prop-2-ynoic acid

• ChemBase ID: 87502
• Molecular Formular: C3H2O2
• Molecular Mass: 70.04678
• Monoisotopic Mass: 70.0054793
• SMILES: OC(=O)C#C
• Canonical SMILES: OC(=O)C#C
• InChI: InChI=1S/C3H2O2/c1-2-3(4)5/h1H,(H,4,5)
• InChIKey: UORVCLMRJXCDCP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-ynoic acid
• IUPAC Traditional name: propiolic acid
• Synonyms: Propiolic acid; Acetylenecarboxylic acid; Prop-2-ynoic acid; Propynoic acid; Propiolic acid; Acetylene carboxylic acid; Propargylic acid; 'acetylene mono-carboxylic acid; 2-Propynoic acid; PROPIOLIC ACID; 2-丙炔酸; 乙炔羧酸; 丙炔酸

Database IDs

• CAS Number: 471-25-0
• EC Number: 207-437-8
• MDL Number: MFCD00004360
• Beilstein Number: 878176
• Merck Index: 147824
• PubChem SID: 24898598; 162074542; 24887911
• PubChem CID: 10110
• CHEMBL: 1213530
• Wikipedia Title: Propiolic_acid

CALCULATED PROPERTIES

• Acid pKa: 1.9903686
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -3.0365708
• LogD (pH = 7.4): -3.341814
• Log P: 0.18196973
• Molar Refractivity: 15.784 cm^3
• Polarizability: 5.772807 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 16-18 °C(lit.); 16-18°C°C; 18°C; 9 °C
• Boiling Point: 102 °C/200 mmHg(lit.); 102°C°C/200mm; 102°C/200mm; 144 °C (decomp.)
• Flash Point: 136.4 °F; 58 °C; 58°C°C; 58°C(136°F)
• Density: 1.1325 g/cm^3; 1.135 g/mL at 20 °C; 1.136; 1.138; 1.138 g/mL at 25 °C(lit.)
• Refractive Index: 1.4310; 1.4330; n20/D 1.431; n20/D 1.431(lit.)

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Toxic/Corrosive/Flammable/Keep Cold
• RTECS: UD9300000
• European Hazard Symbols: Toxic (T); Highly toxic (T+)
• UN Number: 2810; 2920; UN2920
• German water hazard class: 3
• Hazard Class: 6.1; 8
• Packing Group: 2; II; III
• Australian Hazchem: 2X
• Risk Statements: 24/25-34; R:25
• Safety Statements: 20-23-26-27-36/37/39-45-60; 26-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T1
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 153
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H301-H310-H314; H301-H310-H314-H318-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P280-P301 + P310-P302 + P350-P305 + P351 + P338-P310; P280-P302 + P350-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2920 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (T); 95%; 98+%
• Grade: technical
• Impurities: ≤6.0% acetic acid
• Linear Formula: HC≡CCOOH

DETAILS

MP Biomedicals - 05217156

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156397

Yellow liquid.
When coenzyme A is derivatized with this product, it becomes an inactivator of acyl-CoA dehydrogenase.

Sigma Aldrich - P51400

Packaging
5, 25, 100 g in glass bottle
Application
Reagent employed in the synthesis of transition metal complexes,1 haloalkyl propiolates,2,3 and halopropenoates.4

REFERENCES

• Freund, K., et al., Biochem. , 24 : 5996 (1985).
• Alkylation of the dilithio-derivative leads to higher 2-alkynoic acids. Reaction with epoxides, partial reduction (Lindlar) of the triple bond and cyclization has been used in the synthesis of unsaturated lactones: Tetrahedron Lett., 2615 (1974); J. Org. Chem., 40, 1610 (1975).