bicyclo[3.2.1]octane-2,4-dione Chemical Properties

Melting point:

123.5 °C

Boiling point:

275.8±13.0 °C(Predicted)

Density 

1.191±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

10.30±0.20(Predicted)

color 

Pale Beige to Light Brown

InChI

InChI=1S/C8H10O2/c9-7-4-8(10)6-2-1-5(7)3-6/h5-6H,1-4H2

InChIKey

VCYHIHMHWASQAB-UHFFFAOYSA-N

SMILES

C12CC(CC1)C(=O)CC2=O

bicyclo[3.2.1]octane-2,4-dione Usage And Synthesis

Uses

Bicyclo[3.2.1]??octane-??2,??4-??dione is an impurity of the herbicide Benzobicyclon (B366140), Hydrolysate which is used in rice fields.

Synthesis

Preparation of bicyclo[3.2.1]octane-2,4-dione: To a chlorobenzene solution containing 29 g (6.3% w/w, absolute mass 1.83 g, 9.1 mmol) of bromo-bicyclo[3.2.1]oct-3-en-2-one was added 50 ml of acetonitrile and 100 ml of 10% sulphuric acid, and the reaction mixture was stirred for 90 min at reflux temperature (~70 °C). Subsequently, another 50 ml of acetonitrile was added and stirring was continued for 17 hours until the reaction was complete (the progress of the reaction was monitored by HPLC). Upon completion of the reaction, acetonitrile and most of the chlorobenzene were removed using a rotary evaporator. The residue was extracted with 100 ml of ethyl acetate and the aqueous phase was separated. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuum to remove the solvent, resulting in 0.86 g (68% yield) of bicyclo[3.2.1]octane-2,4-dione. Mass spectral (MS) data: 138 (M+), 109, 96, 81, 68, 55, 39. 1H NMR (CDCl3) data: 1.80-2.15 (m, 6H), 2.95 (s, 2H), 3.05-3.15 (d, 1H), 3.20-3.30 (d, 1H).

References

[1] Patent: WO2005/105717, 2005, A1. Location in patent: Page/Page column 7-8

bicyclo[3.2.1]octane-2,4-dione(74896-14-3)Related Product Information

• 2,3-NORBORNANEDICARBOXYLIC ACID
• BICYCLO[2.2.1]HEPTANE-2-CARBOXYLIC ACID
• bicyclo[1.1.1]pentan-1-ylmethanol
• Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester
• Bicyclo[2.2.2]octane-1,4-dimethanol
• ETHYL 5-NORBORNENE-2-CARBOXYLATE (MIXTURE OF ENDO AND EXO)
• 5-Norbornene-2-carboxamide
• Bicyclo[3.1.0]hexan-3-ol
• Bicyclo[1.1.1]pentane-1-carboxylic acid, methyl ester (9CI)
• 4-Aminobenzocyclobutene
• 4-Hydroxymethylbenzocyclobutene
• 4-Carboxylbenzocyclobutene
• bicyclo[1.1.1]pentane-1,3-dicarbonitrile
• Bicyclo[1.1.1]pentane-1-sulfonamide
• Bicyclo[1.1.1]pentane-1,3-dicarboxamide
• Bicyclo[1.1.1]pentane-1-carboxamide
• 5-Norbornene-2-carbonitrile
• Hexane