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| | 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile Basic information |
| Product Name: | 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile | | Synonyms: | 2-[1-(ethanesulfonyl)azetidin-3-ylidene]acetonitrile;[1-(ethylsulfonyl)azetidin-3-ylidene]acetonitrile;2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile;2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile ISO 9001：2015 REACH;Baricitinib-010;2-(1-ETHYLSULFONY)AZETIDIN-3-YLIDENE)ACETONITRILE;Baricitinib intermediates 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile;(1-Ethanesulfonyl-azetidin-3-ylidene)-acetonitrile | | CAS: | 1187595-85-2 | | MF: | C7H10N2O2S | | MW: | 186.23 | | EINECS: | 258-714-6 | | Product Categories: | 1187595-85-2 | | Mol File: | 1187595-85-2.mol |  |
| | 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile Chemical Properties |
| Melting point | 67-69°C | | Boiling point | 360.8±52.0 °C(Predicted) | | density | 1.33±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly) | | pka | -8.49±0.20(Predicted) | | form | Solid | | color | Off-White to Light Yellow | | InChI | InChI=1S/C7H10N2O2S/c1-2-12(10,11)9-5-7(6-9)3-4-8/h3H,2,5-6H2,1H3 | | InChIKey | HQUIOHSYUKWGOM-UHFFFAOYSA-N | | SMILES | C(#N)/C=C1\CN(S(CC)(=O)=O)C\1 |
| | 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile Usage And Synthesis |
| Uses | 2-(1-(Ethylsulfonyl)azetidin-3-ylidene)acetonitrile is an intermediate in the synthesis of Baricitinib, a JAK 1 and 2 inhibitor used in the treatment of rheumatoid arthritis. | | Synthesis | 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile is synthesized by
first treating azetidine-3-ol hydrochloride with an equimolar
equivalent of an alkanesulfonyl chloride, preferably ethanesulfonyl
chloride, to give l-ethylsulfonylazetidin-3-ol. Preferably, the
reaction is performed in a biphasic solution comprising a mixture of an
organic phase and a aqueous phase, preferably THF with an aqueous
solution which is basic, while maintaining the solution at room
temperature or a temperature slightly below room temperature, preferably
20 °C. The reaction is followed to completion using standard monitoring
techniques. Typically, the reaction is complete within 1 to 5 hours.
The organic layer is removed, preferably by distillation, and the
aqueous layer is extracted with an appropriate solvent such as toluene,
p-cymene, and CPME. Preferably the extraction solvent is toluene.
Alternatively, the toluene extractions can be excluded if
recrystallization of 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile is performed. 
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| | 2-(1-(ethylsulfonyl)azetidin-3-ylidene)acetonitrile Preparation Products And Raw materials |
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