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tert-Butyl isothiocyanate

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Identification
Molecular formula
C5H9NS
CAS number
19721-41-0
IUPAC name
2-isothiocyanato-2-methyl-propane
State
State

This compound is a liquid at room temperature.

Melting point (Celsius)
-56.00
Melting point (Kelvin)
217.10
Boiling point (Celsius)
136.50
Boiling point (Kelvin)
409.70
General information
Molecular weight
115.20g/mol
Molar mass
129.2180g/mol
Density
0.8870g/cm3
Appearence

Tert-Butyl isothiocyanate is a colorless to pale yellow liquid. It has a pungent odor characteristic of isothiocyanates.

Comment on solubility

Solubility of 2-isothiocyanato-2-methyl-propane

When it comes to the solubility of 2-isothiocyanato-2-methyl-propane (also known as isothiocyanato isobutene), several key factors need to be considered:

  • Polarity: This compound features a polar functional group due to the isothiocyanate (–N=C=S) moiety, which often promotes solubility in polar solvents.
  • Solvent Compatibility: 2-isothiocyanato-2-methyl-propane demonstrates reasonable solubility in polar aprotic solvents such as dimethyl sulfoxide (DMSO) and acetonitrile, while showing limited solubility in nonpolar solvents.
  • Temperature Effects: As with many organic compounds, higher temperatures generally increase solubility, allowing for better interactions between solute and solvent.
  • Hydrogen Bonding: The possibility for hydrogen bonding due to the presence of nitrogen can enhance solubility in suitable solvents.
  • Practical Applications: The solubility characteristics of this compound make it useful in various chemical syntheses and reactions, particularly where polar media are advantageous.

In conclusion, the solubility of 2-isothiocyanato-2-methyl-propane is notably influenced by its molecular structure and the solvent environment, making it a fascinating compound for both theoretical and practical considerations in chemistry.

Interesting facts

Interesting Facts about 2-Isothiocyanato-2-methylpropane

2-Isothiocyanato-2-methylpropane, also known as an isothiocyanate compound, belongs to a fascinating class of chemicals that are rich in biological activity. Here are some intriguing aspects of this compound:

  • Unique Functional Group: The presence of the isothiocyanate functional group (–N=C=S) is noteworthy as it imparts unique reactivity and properties, often leading to applications in various fields such as agriculture and pharmaceuticals.
  • Biological Significance: Isothiocyanates are known for their role in plant defense mechanisms and are abundant in cruciferous vegetables. They exhibit anti-cancer properties, making compounds like 2-isothiocyanato-2-methylpropane of great interest in cancer research.
  • Chemical Synthesis: This compound can be synthesized through the reaction of a corresponding amine with carbon disulfide, followed by the introduction of a haloor using thiophosgene. This method highlights its accessibility for experimental chemistry.
  • Reactants and Products: Isothiocyanates can undergo a variety of reactions including hydrolysis, yielding thioureas upon reaction with nucleophiles, showcasing their versatility in organic synthesis.
  • Flavor and Aroma: Compounds in the isothiocyanate family often contribute to the pungent aroma associated with mustard and radishes, making them interesting compounds from a sensory perspective.

In summary, 2-isothiocyanato-2-methylpropane is not just a chemical entity but a compound of biological significance and practical applications, making it a subject of ongoing research and interest in the field of chemistry.

Synonyms
tert-Butyl isothiocyanate
590-42-1
Propane, 2-isothiocyanato-2-methyl-
EINECS 209-682-6
209-682-6
2-Isothiocyanato-2-methylpropane
t-Butyl isothiocyanate
tert.-Butyl Isothiocyanate
2-isothiocyanato-2-methyl-propane
MFCD00004816
1,1-Dimethylethyl isothiocyanate; tert-Butyl isothiocyanate
tert-butylisothiocyanate
tert butyl isothiocyanate
tert-butyliso thiocyanate
butyl isothiocyanate, tert-
T-BUTYLISOTHIOCYANATE
tertiary butyl isothiocyanate
SCHEMBL330601
CHEMBL1908216
DTXSID9060441
tert-Butyl isothiocyanate, 99%
2-Isothiocyanato-2-methylpropane #
Isothiocyanic acid, tert-butyl ester
BBL027481
STL371937
AKOS000101196
AS-16156
BP-12928
DB-053309
NS00034069
EN300-49543
D95911
A832130
InChI=1/C5H9NS/c1-5(2,3)6-4-7/h1-3H
F8889-8274