2-Butynoic acid

2-Butynoic acid - Names and Identifiers

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

2-Butynoic acid - Physico-chemical Properties

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.

2-Butynoic acid - Risk and Safety

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

2-Butynoic acid - Nature

Open Data Verified Data

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.

Last Update：2024-01-02 23:10:35

2-Butynoic acid - Preparation Method

Open Data Verified Data

acetylene dicarboxylic acid (or its potassium salt) is prepared by heating to boiling with water.
a,a-sodium propynyl is prepared by reacting allyl chloride with sodium metal, which is then treated with CO2 and finally acidified.

Last Update：2022-01-01 10:31:31

2-Butynoic acid - Introduction

Used in a series of reactions to synthesize fibers, such as the cyclic acylation of phenols to cyclic ketones or chromones, and the cyclization of γ-butyrolactone.

Last Update：2022-10-16 17:26:44

2-Butynoic acid - Use

Open Data Verified Data

can be used for the preparation of dibromocrotonic acid, ethoxycrotonic acid, butynic acid ethyl ester, butynyl (acid) chloride and butynyl (acid) amide.

Last Update：2022-01-01 10:31:31

2-Butynoic acid - Safety

Open Data Verified Data

storage and transportation according to general chemical regulations.

Last Update：2022-01-01 10:31:32

2-Butynoic acid - Reference Information

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]

Last Update：2024-04-09 20:52:54

Shanghai Worldyang Chemical Co.,Ltd.

2-Butynoic acid

2-butynoic acid

CAS: 590-93-2

Molecular Formula: C4H4O2

2-Butynoic acid - Names and Identifiers

2-Butynoic acid - Physico-chemical Properties

2-Butynoic acid - Risk and Safety

2-Butynoic acid - Nature

Open Data Verified Data

2-Butynoic acid - Preparation Method

Open Data Verified Data

2-Butynoic acid - Introduction

2-Butynoic acid - Use

Open Data Verified Data

2-Butynoic acid - Safety

Open Data Verified Data

2-Butynoic acid - Reference Information

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2-Butynoic acid Request for Quotation

2-butynoic acid

CAS: 590-93-2

Molecular Formula: C4H4O2

2-Butynoic acid - Names and Identifiers

2-Butynoic acid - Physico-chemical Properties

2-Butynoic acid - Risk and Safety

2-Butynoic acid - Nature

Open Data Verified Data

2-Butynoic acid - Preparation Method

Open Data Verified Data

2-Butynoic acid - Introduction

2-Butynoic acid - Use

Open Data Verified Data

2-Butynoic acid - Safety

Open Data Verified Data

2-Butynoic acid - Reference Information

Supplier List

2-Butynoic acid