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

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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

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Safety

RIDADR: UN 3439 6.1/PG III
HazardClass: 6.1
PackingGroup: III
HS Code: 2933998090

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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.

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N-Bromosuccinimide Price

TCI Chemical

Product number: B5217
Product name: 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
Purity: >95.0%(GC)
Packaging: 200mg
Price: $47
Updated: 2025/07/31

TCI Chemical

Product number: B5217
Product name: 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
Purity: >95.0%(GC)
Packaging: 1g
Price: $133
Updated: 2025/07/31

TRC

Product number: B117850
Product name: 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
Packaging: 1g
Price: $45
Updated: 2021/12/16

TRC

Product number: B117850
Product name: 1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine
Packaging: 25g
Price: $340
Updated: 2021/12/16

AK Scientific

Product number: J56933
Product name: 1-Boc-3-(cyanomethylene)azetidine
Packaging: 1g
Price: $14
Updated: 2021/12/16

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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.

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

Raw materials

Preparation Products

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1-Boc-3-(cyanomethylene)azetidine Suppliers

Americas 1 Canada 1 China 201 Europe 1 India 5 Japan 1 United Kingdom 1 United States 9 Global 220

Beijing Cooperate Pharmaceutical Co.,Ltd

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View Lastest Price from 1-Boc-3-(cyanomethylene)azetidine manufacturers

Hefei Lbao Physical & Chemical Science Co.,Ltd

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

Shaanxi Didu New Materials Co. Ltd

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

Cangzhou Kangrui Pharma Tech Co. Ltd.,

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

1153949-11-1, 1-Boc-3-(cyanomethylene)azetidineRelated Search:

3,5-Dimethyl-piperazine-1-carboxylic acid tert-butyl ester 1-N-Boc-3-hydroxyazetidine (R)-1-Boc-2-cyanopyrrolidine tert-butyl 4-(2-fluoro-5-((4-oxo-3,4-dihydrophthalazin-1-yl)Methyl)benzoyl)piperazine-1-carboxylate 4-[6-(6-BROMO-8-CYCLOPENTYL-5-METHYL-7-OXO-7,8-DIHYDRO-PYRIDO[2,3-D]PYRIMIDIN-2-YLAMINO)-PYRIDIN-3-YL]-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER 3-(4-AMINO-PHENYL)-PIPERIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER N-Boc-pyrroline tert-butyl 3-broMo-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxylate tert-Butyl 4-broMo-1H-pyrrolo[2,3-c]pyridine-1-carboxylate Baricitinib tert-butyl 3-oxidanyl-3-pyridin-2-yl-azetidine-1-carboxylate tert-butyl 4-((4'-chloro-5,5-diMethyl-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)Methyl)piperazine-1-carboxylate 1-Boc-Azetidine-3-yl-methanol tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate tert-butyl 2,2,4,8-tetraMethyl-1,2,3,4-tetrahydroquinolin-7-ylcarbaMate tert-butyl 3-(4-(7-carbamoyl-2H-indazol-2-yl)phenyl)piperidine-1-carboxylate tert-butyl 2-(1-(3,4-difluoro-2-((2-fluoro-4-iodophenyl)aMino)benzoyl)-3-hydroxyazetidin-3-yl)piperidine-1-carboxylate tert-butyl 2-(3-hydroxy-1-(2,2,2-trifluoroacetyl)azetidin-3-yl)piperidine-1-carboxylate

1-Boc-3-(cyanomethylene)azetidine

3-Cyanomethylene-azetidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-(cyanoMethylene)azetidine-1-carboxylate

tert-butyl 3-(cyanoMethylidene)azetidine-1-carboxylate

3-(Cyanomethylene)-1-azetidinecarboxylic acid tert-butyl ester

1-(<i>tert</i>-Butoxycarbonyl)-3-(cyanomethylene)azetidine

P-Hydroxy phenyl butanone (Raspberry ketone)

tert-Butyl 3-(cyanomethylene)

1-(tert-Butoxycarbonyl)-3-(cyanomethylene)azetidine

1-Azetidinecarboxylic acid, 3-(cyanomethylene)-, 1,1-dimethylethyl ester

Baricitinib Impurity 10

benzyl 3-(cyanomethylene)azetidine-1-carboxylate

Baricitinib-013

ert-butyl3-(cyanomethylidene)azetidine-1-carboxylate

1-Boc-3-(cyanomethylene)azetidine - [C12524]

1153949-11-1

1153649-11-1