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HomeProduct name list3-Hydroxyazetidine hydrochloride

3-Hydroxyazetidine hydrochloride

  • CAS NO.:18621-18-6
  • Empirical Formula: C3H8ClNO
  • Molecular Weight: 109.55
  • MDL number: MFCD02683887
  • EINECS: 628-004-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-24 21:11:45
3-Hydroxyazetidine hydrochloride Structural

What is 3-Hydroxyazetidine hydrochloride?

Description

3-Hydroxyazetidine hydrochloride is an azaecyclobutane compound that is an essential intermediate in the synthesis of Brectinib, which is obtained through a multi-step reaction. Brectinib was approved by the European Union. The monotherapy or in combination with methotrexate for the treatment of adult patients with moderate to severe active rheumatoid arthritis with inadequate or intolerant relief from one or more antirheumatic drugs. It is also the first JAK inhibitor approved in the European Union for treating rheumatoid arthritis.

Chemical properties

white crystal

The Uses of 3-Hydroxyazetidine hydrochloride

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.

Synthesis

A solution of l-(diphenylmethyl)-3-hydroxy azetidine hydrochloride (11.8 g) in absolute ethanol (700 mL) was hydrogenated at room temperature over Pd(OH)2/C in a Parr shaker (4 atm). After 12 hr the catalyst was filtered off and the filtrate evaporated to dryness to give3-hydroxyazetidine hydrochloride (4.20 g, 94%).

Preparation method

3-Hydroxyazetidine hydrochloride is the common drug intermediate of outbalance; for the preparation of 3-hydroxy azetidine hydrochloride, bibliographical information be that hydrogenation makes so that the N-benzyl-the 3-hydroxy azetidine is as raw material. However, hydrogenation is mixed and disorderly, which is difficult to purify, and the purifying of the finished product is the method of column chromatography. Or with N, N-diphenyl-methyl-3-hydroxy azetidine is raw material, and hydrogenation makes. However, the byproduct of hydrogenation (ditane) is challenging to remove, and the purifying of the finished product is also the method with column chromatography, and the employed raw material is all more expensive, making the cost compared to the product high. A method comprises taking t-butylamine and epichlorohydrin as raw materials and performing a cyclization reaction, an acetyl reaction, and a desacetyl reaction successively to give 3-hydroxyazetidine hydrochloride. The product is high in purity and is a white solid.

Properties of 3-Hydroxyazetidine hydrochloride

Melting point: 85-90 °C
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
solubility  DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form  Solid
color  White to Off-White
Water Solubility  Soluble in water, DMSO, methanol.
Sensitive  Hygroscopic
Stability: Hygroscopic
InChI InChI=1S/C3H7NO.ClH/c5-3-1-4-2-3;/h3-5H,1-2H2;1H
CAS DataBase Reference 18621-18-6(CAS DataBase Reference)

Safety information for 3-Hydroxyazetidine hydrochloride

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H318:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.

Computed Descriptors for 3-Hydroxyazetidine hydrochloride

InChIKey UQUPQEUNHVVNKW-UHFFFAOYSA-N
SMILES C1(O)CNC1.Cl

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JSK Chemicals

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Rivashaa Agrotech Biopharma Pvt. Ltd.

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ALS INDIA LIFE SCIENCES

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