ChemicalBook > CAS DataBase List > BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE

BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE

Product Name
BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE
CAS No.
128117-22-6
Chemical Name
BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE
Synonyms
1-Cbz-3-hydroxyazetidine;N-Cbz-3-hydroxyazetidine;1-N-CBZ-3-HYDROXYAZETIDINE;1-BOC-3-Hydroxyl-azetidine;BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLA;1-Benzyloxycarbonyl-3-hydroxyazetidine;BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE;Phenylmethyl 3-hydroxyazetidine-1-carboxylate;3-Hydroxy-azetidine-1-carboxylic acid benzyl ester;3-Hydroxy-azetidine-1-carboxylic acid benzyl ester 96%
CBNumber
CB7850884
Molecular Formula
C11H13NO3
Formula Weight
207.23
MOL File
128117-22-6.mol
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BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE Property

Boiling point:
356.7±42.0 °C(Predicted)
Density 
1.317
Flash point:
169.5℃
storage temp. 
2-8°C
form 
solid
pka
14.14±0.20(Predicted)
color 
White
InChI
InChI=1S/C11H13NO3/c13-10-6-12(7-10)11(14)15-8-9-4-2-1-3-5-9/h1-5,10,13H,6-8H2
InChIKey
XJWSNDGCJMGHSR-UHFFFAOYSA-N
SMILES
N1(C(OCC2=CC=CC=C2)=O)CC(O)C1
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Safety

HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

TRC
Product number
B535213
Product name
Benzyl3-Hydroxyazetidine-1-carboxylate
Packaging
10mg
Price
$45
Updated
2021/12/16
ChemScene
Product number
CS-M1634
Product name
1-Azetidinecarboxylicacid,3-hydroxy-,phenylmethylester
Purity
99.39%
Packaging
25g
Price
$46
Updated
2021/12/16
Matrix Scientific
Product number
068544
Product name
1-Azetidinecarboxylic acid
Purity
3-hydroxy-phenylmethyl ester>95%
Packaging
5g
Price
$20
Updated
2021/12/16
AK Scientific
Product number
X9721
Product name
1-Cbz-3-Hydroxyazetidine
Packaging
5g
Price
$27
Updated
2021/12/16
SynQuest Laboratories
Product number
4H56-1-LD
Product name
1-Cbz-3-hydroxyazetidine
Packaging
5G
Price
$55
Updated
2021/12/16
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BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE Chemical Properties,Usage,Production

Synthesis

18621-18-6

501-53-1

128117-22-6

General procedure for the synthesis of 1-Benzyloxycarbonyl-3-hydroxyazetidine from 3-hydroxyazetidine hydrochloride and benzyl chloroformate: K2CO3 (63.1 g, 0.46 mol) was added to a mixed solution of water (150 mL) and THF (300 mL) containing azetidin-3-ol hydrochloride (25 g, 0.23 mol). The reaction mixture was stirred at 20-25 °C for 30 min. Subsequently, benzyl chloroformate (40.9 g, 0.24 mol) was added slowly and dropwise over 30 min. The reaction mixture was first stirred at 0-5°C and then continued to stir overnight at 20-25°C. Upon completion of the reaction, THF was removed under reduced pressure using a rotary evaporator at 30 °C. The remaining mixture was extracted with ethyl acetate (2 × 150 mL). The organic layers were combined, washed with water (1 × 50 mL), dried with Na2SO4 and concentrated. The residue was purified by silica gel fast column chromatography using ethyl acetate-heptane (1:1 and 4:1) sequentially as eluent to afford the target product, 1-benzyloxycarbonyl-3-hydroxyazetidine (47.3 g, 100%), as a clear oil. The product was characterized by 1H NMR (300 MHz, CDCl3), 13C NMR (75 MHz, CDCl3), IR and ES-HRMS, and the data were consistent with the expected structure.

References

[1] Organic Process Research and Development, 2009, vol. 13, # 1, p. 54 - 59
[2] Patent: WO2010/36329, 2010, A2. Location in patent: Page/Page column 16-17; 21
[3] Chemical Communications, 2012, vol. 48, # 45, p. 5578 - 5580
[4] Patent: WO2016/128529, 2016, A1. Location in patent: Paragraph 0800; 0801; 0802
[5] Patent: WO2014/32, 2014, A1. Location in patent: Page/Page column 33

BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE Preparation Products And Raw materials

Raw materials

Preparation Products

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BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE Suppliers

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128117-22-6, BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATERelated Search:

3-CARBOXYMETHOXY-AZETIDINE-1-CARBOXYLIC ACID BENZYL ESTER BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE 3-(TOLUENE-4-SULFONYLOXY)-AZETIDINE-1-CARBOXYLIC ACID BENZYL ESTER

  • BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE
  • N-Cbz-3-hydroxyazetidine
  • 3-Hydroxy-azetidine-1-carboxylic acid benzyl ester
  • 1-Cbz-3-hydroxyazetidine
  • 1-Azetidinecarboxylic acid 3-hydroxy-, phenylMethyl ester
  • Phenylmethyl 3-hydroxyazetidine-1-carboxylate
  • 1-Benzyloxycarbonyl-3-hydroxyazetidine
  • 1-N-CBZ-3-HYDROXYAZETIDINE
  • 3-Hydroxy-azetidine-1-carboxylic acid benzyl ester 96%
  • 1-BOC-3-Hydroxyl-azetidine
  • BENZYL 3-HYDROXYAZETIDINE-1-CARBOXYLA
  • 1-Azetidinecarboxylic acid, 3-hydroxy-, phenylmethyl ester - [A0169]
  • 128117-22-6