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CAS No.: | 115-19-5 |
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Name: | 3-Methyl butynol |
Article Data: | 139 |
Molecular Structure: | |
Formula: | C5H8O |
Molecular Weight: | 84.1179 |
Synonyms: | 2-Propyn-1-ol,1,1-dimethyl- (7CI);(1-Hydroxy-1-methylethyl)acetylene;1,1-Dimethyl-2-propyn-1-ol;1,1-Dimethyl-2-propynol;1,1-Dimethylpropargylalcohol;2-Ethynyl-2-propanol;2-Hydroxy-2-methyl-3-butyne;2-Methyl-2-hydroxy-3-butyne;2-Methyl-3-butyn-2-ol;2-Methyl-3-butyne-2-ol;2-Propyne-1,1,1-triol;3-Hydroxy-3-methyl-1-butyne;3-Methyl-1-butyn-3-ol;3-Methyl-3-hydroxy-1-butyne;3-Methyl-3-hydroxybutyne;AB 32;AB 32 (alcohol);Dimethylacetylenecarbinol;Dimethylacetylenylcarbinol;Dimethylethynylcarbinol;Dimethylethynylmethanol;Ethynyldimethylcarbinol;Mebynol;NSC 523;a,a-Dimethylpropargyl alcohol;3-Methyl butynol; |
EINECS: | 204-070-5 |
Density: | 0.91 g/cm3 |
Melting Point: | 3 °C |
Boiling Point: | 104.2 °C at 760 mmHg |
Flash Point: | 25 °C |
Solubility: | miscible in water |
Appearance: | colourless to light yellow liquid |
Hazard Symbols: | Xn |
Risk Codes: | 10-22-41 |
Safety: | 26-39-16 |
Transport Information: | UN 1987 3/PG 2 |
PSA: | 20.23000 |
LogP: | 0.39050 |
Conditions | Yield |
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With sodium In methanol at 0 - 5℃; for 1h; Solvent; Reagent/catalyst; Autoclave; Inert atmosphere; Large scale; | 99.2% |
Stage #1: acetylene With sodium amide In ammonia at -50℃; for 0.5h; Stage #2: acetone at -50 - 25℃; | 87.9% |
Stage #1: acetylene With potassium hydroxide monohydrate In dimethyl sulfoxide at 10 - 15℃; for 7h; Stage #2: acetone In dimethyl sulfoxide at 10 - 15℃; for 9h; Temperature; | 82% |
2-methyl-but-3-yn-2-ol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 12h; | 99% |
acetone
acetylene
A
2-methyl-but-3-yn-2-ol
B
2,5-dihydroxy-2,5-dimethyl-3-hexyne
Conditions | Yield |
---|---|
With potassium hydride In tetrahydrofuran at 30℃; under 759.826 Torr; for 2.25h; | A 7% B 91% |
Stage #1: acetone; acetylene With potassium 2-methylpropan-2-olate In xylene at 28 - 35℃; for 1h; Stage #2: With water Stage #3: With phosphoric acid Product distribution / selectivity; | A 2.3% B 90% |
Stage #1: acetone; acetylene With potassium 2-methylpropan-2-olate In xylene at 10 - 20℃; for 1h; Stage #2: With water Stage #3: With phosphoric acid Product distribution / selectivity; | A 79% B 3% |
Conditions | Yield |
---|---|
Stage #1: acetone; lithium acetylide; 4,4'-di-tert-butylbiphenyl In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran at 20℃; Product distribution / selectivity; | 81% |
Stage #1: acetone; lithium acetylide; naphthalene In tetrahydrofuran at 0℃; for 2h; Stage #2: With water In tetrahydrofuran at 20℃; Product distribution / selectivity; | 56.5% |
2-methyl-propan-1-ol
acetone
acetylene
A
2-methyl-but-3-yn-2-ol
B
2,5-dihydroxy-2,5-dimethyl-3-hexyne
Conditions | Yield |
---|---|
Stage #1: 2-methyl-propan-1-ol With potassium hydride In tetrahydrofuran at 30℃; under 759.826 Torr; for 0.25h; Stage #2: acetone; acetylene In tetrahydrofuran at 30℃; under 759.826 Torr; for 2.25h; | A 74% B 22% |
2-methyl-3-butyn-2-ol 1-ethoxyethyl ether
2-methyl-but-3-yn-2-ol
Conditions | Yield |
---|---|
With N,4-dimethyl-N-vinylbenzenesulfonamide; picAuCl2(III) In dichloromethane at 20℃; for 0.25h; Inert atmosphere; | 60% |
Conditions | Yield |
---|---|
In tetrahydrofuran Heating; | 47% |
Stage #1: acetone; acetylenemagnesium bromide In tetrahydrofuran at 0 - 20℃; Stage #2: With ammonium chloride In tetrahydrofuran; water | |
In tetrahydrofuran at -10 - 20℃; |
Conditions | Yield |
---|---|
at -20℃; | |
at -20℃; |
Reported in EPA TSCA Inventory.
