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| CAS No.: | 67-56-1 |
|---|---|
| Name: | Methanol |
| Article Data: | 2114 |
| Molecular Structure: | |
|
|
|
| Formula: | CH4O |
| Molecular Weight: | 32.0422 |
| Synonyms: | Alcohol, methyl;Carbinol;Methanol cluster;Bieleski's solution;Methyl alcohol;Wood alcohol; |
| EINECS: | 200-659-6 |
| Density: | 0.753 g/cm3 |
| Melting Point: | -98 °C(lit.) |
| Boiling Point: | 48.093 °C at 760 mmHg |
| Flash Point: | 11.111 °C |
| Solubility: | miscible with water |
| Appearance: | Clear, colorless liquid |
| Hazard Symbols: |
 Xn,  T,  F
|
| Risk Codes: | 10-20/21/22-68/20/21/22-39/23/24/25-23/24/25-11-40-36-36/38-23/25 |
| Safety: | 36/37-7-45-16-24/25-23-24 |
| Transport Information: | UN 1170 3/PG 2 |
| PSA: | 20.23000 |
| LogP: | -0.39150 |
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- 99170-93-1N-Methyl-2-oxazolamine
- 717878-06-31-(4-fluorophenyl)-4-nitro-1H-imidazole
- 914458-26-7[5-(2-fluorophenyl)-1-pentyl-1H-pyrrol-3-yl]-1-naphthalenyl-Methanone
- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
| Conditions | Yield |
|---|---|
| With water In aq. phosphate buffer at 20℃; for 1h; pH=7.4; Catalytic behavior; Reagent/catalyst; Electrolysis; Inert atmosphere; Enzymatic reaction; | 100% |
| With cobalt(III) acetylacetonate; hydrogen; bis(trifluoromethanesulfonyl)amide; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran; ethanol at 100℃; under 52505.3 Torr; for 24h; Autoclave; Inert atmosphere; | 59% |
| With C36H54IrN2P2(1+)*C24H20B(1-); hydrogen; sodium hydride In ethanol; toluene at 180℃; under 7500.75 - 45004.5 Torr; for 18h; Autoclave; | 31% |
| Conditions | Yield |
|---|---|
| With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 8h; Product distribution; Ambient temperature; | A n/a B 100% |
| With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 8h; Ambient temperature; | A n/a B 100% |
- 120-61-6
1,4-benzenedicarboxylic acid dimethyl ester
- 104-76-7
2-Ethylhexyl alcohol
A
- 67-56-1
methanol
B
- 63468-13-3
2-ethylhexyl methyl terephthalate
| Conditions | Yield |
|---|---|
| With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 24h; Product distribution; Ambient temperature; | A n/a B 100% |
| With phosphorus pentoxide; potassium carbonate; Aliquat 336 In neat (no solvent) under 20 Torr; for 24h; Ambient temperature; | A n/a B 100% |
| Conditions | Yield |
|---|---|
| With D-glucose; NADH In aq. buffer for 2h; pH=6.85; Catalytic behavior; Solvent; Concentration; pH-value; Ionic liquid; Enzymatic reaction; | 100% |
| With carbon monoxide; water; hydrogen at 35 - 250℃; under 825.083 - 75007.5 Torr; Temperature; Pressure; Large scale; | 99.99% |
| With dimethylsulfide borane complex; C24H18BO2P In benzene-d6 at 70℃; under 1520.1 Torr; for 1h; Reagent/catalyst; Inert atmosphere; | 95% |
- 29843-53-6
dimethyl(p-nitrophenyl)sulfonium perchlorate
A
- 67-56-1
methanol
B
- 701-57-5
1-methylthio-4-nitro-benzene
| Conditions | Yield |
|---|---|
| With water at 80℃; Rate constant; other temp.; | A n/a B 100% |
| Conditions | Yield |
|---|---|
| With Methyltrichlorosilane; sodium iodide In acetonitrile at 25℃; for 6h; | A n/a B 100% |
- 113849-79-9
1-(2-Adamantylidene)-1-methoxy-1-phenylmethane
A
- 67-56-1
methanol
B
- 68157-27-7
adamantan-2-yl(phenyl)methanone
| Conditions | Yield |
|---|---|
