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Propiolic acid

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Name

Propiolic acid

EINECS 207-437-8
CAS No. 471-25-0 Density 1.241 g/cm3
PSA 37.30000 LogP -0.29580
Solubility miscible with water Melting Point 16-18 °C(lit.)
Formula C3H2O2 Boiling Point 139.7 °C at 760 mmHg
Molecular Weight 70.0477 Flash Point 58.9 °C
Transport Information UN 2920 8/PG 2 Appearance viscous yellow liquid
Safety 26-36/37/39-45-24/25-7/9 Risk Codes 24/25-34-25-23/24/25
Molecular Structure Molecular Structure of 471-25-0 (Propiolic acid) Hazard Symbols ToxicT
Synonyms

Propiolicacid (6CI,8CI);2-Propyne-1-carboxylic acid;Acetylenecarboxylic acid;Acetylenemonocarboxylic acid;Carboxyacetylene;NSC 16152;Propargylic acid;

Article Data 54

Propiolic acid Synthetic route

2450-71-7

Propargylamine

471-25-0

Propiolic acid

Conditions
ConditionsYield
Stage #1: Propargylamine With sodium nitrate at 30 - 45℃; for 3.33h;
Stage #2: With diethyleneglycol diacetate; antimonypentachloride at 56℃; for 0.833333h; Temperature;
94%
107-19-7

propargyl alcohol

471-25-0

Propiolic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; copper(l) chloride In decane; acetonitrile at 20℃; for 5h;93%
With sodium hydroxide; sodium hypochlorite; TEMPOL In water; ethyl acetate at 15 - 20℃; pH=8.5; Aqueous phophate buffer;92%
With sodium hydroxide; sodium hypochlorite; disodium hydrogenphosphate; phosphoric acid; TEMPOL In water at 5 - 10℃; pH=7 - 10; Aqueous phophate buffer;83%
107-19-7

propargyl alcohol

A

4383-39-5

Propiolsaeure-(2-propinyl)ester

B

471-25-0

Propiolic acid

Conditions
ConditionsYield
With sodium hydroxide; sodium hypochlorite; sulfuric acid; TEMPOL In water at 5 - 10℃; pH=8 - 10;A 0.9%
B 83%
With sodium hydroxide; sodium hypochlorite; sulfuric acid; TEMPOL; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water at 5 - 10℃; pH=8 - 10;A 1.3%
B 46%
584-99-6

trans-2-bromobutenedioic acid

471-25-0

Propiolic acid

Conditions
ConditionsYield
With water at 140℃;
644-80-4

cis-2-bromobutenedioic acid

471-25-0

Propiolic acid

Conditions
ConditionsYield
With water at 140℃;
1066-26-8

sodium acetylide

15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

471-25-0

Propiolic acid

1066-26-8

sodium acetylide

471-25-0

Propiolic acid

Conditions
ConditionsYield
With carbon dioxide under 38000 - 45600 Torr;
142-45-0

Acetylenedicarboxylic acid

471-25-0

Propiolic acid

4301-14-8

acetylenemagnesium bromide

471-25-0

Propiolic acid

Conditions
ConditionsYield
With carbon dioxide
With diethyl ether; carbon dioxide
124-38-9

carbon dioxide

1066-26-8

sodium acetylide

471-25-0

Propiolic acid

Propiolic acid Consensus Reports

Reported in EPA TSCA Inventory.

Propiolic acid Specification

The Propiolic acid with CAS registry number of 471-25-0 is also known as 2-Propynoic acid. The IUPAC name is Prop-2-ynoic acid. It belongs to product categories of Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Acetylenes; Acetylenic Carboxylic Acids & Their Derivatives; Diyne Compounds (LB Films); Functional Materials; LB Films. Its EINECS registry number is 207-437-8. In addition, the formula is C3H2O2 and the molecular weight is 70.05. This chemical is a colorless liquid and slightly soluble in water. What's more, this chemical should be sealed in ventilated and dry place away from oxidants at the temperature of 2-8 °C.

Physical properties about Propiolic acid are: (1)ACD/LogP: 0.296; (2)ACD/LogD (pH 5.5): -3.01; (3)ACD/LogD (pH 7.4): -3.45; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.456; (11)Molar Refractivity: 15.34 cm3; (12)Molar Volume: 56.446 cm3; (13)Polarizability: 6.081 10-24cm3; (14)Surface Tension: 52.9939994812012 dyne/cm; (15)Density: 1.241 g/cm3; (16)Flash Point: 58.889 °C; (17)Enthalpy of Vaporization: 41.587 kJ/mol; (18)Boiling Point: 139.725 °C at 760 mmHg; (19)Vapour Pressure: 3.65499997138977 mmHg at 25°C

Preparation of Propiolic acid: it is prepared by reaction of acetylene sodium with carbon dioxide. The reaction occurs at the temperature below 90 °C and the pressure 3.55-7.09 MPa.

Propiolic acid is prepared by reaction of acetylene sodium with carbon dioxide.

Uses of Propiolic acid: it is used for organic synthesis. For example, it is used to produce 3c-phenylselanyl-acrylic acid by reaction with benzeneselenol. The reaction occurs with reagent NaOMe and solvent ethanol at the temperature of 60 °C for 2 hours. The yield is about 80.3%.

Propiolic acid is used to produce 3c-phenylselanyl-acrylic acid by reaction with benzeneselenol.

When you are using this chemical, please be cautious about it. As a chemical, it is toxic by inhalation, in contact with skin and if swallowed. Besides, it may cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. After using it, keep container tightly closed and in a well-ventilated place. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C#CC(=O)O
2. InChI: InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)
3. InChIKey: UORVCLMRJXCDCP-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 skin 100mg/kg (100mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
mouse LD50 intraperitoneal 25mg/kg (25mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
mouse LD50 oral 100mg/kg (100mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
rat LD50 intraperitoneal 25mg/kg (25mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.
rat LD50 oral 100mg/kg (100mg/kg)   "Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2C, Pg. 4953, 1982.

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