Product Name

  • Name

    1-Benzhydrylazetidin-3-one

  • EINECS
  • CAS No. 40320-60-3
  • Density 1.182 g/cm3
  • Solubility
  • Melting Point 75.0 to 79.0 °C
  • Formula C16H15NO
  • Boiling Point 351.9 °C at 760 mmHg
  • Molecular Weight 237.301
  • Flash Point 156.1 °C
  • Transport Information
  • Appearance
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 40320-60-3 (1-Benzhydrylazetidin-3-one)
  • Hazard Symbols
  • Synonyms 1-(1,1-Diphenylmethyl)azetidin-3-one;1-(Diphenylmethyl)-3-azetidinone;1-[Bis(phenyl)methyl]azetidin-3-one;N-Benzhydrylazetidin-3-one;N-Diphenylmethylazetidin-3-one;
  • PSA 20.31000
  • LogP 2.59860

Synthetic route

1-(diphenylmethyl)-3-hydroxyazetidine
18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -78℃; for 1h;
Stage #2: With triethylamine In dichloromethane		96%
With oxalyl dichloride; dimethyl sulfoxide at -78℃; Swern oxidation;93%
With sulfur trioxide pyridine complex; triethylamine In dimethyl sulfoxide at 10 - 30℃;92.4%
sulphur trioxide pyridine

sulphur trioxide pyridine

1-(diphenylmethyl)-3-hydroxyazetidine
18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide89%
1-(diphenylmethyl)-3-azetidinol hydrochloride
90604-02-7

1-(diphenylmethyl)-3-azetidinol hydrochloride

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
With sulfur trioxide pyridine complex; triethylamine In dimethyl sulfoxide at 0 - 20℃;82%
With sulfur trioxide pyridine complex; triethylamine In tetrahydrofuran; dimethyl sulfoxide at 0 - 20℃; for 2h;67%
With sulfur trioxide pyridine complex; triethylamine In dimethylsulfoxide-d6 for 2h;66%
pyridine-2-sulfonic acid
15103-48-7

pyridine-2-sulfonic acid

1-(diphenylmethyl)-3-hydroxyazetidine
18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
With triethylamine In dimethyl sulfoxide at 50℃; for 0.666667h;60%
aminodiphenylmethane hydrochloride
5267-34-5

aminodiphenylmethane hydrochloride

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NaOH / H2O; CH2Cl2 / 12 h / 20 °C
1.2: 51 percent / methanol / 72 h / 20 °C
2.1: alkaline aq. solution; CH2Cl2 / 1 h / 20 °C
2.2: 50 percent / SO3*pyridine; TEA / dimethylsulfoxide / 2 h / 20 °C
View Scheme
Benzhydrylamine
91-00-9

Benzhydrylamine

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2.) 1 N NaOH / 1.) a) RT, 3 d, b) reflux, 72 h, 2.) Et2O
2: 67 percent / pyridine, phosphoric acid, dicyclohexylcarbodiimide, DMSO / CH2Cl2 / 2 h / Ambient temperature
View Scheme
1-benzhydryl-3-hydroxy-azetidine-3-carbonitrile
686347-59-1

1-benzhydryl-3-hydroxy-azetidine-3-carbonitrile

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
With sodium hydroxide; dihydrogen peroxide; dimethyl sulfoxide In methanol; water at 45℃; for 0.166667h; Product distribution / selectivity;
oxalyl dichloride
79-37-8

oxalyl dichloride

1-(diphenylmethyl)-3-azetidinol hydrochloride
90604-02-7

1-(diphenylmethyl)-3-azetidinol hydrochloride

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide; ethyl acetate
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

3-oxo-azetidine-1-carboxylic acid ethyl ester
105258-88-6

3-oxo-azetidine-1-carboxylic acid ethyl ester

Conditions
ConditionsYield
In benzene Heating;100%
isonipecotic acid
498-94-2

isonipecotic acid

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid
874800-95-0

1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxylic acid

Conditions
ConditionsYield
With methanol; polymer-bound trimethyl ammonium cyanoborohydride; acetic acid at 120℃; for 0.0833333h; Polystyrene; Microwave irradiation;100%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

