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1-bromo-3,3-dimethylbutan-2-one

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Identification
Molecular formula
C6H11BrO
CAS number
815-55-8
IUPAC name
1-bromo-3,3-dimethyl-butan-2-one
State
State

At room temperature, 1-bromo-3,3-dimethylbutan-2-one is typically in a liquid state.

Melting point (Celsius)
-20.00
Melting point (Kelvin)
253.15
Boiling point (Celsius)
157.00
Boiling point (Kelvin)
430.15
General information
Molecular weight
165.06g/mol
Molar mass
165.0320g/mol
Density
1.2180g/cm3
Appearence

1-Bromo-3,3-dimethylbutan-2-one appears as a colorless to pale yellow liquid. It may have a sharp odor typical of organobromine compounds.

Comment on solubility

Solubility of 1-bromo-3,3-dimethyl-butan-2-one

1-bromo-3,3-dimethyl-butan-2-one, with the chemical formula C7H13BrO, presents unique characteristics regarding its solubility. This compound is predominantly a medium-sized organic molecule, which impacts its interaction with solvents.

When discussing solubility, consider the following points:

  • Solvent Polarity: Due to its bromine atom and carbonyl group, this compound is somewhat polar. Thus, it tends to have better solubility in polar solvents such as alcohols and acetone.
  • Hydrophobic Interactions: The long carbon chain combined with the branched structure may lead to increased hydrophobicity, making it less soluble in non-polar environments like hexane.
  • Temperature Considerations: Solubility may also increase with an increase in temperature, as indicated by the general rule that compounds typically dissolve better at elevated temperatures.
  • Atmospheric Conditions: The presence of moisture can affect solubility, particularly because the carbonyl (C=O) group can participate in hydrogen bonding with water molecules.

Overall, 1-bromo-3,3-dimethyl-butan-2-one is anticipated to have a varied solubility profile depending on the quality and characteristics of the solvent used. As stated, it will likely dissolve readily in polar solvents and show limited solubility in non-polar conditions. Further experimental validation would provide more insight into its precise solubility characteristics.

Interesting facts

Interesting Facts about 1-Bromo-3,3-Dimethyl-Butan-2-One

1-Bromo-3,3-dimethyl-butan-2-one, often referred to in scientific literature as a versatile intermediate in organic synthesis, possesses unique properties that make it a subject of interest for chemists:

  • Synthetic Applications: This compound serves as an important building block in the synthesis of pharmaceuticals and agrochemicals. Its bromine atom facilitates various nucleophilic substitution reactions, allowing for the introduction of different functional groups.
  • Structural Significance: The presence of both a ketone functional group and a bromine atom in its structure makes 1-bromo-3,3-dimethyl-butan-2-one a valuable candidate for studies in reactivity and mechanism. The steric hindrance provided by the two methyl groups can significantly influence reaction rates and pathways.
  • Selective Reactivity: The ketonic group is an electrophile, which opens avenues for carbon-carbon bond formation through reactions like the Grignard reaction, illustrating the compound's versatility in organic synthesis.
  • Chirality Consideration: As a compound containing a chiral center, it can give rise to stereoisomers, emphasizing its significance in stereochemistry studies and applications in drug design where enantiomeric purity is paramount.
  • Historical Context: The bromination reactions that lead to the synthesis of this compound have been studied since the early 20th century, showcasing its longstanding utility in organic laboratories.

Overall, 1-bromo-3,3-dimethyl-butan-2-one exemplifies how relatively simple organic compounds can be harnessed for a variety of applications through clever synthetic strategies and a deep understanding of their chemical properties.

Synonyms
1-Bromopinacolone
5469-26-1
1-Bromo-3,3-dimethylbutan-2-one
1-Bromo-3,3-dimethyl-2-butanone
Bromopinacolone
1-Bromopinacolin
Bromomethyl tert-butyl ketone
Bromopinacolin
Pivaloylmethyl bromide
tert-Butyl bromomethyl ketone
2-BUTANONE, 1-BROMO-3,3-DIMETHYL-
NSC 25307
FU9GTL96KB
EINECS 226-794-0
alpha-Bromopinacolone
BRN 0506485
1-bromo-2-pinacolone
.alpha.-Bromopinacolone
NSC-25307
3,3-Dimethyl-2-oxobutyl bromide
DTXSID50203145
4-01-00-03314 (Beilstein Handbook Reference)
omega-Brompinakolin
omega-Brompinakolin [German]
DTXCID50125636
sairzmwxvjebmo-uhfffaoysa-n
1-Bromo-3,3-DiMethyl-Butan-2-One
MFCD00000206
omega- Brompinakolin
omega- Brompinakolin [German]
bromopinacoline
l-bromopinacolone
1- bromopinacolone
1-bromo-pinacolone
UNII-FU9GTL96KB
Bromomethyl-t-butyl ketone
Bromomethyl tert-butylketone
bromomethyl-tert-butylketone
bromomethyl-tert-butyl ketone
1-Bromopinacolone, >=97%
SCHEMBL112282
1-bromo-3,3-dimethy 2-butanone
4-bromo-2,2-dimethylbutan-3-one
BCP19288
NSC25307
1-bromo -3,3-dimethylbutan-2-one
AKOS000210502
AS-16064
FB167518
1-Bromopinacolone, technical grade, ~90%
DB-008054
1-Bromopinacolone, purum, >=97.0% (GC)
B1490
CS-0199161
NS00033175
EN300-21881
F16652