Name | 2-butynoic acid |
Synonyms | NSC 174116 but-2-ynoate TETROLIC ACID 2-butynoic acid 2-Butynoic acid 2-BUTYNOIC ACID but-2-ynoic acid BUT-2-YNOIC ACID Tetrolic acid (8CI) 3-Methylpropiolic acid 1-Propynecarboxylic acid Methylacetylenecarboxylic acid |
CAS | 590-93-2 |
EINECS | 209-695-7 |
InChI | InChI=1/C4H4O2/c1-2-3-4(5)6/h1H3,(H,5,6)/p-1 |
InChIKey | LUEHNHVFDCZTGL-UHFFFAOYSA-N |
Molecular Formula | C4H4O2 |
Molar Mass | 84.07 |
Density | 0,9641 g/cm3 |
Melting Point | 78-80 °C (lit.) |
Boling Point | 200-203°C |
Flash Point | 200-203°C |
Water Solubility | Soluble in water. Slightly soluble in methanol and chloroform. |
Solubility | water: soluble50mg/mL, clear to very slightly hazy, colorless to very faintly yellow |
Vapor Presure | 0.117mmHg at 25°C |
Appearance | White to yellow powder |
Color | White to yellow |
BRN | 1740205 |
pKa | 2.62(at 25℃) |
Storage Condition | Sealed in dry,2-8°C |
Refractive Index | 1.3918 (estimate) |
MDL | MFCD00004363 |
Use | This product is for scientific research only and shall not be used for other purposes. |
Hazard Symbols | C - Corrosive![]() |
Risk Codes | R34 - Causes burns R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S27 - Take off immediately all contaminated clothing. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
UN IDs | UN 3261 8/PG 2 |
WGK Germany | 3 |
TSCA | Yes |
HS Code | 29161900 |
Hazard Class | 8 |
Packing Group | II |
colorless plate-like crystals, melting point about 76 °c. Boiling Point 202. 85 °c. The molar heat of combustion was 2270 J/mol. It has the dual characteristics of alkynes and carboxylic acids, and can carry out reduction, addition, oxidation, esterification and cyclization, and the formation of salts and acid chlorides.
can be used for the preparation of dibromocrotonic acid, ethoxycrotonic acid, butynic acid ethyl ester, butynyl (acid) chloride and butynyl (acid) amide.
storage and transportation according to general chemical regulations.
NIST chemical information | information provided by: webbook.nist.gov (external link) |
EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
Introduction | 2-butyneic acid is colorless, plate-like and crystalline. Boiling point 202.85 °c. Melting point 76 °c. Molar heat of combustion 2270.7J/mol. It has the dual characteristics of alkynes and carboxylic acids, and can carry out reduction, addition, oxidation, esterification and cyclization, and the formation of salts and acid chlorides. |
Use | 2-butyneic acid as a reagent in the synthesis of BMS 911543(B596075); A potent JAK2 inhibitor, can be used for the treatment of abnormal bone marrow hyperplasia. 2-butyneic acid can also be used to prepare chirally pure 1,2,3, 4-tetrahydroisoquinoline analogs as anticancer agents. 2-butyneic acid can be used for the preparation of Dibromo crotonic acid, ethoxy crotonic acid, butynic acid ethyl ester, butynyl (acid) chloride and butynyl (acid) amide. |
preparation method | (1) the acetylene dicarboxylic acid (or its potassium salt) is prepared by heating to boiling with water. (2) α, α-dichloropropene was reacted with metallic sodium to obtain propynyl sodium, which was then treated with CO2 and finally acidified. |
production method | 1. Acetylene dicarboxylic acid (or its potassium salt) is prepared by heating to boiling with water. 2. Α, α-dichloropropene is reacted with metallic sodium to obtain propynyl sodium, which is then treated with CO2 and finally acidified. 