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Ethyl 3,5-dichloro-4-hydroxybenzoate

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Identification
Molecular formula
C9H8Cl2O3
CAS number
43106-88-5
IUPAC name
ethyl 3,5-dichloro-4-hydroxy-benzoate
State
State

At room temperature, this compound is typically a solid.

Melting point (Celsius)
81.50
Melting point (Kelvin)
354.65
Boiling point (Celsius)
343.10
Boiling point (Kelvin)
616.25
General information
Molecular weight
249.07g/mol
Molar mass
249.0710g/mol
Density
1.4590g/cm3
Appearence

Ethyl 3,5-dichloro-4-hydroxybenzoate typically appears as a pale yellow to off-white crystalline solid. It may also appear slightly granular or powdery in texture.

Comment on solubility

Solubility of Ethyl 3,5-Dichloro-4-Hydroxybenzoate

Ethyl 3,5-dichloro-4-hydroxybenzoate, often referred to as a derivative of salicylic acid, exhibits interesting solubility characteristics that can impact its applications in various chemical processes. The solubility of this compound can be attributed to several factors, including:

  • Polarity: The presence of both dichloro and hydroxy groups on the aromatic ring increases the polarity of the molecule, which can enhance interactions with polar solvents.
  • Hydrogen Bonding: The hydroxy group (-OH) can act as a hydrogen bond donor, potentially increasing solubility in polar solvents such as water.
  • Steric Hindrance: The bulky nature of the ethyl group may affect how the compound interacts with solvents, influencing its overall solubility.

Generally, ethyl 3,5-dichloro-4-hydroxybenzoate tends to have higher solubility in organic solvents compared to water. It is soluble in solvents such as:

  • Alcohols: Particularly in ethanol and methanol due to similar polar characteristics.
  • Aromatics: Compounds like benzene and toluene can dissolve it well due to compatible interactions.

Conversely, its solubility in water is limited, often necessitating the use of co-solvents or surfactants for effective dissolution. This unique solubility profile makes ethyl 3,5-dichloro-4-hydroxybenzoate an intriguing compound for study in fields such as pharmaceuticals and agrochemicals.

Interesting facts

Interesting Facts about Ethyl 3,5-Dichloro-4-Hydroxybenzoate

Ethyl 3,5-dichloro-4-hydroxybenzoate, a member of the benzoate ester family, showcases a fascinating interplay of chemical structure and functionality. Here are some engaging insights:

  • Origin of the Compound: This compound is synthesized from the esterification of 3,5-dichloro-4-hydroxybenzoic acid with ethanol. The introduction of chlorine atoms enhances its reactivity and biological activity.
  • Biological Significance: Ethyl 3,5-dichloro-4-hydroxybenzoate is recognized for its use in various biological applications, including studies in pharmacology and agrochemicals. Its chlorine substitutions often enhance herbicidal properties, making it relevant in agricultural chemistry.
  • Utility as an Intermediate: This compound serves as a vital intermediate in the synthesis of a variety of organic compounds, playing a pivotal role in the creation of pharmaceuticals and agrochemicals.
  • Environmental Considerations: With chlorinated compounds, there are environmental concerns related to their persistence and toxicity. Thus, understanding their behavior in the environment is crucial for sustainable usage.
  • Structure-Activity Relationship: Researchers often study the structure-activity relationship (SAR) of such compounds to predict their biological activity based on structural components. In the case of this compound, the positioning of the hydroxy and chloro groups is significant for its efficacy.

Overall, the study of ethyl 3,5-dichloro-4-hydroxybenzoate not only reveals its chemical intricacies but also emphasizes the importance of responsibly managing compounds that have notable biological activity. As emphasized by chemists, "The magic of chemistry lies in the details of molecular interactions." Exploring these details can lead to significant advancements in many fields.

Synonyms
Ethyl 3,5-dichloro-4-hydroxybenzoate
17302-82-8
3,5-Dichloro-4-hydroxybenzoic acid ethyl ester
BENZOIC ACID, 3,5-DICHLORO-4-HYDROXY-, ETHYL ESTER
BAZ7VD16EK
EINECS 241-331-2
NSC 74473
BRN 2649965
NSC-74473
DTXSID20169502
3-10-00-00363 (Beilstein Handbook Reference)
ETHYL 4-HYDROXY-3,5-DICHLOROBENZOATE
DTXCID9091993
241-331-2
MFCD00016420
3,5-dichloro-4-hydroxy-benzoic acid ethyl ester
Ethyl 4-Hydroxy-3,5-dichlorobenzoate; NSC 74473
NSC74473
ethyl 3,5-dichloro-4-hydroxy-benzoate
UNII-BAZ7VD16EK
SCHEMBL691510
WLN: QR BG FG DVO2
HMS1748G09
SBB053719
AKOS001042102
FE71260
PS-3157
SY048420
DB-014794
CS-0063145
D0374
NS00025669
ST50307848
EN300-16192
D73276
Benzoic acid,5-dichloro-4-hydroxy-, ethyl ester
SR-01000046977
SR-01000046977-1
Z54462278
InChI=1/C9H8Cl2O3/c1-2-14-9(13)5-3-6(10)8(12)7(11)4-5/h3-4,12H,2H2,1H