| With tris-p-bromophenyl ammoniumyl hexachloroantimonate In dichloromethane for 3h; | A n/a B 100% |
A
- 67-56-1
methanol
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In benzene for 0.5h; pinacol rearrangement; | A n/a B 100% |
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In benzene at 25℃; for 0.5h; pinacol rearrangement; | A n/a B 100% |
- 64-17-5Ethanol
- 141-78-6Ethyl acetate
- 7757-82-6Sodium sulfate
- 12125-02-9Ammonium chloride
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- 9003-11-6Polyethylene-polypropylene glycol
- 121062-08-6Melanotan II
- 7647-14-5Sodium chloride
- 104987-11-3Tacrolimus
- 141-53-7Sodium formate
- 8001-54-5Quaternary ammonium compounds, alkylbenzyldimethyl, chlorides
- 9003-39-8Povidone
- 10161-34-9Trenbolone acetate
- 402957-28-2Telaprevir
- 68-19-9Cyanocobalamin
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History
Pure methanol, however, was first isolated in 1661 by Robert Boyle, when he produced it via the distillation of boxwood. It later became known as pyroxylic spirit. In 1834, the French chemists Jean-Baptiste Dumas and Eugene Peligot determined its elemental composition. The term "methyl" was derived in about 1840 by back-formation from methylene, and was then applied to describe "methyl alcohol." This was shortened to "methanol" in 1892 by the International Conference on Chemical Nomenclature. In 1923, the German chemists Alwin Mittasch and Mathias Pier, working for BASF developed a means to convert synthesis gas (a mixture of carbon monoxide, carbon dioxide, and hydrogen) into methanol. Modern methanol production has been made more efficient through use of catalysts (commonly copper) capable of operating at lower pressures, the modern low pressure methanol (LPM) was developed by ICI in the late 1960s with the technology now owned by Johnson Matthey who is a leading licensor of methanol technology.
The use of methanol as a motor fuel received attention during the oil crises of the 1970s due to its availability, low cost, and environmental benefits. By the mid-1990s, over 20,000 methanol "flexible fuel vehices" capable of operating on methanol or gasoline were introduced in the U.S. In 2006 astronomers using the MERLIN array of radio telescopes at Jodrell Bank Observatory discovered a large cloud of methanol in space, 300 billion miles across.
Consensus Reports
Community Right-To-Know List. Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
Standards and Recommendations
OSHA PEL: TWA 200 ppm; STEL 250 ppm (skin)
ACGIH TLV: TWA 200 ppm; STEL 250 ppm (skin); BEI: 15 mg/L of methanol in urine at end of shift
DFG MAK: 200 ppm (270 mg/m3); BAT: 30 mg/L in urine at end of shift
NIOSH REL: TWA 200 ppm; CL 800 ppm/15M
DOT Classification: 3; Label: Flammable Liquid, Poison
Analytical Methods
For occupational chemical analysis use NIOSH: Methanol, 2000.
Specification
Methanol, also known as methyl alcohol, is a colorless, flammable, toxic liquid with a faintly sweet pungent odor like that of ethyl alcohol. It is miscible with water, ethanol, ether, benzene, ketones, and most other organic solvents, and can dissolve many inorganic salts. Methanol is the simplest alcohol used in the manufacture of formaldehyde and acetic acid, in chemical synthesis, antifreeze, and as a solvent. Ingestion of methanol is toxic and may cause blindness.
