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Iminodibenzyl

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Name

Iminodibenzyl

EINECS 207-787-1
CAS No. 494-19-9 Density 1.085 g/cm3
PSA 12.03000 LogP 3.66680
Solubility N/A Melting Point 105-108 °C(lit.)
Formula C14H13N Boiling Point 327.7 °C at 760 mmHg
Molecular Weight 195.264 Flash Point 161.3 °C
Transport Information N/A Appearance Yellowish to beige crystalline powder
Safety 22-24/25-39-26-36/37/39-27 Risk Codes 36-36/37/38
Molecular Structure Molecular Structure of 494-19-9 (Iminodibenzyl) Hazard Symbols IrritantXi
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;

Article Data 34

Iminodibenzyl Synthetic route

13080-75-6

5-acetyliminodibenzyl

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
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
ConditionsYield
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
256-96-2

dibenzoazepine

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
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%
256-96-2

dibenzoazepine

A

611-64-3

9-methyl-acridine

B

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
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
ConditionsYield
In acetonitrile electrolysis (Et4NClO4, Hg-dropelectrode);90%

10,11-dihydro-dibenzo[b,f]azepine-5-carboxylic acid prop-2-ynyl ester

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
With benzyltriethylammonium tetrathiomolybdate In acetonitrile at 25℃; for 0.75h; sonicated;88%

C18H19NO

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
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

C14H13Br2N

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
With C55H46N4O4W; potassium carbonate; N-ethyl-N,N-diisopropylamine In acetonitrile for 12h; Inert atmosphere; Irradiation;68%

C21H25NO

494-19-9

9,10-dihydrodibenzazepine

Conditions
ConditionsYield
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
ConditionsYield
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

Iminodibenzyl Chemical Properties

Molecular Structure:

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

Iminodibenzyl 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.

Iminodibenzyl Production

Derived by o-nitrotoluene with condensation, reduction, cyclization .

Iminodibenzyl 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,

Iminodibenzyl Consensus Reports

Reported in EPA TSCA Inventory.

Iminodibenzyl 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

Iminodibenzyl 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.

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