1-Boc-3-Cyanoazetidine Chemical Properties

Melting point:

68-71°C

Boiling point:

290.2±33.0 °C(Predicted)

Density 

1.11±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

-4.29±0.40(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C9H14N2O2/c1-9(2,3)13-8(12)11-5-7(4-10)6-11/h7H,5-6H2,1-3H3

InChIKey

WEFREESWPHICPL-UHFFFAOYSA-N

SMILES

N1(C(OC(C)(C)C)=O)CC(C#N)C1

CAS DataBase Reference

142253-54-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38-52-36-22

Safety Statements 

26-36/37/39-36/37-9

RIDADR 

3439

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

2933998090

1-Boc-3-Cyanoazetidine Usage And Synthesis

Uses

1-?(N-?Boc)?-?3-?cyanoazetidine can be used as reagent/reactant for preparation and SAR of pyridinylmethanol derivatives as TRPV3 antagonists. It can also be used as reagent/reactant for preparation of substituted pyridines via nucleophilic aromatic substitution of cyanopyridines with disubstituted esters and nitriles.

Synthesis

Step 1: 3-Cyanonitrile azetidine hydrochloride (3.64 g, 30.7 mmol) was suspended in 77 mL of dichloromethane. Triethylamine (4.3 mL, 30.7 mmol) was added to the suspension, followed by batchwise addition of di-tert-butyl dicarbonate (8.0 g, 36.8 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was diluted with aqueous hydrochloric acid and dichloromethane. The organic and aqueous layers were separated and the aqueous layer was extracted with dichloromethane. All organic layers were combined, washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give 5.5 g (98% yield) of tert-butyl 3-cyanoazetidine-1-carboxylate.

References

[1] Patent: US2011/230462, 2011, A1. Location in patent: Page/Page column 64-65
[2] Patent: WO2011/61214, 2011, A1. Location in patent: Page/Page column 50
[3] Patent: WO2013/152065, 2013, A2. Location in patent: Page/Page column 27

1-Boc-3-Cyanoazetidine(142253-54-1)Related Product Information

• Sodium cyanoborohydride
• Cyhalofop-butyl
• Butyl acetate
• ISOBUTANE
• 2-Butoxyethanol
• RESMETHRIN
• tert-Butanol
• Buprofezin
• Azetidine
• n-Butane
• Diethylene glycol monobutyl ether
• 1-Chloro-2-methylpropane
• ETHYL 2-CYANOACRYLATE
• tert-Butyl acetate
• tert-Butyl peroxyacetate
• Methylene dithiocyanate
• Butyl acrylate
• tert-butyl 3-bromoazetidine-1-carboxylate