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Benzothiophen-2-ylboronic acid

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Identification
Molecular formula
C8H7BO2S
CAS number
17406-02-1
IUPAC name
benzothiophen-2-ylboronic acid
State
State

At room temperature, Benzothiophen-2-ylboronic acid is found in a solid state. It is usually a finely powdered substance that should be handled with care to prevent inhalation or contact with skin.

Melting point (Celsius)
155.00
Melting point (Kelvin)
428.15
Boiling point (Celsius)
362.00
Boiling point (Kelvin)
635.15
General information
Molecular weight
164.99g/mol
Molar mass
164.9940g/mol
Density
1.3600g/cm3
Appearence

Benzothiophen-2-ylboronic acid typically appears as a white to off-white solid powder. This compound is used in various chemical reactions, including Suzuki couplings, and due to its solid nature, it is quite stable when stored under appropriate conditions.

Comment on solubility

Solubility of Benzothiophen-2-ylboronic Acid (C8H7BO2S)

Benzothiophen-2-ylboronic acid exhibits unique solubility characteristics that are essential for its applications in organic chemistry and materials science. Its solubility can be influenced by several factors, including:

  • Polarity: The presence of both the boronic acid group and the benzothiophene structure contributes to its moderate polarity. This polarity can enhance solubility in polar solvents.
  • Solvent Interactions: Benzothiophen-2-ylboronic acid is typically more soluble in organic solvents such as ethanol, dimethyl sulfoxide (DMSO), and acetone. In contrast, it has limited solubility in non-polar solvents.
  • pH Dependence: The solubility is also strongly pH-dependent due to the acidic nature of the boronic acid group; increasing pH can lead to deprotonation, enhancing solubility.

In practical terms, it is important to consider the following:

  1. Application Efficiency: High solubility in suitable solvents is crucial for reactions involving this compound, as it can facilitate the formation of various boron-containing derivatives.
  2. Handling and Storage: When working with benzothiophen-2-ylboronic acid, ensure that it is stored in a way that maintains its solubility properties, avoiding extreme pH levels that could compromise its stability.

In summary, understanding the solubility of benzothiophen-2-ylboronic acid is key to harnessing its full chemical potential, enabling effective utilization in synthetic methods and applications.

Interesting facts

Interesting Facts about Benzothiophen-2-ylboronic Acid

Benzothiophen-2-ylboronic acid is a fascinating compound that lies at the intersection of organic chemistry and medicinal applications. This boronic acid derivative has garnered attention for its unique structural features and diverse functionality.

Structural Significance

  • The compound contains a benzothiophene moiety, consisting of a fused benzene ring and a thiophene ring, which contributes to its interesting chemical reactivity.
  • The presence of the boronic acid group enhances its ability to participate in cross-coupling reactions, making it a valuable reagent in organic synthesis.
  • Its structure allows for potential interactions with biological targets, which opens avenues for drug discovery and development.

Applications in Drug Discovery

Benzothiophen-2-ylboronic acid has shown promise in several key areas of research:

  • As a potential anticancer agent, it can interact with specific biological pathways to inhibit tumor growth.
  • Its ability to form complexes with various biomolecules may lead to new therapeutic strategies for diseases.
  • This compound serves as a crucial building block for synthesizing pharmaceuticals, particularly in developing kinase inhibitors.

Quote from the Field

As noted by experts, “Boron-containing compounds have long been recognized for their importance in synthetic organic chemistry due to their unique reactivity and ability to form stable complexes.” This statement reinforces the relevance and optimism surrounding benzothiophen-2-ylboronic acid.

In summary, benzothiophen-2-ylboronic acid exemplifies a remarkable compound with significant implications in both synthetic chemistry and medicinal applications, making it a subject of ongoing research and exploration.

Synonyms
98437-23-1
2-benzothienylboronic acid
benzo[b]thiophen-2-ylboronic acid
BENZO[B]THIOPHENE-2-BORONIC ACID
1-Benzothiophen-2-ylboronic acid
benzo(b)thiophene-2-boronic acid
Benzothiophene-2-boronic acid
Thianaphthene-2-boronic acid
1-benzothien-2-ylboronic acid
BENZO[B]THIEN-2-YLBORONIC ACID
Benzo[b]thiophene-2-ylboronic Acid
SME05QG1FJ
MFCD01075674
Benzo(B)thiophen-2-ylboronic acid
CHEMBL34964
benzo[b]thiophen-2-boronic acid
DTXSID80274363
(1-benzothiophen-2-yl)boronic acid
Boronic acid, benzo[b]thien-2-yl-
Benzothiophen-2-ylboronic acid
3fkv
3ixg
benzothiopheneboronic acid
UNII-SME05QG1FJ
2-benzothienyl boronic acid
2-benzothiopheneboronic acid
SCHEMBL8212
thianapthene-2-boronic acid
benzothiophen-2-boronic acid
bezothiophene-2-boronic acid
1-benzothiophen-2-ylboranediol
2-benzo[b]thiopheneboronic acid
benzo[b]thiophene-2-boronicacid
benzo[b]thiophene2-boronic acid
(2-benzo[b]thienyl)boronic acid
BDBM26139
Bnezo[b]thiophen-2-boronic acid
YNCYPMUJDDXIRH-UHFFFAOYSA-
2-benzo[b]thiophene boronic acid
DTXCID50225842
1-benzothiophen-2-yl-boronic acid
benzo[b]-thiophene-2-boronic acid
HMS3604C07
benzo(B) thiophene-2-boronic acid
BBL020712
STK893402
AKOS003585292
Benzo[b]thiophene-2-boronic acid (contains varying amounts of Anhydride)
1-benzothiophen-2-ylboronic acid, 18
AB08143
CS-W018486
DB04360
NCGC00092008-01
NCGC00092008-02
NCGC00092008-03
AS-15065
SY001173
DB-009570
B2893
NS00073510
BENZO[B]THIOPHEN-2-YL-2-BORONIC ACID
EN300-212491
AB01332905-02
Q27095165
Z1255488387
1-Benzothiophen-2-ylboronic acid(contains varying amounts of Anhydride)
Benzo[b]thiophene-2-ylboronic Acid, (contains varying amounts of Anhydride)
InChI=1/C8H7BO2S/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-5,10-11H
671-850-3