(S)-Butane-1,3-diol
(S)-Butane-1,3-diol is a chiral organic compound with the molecular formula C₄H₁₀O₂. It is a diol, meaning it has two hydroxyl (-OH) groups, located on the first and third carbon atoms of a butane chain. The (S) designation indicates that the molecule has a specific stereochemistry, where the configuration around the chiral center (the second carbon) follows the “S” (sinister) arrangement according to the Cahn-Ingold-Prelog priority rules.
Structure:
- The structure of (S)-butane-1,3-diol can be represented as:
HO-CH₂-CH(OH)-CH₂-CH₃- The chiral center is the second carbon (C2), which is bonded to four different groups: a hydroxyl group (-OH), a hydrogen atom (-H), a methylene group (-CH₂-), and an ethyl group (-CH₂-CH₃).
Key Features:
- Chirality: The molecule is chiral due to the presence of the stereocenter at C2. The (S) configuration indicates that the groups around the chiral center are arranged in a specific spatial orientation.
- Hydroxyl Groups: The two hydroxyl groups make the molecule polar and capable of forming hydrogen bonds, which can influence its solubility and reactivity.
- Applications: Diols like (S)-butane-1,3-diol are often used in organic synthesis, as intermediates in the production of polymers, or as solvents. They can also be used in the synthesis of chiral compounds in pharmaceuticals or fine chemicals.
Synthesis:
(S)-Butane-1,3-diol can be synthesized through various methods, including:
- Asymmetric reduction of 1,3-diketones or 1,3-hydroxyketones using chiral catalysts.
- Enzymatic resolution of racemic butane-1,3-diol to isolate the (S)-enantiomer.
Properties:
- Boiling Point: Diols generally have higher boiling points due to hydrogen bonding.
- Solubility: It is likely soluble in water and polar organic solvents due to the presence of hydroxyl groups.
If you need more specific information about its synthesis, reactions, or applications, feel free to ask!
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