1-benzhydryl-3-methylazetidin-3-ol
40320-63-6

1-benzhydryl-3-methylazetidin-3-ol

Conditions
ConditionsYield
In tetrahydrofuran; diethyl ether at 0℃; for 1h;100%
Stage #1: methyl magnesium iodide; N-benzhydryl 3-azetidinone In diethyl ether at 0℃; for 1h; Grignard Reaction;
Stage #2: With methanol In diethyl ether; dichloromethane		68%
(2,8-bis-trifluoromethyl)-4-bromoquinoline
35853-45-3

(2,8-bis-trifluoromethyl)-4-bromoquinoline

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

3-(2,8-bis(trifluoromethyl)-4-quinolinyl)-1-diphenylmethyl-3-azetidinol
260972-91-6

3-(2,8-bis(trifluoromethyl)-4-quinolinyl)-1-diphenylmethyl-3-azetidinol

Conditions
ConditionsYield
With n-butyllithium In water100%
potassium cyanide

potassium cyanide

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

methylamine hydrochloride
593-51-1

methylamine hydrochloride

1-Benzhydryl-3-methylaminoazetidine-3-carbonitrile

1-Benzhydryl-3-methylaminoazetidine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; methylamine hydrochloride With acetic acid In methanol at 20℃; for 0.0833333h;
Stage #2: potassium cyanide at 60℃; for 19h;		100%
Stage #1: N-benzhydryl 3-azetidinone; methylamine hydrochloride With acetic acid In methanol at 20℃; for 0.0833333h;
Stage #2: potassium cyanide at 60℃; for 19h;		100%
Stage #1: N-benzhydryl 3-azetidinone; methylamine hydrochloride With acetic acid In methanol at 20℃; for 0.0833333h;
Stage #2: potassium cyanide In methanol at 60℃; for 19h;		100%
...Expand
potassium cyanide

potassium cyanide

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

dimethyl amine
124-40-3

dimethyl amine

1-Benzhydryl-3-dimethylaminoazetidine-3-carbonitrile
736994-11-9

1-Benzhydryl-3-dimethylaminoazetidine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; dimethyl amine In tetrahydrofuran for 0.0833333h;
Stage #2: potassium cyanide With acetic acid In methanol at 20 - 60℃; for 19.0833h;		100%
Stage #1: N-benzhydryl 3-azetidinone; dimethyl amine In tetrahydrofuran for 0.0833333h;
Stage #2: potassium cyanide With acetic acid In tetrahydrofuran; methanol at 60℃; for 19h;		100%
...Expand
potassium cyanide

potassium cyanide

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

N,N-diethylaniline
91-66-7

N,N-diethylaniline

1-Benzhydryl-3-methylaminoazetidine-3-carbonitrile

1-Benzhydryl-3-methylaminoazetidine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; N,N-diethylaniline With acetic acid In methanol at 20℃; for 0.0833333h;
Stage #2: potassium cyanide In methanol at 60℃; for 19h;		100%
...Expand
potassium cyanide

potassium cyanide

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

ethanamine hydrochloride
557-66-4

ethanamine hydrochloride

1-benzhydryl-3-ethylamino-azetidine-3-carbonitrile
686344-60-5

1-benzhydryl-3-ethylamino-azetidine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; ethanamine hydrochloride With acetic acid In methanol at 20℃; for 0.25h;
Stage #2: potassium cyanide In methanol at 60℃;		100%
...Expand
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

benzyltriphenylphosphonium bromide
1449-46-3

benzyltriphenylphosphonium bromide

3-benzylidene-1-(diphenylmethyl)azetidine
897019-45-3

3-benzylidene-1-(diphenylmethyl)azetidine

Conditions
ConditionsYield
Stage #1: benzyltriphenylphosphonium bromide With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.166667h;
Stage #2: N-benzhydryl 3-azetidinone In dimethyl sulfoxide at 60℃;		100%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

C22H27N3O

C22H27N3O

Conditions
ConditionsYield
at 90℃; for 16h;100%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

N-benzhydryl-3-(hydroxyimino)azetidine
40569-56-0

N-benzhydryl-3-(hydroxyimino)azetidine

Conditions
ConditionsYield
With sodium hydroxide; hydroxylamine hydrochloride In ethanol Heating;99%
With hydroxylamine hydrochloride; sodium carbonate In water at 40℃; for 5h;
With hydroxylamine hydrochloride; sodium acetate In methanol Reflux;
With hydroxylamine hydrochloride; sodium carbonate In water at 40℃; pH=7 - 8;
4-carboxamidopiperidine
39546-32-2

