3-Pyridinemethanol CAS 100-55-0
Introduction：Basic information about 3-Pyridinemethanol CAS 100-55-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
3-Pyridinemethanol Basic information
| Product Name: | 3-Pyridinemethanol |
| Synonyms: | 3-PYRIDYLMETHANOL;3-PYRIDINEMETHANOL;3-Hydroxymethyl pyridine (3-Pyridine methanol);3-(HYDROXYMETHYL)-PYRIDINE97% (GC);ω-hydroxy-3-picoline;3-(HYDROXYMETHYL)PYRIDINE 98%;3-HYDROXYMETHYL PYRIDINE PYRIDIN-3-YL-METHANOL;PYRIDINE-3-METHANOL (3-PYRIDYLCARBINOL) |
| CAS: | 100-55-0 |
| MF: | C6H7NO |
| MW: | 109.13 |
| EINECS: | 202-864-6 |
| Product Categories: | Building Blocks;C6 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines;Heterocycles;Isotope Labelled Compounds;Alkohols;HEXALEN;inhibitor |
| Mol File: | 100-55-0.mol |
3-Pyridinemethanol Chemical Properties
| Melting point | -7 °C |
| Boiling point | 154 °C/28 mmHg (lit.) |
| density | 1.124 g/mL at 25 °C (lit.) |
| vapor pressure | 0.342Pa at 20℃ |
| refractive index | n |
| Fp | >230 °F |
| storage temp. | Inert atmosphere,Room Temperature |
| solubility | 1000mg/l |
| pka | 13.68±0.10(Predicted) |
| form | liquid (clear) |
| color | clear light yellow |
| PH | 7-8 (100g/l, H2O, 20℃) |
| Water Solubility | soluble |
| Sensitive | Hygroscopic |
| Merck | 14,6527 |
| BRN | 107851 |
| Cosmetics Ingredients Functions | TONIC |
| InChI | 1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2 |
| InChIKey | MVQVNTPHUGQQHK-UHFFFAOYSA-N |
| SMILES | OCc1cccnc1 |
| LogP | -0.11 at 25℃ |
| Surface tension | 47.68 mN/m at 23° |
| CAS DataBase Reference | 100-55-0(CAS DataBase Reference) |
| NIST Chemistry Reference | Nicotinyl Alcohol(100-55-0) |
| EPA Substance Registry System | 3-Pyridinemethanol (100-55-0) |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26-36-24/25 |
| WGK Germany | 3 |
| RTECS | UT4690000 |
| F | 3-10-23 |
| Hazard Note | Irritant |
| TSCA | TSCA listed |
| HS Code | 29333999 |
| Storage Class | 10 - Combustible liquids |
| Hazard Classifications | Eye Irrit. 2 |
| Chemical Properties | CLEAR LIGHT YELLOW TO YELLOW LIQUID |
| Originator | Roniacol,Roche,US,1949 |
| Uses | 3-Pyridinemethanol is a useful synthetic intermediate. It can be used in the synthesis of histone deacetylase inhibitors. It can also be used to prepare (phenyl)(cyanopyrazinyl)urea derivatives as possible kinase-1 (Chk1) inhibitors. |
| Uses | 3-Pyridinemethanol can be used as antineoplastic and used in the synthesis of histone deacetylase inhibitors. |
| Application | 3-Pyridinemethanol is a cholesterol-lowering agent with vasodilatory effects. It can be used to treat acroarterial spasm, acrocyanosis, frostbite, migraine, retinal vascular embolism, etc. As a precursor of bioactive compounds, it can be used to study vasodilation mechanisms and cholesterol regulation. |
| Preparation | Using 3-cyanopyridine as the raw material, palladium-carbon catalyst is used for reduction reaction in a hydrogen atmosphere to generate 3-aminomethylpyridine hydrochloride. 3-aminomethylpyridine hydrochloride is converted into 3-Pyridinemethanol by treatment with ethyl nitrite. |
| Definition | ChEBI: 3-pyridinemethanol is a member of the class of pyridines that is pyridine which is substituted by a hydroxymethyl group at position 3. It has a role as a vasodilator agent and an antilipemic drug. It is a member of pyridines and an aromatic primary alcohol. |
