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2,4,6-trimethylbenzenesulfonyl chloride

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Identification
Molecular formula
C9H11ClO2S
CAS number
1393-84-4
IUPAC name
2,4,6-trimethylbenzenesulfonyl chloride
State
State

At room temperature, this compound is typically a solid. It is used frequently in chemical synthesis and research laboratories where precise handling of the solid state is required due to reactive functional groups.

Melting point (Celsius)
48.00
Melting point (Kelvin)
321.15
Boiling point (Celsius)
316.00
Boiling point (Kelvin)
589.15
General information
Molecular weight
202.68g/mol
Molar mass
202.6780g/mol
Density
1.1460g/cm3
Appearence

2,4,6-Trimethylbenzenesulfonyl chloride is a white to off-white crystalline solid. It can also be in the form of a powder and has a characteristic chemical odor. This compound is usually handled in a crystalline form for synthetic purposes, and due to its reactive nature, it is usually stored under an inert atmosphere or moisture-controlled environments to prevent degradation.

Comment on solubility

Solubility of 2,4,6-trimethylbenzenesulfonyl chloride

2,4,6-trimethylbenzenesulfonyl chloride, a sulfonyl chloride compound, exhibits some intriguing solubility characteristics. Here are the key points regarding its solubility:

  • Solvent Preferences: This compound demonstrates good solubility in organic solvents such as acetone, ether, and chloroform. However, it is notably insoluble in water.
  • Polarity Considerations: The solubility behavior can be attributed to its molecular structure, where the hydrophobic aromatic ring hinders interaction with polar solvents.
  • Reactivity: Being a sulfonyl chloride, it can react with water to form hydrochloric acid and sulfonic acids, which emphasizes its limited solubility in aqueous solutions.

In summary, the solubility of 2,4,6-trimethylbenzenesulfonyl chloride is highly dependent on the solvent system employed, favoring polar organic solvents while avoiding interaction with water. Thus, it stands as a prime example of how functional groups and molecular structure influence solubility properties.

Interesting facts

Interesting Facts About 2,4,6-Trimethylbenzenesulfonyl Chloride

2,4,6-Trimethylbenzenesulfonyl chloride is a fascinating compound in the realm of organic chemistry, particularly known for its role as a sulfonylating agent. Here are some engaging aspects to consider:

  • Reactivity: As a sulfonyl chloride, it is highly reactive, making it an important intermediate in the synthesis of sulfonamides and sulfonates. This reactivity allows it to participate in various nucleophilic substitution reactions.
  • Functional Group Importance: The presence of the sulfonyl group (–SO2–) enhances the electrophilic character of the molecule, which can be strategically exploited in synthetic chemistry.
  • Application in Synthesis: 2,4,6-Trimethylbenzenesulfonyl chloride is utilized in the preparation of benzenesulfonamides, which have significant applications in pharmaceuticals and agrochemicals.
  • Steric Hindrance: The three methyl groups on the benzene ring contribute to steric hindrance, which can influence the compound's reactivity profile and selectivity in chemical reactions.

In the words of renowned chemist Frances Arnold, “The best way to predict the future is to invent it.” This compound is a prime example of how the manipulation of molecular structures can lead to innovative reactions and new materials.

Furthermore, its ability to act as a protecting group for amino acids in peptide synthesis showcases its versatility, marking it as an invaluable tool in the chemist's arsenal.

Overall, 2,4,6-trimethylbenzenesulfonyl chloride is not just a compound; it embodies the complex interplay of structure and reactivity that is central to the science of chemistry.

Synonyms
2-Mesitylenesulfonyl chloride
773-64-8
Mesitylenesulfonyl chloride
Benzenesulfonyl chloride, 2,4,6-trimethyl-
EINECS 212-257-8
NSC 403295
BRN 1107601
DTXSID90228019
3-11-00-00346 (Beilstein Handbook Reference)
DTXCID60150510
2-Mesitylenesulfonyl chloride (8CI)
inchi=1/c9h11clo2s/c1-6-4-7(2)9(8(3)5-6)13(10,11)12/h4-5h,1-3h
pvjzbzscgjawng-uhfffaoysa-n
2,4,6-Trimethylbenzenesulfonyl chloride
2,4,6-trimethylbenzene-1-sulfonyl chloride
MESITYLSULFONYL CHLORIDE
2-Mesitylenesulfonylchloride
MFCD00007434
Mesitylenesulphonyl chloride
2,4,6-trimethylphenylsulfonyl chloride
NSC-403295
Mesitylene-2-sulphonyl chloride
mesitylsulfonylchloride
2,4,6-Trimethyl-benzenesulfonyl chloride
mesitylenesulfonylchloride
2-mesitylsulfonyl chloride
mesitylene sulfonyl chloride
SCHEMBL7608
2-mesitylene sulfonyl chloride
2-mesitylene sulphonyl chloride
93TFV87MP5
WLN: WSGR B1 D1 F1
STR02217
2-Mesitylenesulfonyl chloride, 99%
NSC403295
STL199175
2,6-Trimethylbenzenesulfonyl chloride
2,4,6-trimethylbenzenesulfonylchloride
AKOS000431085
2,4,6-Trimethylbenzensulfonyl chloride
CS-W007703
SB21086
2,6-(Trimethylbenzene)sulfonyl chloride
Benzenesulfonyl chloride,4,6-trimethyl-
2,4,6trimethyl benzene sulphonyl chloride
2,4,6 trimethyl benzene sulphonyl chloride
DB-000155
A9792
M0071
NS00037912
2,4,6-trimethylbenzenesulphonic acid chloride
EN300-01722
Q21099516
F0808-2028