ChemicalBook > CAS DataBase List > 1-N-Boc-3-hydroxyazetidine

1-N-Boc-3-hydroxyazetidine

Product Name
1-N-Boc-3-hydroxyazetidine
CAS No.
141699-55-0
Chemical Name
1-N-Boc-3-hydroxyazetidine
Synonyms
TERT-BUTYL 3-HYDROXYAZETIDINE-1-CARBOXYLATE;N-BOC-3-HYDROXYAZETIDINE;Baricitinib-012;JACS-141699-55-0;BUTTPARK 75\04-65;N-Boc-3-Azetidinol;1-Boc-azetidin-3-ol;N-Boc-Azetidin-3-ol;carbamate (ARQ092 RSM2);1-BOC-3-(HYDROXY)AZETIDINE
CBNumber
CB1428146
Molecular Formula
C8H15NO3
Formula Weight
173.21
MOL File
141699-55-0.mol
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1-N-Boc-3-hydroxyazetidine Property

Melting point:
36-43 °C
Boiling point:
253.7±33.0 °C(Predicted)
Density 
1.184±0.06 g/cm3(Predicted)
Flash point:
>110℃
storage temp. 
2-8°C
solubility 
soluble in Methanol
pka
14.16±0.20(Predicted)
form 
Solid
color 
White to light yellow
InChI
InChI=1S/C8H15NO3/c1-8(2,3)12-7(11)9-4-6(10)5-9/h6,10H,4-5H2,1-3H3
InChIKey
XRRXRQJQQKMFBC-UHFFFAOYSA-N
SMILES
N1(C(OC(C)(C)C)=O)CC(O)C1
CAS DataBase Reference
141699-55-0(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-41-22
Safety Statements 
26-36/37/39
WGK Germany 
3
TSCA 
No
HazardClass 
IRRITANT
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H318Causes serious eye damage

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

Sigma-Aldrich
Product number
694347
Product name
1-Boc-3-hydroxyazetidine
Purity
97%
Packaging
5g
Price
$111
Updated
2025/07/31
Sigma-Aldrich
Product number
694347
Product name
1-Boc-3-hydroxyazetidine
Purity
97%
Packaging
1g
Price
$26.2
Updated
2023/06/20
TCI Chemical
Product number
B2922
Product name
1-(tert-Butoxycarbonyl)-3-hydroxyazetidine
Purity
>96.0%(GC)
Packaging
1g
Price
$36
Updated
2025/07/31
TCI Chemical
Product number
B2922
Product name
1-(tert-Butoxycarbonyl)-3-hydroxyazetidine
Purity
>96.0%(GC)
Packaging
5g
Price
$69
Updated
2025/07/31
TRC
Product number
T135520
Product name
tert-Butyl3-Hydroxyazetidine-1-carboxylate
Packaging
500mg
Price
$60
Updated
2021/12/16
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1-N-Boc-3-hydroxyazetidine Chemical Properties,Usage,Production

Chemical Properties

white powder

Uses

1-N-Boc-3-hydroxyazetidine is a non-cleavable ADC linker used in the synthesis of antibody-drug conjugates (ADCs). 1-N-Boc-3-hydroxyazetidine is also a alkyl chain-based PROTAC linker that can be used in the synthesis of PROTACs

Synthesis

18621-17-5

24424-99-5

141699-55-0

General procedure for the synthesis of N-Boc-3-hydroxyazetidine from 1-diphenylmethyl-3-hydroxyazetidine and di-tert-butyl dicarbonate: (1) Dissolve 1-diphenylmethyl-3-hydroxyazetidine (10.0 g, 41.8 mmol) in methanol (300 ml), add 10% palladium-carbon catalyst (10.0 g), and carry out the catalytic hydrogenation reaction at room temperature for 3 hours. After completion of the reaction, the catalyst was removed by filtration. To the filtrate was added di-tert-butyl dicarbonate (18.2 g, 83.6 mmol) and stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the eluent being hexane: ethyl acetate (1:1→1:2) to afford 1-tert-butoxycarbonyl-3-hydroxyazetidine (7.05 g, 97% yield). (2) To a solution of 1-tert-butoxycarbonyl-3-hydroxyazetidine (2.5 g, 14.4 mmol) in dimethylformamide (125 ml) was added sodium hydride (55% oil dispersion) under ice bath conditions. The ice bath was stirred for 10 minutes followed by 30 minutes at room temperature. Subsequently, iodomethane (1.79 ml, 28.8 mmol) was added to the ice bath and the ice bath was stirred for 10 minutes followed by 1 hour at room temperature. After completion of the reaction, 10% aqueous acetic acid solution was added to the ice bath and stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and 10% aqueous sodium chloride solution. The organic layer was washed sequentially with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography with hexane:ethyl acetate (2:1) as eluent to afford 1-tert-butoxycarbonyl-3-methoxyazetidine (2.18 g, 81% yield) as a colorless oil.1H-NMR (400 MHz, CDCl3): δ (ppm) 4.16-4.10 (1H, m), 4.09-4.03 (2H, m ), 3.82 (2H, dd, J = 10.2,4.4Hz), 3.28 (3H, s), 1.44 (9H, s).

