| Identification | More | [Name]
1-Boc-3-Cyanoazetidine | [CAS]
142253-54-1 | [Synonyms]
1-N-BOC-3-CYANO-AZETIDINE
3-CYANO-1-BOC-AZETIDINE
3-CYANO-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
N-T-BOC-3-CYANOAZETIDINE
TERT-BUTYL 3-CYANOAZETIDINE-1-CARBOXYLATE
N-Boc-3-Cyanoazetidine
1-Boc-3-cyanoazetidine | [EINECS(EC#)]
640-760-6 | [Molecular Formula]
C9H14N2O2 | [MDL Number]
MFCD06796640 | [Molecular Weight]
182.22 | [MOL File]
142253-54-1.mol |
| Chemical Properties | Back Directory | [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 Data | Back Directory | [Hazard Codes ]
Xi,Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S36/37:Wear suitable protective clothing and gloves .
S9:Keep container in a well-ventilated place . | [RIDADR ]
3439 | [WGK Germany ]
3 | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
2933998090 |
| Hazard Information | Back Directory | [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 |
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