• Name

  1-(Diphenylmethyl)-3-hydroxyazetidine

• EINECS 606-074-6
• CAS No. 18621-17-5
• Article Data42
• CAS DataBase
• Density 1.189 g/cm³
• Solubility
• Melting Point 106 °C
• Formula C₁₆H₁₇NO
• Boiling Point 353.8 °C at 760 mmHg
• Molecular Weight 239.317
• Flash Point 101.7 °C
• Transport Information
• Appearance white solid
• Safety 26-37/39
• Risk Codes 36/37/38
• Molecular Structure
• Hazard Symbols Xi,C
• Synonyms 1-Benzhydryl-3-azetanol;1-Benzhydryl-3-hydroxyazetidine;1-Benzhydrylazetidin-3-ol;3-Hydroxy-1-(diphenylmethyl)azetidine;N-(Diphenylmethyl)-3-hydroxyazetidine;N-(Diphenylmethyl)azetidin-3-ol;3-Azetidinol,1-(diphenylmethyl)-;
• PSA 23.47000
• LogP 2.39040

Synthetic route

91-00-9

Benzhydrylamine

106-89-8

epichlorohydrin

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

Conditions

Conditions	Yield
With sodium carbonate In isopropyl alcohol for 12h; Solvent; Temperature; Reagent/catalyst; Reflux;	88.2%
In methanol for 72h; Inert atmosphere;	83%
With hydrogenchloride In N,N-dimethyl-formamide	74%

40320-60-3

N-benzhydryl 3-azetidinone

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

Conditions

Conditions	Yield
With methanol; sodium tetrahydroborate at 0 - 20℃;	86.2%
With sodium tetrahydroborate

C29H29NOSi

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

Conditions

Conditions	Yield
With Nonafluorobutanesulfonyl fluoride; TPGS-750-M In propan-1-ol; water at 50℃; for 24h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	80%

63477-43-0

3-chloro-1-diphenylmethylamino-2-hydroxypropane

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 0 - 90℃;	75%
With triethylamine In acetonitrile for 49h; Reflux;	65%
In ethanol for 3h; Heating / reflux;
With triethylamine In methanol; acetonitrile Reflux;

552-82-9

benzhydrylidene(methyl)amine

106-89-8

epichlorohydrin

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

Conditions

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 95℃; for 72h;	74%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

124-63-0

methanesulfonyl chloride

33301-41-6

1-benzhydryl-3-azetidinyl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2h;	100%
With triethylamine In dichloromethane at 0℃;	100%
With triethylamine In dichloromethane at 20℃; for 1h; Product distribution / selectivity;	100%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

124-63-0

methanesulfonyl chloride

106859-45-4

1-(Diphenylmethyl)-3-azetidinol methanesulfonate (ester) hydrochloride

Conditions

Conditions	Yield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine; methanesulfonyl chloride With triethylamine In benzene at 0 - 20℃; Stage #2: With hydrogenchloride In diethyl ether at 0℃;	100%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

90604-02-7

1-(diphenylmethyl)-3-azetidinol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In ethyl acetate at 20℃; for 0.166667h;	100%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

1538-75-6

2,2-dimethylpropanoic anhydride

141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

Conditions

Conditions	Yield
With hydrogen; 20% Pd(OH)2 on carbon In ethyl acetate under 760.051 Torr; for 24h;	100%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

18162-48-6

tert-butyldimethylsilyl chloride

391910-20-6

3-((tert-butyldimethylsilyl)oxy)-1-(diphenylmethyl)azetidine

Conditions

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 0.5h;	100%
With 1H-imidazole In dichloromethane at 20℃; for 3h;	99.8%
With 1H-imidazole In N,N-dimethyl-formamide; toluene at 0 - 20℃; for 22h;	53%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