IC 50

Non-cleavable Linker

References

[1] Beck A, et al. Strategies and challenges for the next generation of antibody-drug conjugates. Nat Rev Drug Discov. 2017;16(5):315-337. DOI:10.1038/nrd.2016.268
[2] Nalawansha DA, et al. PROTACs: An Emerging Therapeutic Modality in Precision Medicine. Cell Chem Biol. 2020;27(8):998-985. DOI:10.7554/eLife.57277

1-N-Boc-3-hydroxyazetidine Preparation Products And Raw materials

Raw materials

3-Hydroxyazetidine hydrochloride Acetonitrile Ammonium formate Toluene Di-tert-butyl dicarbonate Triethylamine Benzophenone Palladium Ethyl acetate Hydrochloric acid Hydrogen Dichloromethane Methanol Epichlorohydrin PETROLEUM ETHER Citric acid

Preparation Products

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View Lastest Price from 1-N-Boc-3-hydroxyazetidine manufacturers

Henan Aochuang Chemical Co.,Ltd.
Product
1-N-Boc-3-hydroxyazetidine 141699-55-0
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
1Ton
Release date
2022-10-08
Henan Fengda Chemical Co., Ltd
Product
1-N-Boc-3-hydroxyazetidine 141699-55-0
Price
US $101.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-28
Hong Kong Tiansheng New Material Trading Co., Ltd
Product
1-Boc-3-hydroxyazetidine 141699-55-0
Price
US $8.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
98%
Supply Ability
10KG
Release date
2021-09-24

141699-55-0, 1-N-Boc-3-hydroxyazetidineRelated Search:

tert-Butyl peroxyacetate Cyhalofop-butyl 1-Bromobutane tert-Butyl acetate Butyl acetate Azetidine n-Butane Diethylene glycol monobutyl ether RESMETHRIN 1-Chloro-2-methylpropane 2-Butoxyethanol Buprofezin ISOBUTANE tert-Butanol N-Boc-3-pyrrolidinone N-BOC-3-AZA-HEPTAN-1-ONE Butyl acrylate tert-Butyl 4-broMo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate

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  • JACS-141699-55-0
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  • 1-Boc-3-hydroxyazetidine tert-Butyl 3-Hydroxyazetidine-1-carboxylate 3-Hydroxyazetidine-1-carboxylic Acid tert-Butyl Ester
  • tert-Butyl 3-hydroxyazetidine-1-carboxylate, 1-(tert-Butoxycarbonyl)-3-hydroxyazetidine
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  • carbamate (ARQ092 RSM2)
  • 3-hydroxy-1-azetidinecarboxylic acid tert-butyl ester
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  • N-Boc-Azetidin-3-ol
  • 1-azetidinecarboxylic acid, 3-hydroxy-, 1,1-dimethylethyl
  • N-Boc-3-Azetidinol
  • 1-(tert-Butoxycarbonyl)-3-hydroxyazetidine &gt
  • Baricitinib-012
  • 1-N-Boc-3-hydroxyazetidine ISO 9001：2015 REACH
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  • tert-butyl-3-hydroxyazetidine-4-carboxylate
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  • tert-Butyl 3-hydroxyazetidine-1-carboxylate - [B5483]
  • 141699-55-0
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  • CMLLYL
  • Ring Systems
  • B-Amino
  • Azetidines
  • Simple 4-Membered Ring Compounds