2,5-Dimethyl-2,5-hexanediol
2,5-DIMETHYLHEXANE-2,5-DIOL · 2,5-Hexanediol, 2,5-dimethyl- · 1,1,4,4-Tetramethyl-1,4-butanediol · nsc5595 · ai3-20685 · 5-hexanediol · -2,5-hexanedioL · DiMethyl-2,5-hexan
Identifiers & Physical Properties
| CAS No. | 110-03-2 |
|---|---|
| Molecular formula | C8H18O2 |
| Average molar mass | 146.23 g/mol |
| Monoisotopic mass | 146.13067981 g/mol |
| SMILES | CC(C)(O)CCC(C)(C)O |
| InChIKey | ZWNMRZQYWRLGMM-UHFFFAOYSA-N |
| PubChem CID | 8031 |
| ChEMBL | CHEMBL1476371 |
| EC No. | 203-731-5 |
| DTXSID | DTXSID0026830 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 40.5 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 3 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 91 |
| Density | 0.898 G/ML @ 20 °C0,898 g/cm3 |
| Color/Form | PRISMS FROM ETHYL ACETATE, FLAKES FROM PETROLEUM ETHERWHITE CRYSTALS |
| Solubility | SOL IN WATERVERY SOL IN ALCOHOL, HOT BENZENE, CHLOROFORMSOL IN ACETONEINSOL IN CARBON TETRACHLORIDE, KEROSENESOLUBLE |
| Boiling point | 118 °C @ 15 MM HG214-215 °C (lit.) |
| Melting point | 92 °C86-90 °C (lit.) |
| Physical Description | Large CrystalsCBIWhite solid[HSDB] Crystalline flakes[MSDSonline] |
| Kovats Retention Index | 916 |
| Vapor pressure | 0.18Pa at 20℃ |
| Refractive index | 1.4429 (estimate) |
| Flash point | 126 °C |
| Storage conditions | Keep in dark place,Sealed in dry,Room Temperature |
| Physical state | Crystalline Flakes |
| pKa (acidity coefficient) | 15.07±0.29(Predicted) |
| Color | White |
| Odor | mild camphor |
| BRN | 1361437 |
| Henry's law constant | 1.4×101 mol/(m3Pa) at 25℃, Zhang et al. (2010) |
| InChI | 1S/C8H18O2/c1-7(2,9)5-6-8(3,4)10/h9-10H,5-6H2,1-4H3 |
| InChIKey | ZWNMRZQYWRLGMM-UHFFFAOYSA-N |
| SMILES | CC(C)(O)CCC(C)(C)O |
| LogP (partition coefficient) | 0.21 at 23℃ |
| CAS DataBase Reference | 110-03-2(CAS DataBase Reference) |
| FDA UNII | 3PNB2S8721 |
| NIST Chemistry Reference | 2,5-Hexanediol, 2,5-dimethyl-(110-03-2) |
| EPA Substance Registry System | 2,5-Hexanediol, 2,5-dimethyl- (110-03-2) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H319 |
| GHS precautionary statements | P264-P280-P305+P351+P338-P337+P313 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Safety statements (S) | 22-24/25 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29053980 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2 |
| Hazardous substances data | 110-03-2(Hazardous Substances Data) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH315 (16.5%): Causes skin irritation [Warning Skin corrosion/irritation]H318 (78.9%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P264, P264+P265, P280, P302+P352, P305+P354+P338, P317, P321, P332+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 133 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.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. |
|---|---|
| Regulatory information | Chemical: 2,5-Hexanediol, 2,5-dimethyl-2,5-Hexanediol, 2,5-dimethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2,5-Hexanediol, 2,5-dimethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)SP - indicates a substance that is identified in a proposed Significant New Use Rule.Status: Active Update: 04-04-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/142632,5-Dimethyl-2,5-hexanediol: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | May cause irritation[MSDSonline] |
| Hazard Classes and Categories | Skin Irrit. 2 (16.5%)Eye Dam. 1 (78.9%) |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29053980 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Safety statements (S) | 22-24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H319 |
| REACH registrations | Active |
| Hazard class | Eye Irrit. 2 |
| GHS precautionary statements | P264-P280-P305+P351+P338-P337+P313 |
| Hazardous substances data | 110-03-2(Hazardous Substances Data) |
Applications & Uses
Uses
2,5-Dimethyl-2,5-hexanediol is used as an intermediate in the preparation of 2.5-Dimethyl-2.5-bis(tertbutyl-peroxy)hexane to produce polyethylene copolymers and polyethylene rubbers. It is also could be used to prepared nickel-containing Complex Reducing Agents (termed NiCRA)[1].
Uses
2,5-Dimethyl-2,5-hexanediol was used in the synthesis of six- and seven-membered heterocyclic boron compounds containing intramolecular N-B bond.
General Description
2,5-Dimethyl-2,5-hexanediol on heteropoly acid catalyzed dehydration yields cyclic ethers via stereospecific intramolecular SN2 mechanism. It reacts with nitriles in concentrated sulfuric acid to yield Δ1-pyrrolines.
Preparation & Synthesis
Preparation
The raw materials 2,5-Dimethyl-3-hexyne-2,5-diol (37.4 g, 263 mmol), ethyl acetate (60 mL), and Pd/C catalyst (0.285 g, 2.63 mmol, 1 mol %) were added to an autoclave. The hydrogen gas was slowly added to 10 bar. When the hydrogenation reaction was performed for 12 hours and then removed the hydrogen gas. Finally, 2,5-Dimethyl-2,5-hexanediol is obtained by purification.