4-carboxamidopiperidine

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxamide
957054-82-9

1-[1-(diphenylmethyl)azetidin-3-yl]piperidine-4-carboxamide

Conditions
ConditionsYield
With methanol; polymer-bound trimethyl ammonium cyanoborohydride; acetic acid at 120℃; for 0.0833333h; Polystyrene; Microwave irradiation;99%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

methyl trifluoromethanesulfonate
333-27-7

methyl trifluoromethanesulfonate

1-(Diphenylmethyl)-1-methyl-3-oxoazetidinium trifluoromethanesulfonate

1-(Diphenylmethyl)-1-methyl-3-oxoazetidinium trifluoromethanesulfonate

Conditions
ConditionsYield
In dichloromethane at 20℃;98%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

methyl chloroformate
79-22-1

methyl chloroformate

methyl 3-oxoazetidine-1-carboxylate

methyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
In dichloromethane for 15h; Heating;97%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

3-butene-1-amine
2524-49-4

3-butene-1-amine

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
72824-04-5

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

(3-allyl-1-benzhydryl-azetidin-3-yl)-but-3-enyl-amine

(3-allyl-1-benzhydryl-azetidin-3-yl)-but-3-enyl-amine

Conditions
ConditionsYield
With 4A MS In toluene at 80℃;96%
...Expand
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

methylmagnesium chloride
676-58-4

methylmagnesium chloride

1-benzhydryl-3-methylazetidin-3-ol
40320-63-6

1-benzhydryl-3-methylazetidin-3-ol

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; methylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 1.83333h;
Stage #2: With water; ammonium chloride In tetrahydrofuran; ethyl acetate		96%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

C16H16N2O*ClH
1375075-83-4

C16H16N2O*ClH

Conditions
ConditionsYield
With hydroxylamine hydrochloride96%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

tert-butyl 2-[1-(diphenylmethyl)azetidin-3-ylidene]hydrazinecarboxylate
1025713-55-6

tert-butyl 2-[1-(diphenylmethyl)azetidin-3-ylidene]hydrazinecarboxylate

Conditions
ConditionsYield
With acetic acid In methanol at 0℃; for 16h;94%
With acetic acid In methanol for 18h;82%
With acetic acid In methanol at 20℃;30%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

(S)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester
147081-29-6

(S)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester

tert-butyl (3S)-4-(1-(diphenylmethyl)azetidin-3-yl)-3-methylpiperazine-1-carboxylate

tert-butyl (3S)-4-(1-(diphenylmethyl)azetidin-3-yl)-3-methylpiperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; (S)-3-methyl-piperazine-1-carboxylic acid tert-butyl ester With acetic acid In tetrahydrofuran at 20℃; for 1.66667h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 13.75h;		93%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

2-((difluoromethyl)sulfinyl)pyridine
1219454-89-3

2-((difluoromethyl)sulfinyl)pyridine

1-benzhydryl-3-(difluoro(pyridin-2-ylsulfonyl)methyl)azetidin-3-ol

1-benzhydryl-3-(difluoro(pyridin-2-ylsulfonyl)methyl)azetidin-3-ol

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -98℃; for 0.5h; Schlenk technique; Inert atmosphere;93%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

methylmagnesium bromide
75-16-1

methylmagnesium bromide

1-benzhydryl-3-methylazetidin-3-ol
40320-63-6

1-benzhydryl-3-methylazetidin-3-ol

Conditions
ConditionsYield
In tetrahydrofuran at -78 - 20℃;92%
In tetrahydrofuran; diethyl ether at 0℃; for 2h;89%
In tetrahydrofuran at 0 - 20℃; for 2.33333h;84%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

dimethyl amine
124-40-3

dimethyl amine

3-(dimethylamino)-1-(diphenylmethyl)azetidine
55438-79-4

3-(dimethylamino)-1-(diphenylmethyl)azetidine

Conditions
ConditionsYield
With hydrogen; 5% palladium over charcoal In methanol; water92%
With hydrogen; 5% palladium over charcoal In methanol92%
With hydrogen; 5%-palladium/activated carbon In methanol; water92%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

dimethyl 2,2-di(but-2-yn-1-yl)malonate
107428-05-7

dimethyl 2,2-di(but-2-yn-1-yl)malonate

(1Z,6Z)-dimethyl 3-benzhydryl-1,6-dimethyl-5-oxo-4,5,7,9-tetrahydro-2H-cyclopenta[d]azocine-8,8(3H)-dicarboxylate

