prop-2-yn-1-ol

• ChemBase ID: 123300
• Molecular Formular: C3H4O
• Molecular Mass: 56.06326
• Monoisotopic Mass: 56.02621475
• SMILES: C(#C)CO
• Canonical SMILES: OCC#C
• InChI: InChI=1S/C3H4O/c1-2-3-4/h1,4H,3H2
• InChIKey: TVDSBUOJIPERQY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: prop-2-yn-1-ol
• IUPAC Traditional name: propargyl alcohol
• Synonyms: prop-2-yn-1-ol; 2-Propyn-1-ol; Propargyl alcohol; Propargyl alcohol; 2-丙炔-1-醇; 炔丙醇

Database IDs

• CAS Number: 107-19-7
• EC Number: 203-471-2
• MDL Number: MFCD00002912
• Beilstein Number: 506003
• Merck Index: 147809
• PubChem SID: 162217653; 24898591
• PubChem CID: 7859
• CHEBI ID: 28905
• Chemspider ID: 21106466
• KEGG ID: C05986
• Wikipedia Title: Propargyl_alcohol

CALCULATED PROPERTIES

• Acid pKa: 13.649209
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): -0.29049402
• LogD (pH = 7.4): -0.29049426
• Log P: -0.29049402
• Molar Refractivity: 15.8415 cm^3
• Polarizability: 5.783386 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -51 - °C; -53 °C(lit.); -53°C
• Boiling Point: 114 - 115°C; 114-115 °C(lit.); 114-115°C
• Flash Point: 33 °C; 33°C(91°F); 91.4 °F
• Density: 0.949; 0.963 g/mL at 25 °C(lit.); 0.9715 g/cm3
• Refractive Index: 1.4320; n20/D 1.432(lit.)
• Vapor Pressure: 11.6 mmHg ( 20 °C)
• Vapor Density: 1.93 (vs air)

Safety Information

• RTECS: UK5075000
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2929; UN2929
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 1; II
• Risk Statements: 10-23/24/25-34-51/53
• Safety Statements: 1/2-26-28-36-45-61; 26-28-36-45-61
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS06; GHS09
• GHS Signal Word: Danger
• NFPA704:
  

  3

  4

  3
• GHS Hazard statements: H226-H301-H311-H314-H331-H411; H301-H311-H331-H314-H226-H411
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A; P261-P273-P280-P301 + P310-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 2929 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: 99%
• Linear Formula: HC≡CCH2OH

DETAILS

Sigma Aldrich - P50803

Packaging
1 L in glass bottle
100, 500 mL in glass bottle

REFERENCES

• Useful 3-carbon fragment in acetylene coupling reactions. The hydroxyl group can be protected as its THP ether; see, e.g.: Org. Synth., 76, 178 (1998), or 1-ethoxyethyl ether (see Ethyl vinyl ether, A15691): Org. Synth., 76, 199 (1998). C-Alkylation can also be accomplished without O-protection by using 2 equivalents of base (LiNH₂); see, e.g., J. Chem. Soc., Perkin 1, 85 (1988); Org. Synth. Coll., 8, 415 (1993).
• O-methylation, followed by treatment with t-BuOK affords methoxyallene, a valuable reactive intermediate. It undergoes Pd-catalyzed O-coupling with alcohols to give the corresponding 1-methoxyallyl ethers: Synlett, 192 (1998). Lithiation leads to 1-lithio-1-methoxyallene: J. Org. Chem., 50, 5308 (1985); 58, 6377 (1993). For a brief feature on methoxyallene with further examples, see: Synlett, 1697 (2000).