p-Toluenesulfonyl chloride p-Toluenesulfonyl chloride
Structural formula
| Business number | 02E7 |
|---|---|
| Molecular formula | C7H7ClO2S |
| Molecular weight | 190.70 |
| label |
Toluene sulfone chloride, 4-Toluenesulfonyl chloride, 4-methylbenzenesulfonyl chloride, Tosyl chloride, 4-Toluene sulfonyl chloride, TsCl, Plasticizers; Phenol determination |
Numbering system
CAS number:98-59-9
MDL number:MFCD00007450
EINECS number:202-684-8
RTECS number:None
BRN number:607898
PubChem number:24889256
Physical property data
1. Characteristics: White rhombus-shaped crystals with pungent odor. [11]
2. Melting point (℃): 67~71[12]
3. Boiling point (℃) : 145~146 (2.0kPa) [13]
4. Relative density (water = 1): 1.33[14]
5. Saturated vapor pressure (kPa): 0.13 (88℃)[15]
6. Octanol/water partition coefficient: 3.49[16]
7. Flash point (℃): 110[17]
8. Solubility: insoluble in water, easily soluble in ethanol , ether, benzene. [18]
Toxicological data
1. Acute toxicity No data available
2. Irritation No data available
Ecological data
1. This substance is slightly harmful to water.
2. Ecotoxicity No information available
3. Biodegradability[19] MITI-I test, initial concentration 100ppm, sludge concentration 30ppm, 93% degradation after 3 weeks.
4. Non-biodegradability No information available
Molecular structure data
1. Molar refractive index: 45.02
2. Molar volume (cm3/mol): 142.3
3. Isotonic specific volume (90.2K ): 360.4
4. Surface tension (dyne/cm): 41.0
5. Polarizability: 17.84
Compute chemical data
1. Reference value for hydrophobic parameter calculation (XlogP): None
2. Number of hydrogen bond donors: 0
3. Number of hydrogen bond acceptors: 2
4. Number of rotatable chemical bonds: 1
5. Number of tautomers: none
6. Topological molecule polar surface area 42.5
7. Number of heavy atoms: 11
8. Surface charge: 0
9. Complexity: 209
10. Number of isotope atoms: 0
11. Determine the number of atomic stereocenters: 0
12. Uncertain number of atomic stereocenters: 0
13. Determine the number of chemical bond stereocenters: 0
14. Number of uncertain chemical bond stereocenters: 0
15. Number of covalent bond units: 1
Properties and stability
1. Stability[20] Stable
2. Incompatible substances[21] Strong oxidants, strong alkali
3. Avoid contactConditions[22] Moist air, heat
4. Polymerization hazard[23] No polymerization
5. Decomposition products[24] Sulfur oxide, hydrogen chloride
Storage method
Storage Precautions[25] Store in a cool and dry place. Well-ventilated warehouse. Keep away from fire and heat sources. The packaging must be sealed and protected from moisture. They should be stored separately from oxidants, alkalis, and food chemicals, and avoid mixed storage. Equipped with the appropriate variety and quantity of fire equipment. Suitable materials should be available in the storage area to contain spills.
Synthesis method
1. During the chlorosulfonation of toluene to produce o-toluenesulfonyl chloride, p-toluenesulfonyl chloride is also produced. From the filter cake after separation of o-toluenesulfonyl chloride, p-toluenesulfonyl chloride is purified.
2. Wash the crushed industrial p-toluenesulfonyl chloride with hot water at 40-50°C until there is no ortho-oil, and then recrystallize it with acetone.
Purpose
1.Used in organic synthesis and dye preparation. Used as plasticizer and analytical reagent for the determination of primary amines, secondary amines and phenols.
2. The most important use of TsCl in organic chemistry is as a sulfonylation reagent for alcohol compounds. The results of the optimization of reaction conditions show that 1 equivalent of alcohol can be converted into a sulfonylated product (Formula 1) with the highest yield in the presence of 2 equivalents of TsCl and 1.5 equivalents of pyridine. The 1,2-diol compound undergoes an epoxidation reaction under the action of TsCl and alkali (formula 2)[2].
Except O-, TsCl can also act on amine compounds to cause sulfonylation reaction on N-. And in the presence of different bases, TsCl can selectively realize the sulfonylation reaction on O– and N– (Formula 3) [3]. In pyridine solvent, the sulfonylation reaction on N– can occur preferentially; in triethylamine solvent, the sulfonylation reaction on O– can occur preferentially.
TsCl can also be used to convert alkenes The reaction of converting propyl alcohol into allyl chloride compounds does not occur the rearrangement reaction of the allyl substrate and the functional group conversion reaction of other active groups (formula 4)[4].
Alkenes or alkynes and TsCl in Under the catalysis of TsOH, β-hydroxysulfonate or β-carbonylsulfonate (formula 5[5], formula 6[6]).
Amino acids under the action of TsCl and pyridine Decarboxylation reaction can occur (Formula 7)[7]. The reaction first generates a sulfonylation intermediate. Under the strong electron-withdrawing effect of the sulfonyl group, intramolecular electron transfer occurs, and a molecule of hydrogen ion and sulfonate is removed to obtain the imine product.
Oxime compounds in TsCl and pyridine The sulfonylated product generated under the action can continue to undergo Beckmann rearrangement reaction to obtain a lactam compound (formula 8)[8].
Primary amide compounds in TsCl and Nitrile (Formula 9) [9] can be obtained under the action of pyridine, while a similar formamide substrate can generate isonitrile (Formula 10) [10] under the action of TsCl and pyridine. sup>.
3. Used in organic synthesis, Manufacture of dyes, saccharin, etc. [26]
