| Identification | More | [Name]
3-Ethynyltoluene | [CAS]
766-82-5 | [Synonyms]
1-ETHYNYL-3-METHYLBENZENE
3-ETHYNYLTOLUENE
3'-METHYLPHENYL ACETYLENE
M-ETHYNYLTOLUENE
M-TOLYLACETYLENE
Benzene,1-ethynyl-3-methyl-
3-Ethynyltoluene~3-Methylphenylacetylene
m-TOLYLACETYLENE (3-Ethynyltoluene)
Benzene, 1-ethynyl-3-methyl-(9CI)
m-Tolylacetylene,97% | [EINECS(EC#)]
628-378-8 | [Molecular Formula]
C9H8 | [MDL Number]
MFCD01318174 | [Molecular Weight]
116.16 | [MOL File]
766-82-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear light yellow to brown liquid | [Boiling point ]
170-175 °C(lit.)
| [density ]
0.900 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5440(lit.)
| [Fp ]
50°C | [storage temp. ]
Flammables area | [form ]
Liquid | [color ]
Clear light yellow to brown | [Specific Gravity]
0.9073 | [BRN ]
2038007 | [InChI]
1S/C9H8/c1-3-9-6-4-5-8(2)7-9/h1,4-7H,2H3 | [InChIKey]
RENYIDZOAFFNHC-UHFFFAOYSA-N | [SMILES]
Cc1cccc(c1)C#C | [CAS DataBase Reference]
766-82-5(CAS DataBase Reference) | [NIST Chemistry Reference]
3-Methylphenylacetylene(766-82-5) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R10:Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin .
R65:Harmful: May cause lung damage if swallowed. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 1993 3/PG 3
| [WGK Germany ]
3
| [HazardClass ]
3 | [PackingGroup ]
III | [HS Code ]
29029090 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Asp. Tox. 1
Eye Irrit. 2
Flam. Liq. 3
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear light yellow to brown liquid | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 43, p. 358, 1978 DOI: 10.1021/jo00396a046
Tetrahedron Letters, 13, p. 5209, 1972 | [Synthesis]
The general procedure for the synthesis of 3-methylphenylacetylene from 3-tolyl(trimethylsilyl)acetylene was as follows: 3-[(trimethylsilyl)ethynyl]toluene (1 mmol), an inorganic base (potassium tert-butanol, sodium tert-butanol, potassium hydroxide, sodium hydroxide, or potassium trimethylsilylated, sodium trimethylsilylated, 0.05 mmol) were added in turn to a 10 mL sealed tube, as well as 2 mL of DMA or DMSO as solvent. The mixture was heated and stirred in an oil bath at 60 °C for 7 h. The reaction progress was monitored by TLC. Upon completion of the reaction, equal amounts of homotrimethylbenzene or n-undecane were added as internal standards for quantitative analysis of the crude product. The exact yields of the products were determined by GC and GC-MS. The yields of the products were 74%, 73%, 74%, 80%, 93%, and 90% when DMSO was used as the solvent and potassium tert-butanol, sodium tert-butanol, potassium hydroxide, sodium hydroxide, or potassium trimethylmethylsilylated, sodium trimethylmethylsilylated were used as the catalysts, respectively. And when DMA was used as the solvent, the yields of the products were 61%, 60%, 63%, 73%, 82%, and 83%, respectively, using the same catalysts. | [References]
[1] Journal of Chemical Research, 2007, # 12, p. 728 - 732
[2] Patent: CN107459438, 2017, A. Location in patent: Paragraph 0054; 0055
[3] Organic Letters, 2014, vol. 16, # 3, p. 948 - 951
[4] Tetrahedron Letters, 1972, vol. 13, # 51, p. 5209 - 5212
[5] Organic letters, 2001, vol. 3, # 2, p. 153 - 155 |
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