Dicyclopropyl ketone
DICYCLOPROPYLMETHANONE · CYCLOPROPYL KETONE · DICYLOPROPYL KETONE · BicyclopropylKetone · DICYCLOPROPYL KETONE · DicyclopropylKetone>DICYCLOPROPYLMETHYLOXIME · Dicyclopropyl ketone,95% · Methanone,dicyclopropyl-
Identifiers & Physical Properties
| CAS No. | 1121-37-5 |
|---|---|
| Molecular formula | C7H10O |
| Average molar mass | 110.15 g/mol |
| Monoisotopic mass | 110.07316494 g/mol |
| SMILES | O=C(C1CC1)C1CC1 |
| InChIKey | BIPUHAHGLJKIPK-UHFFFAOYSA-N |
| PubChem CID | 70721 |
| EC No. | 214-331-5 |
| DTXSID | DTXSID70149910 |
Chemical & Physical Properties
| XLogP | 0.9 |
|---|---|
| Topological polar surface area | 17.1 |
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 2 |
| Heavy atoms | 8 |
| Formal charge | 0 |
| Complexity | 106 |
| SpringerMaterials Properties | Schoenflies notation |
| Melting point | 44.0-44.5 °C |
| Boiling point | 160-162 °C(lit.) |
| Density | 0.977 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.467(lit.) |
| Flash point | 103 °F |
| Storage conditions | Store below +30°C. |
| Physical state | liquid |
| Specific gravity | 0.957 |
| Appearance | Colorless to light yellow Liquid |
| Solubility | Soluble in water. |
| BRN | 774172 |
| Henry's law constant | 3.1×100 mol/(m3Pa) at 25℃, Bagno et al. (1991) |
| InChI | InChI=1S/C7H10O/c8-7(5-1-2-5)6-3-4-6/h5-6H,1-4H2 |
| InChIKey | BIPUHAHGLJKIPK-UHFFFAOYSA-N |
| SMILES | C(C1CC1)(C1CC1)=O |
| CAS DataBase Reference | 1121-37-5(CAS DataBase Reference) |
| FDA UNII | FGQ92KB360 |
| NIST Chemistry Reference | Methanone, dicyclopropyl-(1121-37-5) |
| UNSPSC Code | 12352115 |
| NACRES | NA.22 |
| GHS pictogram | GHS02 |
| Signal word | Warning |
| GHS hazard statements | H226 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243 |
| Hazard symbols | F,Xn |
| Risk statements (R) | 10-36/37/38-20/21/22-5 |
| Safety statements (S) | 16-36-26-3 |
| UN transport number | UN 1224 3/PG 3 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Harmful/Flammable |
| Hazard class | 3Flam. Liq. 3 |
| Packing group | III |
| Customs code | 29142900 |
| Storage class | 3 - Flammable liquids |
| REACH registrations | Active |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
Safety & Regulations
| GHS classification | WarningH226 (100%): Flammable liquid and vapor [Warning Flammable liquids]P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 103 reports by companies from 7 notifications to the ECHA C&L Inventory. |
|---|---|
| Hazard Classes and Categories | Flam. Liq. 3 (100%) |
| Water hazard class (WGK) | 3 |
| UN transport number | UN 1224 3/PG 3 |
| Customs code | 29142900 |
| Risk statements (R) | 10-36/37/38-20/21/22-5 |
| Signal word | Warning |
| GHS pictogram | GHS02 |
| Hazard symbols | F,Xn |
| hazard_note | Harmful/Flammable |
| Safety statements (S) | 16-36-26-3 |
| Hazard class | 3Flam. Liq. 3 |
| Storage class | 3 - Flammable liquids |
| Packing group | III |
| GHS hazard statements | H226 |
| Limited quantities | 5.0 L (1.3 gallons) (liquid) |
| Excepted quantities | Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L) |
| REACH registrations | Active |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243 |
Applications & Uses
Uses
Dicyclopropyl Ketone is used as a reagent in the synthesis of a new class of potent and selective agonists of dimeric carbamoylguanidine-type histamine H2 receptor ligands. Also used in the preparation of chemical space analogs of PNU-282,987 and SSR180711, which have nicotinic receptor activity.
Preparation & Synthesis
Preparation
Preparation of Dicyclopropyl ketoneReaction: To a one liter three-necked flask fitted with a reflux condenser and a metal Hershberg stirrer there was added 600 ml. of 20% sodium hydroxide and 165g . (0.9mole) of 1,7 -dichloro-4-heptanone. The mixture was refluxed for 30 minutes with vigorous stirring, then steam distilled until the characteristic odor of dicyclopropyl ketone was absent from the distillate. The distillate was then saturated with potassium carbonate, the upper layer separated and the water layer extracted once with ether. The combined organic layers were dried over potassium carbonate. after removal of the ether there was dist illed 69g. (70%) of dicyclopropyl ketone, b.p . 69° at 20 mm, nD25 1.4648-1.4654.