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Tosyl chloride

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Identification
Molecular formula
C7H7ClO2S
CAS number
98-59-9
IUPAC name
2-methylbenzenesulfonyl chloride
State
State

At room temperature, tosyl chloride is typically a solid.

Melting point (Celsius)
66.00
Melting point (Kelvin)
339.15
Boiling point (Celsius)
140.00
Boiling point (Kelvin)
413.15
General information
Molecular weight
190.65g/mol
Molar mass
190.6540g/mol
Density
1.2477g/cm3
Appearence

Tosyl chloride is a white to yellow crystalline powder. It is often encountered in the form of crystals or as a crystalline powder, and can exhibit a slight yellow tint when impure.

Comment on solubility

Solubility of 2-methylbenzenesulfonyl chloride

2-methylbenzenesulfonyl chloride, with its unique structure, exhibits particular solubility characteristics that are essential to note:

  • Solubility in Organic Solvents: This compound is highly soluble in many organic solvents, such as acetone, ethyl acetate, and dichloromethane. This property makes it useful in various organic synthesis reactions.
  • Water Solubility: 2-methylbenzenesulfonyl chloride is only sparingly soluble in water. The presence of the sulfonyl chloride group influences its ability to interact with polar solvents.
  • Temperature Dependence: As with many organic compounds, the solubility can be affected by temperature. Increased temperature typically leads to higher solubility in organic solvents.

Overall, while 2-methylbenzenesulfonyl chloride is not water-friendly, its solubility in organic solvents allows for its effective use in synthesis and other chemical applications. Understanding its solubility profile is crucial for successful experimental design and execution.

Interesting facts

Interesting Facts about 2-Methylbenzenesulfonyl Chloride

2-Methylbenzenesulfonyl chloride, often denoted as a reactive sulfonyl chloride, holds significant importance in organic chemistry, particularly in the realm of synthetic pathways. Below are some intriguing aspects of this compound:

  • Reactivity: This compound serves as an electrophilic reagent, facilitating a variety of chemical reactions. It can react with alcohols and amines to form sulfonamides, and it is pivotal in the synthesis of sulfonylureas, a class of compounds used in diabetes treatment.
  • Functional Group Transformation: 2-methylbenzenesulfonyl chloride acts as an efficient sulfonylating agent. It can transform functional groups—particularly alcohols—into sulfonates, which are more reactive and useful in further chemical transformations.
  • Synthesis Applications: In the laboratory, its sulfonyl chloride group is often utilized for the introduction of sulfonyl groups into various aromatic compounds, enhancing their reactivity and allowing the formation of complex molecular architectures.
  • Environmental Considerations: As with many sulfonyl chlorides, it is essential to manage waste derived from reactions involving 2-methylbenzenesulfonyl chloride responsibly, as it can produce hazardous byproducts. Proper safety measures are critical due to its potential reactivity with moisture and the release of hydrochloric acid.

In summary, 2-methylbenzenesulfonyl chloride is not only a versatile reagent in organic synthesis but also prompts a thoughtful approach to laboratory safety and environmental impact. As aptly stated in the field of organic chemistry, "The pathway to innovation is often paved with unique compounds that challenge the boundaries of synthesis."

Synonyms
o-Toluenesulfonyl chloride
133-59-5
2-Methylbenzenesulfonyl chloride
Benzenesulfonyl chloride, 2-methyl-
2-methylbenzene-1-sulfonyl chloride
Toluene-2-sulphonyl chloride
2-Toluenesulfonyl chloride
O-TOLYLSULFONYL CHLORIDE
o-Tosyl chloride
2-methyl-benzenesulfonyl chloride
toluene-2-sulfonyl chloride
2-Methylbenzenesulphonyl chloride
ortho-Toluenesulfochloride
ortho-Toluenesulfonchloride
ortho-Toluenesulfonyl chloride
UNII-341L82E3WG
2-methylphenylsulfonyl chloride
o-methylbenzenesulfonyl chloride
HSDB 5618
NSC 9354
NSC-9354
EINECS 205-113-0
O-Toluenesulfonyl chloride, tech grade
DTXSID7051682
341L82E3WG
O-TOLYLSULFONYL CHLORIDE [HSDB]
MFCD00024874
Benzenesulfonyl chloride, methyl-
2-methylbenzene-1-sulfonylchloride
tolylsulfonyl chloride
toluenesulfonylchloride
toluenesufonyl chloride
toluenesulphonylchloride
toluene sulfonylchloride
toluenesulfonic chloride
orthoToluenesulfochloride
o-toluenesulfonylchloride
Toluenesulphonyl chloride
orthoToluenesulfonchloride
Toluene sulfonyl chloride
toluene sulphonyl chloride
toluene-sulphonyl chloride
Toluene suiphonyl chloride
SCHEMBL4439
orthoToluenesulfonyl chloride
toluenesulfonic acid chloride
toluenesulphonic acid chloride
toluene sulfonic acid chloride
2methylbenzenesulfonyl chloride
DTXCID1030236
Benzenesulfonyl chloride, 2methyl
NSC9354
o-Toluenesulfonyl chloride, 97%
2-methylbenzene-sulphonyl chloride
o-Toluenesulfonyl chloride (8CI)
BBL013805
STK500501
AKOS005207130
FT164705
PS-10915
NS00024295
T0284
EN300-66997
A806639
2-Toluenesulfonyl chloride(contains ca.23% isomer)
Q27256316