| Manufacturing Process | The catalyst is prepared by suspending 5 kg of catalyst grade charcoal in 200liters of water, in a pressure vessel, and adding thereto 25 liters of 4% (as Pdmetal) aqueous palladous chloride. Air is displaced from the vessel and thenhydrogen is passed into the aqueous mixture at a pressure of 3 to 5 psi, whilestirring, until no further absorption is noted and the chloride is completelyreduced to metal. To the aqueous suspension of the palladized charcoal catalyst thus obtainedare added 20.8 kg of 3-cyano-pyridine (96% purity); and then are added 70 liters of a hydrochloric acid solution prepared by diluting 30 liters of 36% HClwith 40 liters of water. This represents approximately 1.75 mols of HCl foreach mol of 3-cyano-pyridine. The suspension is maintained at 10° to 15°Cand stirred continuously while introducing a current of hydrogen at a pressureof 3 to 5 psi. When absorption of hydrogen ceases and the 3-cyanopyridine iscompletely reduced, the reaction mixture is filtered to remove the catalyst.The filter cake is washed with 40 liters of water in two equal portions, and thewash water is added to the filtrate. The combined liquors, which comprise an aqueous hydrochloric acid solutionof 3-aminomethyl-pyridine hydrochloride, are then heated to a temperature of60° to 65°C, and ethyl nitrite gas is passed into the heated solution. The ethylnitrite is generated by placing 20 liters of 90% ethyl alcohol in a suitablevessel, diluting with 200 liters of water, and, while stirring, adding to thedilute alcohol 18.3 kg of nitrosyl chloride at the rate of 2.25 kg per hour. (Theprocess using methyl nitrite is carried out by substituting a stoichiometricallyequivalent quantity of methyl alcohol for the ethyl alcohol.) When all the ethyl nitrite has been added, the reaction mixture is refluxed forapproximately one hour, then concentrated to dryness under reduced pressure(25 to 30 mm Hg) and at a maximum temperature of 70°C. The crystallineresidue is dissolved in 35 liters of water and adjusted to a pH of 8 to 9 byaddition (with cooling and stirring) of 11 to 12 kg of caustic soda. The sodiumchloride formed is filtered off, and the filter cake is washed with 20 liters ofnormal butyl alcohol. This wash liquid is used for the first extraction of theproduct from the aqueous filtrate. The filtrate is then further extracted withfour successive 20-liter portions of n-butyl alcohol. All the extracts are combined and concentrated in vacuo (100°C/20 mm) toremove the n-butyl alcohol. The residue is submitted to fractionation underreduced pressure. The forerun (up to 112°C/2 to 3 mm) consists of a smallamount of n-butyl alcohol and some 3-pyridylcarbinol. The main fraction,boiling at 112° to 114°C/2 to 3 mm, consists of 3-pyridylcarbinol. |
| Brand name | Roniacol (HoffmannLaRoche). |
| Therapeutic Function | Vasodilator |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 28, p. 3261, 1963 DOI: 10.1021/jo01046a538 Synthesis, p. 55, 1987 |
| General Description | 3-Pyridinemethanol, an aromatic primary alcohol, is the key moiety of many bio-active and industrially important compounds. |
| Flammability and Explosibility | Not classified |
| References | [1] Patent: CN107459480, 2017, A. Location in patent: Paragraph 0119-0120 [2] Journal of Organometallic Chemistry, 1982, vol. 224, # 1, p. 21 - 28 [3] ACS Catalysis, 2016, vol. 6, # 6, p. 3998 - 4002 [4] Journal of the Chemical Society, 1953, p. 3733,3736, 3737 [5] Journal of the American Chemical Society, 1951, vol. 73, p. 4925 |
3-Pyridinemethanol Preparation Products And Raw materials
| Raw materials | 3-Cyanopyridine-->Hydrogen-->Nitrosyl chloride-->Ethanol-->Methyl nicotinate-->5-Bromo-3-pyridinecarboxaldehyde-->2-Bromopyridine-5-carbaldehyde-->3-(Aminomethyl)pyridine-->Ethyl nicotinate-->(6-BROMO-PYRIDIN-3-YL)-METHANOL |
| Preparation Products | 3-Pyridineethaneamine-->3-Picolyl chloride hydrochloride-->3-PYRIDINEMETHANOL N-OXIDE-->3-(2-HYDROXYETHYL)PYRIDINE-->3-Ethylpyridine-->3-(4-Fluoro-2-nitro-phenoxymethyl)-pyridine-->Pyridin-3-yl-pyridin-3-ylmethyl-amine-->3-(Methoxymethyl)pyridine-->PyridiniuM, 3-(hydroxyMethyl)-1-Methyl-, iodide-->3-Pyridylmethyl-N-(p-nitrophen-->3-(pyridin-3-yl-methyl)indolin-2-one |
