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Basic Information
CAS No.: 5735-53-5
Name: Benzomorpholine
Article Data: 71
Molecular Structure:
Molecular Structure of 5735-53-5 (Benzomorpholine)
Formula: C8H9NO
Molecular Weight: 135.166
Synonyms: 2,3-Dihydro-1,4-benzoxazine;2,3-Dihydro-4H-1,4-benzoxazine;3,4-Dihydro-2H-1,4-benzoxazine;3,4-Dihydro-2H-benzo[1,4]oxazine;3,4-Dihydro-2H-benzo[b][1,4]oxazine;Benzomorpholine;Phenmorpholine;Phenomorpholine;
Density: 1.095 g/cm3
Boiling Point: 250.6 °C at 760 mmHg
Flash Point: 91 °C
Solubility: Sparingly soluble in water.(0.26 g/L) (25°C),
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 21.26000
LogP: 1.62890
Synthetic route
70801-52-4

1-(2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at -40℃; for 1.16667h;100%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 12h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;81%
With sodium triethylborohydride In tetrahydrofuran at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;81%
19202-00-7

(2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)(phenyl)methanone

A

5735-53-5

1,4-benzoxazine

B

100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium bis(2-methoxyethoxy)aluminium dihydride In ethyl acetate; benzene at -40℃;A 100%
B 100%
42876-07-3

2-(2-aminophenoxy)ethan-1-ol

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate In toluene; butan-1-ol at 120℃; under 22502.3 Torr; for 6h; Schlenk technique; Autoclave;100%
5466-88-6

3,4-dihydro-3-oxo-2H-1,4-benzoxazine

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; hydrogen; caesium carbonate In toluene; butan-1-ol at 120℃; under 22502.3 Torr; for 6h; Schlenk technique; Autoclave;98%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere;92%
Stage #1: 3,4-dihydro-3-oxo-2H-1,4-benzoxazine With lithium aluminium tetrahydride In tetrahydrofuran Heating / reflux;
Stage #2: With sodium hydroxide; water In tetrahydrofuran
79%
70801-52-4

1-(2H-benzo[b][1,4]oxazin-4(3H)-yl)ethanone

A

82756-78-3

4-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazine

B

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With triethyl borane; Triethoxysilane; sodium hydroxide In hexane at 80℃; for 6h; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube;A 7%
B 90%
With Triethoxysilane; sodium triethylborohydride In hexane at 80℃; for 6h; Schlenk technique; Glovebox; Sealed tube; Inert atmosphere;A 90%
B n/a
With Triethoxysilane; sodium triethylborohydride In hexane at 80℃; for 6h; Inert atmosphere; Schlenk technique; High pressure; Sealed tube;A 90%
B n/a
31507-30-9

2-(2-nitrophenoxy)acetonitrile

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid In ethanol at 50℃; under 37503.8 Torr; for 2h;88%
With polymethylhydrosiloxane; palladium dihydroxide In ethanol at 20℃; for 0.5h;73%
87762-20-7

2-<(2-bromophenyl)amino>ethanol

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 24h;87%
With racemic-2-(di-tert-butylphosphino)-1,1′-binaphthyl; palladium diacetate; caesium carbonate In toluene at 50℃; for 24h;87%
438013-84-4

4-(p-toluenesulfonyl)-3,4-dihydro-2H-benzoxazine

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With naphthalene; tetraethylammonium bromide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Electrolysis;87%

tert-butyl (2-phenoxyethyl)(tosyloxy)carbamate

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; trifluoroacetic acid In 2,2,2-trifluoroethanol at 0 - 20℃; for 17h; regioselective reaction;82%
With Rh2(esp)2; trifluoroacetic acid In 2,2,2-trifluoroethanol at 20℃; for 17h; Inert atmosphere;82%
82415-84-7

benzofuran-3(2H)-one oxime

5735-53-5

1,4-benzoxazine

Conditions
ConditionsYield
Stage #1: benzofuran-3(2H)-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With sodium fluoride In hexane; dichloromethane; water at 0℃; for 0.5h;
80%
Stage #1: benzofuran-3(2H)-one oxime With diisobutylaluminium hydride In hexane; dichloromethane at 0 - 20℃; Inert atmosphere;
Stage #2: With water; sodium fluoride In hexane; dichloromethane at 0℃; for 0.5h; Inert atmosphere; regioselective reaction;
80%
With diisobutylaluminium hydride In dichloromethane at 0 - 20℃;80%
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  • 5735-53-5  CAS NO.5735-53-5

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    5735-53-5 CAS NO.5735-53-5

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Specification

The Benzomorpholine, with the cas registry number 5735-53-5, has the systematic name of 3,4-dihydro-2H-1,4-benzoxazine. It belongs to the product categories of Pharmacetical and Heterocycles series. And the molecular formula of the chemical is C8H9NO.

The characteristics of this chemical are as followings: (1)ACD/LogP: 1.64; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.61; (4)ACD/LogD (pH 7.4): 1.64; (5)ACD/BCF (pH 5.5): 9.65; (6)ACD/BCF (pH 7.4): 10.36; (7)ACD/KOC (pH 5.5): 172.8; (8)ACD/KOC (pH 7.4): 185.51; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 12.47 Å2; (13)Index of Refraction: 1.541; (14)Molar Refractivity: 38.76 cm3; (15)Molar Volume: 123.3 cm3; (16)Polarizability: 15.36×10-24cm3; (17)Surface Tension: 40.3 dyne/cm; (18)Density: 1.095 g/cm3; (19)Flash Point: 91 °C; (20)Enthalpy of Vaporization: 48.78 kJ/mol; (21)Boiling Point: 250.6 °C at 760 mmHg; (22)Vapour Pressure: 0.0215 mmHg at 25°C.

Preparation of Benzomorpholine: This chemical can be prepared by 4-acetyl-3,4-dihydro-2H-benzo[1,4]oxazine. The reaction will need reagent 70% Redal, and the menstruum toluene. The reaction time is 70 minutes with temperature of -40°C, and the yield is about 100%. 

Uses of Benzomorpholine: It can react with chloroacetyl chloride to produce 4-chloroacetyl-3,4-dihydro-2H-benzo[1,4]oxazine. This reaction will need reagent pyridine, and the menstruum benzene. And the yield is about 100%.   

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O2c1ccccc1NCC2
(2)InChI: InChI=1/C8H9NO/c1-2-4-8-7(3-1)9-5-6-10-8/h1-4,9H,5-6H2
(3)InChIKey: YRLORWPBJZEGBX-UHFFFAOYAQ