(1Z,6Z)-dimethyl 3-benzhydryl-1,6-dimethyl-5-oxo-4,5,7,9-tetrahydro-2H-cyclopenta[d]azocine-8,8(3H)-dicarboxylate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene In toluene at 0℃; for 8h; Inert atmosphere;92%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

1-(diphenylmethyl)-3-[(trimethylsilyl)oxy]azetidine-3-carbonitrile
151097-25-5

1-(diphenylmethyl)-3-[(trimethylsilyl)oxy]azetidine-3-carbonitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 2h;91%
With triethylamine In dichloromethane at 20℃; for 2h;91%
With triethylamine In dichloromethane at 20℃; for 2h;91%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

1-(but-2-yn-1-yloxy)but-2-yne
55833-53-9

1-(but-2-yn-1-yloxy)but-2-yne

(3aE,9E)-6-benzhydryl-4,9-dimethyl-3,5,6,7-tetrahydrofuro[3,4-d]azocin-8(1H)-one

(3aE,9E)-6-benzhydryl-4,9-dimethyl-3,5,6,7-tetrahydrofuro[3,4-d]azocin-8(1H)-one

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel(0); 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene In toluene at 0℃; for 8h; Inert atmosphere;91%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

(R)-tert-butyl 2-methylpiperazine-1-carboxylate
170033-47-3

(R)-tert-butyl 2-methylpiperazine-1-carboxylate

tert-butyl (2R)-4-(1-(diphenylmethyl)azetidin-3-yl)-2-methylpiperazine-1-carboxylate

tert-butyl (2R)-4-(1-(diphenylmethyl)azetidin-3-yl)-2-methylpiperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: N-benzhydryl 3-azetidinone; (R)-tert-butyl 2-methylpiperazine-1-carboxylate With acetic acid In tetrahydrofuran at 20℃; for 0.416667h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 18.5h;		90%
N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

phenylacetylene
536-74-3

phenylacetylene

C24H21NO

C24H21NO

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: N-benzhydryl 3-azetidinone In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;		90%
4-ethylpiperazine
5308-25-8

4-ethylpiperazine

N-benzhydryl 3-azetidinone
40320-60-3

N-benzhydryl 3-azetidinone

1-(1-(diphenylmethyl)azetidin-3-yl)-4-ethylpiperazine

1-(1-(diphenylmethyl)azetidin-3-yl)-4-ethylpiperazine

Conditions
ConditionsYield
Stage #1: 4-ethylpiperazine; N-benzhydryl 3-azetidinone With acetic acid In tetrahydrofuran at 20℃; for 0.75h;
Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 15h;		89%
Stage #1: 4-ethylpiperazine; N-benzhydryl 3-azetidinone With acetic acid In tetrahydrofuran at 20℃; for 0.75h;
Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 15h;		89%

1-Benzhydrylazetidin-3-one Specification

The 1-Benzhydrylazetidin-3-one, also known as 1-Benzhydryl-3-azetidinone, is an organic compound with the formula C16H15NO. It belongs to the product category of Ring Systems. With the CAS registry number 40320-60-3, its IUPAC name is 1-benzhydrylazetidin-3-one.

Physical properties of 1-Benzhydrylazetidin-3-one: (1)ACD/LogP: 2.12; (2)#H bond acceptors: 2; (3)#Freely Rotating Bonds: 3; (4)Index of Refraction: 1.626; (5)Molar Refractivity: 71.09 cm3; (6)Molar Volume: 200.6 cm3; (7)Surface Tension: 51.5 dyne/cm; (8)Density: 1.182 g/cm3; (9)Flash Point: 156.1 °C; (10)Enthalpy of Vaporization: 59.66 kJ/mol; (11)Boiling Point: 351.9 °C at 760 mmHg; (12)Vapour Pressure: 3.99E-05 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1C(=O)CN1C(C2=CC=CC=C2)C3=CC=CC=C3
(2)InChI: InChI=1S/C16H15NO/c18-15-11-17(12-15)16(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-10,16H,11-12H2
(3)InChIKey: AVUDXLOVIBJFQA-UHFFFAOYSA-N

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