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Home > Encyclopedia > 3-Hydroxyazetidine hydrochloride

3-Hydroxyazetidine hydrochloride

3-Hydroxyazetidine hydrochloride structure

3-Hydroxyazetidine hydrochloride 

structure
  • CAS No:

    18621-18-6

  • Formula:

    C3H7NO.ClH

  • Chemical Name:

    3-Hydroxyazetidine hydrochloride

  • Synonyms:

    3-Azetidinol,hydrochloride (1:1);3-Azetidinol,hydrochloride;3-Hydroxyazetidine hydrochloride;Azetidine-3-ol hydrochloride;Azetidin-3-ol hydrochloride;3-Hydroxyazetedine hydrochloride

  • Categories:

    Pharmaceutical Intermediates  >  Antibacterials

Description

white crystal

3-Hydroxyazetidine hydrochloride Basic Attributes

109.55

109.029442

1592732-453-0

DTXSID30374721

29339900

Characteristics

32.3

0.08130

White Solid

91-92 °C

170.7°C at 760 mmHg

120.4ºC

Soluble in water, DMSO, methanol.

Room temperature.

0.464mmHg at 25°C

Safety Information

IRRITANT

NONH for all modes of transport

3

36/37/38-41-37/38-22

26-36/37/39

C,Xi,Xn

Harmful/Corrosive

P261-P280-P305 + P351 + P338

H302-H315-H318-H335

|Danger|H302 (85.71%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 50 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

3-Hydroxyazetidine hydrochloride Use and Manufacturing

Methods of Manufacturing

A solution of l-(diphenylmethyl)-3-hydroxyazetidine hydrochloride (11.8 g) in absolute ethanol (700 mL) was hydrogenated at room temperature over Pd(OH)2/C in a Parr shaker at 4 atm. After 12 hr the catalyst was filtered off and the filtrate evaporated to dryness to give3-hydroxyazetidine hydrochloride (4.20 g, 94percent). A reaction mixture of N-benzhydrylazetidin-3-ol HCl salt (2.76 g, 10.0 mmol) with palladium hydroxide, 20percent Pd (dry base) on C (400 mg) in 50 mL of MeOH was hydrogenated at 55 psi for 48 h. The reaction mixture was filtered through Celite pad and washed well with MeOH. The filtrate was concentrated under vacuum at room temperature water bath. The residue was treated with ether (3x30 ml) and the solvent is decanted. The solid was air dried to give 571 mg of HCl salt product (2) as white solid (52percent yield). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.33 (s, 1H) 3.63-3.80 (m, 2H) 3.93-4.09 (m, 2H) 4.40-4.58 (m, 1H) 6.18 (d, J=6.32 Hz, 1H).A reaction mixture of N-benzhydrylazetidin-3-ol HCI salt (2.76 g, 10.0 mmol) with palladium hydroxide, 20percent Pd (dry base) on C (400 mg) in 50 mL of MeOH was hydrogenated at 55 psi for 48 h. The reaction mixture was filtered through Celite pad and washed well with MeOH. The filtrate was concentrated under vacuum at room temperature water bath. The residue was treated with ether (3x30ml) and the solvent is decanted. The solid was air dried to give 571 mg of HCI salt product (2-2) as white solid (52percent yield). To a soln of 1-benzhydrylazetan-3-ol (1.0 g, 4.16 mmol) in methanol (20 mL) were added 10percent Pd/C (1.0 g) and 4N HCl in 1, 4-dioxane (2 mL). The mixture was flushed with Ar, and then stirred on Parr apparatus at 40 psi H2 for 6 h at 60°. The mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated and the resulting solid was washed with diethyl ether to give the desired product 0.31 g (68percent). 1H NMR (MeOD-d4): δ 4.17 (m, 1H), 4.22 (m, 2H), 3.91 (m, 2H)

Uses

A useful intermediate in the synthesis of polypeptides

Computed Properties

Molecular Weight:109.55
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:2
Exact Mass:109.0294416
Monoisotopic Mass:109.0294416
Topological Polar Surface Area:32.3
Heavy Atom Count:6
Complexity:33.9
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

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