ethynylbenzene

• ChemBase ID: 92003
• Molecular Formular: C8H6
• Molecular Mass: 102.13324
• Monoisotopic Mass: 102.04695019
• SMILES: C#Cc1ccccc1
• Canonical SMILES: C#Cc1ccccc1
• InChI: InChI=1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H
• InChIKey: UEXCJVNBTNXOEH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethynylbenzene
• IUPAC Traditional name: phenylacetylene
• Synonyms: Ethynylbenzene; Phenylethyne; Phenylacetylene; Phenylacetylene; ETHYNYLBENZENE; 乙炔苯; 苯乙炔

Database IDs

• CAS Number: 536-74-3; 126716-66-3
• EC Number: 208-645-1
• MDL Number: MFCD00008570
• Beilstein Number: 605461
• Merck Index: 143861
• PubChem SID: 24847341; 24887238; 162078701
• PubChem CID: 10821
• CHEMBL: 234833
• Chemspider ID: 10364
• Wikipedia Title: Phenylacetylene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.1240811
• LogD (pH = 7.4): 2.1240811
• Log P: 2.1240811
• Molar Refractivity: 31.2303 cm^3
• Polarizability: 12.969005 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: –45 °C; -45°C; 67 - 69°C
• Boiling Point: 142°C; 142-144 °C; 142-144 °C(lit.); 142-144°C; 142-144°C
• Flash Point: 27 °C; 27°C; 27°C(81°F); 31.1°C; 80.6 °F; 81 °F
• Density: 0.93; 0.93 g/cm3; 0.93 g/mL at 25 °C(lit.); 0.930; 0.930 g/ml
• Refractive Index: 1.5480; n20/D 1.549; n20/D 1.549(lit.)
• Vapor Pressure: 17.6 mm Hg @ 37.7°C; 17.6 mmHg ( 37.7 °C)
• Hydrophobicity(logP): 2.412
• pKa: 28.8

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Flammable/Harmful/Lachrymatory/Moisture Sensitive/Light Sensitive/Keep Cold; Light Sensitive
• RTECS: DA0780000
• European Hazard Symbols: Flammable (F); X; Irritant (Xi); Harmful (Xn)
• UN Number: 1993; 3295; UN3295
• German water hazard class: 1; 3
• Hazard Class: 3
• Packing Group: 3; III
• Australian Hazchem: 3Y
• Risk Statements: 10-36/37-40-65; 10-36/37-65; R:10; R:10-36/37
• Safety Statements: 23-26-36-62; 26-36/37/39-45; 26-36/37-62; S:9-16-26-29; S:9-16-29
• EU Classification: F1
• EU Hazard Identification Number: 3B
• Emergency Response Guidebook(ERG) Number: 128
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H304-H315-H319-H351; H304-H226-H319-H335
• GHS Precautionary statements: P261-P280F-P305+P351+P338-P301+P330+P331-P315; P281-P301 + P310-P305 + P351 + P338-P331
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3295 3/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 95%; 95+%; 97%; 98%; 98+%
• Grade: purum
• Impurities: <1% 1,4-dioxane
• Linear Formula: C6H5CCH

DETAILS

MP Biomedicals - 05212155

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156149

Purity: 98%
1 ml = approx. 0.93 g

Sigma Aldrich - 117706

Application
Terminal acetylene used in the conversion of nitrones to alkynyl hydroxyl amines in the presence of trimethylaluminum.1.
Packaging
25, 100 mL in glass bottle

REFERENCES

• For preparation of the cuprate and references for coupling with aryl halides to give diarylacetylenes, see: Org. Synth. Coll., 6, 916 (1988).
• Conversion to the 1-bromoalkyne has been described: Org. Synth. Coll., 5, 921 (1973). For an improved phase-transfer method, using NaBr/NaOCl, see: J. Org. Chem., 57, 4555 (1992).
• Dimetallation can be accomplished with a 2:1 molar mixture of n-BuLi and KO-t-Bu in THF, the second metallation occurring specifically at the ortho-position. Thus, the bis(TMS)-derivative can be prepared in excellent yield: J. Org. Chem., 55, 1311 (1990).
• For cyanation with CuCN in the presence of TMS chloride and NaI, see: Tetrahedron Lett., 34, 591 (1993).
• Glaser oxidative coupling by Cu(OAc)₂ in pyridine gives diphenylbuta-1,3-diyne: Org. Synth. Coll., 5, 499 (1973).
• For conversion to the Grignard with ethylmagnesium bromide, and subsequent Cu-catalyzed coupling with allyl bromide, see: Org. Synth. Coll., 6, 925 (1988).