Physical properties about Methanol are: (1)ACD/LogP: -0.69; (2)ACD/LogD (pH 5.5): -0.69; (3)ACD/LogD (pH 7.4): -0.69; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 10.04; (7)ACD/KOC (pH 7.4): 10.04; (8)#H bond acceptors: 1; (9)Index of Refraction: 1.311 ; (10)Molar Refractivity: 8.217 cm3; (11)Molar Volume: 42.548 cm3; (12)Polarizability: 3.257 10-24cm3; (13)Surface Tension: 18.8619995117188 dyne/cm; (14)Density: 0.753 g/cm3; (15)Flash Point: 11.111 °C; (16)Enthalpy of Vaporization: 35.21 kJ/mol; (17)Boiling Point: 48.093 °C at 760 mmHg; (18)vapour Pressure: 265.414001464844 mmHg at 25°C
Preparation of Methanol: Before 1926, all methanol was made by distillation of wood. But now, almost all the industrial synthesis of methanol is using catalytic hydrogenation of carbon monoxide under pressure. This process includs gas making, synthetic purification, methanol synthesis and crude methanol rectification. The synthesis gas is most commonly produced from the methane component in natural gas rather than from coal. The purification process of crude methanol includes rectification and chemical treatment. Chemical treatment is using alkali to undermine the impurities which is difficult to be separated in the rectification process, and adjust the pH value. Rectification is removal of the main easily volatile components such as dimethyl ether, and difficultly volatile components such as ethanol, high-carbon alcohol and water. After the crude distillation, purity can achieve more than 98% .
Uses of Methanol:
1. Methanol is especially useful for HPLC, UV/VIS spectroscopy, and LCMS due to its low UV cutoff. It is also a basic organic raw material, which is mainly used to produce formaldehyde, acetic acid, methyl chloride, methylamine, dimethyl sulfate, pesticides (insecticides, acaricides), medicine (sulfonamides, syntomycin, etc.) and other organic products.
2. Methanol can also be mixed with gasoline for use of alternative fuels. The physical and chemical characteristics of methanol offer several advantages as an alternative fuel, including relatively low production cost and a lower risk of flammability compared to gasoline. But it is used on a limited basis to fuel internal combustion engines.
3. Methanol is an important solvent used for paint, varnish, shellac, ink, adhesives, dyes, alkaloids, cellulose acetate, cellulose nitrate, ethyl cellulose, polyvinyl butyral, etc. Methanol is a usually better solvent than ethanol. And it can dissolve many inorganic salts.
4. Methanol is also used as reagent for analysis and chromatography, as reagent of determination of boron, in separation of calcium sulfate and magnesium sulfate, and in separation of strontium bromide and barium bromide. What's more, it can used as antifreeze in pipelines and windshield washer fluid.
When you are using this chemical, please be cautious about it as the following: Methanol is harmful by inhalation, in contact with skin and if swallowed. If ingested, for example, as little as 10 mL of pure methanol can cause permanent blindness by destruction of the optic nerve, and 30 ml is potentially fatal. It has danger of very serious irreversible effects. Methanol is often a component in "bootleg" liquor (illegally brewed and distilled alcohol) and there have been numerous cases in the past in which the consumption of such a drink has been fatal. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Methanol is highly flammable, so people should keep it away from sources of ignition. A hot air gun, a hot plate or even a radiator may be sufficiently hot to ignite the vapour of methanol. So people should be very careful.
