1-Boc-3-(cyanomethylene)azetidine
Uses- Product Name
- 1-Boc-3-(cyanomethylene)azetidine
- CAS No.
- 1153949-11-1
- Chemical Name
- 1-Boc-3-(cyanomethylene)azetidine
- Synonyms
- tert-butyl 3-(cyanoMethylene)azetidine-1-carboxylate;benzyl 3-(cyanomethylene)azetidine-1-carboxylate;3-Cyanomethylene-azetidine-1-carboxylic acid tert-butyl ester;Baricitinib-013;Baricitinib Impurity 10;tert-Butyl 3-(cyanomethylene);1-Boc-3-(cyanomethylene)azetidine;P-Hydroxy phenyl butanone (Raspberry ketone);1-Boc-3-(cyanomethylene)azetidine - [C12524];1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
- CBNumber
- CB22485423
- Molecular Formula
- C10H14N2O2
- Formula Weight
- 194.23
- MOL File
- 1153949-11-1.mol
1-Boc-3-(cyanomethylene)azetidine Property
- Boiling point:
- 309.7±35.0 °C(Predicted)
- Density
- 1.215
- storage temp.
- under inert gas (nitrogen or Argon) at 2-8°C
- form
- powder to crystal
- pka
- -1.88±0.20(Predicted)
- color
- White to Orange to Green
- InChI
- InChI=1S/C10H14N2O2/c1-10(2,3)14-9(13)12-6-8(7-12)4-5-11/h4H,6-7H2,1-3H3
- InChIKey
- BESFCRTTXQYNBW-UHFFFAOYSA-N
- SMILES
- N1(C(OC(C)(C)C)=O)C/C(=C\C#N)/C1
Safety
- RIDADR
- UN 3439 6.1/PG III
- HazardClass
- 6.1
- PackingGroup
- III
- HS Code
- 2933998090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
- Precautionary statements
-
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P321Specific treatment (see … on this label).
P332+P313IF SKIN irritation occurs: Get medical advice/attention.
P362Take off contaminated clothing and wash before reuse.
N-Bromosuccinimide Price
- Product number
- B5217
- Product name
- 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
- Purity
- >95.0%(GC)
- Packaging
- 200mg
- Price
- $47
- Updated
- 2025/07/31
- Product number
- B5217
- Product name
- 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
- Purity
- >95.0%(GC)
- Packaging
- 1g
- Price
- $133
- Updated
- 2025/07/31
- Product number
- B117850
- Product name
- 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
- Packaging
- 1g
- Price
- $45
- Updated
- 2021/12/16
- Product number
- B117850
- Product name
- 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
- Packaging
- 25g
- Price
- $340
- Updated
- 2021/12/16
- Product number
- J56933
- Product name
- 1-Boc-3-(cyanomethylene)azetidine
- Packaging
- 1g
- Price
- $14
- Updated
- 2021/12/16
1-Boc-3-(cyanomethylene)azetidine Chemical Properties,Usage,Production
Uses
1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine is used in the synthesis of baricitinib via Horner-Emmons reaction of tert-butyl-oxoazetidine-carboxylate followed by sulfonamidation, nucleophilic addition. and subsequent Suzuki-coupling reaction.
Description
1-Boc-3-(cyanomethylene)azacyclobutane is an important pharmaceutical intermediate and a multifunctional structural unit, primarily used as a key intermediate in the synthesis of baricitinib, a JAK inhibitor used to treat rheumatoid arthritis and alopecia areata. The synthesis of baricitinib typically involves the Horner-Emmons reaction of this intermediate.
Uses
1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine is used in the synthesis of baricitinib via Horner-Emmons reaction of tert-butyl-oxoazetidine-carboxylate followed by sulfonamidation, nucleophilic addition. and subsequent Suzuki-coupling reaction.
Synthesis
398489-26-4
50586-62-4
1153949-11-1
Under nitrogen protection, 24.8 g of cyanomethyl diethyl phosphate and 300 mL of anhydrous tetrahydrofuran were added to a 1000 mL four-necked flask. The reaction mixture was cooled to -15 to -10 °C under nitrogen protection and 128.5 mL of 1.0 M potassium tert-butanolate in tetrahydrofuran solution was slowly added while controlling the temperature below -5 °C. After addition, the reaction continued to be stirred at -10 to -5 °C for 3 hours. Subsequently, keeping the temperature below -5 °C, a tetrahydrofuran solution of 1-Boc-3-azetidinone was added slowly and dropwise (20.0 g 1-Boc-3-azetidinone dissolved in 67 mL of tetrahydrofuran). After dropwise addition, the reaction temperature was maintained at -10 to -5°C with continued stirring for 2 hours. Next, the reaction mixture was slowly warmed to 25 to 30 °C and stirred at this temperature for 16 hours. Upon completion of the reaction, the layers were separated by slowly adding 300 mL of 12.5% aqueous sodium chloride solution. The aqueous phase was extracted with 300 mL of ethyl acetate. The organic phases were combined and washed with 200 mL of brine. A final 20.65 g white solid product tert-butyl 3-(cyanomethylene)azetidine-1-carboxylate was obtained in 91% yield.
References
[1] Patent: CN108752254, 2018, A. Location in patent: Paragraph 0097-0099
[2] Patent: WO2013/36611, 2013, A1. Location in patent: Page/Page column 28; 29
[3] Patent: US2016/333015, 2016, A1. Location in patent: Paragraph 0055; 0056; 0081; 0082; 0105; 0106; 0134; 0135
1-Boc-3-(cyanomethylene)azetidine Preparation Products And Raw materials
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View Lastest Price from 1-Boc-3-(cyanomethylene)azetidine manufacturers
- Product
- 1-Boc-3-(cyanomethylene)azetidine 1153949-11-1
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- Customise
- Release date
- 2025-11-28
- Product
- 1-Boc-3-(cyanomethylene)azetidine 1153949-11-1
- Price
- US $1.50/g
- Min. Order
- 1g
- Purity
- 99.0% Min
- Supply Ability
- 100 Tons
- Release date
- 2025-09-25
- Product
- tert-Butyl 3-(cyanomethylene)azetidine-1-carboxylate 1153949-11-1
- Price
- US $0.00-0.00/g
- Min. Order
- 500g
- Purity
- 98%
- Supply Ability
- 100kgs
- Release date
- 2024-12-27