3-Hydroxyazetidine hydrochloride

Iupac Name：azetidin-3-ol;hydrochloride

Molecular Weight：109.553

Modify Date.: 2022-11-22 21:17

Introduction: 3-Hydroxyazetidine hydrochloride is a useful intermediate in the synthesis of polypeptides. 3-Hydroxyazetidine hydrochloride Preparation Products And Raw materials Raw materials View more+

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1. Names and Identifiers

1.1 Name: 3-Hydroxyazetidine hydrochloride
1.2 Synonyms: 3 HYDROXY AZETIDINE HYDROCHLORIDE 3-AZETIDINOL HYDROCHLORIDE 3-Azetidinol hydrochloride (1:1) 3-Azetidinol, hydrochloride (1:1) 3-hydroxy-1-azetidine hydrochloride 3-hydroxyazacyclobutane hydrochloride 3-HYDROXYAZETIDINE HCL 3-hydroxyazetidine monohydrochloride 3-Hydroxyazetidine-HCl 3-hydroxyazetidinium chloride AZETAN-2-ONE azetidin-3-ol hcl AZETIDIN-3-OL HYDROCHLORIDE azetidin-3-ol monohydrochloride AZETIDIN-3-OL, HYDROCHLORIDE SALT azetidin-3-ol-hydrochloride BUTTPARK 75\04-67 MFCD02683887

1.3 CAS No.: 18621-18-6

1.4 CID: 2759290

1.5 EINECS(EC#): 1592732-453-0

1.6 Molecular Formula: C3H8ClNO (isomer)

1.7 Inchi: InChI=1S/C3H7NO.ClH/c5-3-1-4-2-3;/h3-5H,1-2H2;1H

1.8 InChkey: UQUPQEUNHVVNKW-UHFFFAOYSA-N

1.9 Canonical Smiles: C1C(CN1)O.Cl

1.10 Isomers Smiles: C1C(CN1)O.Cl

2. Properties

2.1 Density: 1.1010

2.1 Melting point: 85-90 °C

2.1 Boiling point: 170.7 °C at 760 mmHg

2.1 Flash Point: 120.4 °C

2.1 Precise Quality: 109.02900

2.1 PSA: 32.26000

2.1 logP: 0.08130

2.1 Appearance: White Solid

2.2 Storage: Hygroscopic. Ambient temperatures.

2.3 Chemical Properties: white crystal

2.4 Color/Form: White to Yellow Solid

2.5 Water Solubility: Soluble in water, DMSO, methanol.

2.6 StorageTemp: Keep in dark place,Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 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)

3.2 Usage: 3-Hydroxyazetidine hydrochloride is a useful intermediate in the synthesis of polypeptides. 3-Hydroxyazetidine hydrochloride Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Symbol: GHS05, GHS07

4.1 Hazard Codes: C; Xi; Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: 26-36/37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H302-H315-H318-H335

4.1 RIDADR: UN1759

4.1 Caution Statement: P261-P280-P305 + P351 + P338

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes:??C,Xi,Xn
Risk Statements: 36/37/38-41-37/38-22
R36/37/38:Irritating to eyes, respiratory system and skin.?
R41:Risk of serious damage to the eyes.?
R37/38:Irritating to respiratory system and skin.?
R22:Harmful if swallowed.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
Hazard Note: Harmful/Corrosive
HazardClass: irritant

4.2 Sensitive: Hygroscopic

4.3 Specification: ?3-Hydroxyazetidine Hydrochloride ,? its cas register number is 18621-18-6. It also can be called azetidin-3-ol-hydrochloride ; azetidin-3-ol hydrochloride ; 3-hydroxy-Azetidine hydrochloride ; 1-azoniacyclobutan-3-ol ; 3-(Hydroxy)azetidine Hydrochloride ; azetidin-3-ol ; 3-Hydroxyazetidine HCl ; Azetidin-3-ol hydrochloride (1:1) ; Azetidin-3-olhydrochlorid(1:1) ; 3-azetidinol, hydrochloride (1:1) .?3-Hydroxyazetidine Hydrochloride is?a useful intermediate in the synthesis of polypeptides.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Serious eye damage, Category 1

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H318 Causes serious eye damage H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

18621-18-6Total: 7 Synthesis Route

90604-02-7 104 Suppliers

18621-18-6 248 Suppliers

Literatures:
Isoda, Takeshi; Ushirogochi, Hideki; Satoh, Koichi; Takasaki, Tsuyoshi; Yamamura, Itsuki; Sato, Chisato; Mihira, Ado; Abe, Takao; Tamai, Satoshi; Yamamoto, Shigeki; Kumagai, Toshio; Nagao, Yoshimitsu Journal of Antibiotics, 2006 , vol. 59, # 4 p. 241 - 247
Yield: ~99%

19540-05-7

18621-18-6 248 Suppliers

Literatures:
Tetrahedron Letters, , vol. 40, # 19 p. 3761 - 3764
Yield: null

54881-13-9 72 Suppliers

18621-18-6 248 Suppliers

Literatures:
WO2006/15194 A2, ; Page/Page column 14 ;
Yield: null

View all

8. Precursor and Product

precursor:

90604-02-7

18621-17-5

54881-13-9

19540-05-7

848438-92-6

143329-27-5

223382-13-6

product :

161715-27-1

128117-22-6

154010-96-5

141890-67-7

141699-55-0

189279-58-1

9. Other Information

9.0 Chemical Properties: white crystal

9.1 Uses: A useful intermediate in the synthesis of polypeptides

9.2 Usage: 3-Hydroxyazetidine hydrochloride is an building block used in a recent synthesis of a fluoroquinolone antibiotic and a useful intermediate in the synthesis of polypeptides.

9.3 Uses: 3-Hydroxyazetidine hydrochloride is a useful intermediate in the synthesis of polypeptides.

9.4 Storage Conditions: 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)

10. Computational chemical data

Molecular Weight: 109.553g/mol
Molecular Formula: C₃H₈ClNO
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 109.0294416
Monoisotopic Mass: 109.0294416
Complexity: 33.9
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 32.3
Heavy Atom Count: 6
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADccBCIAAEAAAAAAAAAAAAAABYAAAAAAAAAAAAAAAAAAAAAAAAHgAQCAAACBThgAYAAALAAgAAAAAAAAAAAAAAAAAAAIAIAAACEAAAAAAAAAAAEAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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