was when triethoxysilane or polymethylhydrosiloxane (PMHS) was used as the reducing agent:

References

[1] Patent: CN107337573, 2017, A. Location in patent: Paragraph 0022; 0023; 0024; 0025

Iminodibenzyl(494-19-9)Related Product Information

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