9-Anthracenemethanol CAS#: 1468-95-7; ChemWhat Code: 64673
Identification
| Product Name | 9-Anthracenemethanol |
| IUPAC Name | anthracen-9-ylmethanol |
| Molecular Structure |  |
| CAS Registry Number | 1468-95-7 |
| EINECS Number | 215-998-5 |
| MDL Number | MFCD00001264 |
| Beilstein Registry Number | 1873402 |
| Synonyms | 9-hydroxymethylanthracene, 9-Hydroxymethylanthracene, 9-anthracenylmethanol;1468-95-7 |
| Molecular Formula | C15H12O |
| Molecular Weight | 208.26 |
| InChI | InChI=1S/C15H12O/c16-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)15/h1-9,16H,10H2 |
| InChI Key | JCJNNHDZTLRSGN-UHFFFAOYSA-N |
| Canonical SMILES | c1ccc2c(c1)cc3ccccc3c2CO |
Physical Data
| Appearance | Light yellow powder |
| Solubility | Soluble in hot methanol very faint turbidity. |
| Refractive index | 1.5361 |
| Melting Point, °C | Solvent (Melting Point) |
| 161 – 162 | benzene |
| 159 – 162 | |
| 158 – 160 | |
| 164 – 165 | ethanol, petroleum ether |
| 162 – 163 | |
| 138 – 140 | |
| 270 | |
| 156 – 158 | methanol, H2O |
| Density, g·cm-3 | Measurement Temperature, °C |
| 22.84 | |
| 1.3 |
| Description (Association (MCS)) | Solvent (Association (MCS)) | Comment (Association (MCS)) | Partner (Association (MCS)) |
| Association with compound | Association with compound | Ratio of solvents: 9:1 | C40H36N4(4+)*4Cl(1-) |
| Association with compound | Association with compound | Ratio of solvents: 9:1 | C53H48N4(4+)*4Cl(1-) |
| Association with compound | Association with compound | Ratio of solvents: 9:1 | trans-4,4′-vinylenebis(1-benzylpyridinium) dichloride |
| Association with compound | Association with compound | Ratio of solvents: 9:1 | C50H44N4(4+)*4Cl(1-) |
Spectra
| Description (NMR Spectroscopy) | Nucleus (NMR Spectroscopy) | Solvents (NMR Spectroscopy) | Temperature (NMR Spectroscopy), °C | Frequency (NMR Spectroscopy), MHz |
| Spectrum | 13C | dimethylsulfoxide-d6 | ||
| Chemical shifts, Spectrum | 1H | dimethylsulfoxide-d6 | 25 | 400.13 |
| Chemical shifts | 1H | chloroform-d1 | 400 | |
| Chemical shifts, Spectrum | 13C | chloroform-d1 | 100 | |
| Chemical shifts | 1H | dimethylsulfoxide-d6 | 300 | |
| Chemical shifts | 1H | [D3]acetonitrile | ||
| Chemical shifts | 1H | CDCl3 | 200 | |
| Spin-spin coupling constants | acetone-d6 | |||
| NMR |
| Description (IR Spectroscopy) | Solvent (IR Spectroscopy) | Original Text (IR Spectroscopy) | Comment (IR Spectroscopy) | Signals, cm-1 |
| Bands | potassium bromide | FTIR (cm-1): 3442 (CH2-OH, stretching); 3003 (w, aromatic C-H stretching); 1490 (s, C=C stretching); 738 (s, aromatic C-H out-of-plane bending) | 3442, 3003, 1490, 738 | |
| ATR (attenuated total reflectance), Bands | ||||
| Bands, Spectrum | potassium bromide | |||
| Bands | KBr | 3380 – 1050 cm**(-1) | ||
| Bands | CCl4 | 3616 – 13 cm**(-1) |
| Description (Mass Spectrometry) |
| electron impact (EI), spectrum |
| high resolution mass spectrometry (HRMS), electrospray ionisation (ESI), liquid chromatography mass spectrometry (LCMS), time-of-flight mass spectra (TOFMS), spectrum |
| MALDI-TOF (Matrix assisted laser desorption ionization – time of flight), Spectrum |
| Description (UV/VIS Spectroscopy) | Solvent (UV/VIS Spectroscopy) | Absorption Maxima (UV/VIS), nm |
