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tert-Butyl mercaptan

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Identification
Molecular formula
C4H10S
CAS number
75-66-1
IUPAC name
2-methylpropane-2-thiol
State
State

At room temperature, tert-butyl mercaptan is a liquid.

Melting point (Celsius)
-0.50
Melting point (Kelvin)
272.70
Boiling point (Celsius)
64.00
Boiling point (Kelvin)
337.00
General information
Molecular weight
90.19g/mol
Molar mass
90.1860g/mol
Density
0.8360g/cm3
Appearence

Appearance: tert-Butyl mercaptan is a colorless liquid with a strong odor reminiscent of garlic or skunky smell. It is often used as an odorant for natural gas identification.

Comment on solubility

Solubility of 2-Methylpropane-2-thiol

2-Methylpropane-2-thiol, also known as tert-butyl mercaptan, displays interesting solubility characteristics primarily due to its structure and functional group. Here are some key points to consider:

  • Polar versus Nonpolar: The presence of the thiol (-SH) group indicates that this compound has some polar characteristics, which enables it to interact with polar solvents.
  • Solvent Preference: 2-Methylpropane-2-thiol is generally soluble in polar organic solvents such as alcohols and ethers. However, it exhibits limited solubility in water.
  • Hydrophobic Behavior: The hydrocarbon tail contributes to hydrophobic interactions, making the compound less favorable for dissolution in aqueous solutions.
  • Concentration Considerations: While the compound may not be highly soluble in water, it can form emulsions or be solubilized at higher concentrations in nonpolar solvents.

As a result, we can conclude that 2-methylpropane-2-thiol has a modest solubility profile, predominantly favoring nonpolar and polar organic solvents, while being sparingly soluble in water, showcasing the balance between its polar thiol group and nonpolar hydrocarbon backbone.

Interesting facts

Interesting Facts about 2-Methylpropane-2-thiol

2-Methylpropane-2-thiol, commonly known for its distinctive odor, is an important compound in the realm of organic chemistry. This compound belongs to the class of thiols, which are characterized by the presence of a sulfur-containing functional group. Here are some intriguing aspects of 2-methylpropane-2-thiol:

  • Distinctive Odor: One of the most notable features of 2-methylpropane-2-thiol is its strong, skunky smell, which is often compared to that of rotten cabbage or garlic. This pungent aroma makes it an excellent candidate for use as an odorant in the gas industry, helping to detect gas leaks.
  • Biological Role: Thiols, including 2-methylpropane-2-thiol, play a crucial role in biological processes. They are involved in the structure of certain proteins and enzymes, contributing to the stability and activity of these biomolecules.
  • Synthesis Pathways: The synthesis of 2-methylpropane-2-thiol can be achieved through various methods, including the reaction of alkenes with hydrogen sulfide in the presence of catalysts. Understanding these pathways is essential for researchers looking to create thiol compounds efficiently.
  • Industrial Applications: Beyond its use in gas detection, 2-methylpropane-2-thiol has applications in the production of pharmaceuticals and agricultural chemicals. Its unique properties make it valuable in organic synthesis and formulation.
  • Health Implications: While thiols are essential in many biochemical contexts, care must be taken when handling 2-methylpropane-2-thiol due to its high toxicity in concentrated forms. It is crucial for chemists and students to understand safety precautions when working with this compound.

In summary, 2-methylpropane-2-thiol not only serves practical applications in safety and industry but also offers fascinating insights into the complex world of organic compounds. As with many chemical entities, it embodies the dual nature of being both useful and hazardous, which demands a comprehensive understanding from both scientists and students alike.

Synonyms
tert-Butyl mercaptan
75-66-1
Tertiary Butyl Mercaptan
2-Methyl-2-propanethiol
2-Methylpropane-2-thiol
tert-Butylthiol
tert-Butanethiol
2-Propanethiol, 2-methyl-
T-BUTYL MERCAPTAN
tert-Butylmercaptan
t-Butylmercaptan
1,1-Dimethylethanethiol
2-Isobutanethiol
tertiary-Butyl mercaptan
tertbutanethiol
HSDB 1611
tert-butyl thiol
EINECS 200-890-2
UNII-489PW92WIV
BRN 0505947
tert-C4H9SH
DTXSID0026418
tert-Butyl hydrosulfide
2-Methyl-2-propylthiol
2-methyl-propane-2-thiol
BUTANETHIOL, TERT-
489PW92WIV
DTXCID906418
EC 200-890-2
TERT-BUTYL MERCAPTAN [MI]
4-01-00-01634 (Beilstein Handbook Reference)
3374-16-1
16528-55-5
TBM
t-BuSH
tbutylmercaptan
tertButylthiol
t-butanethiol
2Isobutanethiol
tButyl mercaptan
tertbutylmercaptan
terbutyl mercaptan
tBuSH
tert.-butylmercaptan
2Methyl2propanethiol
MFCD00004857
tert. butyl mercaptan
tert.-butyl mercaptan
tertiaryButyl mercaptan
HS-t-Bu
1,1Dimethylethanethiol
2-methyl-2propanethiol
2Propanethiol, 2methyl
2-methylpropan-2-thiol
CHEMBL3182458
2-Methyl-2-propanethiol, 99%
Tox21_200874
NSC229569
STL264247
AKOS000121277
AT13962
FM43308
NSC-229569
CAS-75-66-1
NCGC00248858-01
NCGC00258428-01
DB-000158
M0405
NS00002616
EN300-21408
Q973473
F0001-1902