2,6-Dimethylol-p-cresol
(2-Hydroxy-5-Methyl-1,3-phenylene)diMethanol · 2,6-Dimethylol-4-methylphenol · 2,6-BIS(HYDROXYMETHYL)-4-CRESOL · 2-HYDROXY-5-METHYL-1,3-BENZENEDIMETHANOL · 3,5-bis(hydroxymethyl)-p-cresol · 2,6-BIS(HYDROXYMETHYL)-4-METHYLPHENOL · 1,3-Benzenedimethanol, 2-hydroxy-5-methyl- · AKOS BC-1882
Identifiers & Physical Properties
| CAS No. | 91-04-3 |
|---|---|
| Molecular formula | C9H12O3 |
| Average molar mass | 168.19 g/mol |
| Monoisotopic mass | 168.07864424 g/mol |
| SMILES | Cc1cc(CO)c(O)c(CO)c1 |
| InChIKey | KUMMBDBTERQYCG-UHFFFAOYSA-N |
| PubChem CID | 7039 |
| EC No. | 202-036-4 |
| DTXSID | DTXSID2059017 |
Chemical & Physical Properties
| XLogP | 0.7 |
|---|---|
| Topological polar surface area | 60.7 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 2 |
| Heavy atoms | 12 |
| Formal charge | 0 |
| Complexity | 124 |
| SpringerMaterials Properties | Chemical shift |
| Melting point | 128-130 °C(lit.) |
| Boiling point | 237.12°C (rough estimate) |
| Density | 1.0812 (rough estimate) |
| Vapor density | 5.8 (vs air) |
| Refractive index | 1.4371 (estimate) |
| Storage conditions | Sealed in dry,Room Temperature |
| Solubility | very faint turbidity in THF |
| Physical state | powder to crystal |
| pKa (acidity coefficient) | 10.20±0.23(Predicted) |
| Color | White to Yellow to Orange |
| BRN | 1240237 |
| InChI | InChI=1S/C9H12O3/c1-6-2-7(4-10)9(12)8(3-6)5-11/h2-3,10-12H,4-5H2,1H3 |
| InChIKey | KUMMBDBTERQYCG-UHFFFAOYSA-N |
| SMILES | C1(CO)=CC(C)=CC(CO)=C1O |
| CAS DataBase Reference | 91-04-3(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | Q99HT08S5N |
| NIST Chemistry Reference | A1,a3-mesityllenediol, 2-hydroxy-(91-04-3) |
| EPA Substance Registry System | 1,3-Benzenedimethanol, 2-hydroxy-5-methyl- (91-04-3) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Target organs | Respiratory system |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-37/39 |
| Water hazard class (WGK) | 3 |
| RTECS number | CZ6440000 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29072990 |
| Storage class | 11 - Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 2.1% (1 of 47) of reports.WarningH315 (97.9%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Chemical: 1,3-Benzenedimethanol, 2-hydroxy-5-methyl- |
| Hazard Classes and Categories | Skin Irrit. 2 (97.9%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | CZ6440000 |
| Customs code | 29072990 |
| Risk statements (R) | 36/37/38 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-37/39 |
| Storage class | 11 - Combustible Solids |
| Target organs | Respiratory system |
| GHS hazard statements | H315-H319-H335 |
| Hazard class | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Applications & Uses
Uses
2,6-Bis(hydroxymethyl)-p-cresol was used as a bridging ligand in binuclear oxovanadium(V) compound, which on exposure to white light and aerial oxygen forms an oligomeric compound.
Preparation & Synthesis
Preparation
The synthesis method for 2,6-Bis(hydroxymethyl)-p-cresol is as follows:Aqueous formaldehyde (21.5 g, 37%) is added to a solution of p-cresol (10.8 g, 0.1 mol) and NaOH (5.0 g) in HO (20 mL).The mixture is stirred at room temperature for 24 hours.The mixture is filtered and washed with saturated aqueous NaCl (100 mL).The resulting salt is dissolved in water (400 mL) and neutralized with acetic acid.Pale pink crystals are obtained and filtered.The crystals are washed with H2O and dissolved in hot ethyl acetate (40 mL).The solution is dried over Na2SO4 and filtered while still hot.The solution is concentrated to 27 mL and recrystallized overnight.The product crystals are filtered and washed with cold ethyl acetate.The crystals are air dried.