| Spectrum | aq. phosphate buffer | |
| Spectrum | acetonitrile | 243.6 |
| Spectrum | ethanol | 244.5 |
| Spectrum | aq. buffer, ethanol | 253, 315, 330, 346, 364, 384 |
| H2O | 366 | |
| Absorption maxima | 383 |
| Description (Raman Spectroscopy) |
| Spectrum, Bands |
Route of Synthesis (ROS)
| Conditions | Yield |
| With Silphos; bromine In acetonitrile for 0.75h; Heating; | 97% |
| With sulfuric acid; hydrogen bromide; sodium bromide In diethyl ether | 96% |
| With phosphorus tribromide In toluene at 0 – 20℃; | 94% |
| With phosphorus tribromide In toluene at 0 – 20℃; Inert atmosphere; | 94% |
| With phosphorus tribromide In toluene at 0℃; for 1h; Inert atmosphere; | 92% |
Safety and Hazards
| Pictogram(s) |  |
| Signal | Warning |
| GHS Hazard Statements | H341 (100%): Suspected of causing genetic defects [Warning Germ cell mutagenicity] Information may vary between notifications depending on impurities, additives, and other factors. |
| Precautionary Statement Codes | P201, P202, P281, P308+P313, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
Other Data
| Transportation | NONH for all modes of transport |
| Under the room temperature and away from light | |
| HS Code | 290629 |
| Storage | Under the room temperature and away from light |
| Market Price | USD |
| Druglikeness | |
| Lipinski rules component | |
| Molecular Weight | 208.26 |
| logP | 3.743 |
| HBA | 1 |
| HBD | 1 |
| Matching Lipinski Rules | 4 |
| Veber rules component | |
| Polar Surface Area (PSA) | 20.23 |
| Rotatable Bond (RotB) | 1 |
| Matching Veber Rules | 2 |
| Bioactivity |
| In vitro: Efficacy |
| Quantitative Results |
| pX | Parameter | Value (quant) | Unit | Effect |
| 4.6 | EC50 | 5.3 | μg/ml | antibiotic agent |
| 4.52 | EC50 | 6.3 | μg/ml | antibiotic agent |
| 3.82 | EC50 | 11.3 | μg/ml | antibiotic agent |
| Quantitative Results | ||
| 1 of 2 | Effect | Mutagenic |
| Biological material | Salmonella enterica serovar Typhimurium | |
| Assay Description | Bioassay : PAPS-3′-phosphoadenosine-5′-phosphosulfate bacteria were grown overnight in Nutrient Broth No.2; titer of 6 to 10×109 bacteria; bacterial suspension and test comp. (in DMSO) added to glass tube, cont. cytosol, PAPS, buffer B; 37 deg C, pH 7.4; dark | |
| Results | addition of rat liver cytosol, PAPS and Cl– led to strong mutagenic effects of test comp.; test comp. activated by cytosol of V79rSTa-1, V79rSTa-2 | |
| 2 of 2 | Effect | Mutagenic |
| Biological material | Salmonella enterica serovar Typhimurium | |
| Assay Description | Bioassay : Ames test conditions in presence of 3′-phosphoadenosine-5′-phosphosulphate, cofactor for sulphotransferases and varying amounts of hepatic cytosols from 3-y-old child, adult female, adult male and one unknown | |
| Results | activation to mutagen by human hepatic sulphotransferases |
| Use Pattern |
| 9-Anthracenemethanol CAS 1468-95-7 as producing propylene oxide |
| 9-Anthracenemethanol CAS 1468-95-7 as photosensitizer of dental composition for making dental prostheses and for dental restoration |
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| Caming Pharmaceutical Ltd | http://www.caming.com/ |
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