3. Preparation Method: 3-picolinolin-5-one (3): add ethyl acetoacetate (2)65g(0.5mol) to a reaction bottle equipped with a stirrer, a thermometer and a dropping funnel, A solution of 98% to 100% water and 25g(0.5mol) of hydrazine dissolved in 40ml of absolute ethanol was slowly added dropwise. The temperature was raised to 60 °c during the dropwise addition and kept at this temperature range until the addition was complete with the appearance of crystals. After the addition was complete, the reaction was continued to stir at room temperature for 1H. Cooling in an ice-water bath, Suction filtration, washing with cold ethanol, and drying gave 43g of 3-methylpyrazolin-5-one (3) at mp222 ° C. In 90% yield. 4, 4-dibromo-3-methylpyridin-5-one (4): In a reaction flask equipped with a stirrer, a thermometer and a dropping funnel, addition of 3-methylpyridin-5-one (3)20g(0.2mol), 80ml of glacial acetic acid, and a solution of 32G (0.2mol) of bromine dissolved in 20ml of glacial acetic acid was slowly added dropwise with stirring. After the addition, 50ml of water was added. A solution of 32G (0.2mol) of bromine in 20ml of glacial acetic acid was added dropwise. After the addition, it was left overnight at room temperature. The precipitation was completed by the addition of water. Suction filtration, washing with distilled water to neutral. After drying, 41g of 4, 4-dibromo-3-methylpyrazolin-5-one (4) was obtained, mp130 ~ 132 °c, yield 79%. 2-butyneic acid (1): In a reaction flask equipped with a stirrer and a thermometer, 20g of sodium hydroxide and 500ml of water were added, and the solution was cooled to 0-5 °c in an ice salt bath. 34G (0.132mol) of compound (4) were added in portions over about 10min. After dissolution, an orange-red solution was formed, and nitrogen was generated. The temperature of the reaction solution slightly increased. Continue 0~5 c reaction 1H, and then at room temperature reaction 1H. Acidified to acidic with concentrated hydrochloric acid under cooling. It was extracted with diethyl ether overnight using a continuous extractor. The ether extract was dried over anhydrous sodium sulfate and the ether was distilled off to give an orange oil. Place in a vacuum dryer until the oil solidifies as an orange solid. The solid was extracted with hot petroleum ether components, and the petroleum ether was concentrated to 50ml to precipitate off-white crystals, MP 74-75 °c. It is dissolved in a small amount of hot petroleum ether, and then add the same volume of petroleum ether, cooling crystallization, pure 2-butyneic acid (1)5.9g, MP 75~76 deg C, the yield of 54%. [1] 4. Preparation Method: In the reaction bottle equipped with a stirrer, 1500ml of liquid ammonia was added, one small particle of iron nitrate monohydrate was crystallized, acetone-dry ice was cooled, and 23g(1mol) of sodium metal was added in portions. Propyne (2) gas 44-48g(1.1-1.2mol) was introduced with rapid stirring. The ammonia was left to volatilize overnight. Dry ammonia gas was introduced to drive up the ammonia (finally, it could be heated in a hot water bath). 1000mL of dry THF, 500ml of diethyl ether were added and dry carbon dioxide gas was passed through with stirring. 8h after the absorption of carbon dioxide becomes very slow. It was noted that the solid formed in the reaction flask was crushed as much as possible, and the reaction was continued to be stirred overnight with introduction of carbon dioxide. The solvent was removed under reduced pressure, 200ml of water was added and the mixture was extracted with ether. The aqueous layer was added with 200g of crushed ice and acidified to acidity with hydrochloric acid. In a continuous extractor with ether extraction 24~36H. The ether layer was separated, the solvent was distilled off, and vacuum dried in a desiccator containing concentrated sulfuric acid for 2 days to obtain 58-60g of crude product in a yield of 69%-71%. Recrystallization was carried out with 50% ml of hexane and decolorized with activated carbon to obtain 42-50g of compound (1) in a yield of 59%. [2] |