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
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)
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
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.
N-Bromosuccinimide Price
- Product number
- 694347
- Product name
- 1-Boc-3-hydroxyazetidine
- Purity
- 97%
- Packaging
- 5g
- Price
- $111
- Updated
- 2025/07/31
- Product number
- 694347
- Product name
- 1-Boc-3-hydroxyazetidine
- Purity
- 97%
- Packaging
- 1g
- Price
- $26.2
- Updated
- 2023/06/20
- Product number
- B2922
- Product name
- 1-(tert-Butoxycarbonyl)-3-hydroxyazetidine
- Purity
- >96.0%(GC)
- Packaging
- 1g
- Price
- $36
- Updated
- 2025/07/31
- Product number
- B2922
- Product name
- 1-(tert-Butoxycarbonyl)-3-hydroxyazetidine
- Purity
- >96.0%(GC)
- Packaging
- 5g
- Price
- $69
- Updated
- 2025/07/31
- Product number
- T135520
- Product name
- tert-Butyl3-Hydroxyazetidine-1-carboxylate
- Packaging
- 500mg
- Price
- $60
- Updated
- 2021/12/16
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
Preparation Products
1-N-Boc-3-hydroxyazetidine Suppliers
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- Switzerland
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View Lastest Price from 1-N-Boc-3-hydroxyazetidine manufacturers
- 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
- 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
- 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