You can still convert the following datas into molecular structure:
(1)SMILES:CO;
(2)Std. InChI:InChI=1S/CH4O/c1-2/h2H,1H3;
(3)Std. InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LCLo | inhalation | 44gm/m3/6H (44000mg/m3) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: MUSCLE WEAKNESS GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933. |
| cat | LDLo | intravenous | 4641mg/kg (4641mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 16, Pg. 1, 1920. | |
| dog | LDLo | oral | 7500mg/kg (7500mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1365, 1935. | |
| frog | LDLo | parenteral | 59gm/kg (59000mg/kg) | PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 50, Pg. 296, 1935. |
| guinea pig | LD50 | intraperitoneal | 3556mg/kg (3556mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| hamster | LD50 | intraperitoneal | 8555mg/kg (8555mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| human | LDLo | oral | 143mg/kg (143mg/kg) | SENSE ORGANS AND SPECIAL SENSES: OPTIC NERVE NEUROPATHY: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING | "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 382, 1969. |
| human | LDLo | oral | 428mg/kg (428mg/kg) | BEHAVIORAL: HEADACHE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974. |
| human | TCLo | inhalation | 300ppm (300ppm) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE BEHAVIORAL: HEADACHE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974. |
| human | TCLo | inhalation | 86000mg/m3 (86000mg/m3) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES LUNGS, THORAX, OR RESPIRATION: COUGH | Archiv fuer Gewerbepathologie und Gewerbehygiene. Vol. 5, Pg. 1, 1933. |
| man | LDLo | oral | 6422mg/kg (6422mg/kg) | BRAIN AND COVERINGS: "CHANGES IN CIRCULATION (HEMORRHAGE, THROMBOSIS, ETC.)" LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING | Canadian Medical Association Journal. Vol. 128, Pg. 14, 1983. |
| man | LDLo | unreported | 868mg/kg (868mg/kg) | "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970. | |
| man | TDLo | oral | 3571uL/kg (3.571mL/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA BLOOD: OTHER CHANGES | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 2095, 1993. |
| man | TDLo | oral | 9450uL/kg (9.45mL/kg) | SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE BEHAVIORAL: GENERAL ANESTHETIC | American Journal of Emergency Medicine. Vol. 16, Pg. 538, 1998. |
| man | TDLo | oral | 3429mg/kg (3429mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE | Acta Medica Scandinavica. Vol. 212, Pg. 5, 1982. |
| monkey | LCLo | inhalation | 1000ppm (1000ppm) | Industrial and Engineering Chemistry. Vol. 23, Pg. 931, 1931. | |
| monkey | LD50 | oral | 7gm/kg (7000mg/kg) | BEHAVIORAL: MUSCLE WEAKNESS BEHAVIORAL: ATAXIA BEHAVIORAL: COMA | Toxicology and Applied Pharmacology. Vol. 3, Pg. 202, 1961. |
| monkey | LDLo | skin | 393mg/kg (393mg/kg) | Industrial and Engineering Chemistry. Vol. 23, Pg. 931, 1931. | |
| mouse | LCLo | inhalation | 50gm/m3/2H (50000mg/m3) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 80, 1982. | |
| mouse | LD50 | intraperitoneal | 10765mg/kg (10765mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| mouse | LD50 | intravenous | 4710mg/kg (4710mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| mouse | LD50 | oral | 7300mg/kg (7300mg/kg) | Toxicology. Vol. 25, Pg. 271, 1982. | |
| mouse | LD50 | subcutaneous | 9800mg/kg (9800mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. | |
| rabbit | LD50 | intraperitoneal | 1826mg/kg (1826mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| rabbit | LD50 | intravenous | 8907mg/kg (8907mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| rabbit | LD50 | oral | 14200mg/kg (14200mg/kg) | FAO Nutrition Meetings Report Series. Vol. 48A, Pg. 105, 1970. | |
| rabbit | LD50 | skin | 15800mg/kg (15800mg/kg) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974. | |
| rat | LC50 | inhalation | 64000ppm/4H (64000ppm) | Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 74, 1974. | |
| rat | LD50 | intraperitoneal | 7529mg/kg (7529mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| rat | LD50 | intravenous | 2131mg/kg (2131mg/kg) | EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985. | |
| rat | LD50 | oral | 5628mg/kg (5628mg/kg) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 19(11), Pg. 27, 1975. | |
| women | TDLo | oral | 4gm/kg (4000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE LUNGS, THORAX, OR RESPIRATION: DYSPNEA GASTROINTESTINAL: NAUSEA OR VOMITING | Acta Medica Scandinavica. Vol. 212, Pg. 5, 1982. |