76-05-1

trifluoroacetic acid

638216-99-6

3-hydroxyazetidin-1-ium 2,2,2-trifluoroacetate

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In methanol for 24h;	99%

232599-02-9

1-benzhydryl-3-(4-chlorobenzyloxy)azetidine

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

102-47-6

3,4-Dichlorophenylmethyl chloride

232599-04-1

3-(3,4-Dichlorobenzyloxy)-1-(diphenylmethyl)azetidine

Conditions

Conditions	Yield
	92%

...Expand

232599-02-9

1-benzhydryl-3-(4-chlorobenzyloxy)azetidine

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

402-23-3

1-bromomethyl-3-trifluoromethylbenzene

232599-06-3

3-(3-(Trifluoromethyl)benzyloxy)-1-(diphenylmethyl)azetidine

Conditions

Conditions	Yield
	91%

...Expand

617-88-9

2-Chloromethylfuran

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

1309208-08-9

1-benzhydryl-3-(furan-2-ylmethoxy)azetidine

Conditions

Conditions	Yield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: 2-Chloromethylfuran In N,N-dimethyl-formamide; mineral oil at 20℃;	91%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

36476-84-3

3-bromo-1-benzhydrylazetidine

Conditions

Conditions	Yield
With pyridine; phosphorus tribromide In 1,2-dichloro-ethane at 0 - 10℃; for 7h; Solvent; Reagent/catalyst; Concentration;	90%
Multi-step reaction with 2 steps 1: 89 percent / pyridine 2: 81 percent / LiBr, Li2CO3 / tetrahydrofuran View Scheme

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

100-39-0

benzyl bromide

3-(benzyloxy)-1-(diphenylmethyl)azetidine

Conditions

Conditions	Yield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 60℃; for 18h; Inert atmosphere;	90%
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: benzyl bromide In tetrahydrofuran; mineral oil at 60℃; for 18h;	85%
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide; mineral oil at 0 - 80℃;	24%

sulphur trioxide pyridine

sulphur trioxide pyridine

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

40320-60-3

N-benzhydryl 3-azetidinone

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide	89%

89581-84-0

2-chloro-3-(chloromethyl)pyridine

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

1357305-91-9

3-(2-chloropyrid-3-ylmethoxy)-1-benzhydrylazetidine

Conditions

Conditions	Yield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Stage #2: 2-chloro-3-(chloromethyl)pyridine In tetrahydrofuran; dimethyl sulfoxide; mineral oil at 20 - 50℃; for 21.5h;	89%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

106-96-7

propargyl bromide

C19H19NO

Conditions

Conditions	Yield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran; mineral oil at 60℃; for 18h;	87%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

10133-20-7

2-bromomethylbenzo[b]thiophene

1309208-65-8

1-benzhydryl-3-(benzo[b]thiophen-2-ylmethoxy)azetidine

Conditions

Conditions	Yield
Stage #1: 1-(diphenylmethyl)-3-hydroxyazetidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: 2-bromomethylbenzo[b]thiophene In N,N-dimethyl-formamide; mineral oil at 20℃; for 3h;	85%

232599-02-9

1-benzhydryl-3-(4-chlorobenzyloxy)azetidine

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

459-46-1

4-Fluorobenzyl bromide

232599-11-0

3-(4-Fluorobenzyloxy)-1-(diphenylmethyl)azetidine

Conditions

Conditions	Yield
	83%

...Expand

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

352-33-0

1-Chloro-4-fluorobenzene

3-(4-chlorophenoxy)-1-(diphenylmethyl)azetidine

Conditions

Conditions	Yield
In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; mineral oil	82.4%
In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; ethanol; mineral oil	82.4%

18621-17-5

1-(diphenylmethyl)-3-hydroxyazetidine

104-83-6

1-Chloro-4-(chloromethyl)benzene

232599-02-9

1-benzhydryl-3-(4-chlorobenzyloxy)azetidine

Conditions

Conditions	Yield
With NaH In N,N-dimethyl-formamide	80%

1-(Diphenylmethyl)-3-hydroxyazetidine Chemical Properties

1-(Diphenylmethyl)-3-hydroxyazetidine Uses

1-(Diphenylmethyl)-3-hydroxyazetidine Safety Profile

1-(Diphenylmethyl)-3-hydroxyazetidine Specification