3-Hydroxy-3-methyl-2-butanone
3-Hydroxy-3-methylbutan-2-one · Methylacetoin · 3-Methylacetoin · 3-HYDROXY-3-METHYL-2 · Dimethylacetylcarbinol · ACETYLDIMETHYLCARBINOL · 2-Methylbutan-2-ol-3-one · 3-hydroxy-3-ethylbutanone
Identifiers & Physical Properties
| CAS No. | 115-22-0 |
|---|---|
| Molecular formula | C5H10O2 |
| Average molar mass | 102.13 g/mol |
| Monoisotopic mass | 102.06807956 g/mol |
| SMILES | CC(=O)C(C)(C)O |
| InChIKey | BNDRWEVUODOUDW-UHFFFAOYSA-N |
| PubChem CID | 8261 |
| ChEBI | CHEBI:179407 |
| EC No. | 204-073-1 |
| DTXSID | DTXSID60870468 |
Chemical & Physical Properties
| XLogP | -0.1 |
|---|---|
| Topological polar surface area | 37.3 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 1 |
| Heavy atoms | 7 |
| Formal charge | 0 |
| Complexity | 84 |
| Physical Description | Colorless liquid[Alfa Aesar MSDS] |
| Kovats Retention Index | 77877969170012621246123812431247 |
| Melting point | 84-85 °C |
| Boiling point | 140-141 °C (lit.) |
| Density | 0.971 g/mL at 25 °C (lit.) |
| Refractive index | n20/D 1.415(lit.) |
| Flash point | 108 °F |
| Storage conditions | Flammables area |
| Solubility | Soluble in chloroform. |
| pKa (acidity coefficient) | 13.28±0.29(Predicted) |
| Physical state | Liquid |
| Color | Clear colorless to yellow or light red |
| BRN | 1616385 |
| InChI | 1S/C5H10O2/c1-4(6)5(2,3)7/h7H,1-3H3 |
| InChIKey | BNDRWEVUODOUDW-UHFFFAOYSA-N |
| SMILES | CC(=O)C(C)(C)O |
| LogP (partition coefficient) | 0.112 (est) |
| CAS DataBase Reference | 115-22-0(CAS DataBase Reference) |
| EPA Substance Registry System | 2-Butanone, 3-hydroxy-3-methyl- (115-22-0) |
| UNSPSC Code | 12352100 |
| GHS pictogram | GHS02 |
| Signal word | Warning |
| GHS hazard statements | H226 |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Risk statements (R) | 10 |
| Safety statements (S) | 23-24/25-22 |
| UN transport number | UN 1224 3/PG 3 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Hazard class | 3Flam. Liq. 3 |
| Packing group | III |
| Customs code | 29144000 |
| Storage class | 3 - Flammable liquids |
| 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 45 reports by companies from 2 notifications to the ECHA C&L Inventory.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazards summary | An irritant[Alfa Aesar MSDS] See Diacetone alcohol. |
| Hazard Classes and Categories | Flam. Liq. 3 (100%) |
| Adverse effects | Neurotoxin - Acute solvent syndrome |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 1224 3/PG 3 |
| Customs code | 29144000 |
| Risk statements (R) | 10 |
| Signal word | Warning |
| GHS pictogram | GHS02 |
| Safety statements (S) | 23-24/25-22 |
| 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) |
| GHS precautionary statements | P210-P233-P240-P241-P242-P243 |
Applications & Uses
Uses
3-Hydroxy-3-methyl-2-butanone used to produce 2,5-dihydroxy-2-methyl-heptan-3-one, laboratory chemicals.
Preparation & Synthesis
Preparation
synthesis of 3-Hydroxy-3-methyl-2-butanone: 19ml of concentrated sulfuric acid (98wt%) was slowly mixed with 100ml of water, then 13g of yellow mercury oxide was added within 1.5h, 84g (1.0mol) of 2-methyl-3-butyn-2-ol was added dropwise to the sulfuric acid solution containing mercury oxide at 65-75°C, Then the reaction was stirred at 65-75°C for 30min, cooled to room temperature after the reaction was completed, the reaction product was subjected to suction filtration, the filtrate after suction filtration was extracted with ether (3×20ml), and the organic phase after extraction was water and hydrogen carbonate respectively. Washed with sodium solution, the washed organic phase was dried with anhydrous magnesium sulfate, and then filtered, the filtered filtrate was concentrated by rotary evaporation and then distilled, and the 140°C fraction was collected, 45.6 g of light yellow liquid was obtained as 3-hydroxy-3-methyl-2-butanone, and the yield was 32.2%.