| Identification | More | [Name]
3-Butynyl 4-methylbenzenesulfonate | [CAS]
23418-85-1 | [Synonyms]
3-(1-BUTYNYL)-4-TOLUENESULPHONATE
3-BUTYNYL 4-TOLUENESULFONATE
3-BUTYNYL P-TOLUENESULFONATE
3-BUTYNYL P-TOLUENESULPHONATE
3-BUTYNYL TOSYLATE
BUT-3-YNYL 4-METHYLBENZENESULFONATE
P-TOLUENESULFONIC ACID 3-BUTYNYL ESTER
TIMTEC-BB SBB008912
3-(1-Butynyl)-4-toluenesulphonate 98%
3-BUTYNYL P-TOLUENESULPHONATE 96%
3-Butynyl 4-methylbenzenesulfonate | [EINECS(EC#)]
627-850-0 | [Molecular Formula]
C11H12O3S | [MDL Number]
MFCD00041687 | [Molecular Weight]
224.28 | [MOL File]
23418-85-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Clear slightly yellow liquid | [Melting point ]
42-45° | [Boiling point ]
128°C 0,01mm | [density ]
1.27 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.519(lit.)
| [Fp ]
>65°C | [storage temp. ]
Refrigerator (+4°C) | [solubility ]
Dichloromethane, Methanol | [form ]
Liquid | [color ]
Clear slightly yellow | [Specific Gravity]
1.270 | [BRN ]
3304257 | [InChI]
1S/C11H12O3S/c1-3-4-9-14-15(12,13)11-7-5-10(2)6-8-11/h1,5-8H,4,9H2,2H3 | [InChIKey]
STOASOOVVADOKH-UHFFFAOYSA-N | [SMILES]
Cc1ccc(cc1)S(=O)(=O)OCCC#C | [CAS DataBase Reference]
23418-85-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [HS Code ]
29041000 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear slightly yellow liquid | [Uses]
An organic sulfur compound, 3-Butynyl p-toluenesulfonate can be used for controlling harmful arthropod.
| [Synthesis]
A hexane solution of n-butyllithium (n-BuLi, 2.80 mL, 2.60 M, 7.27 mmol) was slowly added dropwise to a tetrahydrofuran (THF, 7.5 mL) solution of 3-butyn-1-ol (0.50 mL, 6.61 mmol) at -78 °C. The reaction mixture was kept at -78 °C for 5 min before warming up to 0 °C and continued stirring for 30 min. Subsequently, a solution of p-Toluenesulfonyl chloride (p-TsCl, 1.51 g, 7.93 mmol) in THF (8 mL) was added and the reaction continued to be stirred at 0 °C for 30 min. Upon completion of the reaction, the reaction was quenched by the addition of water (2 mL) and the mixture was extracted with ether (Et2O, 3 × 10 mL). The organic phases were combined, dried with anhydrous sodium sulfate (Na2SO4), and concentrated under reduced pressure to remove the solvent to afford 3-butynyl p-toluenesulfonate (1.41 g, 95% yield) as a light yellow oil. The product was confirmed by nuclear magnetic resonance hydrogen spectroscopy (1H NMR, 400 MHz, CDCl3): δ 7.78 (d, J = 8.0 Hz, 2H), 7.33 (d, J = 8.0 Hz, 2H), 4.08 (t, J = 7.1 Hz, 2H), 2.53 (dt, J = 7.1, 2.6 Hz, 2H), 2.43 (s, 3H), 1.95 ( t, J = 2.6 Hz, 1H); nuclear magnetic resonance carbon spectrum (13C NMR, 100 MHz, CDCl3): δ 145.0, 132.7, 129.9, 127.9, 78.3, 70.7, 67.4, 21.6, 19.4; infrared spectra (IR, pure): 3290, 2962, 2919, 1598, 1359, 1190, 1176, 980, 904, 815 cm-1; mass spectra (ESI): m/z 247.0399 [C11H12O3S (M+23) theoretical value 247.0400], 471 (base), 247, 225. | [IC 50]
Cleavable Linker | [References]
[1] Nucleosides and Nucleotides, 1994, vol. 13, # 9, p. 2021 - 2034
[2] Synlett, 2001, # 12, p. 1971 - 1973
[3] Tetrahedron Letters, 2011, vol. 52, # 43, p. 5589 - 5592
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 15, p. 3080 - 3091
[5] Chemical Communications, 2010, vol. 46, # 30, p. 5476 - 5478 |
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