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256-96-2

Basic Information
CAS No.: 256-96-2
Name: Iminostilbene
Article Data: 40
Molecular Structure:
Molecular Structure of 256-96-2 (Iminostilbene)
Formula: C14H11N
Molecular Weight: 193.248
Synonyms: 2,2'-Iminostilbene;5-Azadibenzo[a,e]cycloheptatriene;5H-Dibenzo[b,f]azepine;Dibenz[b,f]azepine;NSC 123458;RP 9989;Stilbene, 2,2'-imino-;
EINECS: 205-970-0
Density: 1.116 g/cm3
Melting Point: 197-201 °C
Boiling Point: 349.1 °C at 760 mmHg
Flash Point: 178.4 °C
Solubility: dioxane: 50 mg/mL, clear
Appearance: Yellow to orange-yellow fine powder
Hazard Symbols: CorrosiveC,IrritantXi,DangerousN,HarmfulXn
Risk Codes: 34-51/53-22-36/37/38
Safety: 26-36/37/39-45-61-27
Transport Information: UN 3265 8/PG 2
PSA: 12.03000
LogP: 4.05200
Synthetic route
2039-88-5

2-bromostyrene

95-51-2

2-Chloroaniline

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;99%
19209-60-0

N-acetyl iminostilbene

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;99%
Stage #1: N-acetyl iminostilbene With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h;
Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;
99%
Multi-step reaction with 2 steps
1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube
2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube
View Scheme
13066-19-8

2-(2-phenylethenyl)benzenamine

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With phosphoric acid at 100 - 300℃; for 2h; Temperature; Reagent/catalyst; Inert atmosphere; Industrial scale;98.9%
494-19-9

9,10-dihydrodibenzazepine

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With 1-methyl-2-nitrobenzene; palladium on activated charcoal at 230℃; for 1.5h; Rate constant; Kinetics; Thermodynamic data; var. hydrogen acceptors (also without acceptor); ΔH(excit.), ΔS(excit.); var. temp. and time;98.2%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h;24%
Stage #1: 9,10-dihydrodibenzazepine With N-Bromosuccinimide
Stage #2: With pyridine
78943-58-5

N-benzyl-5H-dibenzoazepine

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol at 35 - 40℃; under 1500.15 - 2250.23 Torr; for 5h; Autoclave;97%
10464-31-0

5H-N-benzyl-10,11-dihydrobenzazepin-10-one

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With 5%-palladium/activated carbon; hydrogen In methanol at 45 - 50℃; under 7500.75 - 9000.9 Torr; for 5h; Autoclave;94.5%
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / 4 h / 40 - 45 °C
2: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 35 - 40 °C / 1500.15 - 2250.23 Torr / Autoclave
View Scheme
33948-22-0

5H-dibenz[b,f]azepine-5-carbonylchloride

256-96-2

dibenzoazepine

Conditions
ConditionsYield
In acetonitrile electrolysis (Et4NClO4, Hg-dropelectrode);92%
75272-34-3

10-bromo-dibenz[b,f]azepine

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With tetraethylammonium perchlorate In water; N,N-dimethyl-formamide cathode: Hg, working potential: -1.85 V, charge: 2.0-2.1 F/mol, 4-5 h;89%
298-46-4

carbamazepin

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With tetraethoxy tellurium(IV) In tetrachloromethane for 3h; Heating;85%
With hydrogenchloride In water for 12h; Reagent/catalyst; Darkness;
With carbon dioxide at 160 - 200℃;
16096-33-6

1-phenyl-1H-indole

256-96-2

dibenzoazepine

Conditions
ConditionsYield
With methanesulfonic acid at 90℃; for 7h; Temperature;83.4%
With polyphosphoric acid at 100℃;67%
With PPA at 75 - 85℃; for 55h; Mechanism; substituent effect discussed;43%
With PPA at 75 - 85℃; for 55h;43%
With methanesulfonic acid; phosphorus pentoxide In toluene at 120℃; for 6h;
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Specification

The IUPAC name of this chemical is 11H-benzo[b][1]benzazepine. With the CAS registry number 256-96-2, it is also named as 2,2'-Iminostilbene. The product's categories are Stilbenes (substituted); Heterocyclic Compounds. It is yellow to orange-yellow fine powder which is soluble in acid, alkali, toluene, DMF and pyridine, slightly soluble in alcohol.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 4.11; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 4.11; (4)ACD/LogD (pH 7.4): 4.11; (5)ACD/BCF (pH 5.5): 785.39; (6)ACD/BCF (pH 7.4): 785.52; (7)ACD/KOC (pH 5.5): 4110.41; (8)ACD/KOC (pH 7.4): 4111.06; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.626; (13)Molar Refractivity: 61.35 cm3; (14)Molar Volume: 173.1 cm3; (15)Polarizability: 24.32×10-24 cm3; (16)Surface Tension: 46 dyne/cm; (17)Enthalpy of Vaporization: 59.36 kJ/mol; (18)Vapour Pressure: 4.81E-05 mmHg at 25°C; (19)Exact Mass: 193.089149; (20)MonoIsotopic Mass: 193.089149; (21)Topological Polar Surface Area: 12; (22)Heavy Atom Count: 15; (23)Complexity: 222.

Preparation of 11H-Benzo[b][1]benzazepine: It can be derived by the elimination of 10,11-Dihydro-5H-dibenzo[b,f]azepine.

Uses of 11H-Benzo[b][1]benzazepine: It is used as pharmaceutical intermediates for the synthesis of specific analgesic and antipsychotic agents. It also can react with 6-bromo-hexanoyl chloride to get 6-bromo-1-dibenzo[b,f]azeπn-5-yl-hexan-1-one. This reaction needs reagent N,N-dimethylaniline and solvent tetrahydrofuran by heating. The reaction time is 1 hours. The yield is 96%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful if swallowed, but also irritating to eyes, respiratory system and skin. And it can cause burns. What's more, this chemical is toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure. 
1. SMILES:c3cc2c(\C=C/c1c(cccc1)N2)cc3
2. InChI:InChI=1/C14H11N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-10,15H 
3. InChIKey:LCGTWRLJTMHIQZ-UHFFFAOYAN