3-OXO-CYCLOBUTANECARBONITRILE Chemical Properties

Boiling point:

249℃

Density 

1.13

Flash point:

105℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Off-white to light brown Solid

InChI

InChI=1S/C5H5NO/c6-3-4-1-5(7)2-4/h4H,1-2H2

InChIKey

MSAGLWTVMUDVDT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

20249-16-5

Safety Information

HS Code 

2926907090

3-OXO-CYCLOBUTANECARBONITRILE Usage And Synthesis

Uses

3-Oxocyclobutyronitrile is an organic compound commonly used as a pharmaceutical intermediate. It can be prepared by oxidation of 3-methylenecyclobutyronitrile, and the oxidants that can be used are sodium periodate and ozone.

Synthesis

Example 37b Synthesis of 3-oxocyclobutanecarbonitrile: Sodium meta-periodate (284 g, 1.32 mol) was added in small batches (over 30-45 min) to 3-methylenecyclobutanecarbonitrile (30 g, 370 mmol) and ruthenium trichloride monohydrate (2.2 mol%, 1.5 g, 7.23 mmol) at 5 °C in a DCM-MeCN-water ( 645mL:645mL:945mL) in a solvent mixture. The reaction mixture was stirred vigorously at room temperature. Subsequently, the organic phase was separated and the aqueous phase was extracted with DCM (3 x 1500 mL). The combined organic extracts were filtered through a small pad of fast silica gel, and the silica gel pad was washed with 2000 mL of DCM. The filtrate was dried over MgSO4, filtered and concentrated under reduced pressure to give 3-oxocyclobutanecarbonitrile (28 g, 100%). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.27 (quin, 1H), 3.57 (d, 4H).

References

[1] Patent: US2012/122843, 2012, A1. Location in patent: Page/Page column 39
[2] Patent: WO2015/179190, 2015, A1. Location in patent: Paragraph 0331
[3] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 13, p. 3947 - 3953
[4] Patent: US2014/80803, 2014, A1. Location in patent: Paragraph 1262
[5] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4926 - 4947

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