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tert-Butyl iodide

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Identification
Molecular formula
C4H9I
CAS number
558-17-8
IUPAC name
2-iodo-2-methyl-propane
State
State

At room temperature, tert-Butyl iodide is a liquid. It is relatively volatile and has a moderate boiling point typical of alkyl iodides.

Melting point (Celsius)
-33.00
Melting point (Kelvin)
240.15
Boiling point (Celsius)
102.00
Boiling point (Kelvin)
375.15
General information
Molecular weight
184.03g/mol
Molar mass
184.0280g/mol
Density
1.6740g/cm3
Appearence

The compound is a colorless to pale yellow liquid that is sensitive to light. It is often stored in brown or amber bottles to protect it from photodegradation.

Comment on solubility

Solubility of 2-iodo-2-methyl-propane

2-iodo-2-methyl-propane, with the chemical formula C5H11I, exhibits distinct solubility characteristics that are noteworthy. Being a halogenated hydrocarbon, this compound has specific interactions with solvents that can be quite fascinating. Here are some key points regarding its solubility:

  • Polarity: 2-iodo-2-methyl-propane is a relatively non-polar molecule due to its hydrocarbon backbone.
  • Solvent Compatibility: It shows greater solubility in non-polar solvents, such as hexane and benzene, compared to polar solvents like water.
  • Temperature Influence: As with many organic compounds, solubility can improve with increasing temperature, as the increased kinetic energy can help disrupt intermolecular forces.
  • Functional Groups: The presence of the iodine atom can lead to some level of dipole interactions, but overall, it does not significantly enhance solubility in polar solvents.
  • Mixtures: When mixed with other halogenated solvents, like chloroform or dichloromethane, the solubility can vary depending on the specific interactions involved.

In summary, while 2-iodo-2-methyl-propane is primarily soluble in non-polar environments, its unique properties as a halogenated compound can lead to interesting solubility behaviors in various chemical contexts. As stated, "like dissolves like" is a guiding principle that perfectly captures its solubility profile.

Interesting facts

Interesting Facts about 2-iodo-2-methyl-propane

2-iodo-2-methyl-propane, also known as tert-butyl iodide, is an intriguing compound that captures the interest of chemists and students alike. Here are some fascinating insights about this compound:

  • Structure and Stability: 2-iodo-2-methyl-propane belongs to the class of alkyl halides, specifically tertiary alkyl halides. Its unique structure features a central carbon atom bonded to three methyl groups and one iodine atom, providing it with increased stability compared to its primary and secondary counterparts.
  • Nucleophilic Substitution Reactions: This compound is often used as a substrate in nucleophilic substitution reactions, making it a popular choice when exploring SN2 and SN1 mechanisms. The ease of iodide leaving allows for efficient reactions with various nucleophiles, such as water, alcohols, and amines.
  • Applications in Organic Synthesis: 2-iodo-2-methyl-propane is used as an important intermediate in the synthesis of a variety of chemical compounds. It plays a vital role in the preparation of pharmaceuticals, agrochemicals, and other functional materials.
  • Historical Significance: The reactivity of halides like 2-iodo-2-methyl-propane has historically contributed to the development of modern organic chemistry. Its study has enhanced the understanding of reaction mechanisms and functional group transformations.
  • Tert-Butyl Group Influences: The tert-butyl group itself is significant in various chemical contexts. It can influence the steric and electronic properties of molecules, affecting reaction pathways and product outcomes.

In summary, 2-iodo-2-methyl-propane showcases the intricate balance between structure and reactivity, providing endless opportunities for exploration in the realm of organic chemistry. As students and scientists dive into the depths of its properties and reactions, they continue to unravel the complexities of chemical interactions.

Synonyms
tert-Butyl iodide
2-Iodo-2-methylpropane
PROPANE, 2-IODO-2-METHYL-
Trimethyliodomethane
t-butyl iodide
EINECS 209-190-1
UNII-E5HY19G10P
BRN 0505950
E5HY19G10P
tert-C4H9I
2-methyl-2-iodopropane
1,1-dimethylethyl iodide
BUTYL IODIDE, TERT-
DTXSID3060328
4-01-00-00300 (Beilstein Handbook Reference)
DTXCID2041969
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inchi=1/c4h9i/c1-4(2,3)5/h1-3h
558-17-8
2-iodo-2-methyl-propane
MFCD00001068
SCHEMBL7251
AKOS009031397
AS-87416
B1072
NS00033406
2-Iodo-2-methylpropane stabilized over copper
D88747
2-Iodo-2-methylpropane (stabilized with Copper chip)
Q25385497
2-Iodo-2-methylpropane, contains copper as stabilizer, 95%