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| CAS No.: | 494-19-9 |
|---|---|
| Name: | Iminodibenzyl |
| Article Data: | 34 |
| Molecular Structure: | |
|
|
|
| Formula: | C14H13N |
| Molecular Weight: | 195.264 |
| Synonyms: | 10,11-Dihydro-5H-dibenz[b,f]azepine;10,11-Dihydro-5H-dibenzo[b,f]azepine;10,11-Dihydrodibenz[b,f]azepine;2,2'-Iminobibenzyl;2,2'-Iminodibenzyl;Iminobibenzyl;NSC 72110; |
| EINECS: | 207-787-1 |
| Density: | 1.085 g/cm3 |
| Melting Point: | 105-108 °C(lit.) |
| Boiling Point: | 327.7 °C at 760 mmHg |
| Flash Point: | 161.3 °C |
| Appearance: | Yellowish to beige crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36-36/37/38 |
| Safety: | 22-24/25-39-26-36/37/39-27 |
| PSA: | 12.03000 |
| LogP: | 3.66680 |
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- 13080-75-6
5-acetyliminodibenzyl
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; | 99% |
| Stage #1: 5-acetyliminodibenzyl 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 / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme |
- 40583-89-9
5-propionyl-10,11-dihydro-5H-dibenzo[b,f]azepine
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; | 99% |
| Stage #1: 5-propionyl-10,11-dihydro-5H-dibenzo[b,f]azepine 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; | 81% |
| 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 |
| Conditions | Yield |
|---|---|
| With [Fe3(1,1,1,3,3,3-hexamethyldisilazan-2-ide)4]Fe(η6-toluene); hydrogen at 20℃; under 1425.14 Torr; for 3h; Inert atmosphere; Glovebox; chemoselective reaction; | 92% |
| With tetraethylammonium perchlorate; ammonium chloride In water; N,N-dimethyl-formamide cathodic (Hg, -2.0 V vs. SCE) reduction; | 82% |
| Conditions | Yield |
|---|---|
| With iodine; hypophosphorous acid In acetic acid for 24h; Heating; | A 92% B 8% |
- 33948-19-5
10,11-dihydro-dibenzo[b,f]azepine-5-carbonyl chloride
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| In acetonitrile electrolysis (Et4NClO4, Hg-dropelectrode); | 90% |
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 25℃; for 0.75h; sonicated; | 88% |
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| Stage #1: C18H19NO 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; | 87% |
| With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; | 86% |
| 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 |
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| With C55H46N4O4W; potassium carbonate; N-ethyl-N,N-diisopropylamine In acetonitrile for 12h; Inert atmosphere; Irradiation; | 68% |
- 494-19-9
9,10-dihydrodibenzazepine
| Conditions | Yield |
|---|---|
| With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube; | 67% |
| Stage #1: C21H25NO 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; | 62% |
| 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 |
- 13080-75-6
5-acetyliminodibenzyl
A
- 494-19-9
9,10-dihydrodibenzazepine
B
- 40583-88-8
11-ethyliminodibenzyl
C
- 64-17-5
ethanol
| Conditions | Yield |
|---|---|
| With Mo2((1)-H)2(OtBu)6; diphenylsilane In toluene for 25h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; Reflux; | A 62% B 36% C n/a |
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Chemistry
Molecular Structure:
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Molecular Formula: C14H13N
Molecular Weight: 195.2597
IUPAC Name: 6,11-Dihydro-5H-benzo[b][1]benzazepine
Synonyms of 5H-Dibenz(b,f)azepine, 10,11-dihydro- (CAS NO.494-19-9): 10,11-Dihydro-5-dibenz(b,f)azepine ; 10,11-Dihydro-5H-dibenz(b,f)azepine ; 10,11-Dihydrodibenz(b,f)azepine ; 2,2'-Iminobibenzyl ; 2,2'-Iminodibenzyl ; 5-20-08-00092 (Beilstein Handbook Reference) ; AI3-39165 ; BRN 0152732 ; EINECS 207-787-1 ; Iminobibenzyl ; Iminodibenzyl ; NSC 72110 ; RP 23669
CAS NO: 494-19-9
Classification Code: Skin / Eye Irritant
Melting point: 105-108 °C
Index of Refraction: 1.602
Molar Refractivity: 61.75 cm3
Molar Volume: 179.8 cm3
Surface Tension: 42.6 dyne/cm
Density: 1.085 g/cm3
Flash Point: 161.3 °C
Enthalpy of Vaporization: 57 kJ/mol
Boiling Point: 327.7 °C at 760 mmHg
Vapour Pressure: 0.000199 mmHg at 25°C
Uses
5H-Dibenz(b,f)azepine, 10,11-dihydro- (CAS NO.494-19-9) is the materials for pharmaceutical intermediates. It can be used for the production of analgesic anti-spasm drug amide hydrochloride microphone. It is also used in synthetic lubricants, high-temperature antioxidant.
Production
Derived by o-nitrotoluene with condensation, reduction, cyclization .
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intravenous | 320mg/kg (320mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#01352, |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Poison by intravenous route. An eye irritant. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes:Xi
Risk Statements:
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
22: Do not breathe dust
24: Avoid contact with skin
25: Avoid contact with eyes
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27: Take off immediately all contaminated clothing28: After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer)
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
Specification
Stability and Reactivity of 5H-Dibenz(b,f)azepine, 10,11-dihydro- (CAS NO.494-19-9):
Conditions to Avoid:incompatible materials.
Chemical Stability:Stable under normal temperatures and pressures.
Incompatibilities with Other Materials:Strong oxidizing agents.
Hazardous Decomposition Products: irritating and toxic fumes and gases,carbon dioxide,hydrogen bromide,Carbon monoxide,nitrogen oxides.