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Pinacol

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Identification
Molecular formula
C6H14O2
CAS number
76-09-5
IUPAC name
2,3-dimethylbutane-2,3-diol
State
State

Pinacol is a solid at room temperature. It is typically encountered as crystalline flakes or powder.

Melting point (Celsius)
45.00
Melting point (Kelvin)
318.15
Boiling point (Celsius)
172.60
Boiling point (Kelvin)
445.75
General information
Molecular weight
118.17g/mol
Molar mass
118.1740g/mol
Density
0.9673g/cm3
Appearence

Pinacol appears as a white crystalline solid. It is known for forming tightly packed crystals that might be prismatic in nature. When pure, it typically does not exhibit any color and has a distinct, sweetish odor akin to glycerol.

Comment on solubility

Solubility of 2,3-dimethylbutane-2,3-diol

2,3-dimethylbutane-2,3-diol, a diol with a branched structure, exhibits interesting solubility properties due to the presence of hydroxyl (-OH) groups. The compound's solubility can be influenced by several factors:

  • Polarity: The hydroxyl groups contribute to the polarity of the molecule, enhancing interactions with polar solvents such as water.
  • Hydrogen Bonding: 2,3-dimethylbutane-2,3-diol can form hydrogen bonds with water molecules, which typically increases solubility.
  • Chain Length and Structure: The branched 2,3-dimethyl structure may limit solubility in nonpolar solvents, making it less soluble compared to straight-chain diols.

Generally, diols are known for their relatively good solubility in water compared to their non-hydroxylated counterparts. As a rule of thumb:

  1. If the number of hydroxyl groups increases, solubility in water tends to increase.
  2. However, the presence of bulky alkyl groups can reduce this solubility due to steric hindrance.

In summary, 2,3-dimethylbutane-2,3-diol is expected to have moderate solubility in water, primarily attributable to its hydroxyl groups, while its branched nature may play a role in limiting solubility in nonpolar solvents. This duality in solubility exemplifies the importance of both molecular structure and functional groups in determining the behavior of chemical compounds in various solvents.

Interesting facts

Interesting Facts About 2,3-Dimethylbutane-2,3-diol

2,3-Dimethylbutane-2,3-diol is a fascinating compound that plays a significant role in organic chemistry, particularly in the study of alcohols. Here are some intriguing aspects of this compound:

  • Chiral Centers: This compound contains two chiral centers, making it optically active. This characteristic allows for the existence of multiple stereoisomers, which can have vastly different chemical properties despite having the same molecular formula.
  • Hydroxyl Groups: The presence of two hydroxyl (–OH) groups contributes to its classification as a diol or glycol. Diols are known for their ability to form hydrogen bonds, leading to unique physical and chemical properties, including higher boiling points compared to similar hydrocarbons.
  • Synthesis: 2,3-Dimethylbutane-2,3-diol can be synthesized through various methods, including the reduction of ketones or the hydrolysis of epoxides. Understanding these synthesis routes is crucial for students venturing into organic synthesis.
  • Applications: This compound is often utilized in the pharmaceutical industry as a precursor for designing more complex molecules. Its reactivity and structure make it a valuable intermediate in organic synthesis.
  • Critical Role in Understanding Reaction Mechanisms: Studying this compound provides insights into stereochemistry and reaction mechanisms that are fundamental in organic chemistry, helping students develop a deeper understanding of molecular interactions.

In summary, 2,3-dimethylbutane-2,3-diol exemplifies the elegance of organic chemistry, showcasing the interplay between structure, stereochemistry, and reactivity. As you delve into the world of alcohols and related compounds, this diol serves as an excellent model for exploring fundamental concepts in both laboratory and theoretical settings.

Synonyms
PINACOL
76-09-5
2,3-Dimethylbutane-2,3-diol
2,3-Dimethyl-2,3-butanediol
Pinacone
2,3-Butanediol, 2,3-dimethyl-
Tetramethylethylene glycol
1,1,2,2-Tetramethylethylene glycol
MFCD00004462
2,3-Dihydroxy-2,3-dimethylbutane
2,3-Dimethyl-2,3-dihydroxybutane
EINECS 200-933-5
UNII-527QE7I5CO
NSC 25943
BRN 1340501
527QE7I5CO
2,3-Dimethyl-butane-2,3-diol
AI3-02251
PINACOL [MI]
NSC-25943
DTXSID3058793
CHEBI:131185
4-01-00-02575 (Beilstein Handbook Reference)
meso-2,3-Dimethyl-2,3-butanediol
75160-24-6
Pinacol, 98%
Pinacol, >=98%
2,3Dimethyl2,3butanediol
SCHEMBL8968
2,3-dimethyl-2,3-butandiol
CHEMBL3289669
DTXCID5047825
WLN: QX1&1&XQ1&1
1,1,2,2Tetramethylethylene glycol
ADA16024
NSC25943
STL256832
AKOS007930158
AC-4658
FP16086
AS-12465
BP-21164
SY001866
CS-0015356
D0691
NS00013152
EN300-39352
D71083
Pinacol Pinacone 2,3-Dimethyl-2,3-butanediol
Q421634
2,3-Dimethyl-2,3-butanediol, Tetramethylethylene glycol
F0001-1921
Z382716052
200-933-5