The IUPAC name of 2-Methyl-3-butyn-2-ol is 2-methylbut-3-yn-2-ol. With the CAS registry number 115-19-5, it is also named as 1,1-Dimethyl-2-propyn-1-ol carbamate. The product's categories are Acetylenes; Acetylenic Alcohols & Their Derivatives; Chemistry, and the other registry numbers are 140705-79-9; 67539-62-2. Besides, it is colourless to light yellow liquid, which should be stored in a cool, sealed and ventilated warehouse. It is stable, but incompatible with strong oxidizing agents. In addition, its molecular formula is C5H8O and molecular weight is 84.12.
Physical properties about 2-Methyl-3-butyn-2-ol are: (1)ACD/LogP: 0.316; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.32; (4)ACD/LogD (pH 7.4): 0.32; (5)ACD/BCF (pH 5.5): 1.02; (6)ACD/BCF (pH 7.4): 1.02; (7)ACD/KOC (pH 5.5): 35.39; (8)ACD/KOC (pH 7.4): 35.39; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.444; (13)Molar Refractivity: 24.542 cm3; (14)Molar Volume: 92.388 cm3; (15)Polarizability: 9.729 10-24cm3; (16)Surface Tension: 33.2760009765625 dyne/cm; (17)Density: 0.911 g/cm3; (18)Flash Point: 25 °C; (19)Enthalpy of Vaporization: 40.008 kJ/mol; (20)Boiling Point: 104.165 °C at 760 mmHg; (21)Vapour Pressure: 17.1840000152588 mmHg at 25°C
Preparation of 2-Methyl-3-butyn-2-ol: this chemical can be prepared by the reaction of Propan-2-one with Ethynylmagnesium bromide.
This reaction needs Tetrahydrofuran by heating. The yield is 47 %.
Uses of 2-Methyl-3-butyn-2-ol: this chemical is an intermediate used in the synthesis of pharmaceuticals, pesticides and terpeneless spice. It can also used as acid corrosion inhibitor, viscosity depressant, viscosity stabilizer, glazing agent and stabilizer of chlorinated hydrocarbons. Additionally, it is used as polymerization inhibitor in silicon rubber. Similarly, it can react with Ethoxyethene to get 3-(1-Ethoxy-ethoxy)-3-methyl-but-1-yne.
This reaction needs Sulfuric acid for 30 min. The yield is 77 %.
When you are using this chemical, please be cautious about it as the following: it is flammable. Please keep away from sources of ignition. It is also harmful if swallowed and risk of serious damage to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. And you should wear eye/face protection.
People can use the following data to convert to the molecule structure.
(1)Canonical SMILES: CC(C)(C#C)O;
(2)InChI: InChI=1S/C5H8O/c1-4-5(2,3)6/h1,6H,2-3H3;
(3)InChIKey: CEBKHWWANWSNTI-UHFFFAOYSA-N;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 2gm/m3 (2000mg/m3) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(4), Pg. 55, 1987. |
mouse | LD50 | oral | 500mg/kg (500mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: ATAXIA BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 31(4), Pg. 55, 1987. |
mouse | LD50 | subcutaneous | 1161mg/kg (1161mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Yakugaku Zasshi. Journal of Pharmacy. Vol. 76, Pg. 181, 1956. |
rat | LD50 | oral | 1950mg/kg (1950mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 115, Pg. 230, 1955. |