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3-Thiopheneboronic acid

CAS：6165-69-1
MW:127.952
MF：C4H5BO2S

suzuki reaction 3-Thiopheneboronic acid Preparation Products And Raw materials Raw materials

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Names and ldentifier
Properties
Use and Manufacturing
Msds
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 3-Thiopheneboronic acid

1.2 Synonyms: (Thiophene-3-yl)boronic acid; 3-Thienylboronic acid; 3-Thiopheneboric acid; 3-Thiophenylboronic acid; B-3-Thienylboronic acid; Boronic acid, 3-thienyl-; Boronic acid, B-3-thienyl-; Thiophen-3-boronic acid; Thiophen-3-ylboronic acid;

1.3 CAS No.: 6165-69-1

1.4 CID: 581760

1.5 Molecular Formula: C4H5BO2S

1.6 Inchi: InChI=1S/C4H5BO2S/c6-5(7)4-1-2-8-3-4/h1-3,6-7H

1.7 InChkey: QNMBSXGYAQZCTN-UHFFFAOYSA-N

1.8 Canonical Smiles: B(C1=CSC=C1)(O)O

1.9 Isomers Smiles: B(C1=CSC=C1)(O)O

2. Properties

2.1 Appearance: white to light yellow crystal powder

2.2 Storage: Store at -20°C.

2.3 Chemical Properties: white to light yellow crystal powder

2.4 Color/Form: Almost white to grayish

2.5 pKa: 8.25±0.10(Predicted)

2.6 StorageTemp: 0-6°C

3. Use and Manufacturing

3.1 Description

3-Thiopheneboronic acid, with the chemical formula C4H5BO2S, has the CAS number 6165-69-1. It appears as a white to off-white solid with no distinct odor. The basic structure of 3-Thiopheneboronic acid consists of a thiophene ring attached to a boronic acid group. This compound is soluble in water and organic solvents such as ethanol and methanol. It is important to handle 3-Thiopheneboronic acid with caution as it may cause irritation to the skin, eyes, and respiratory system. It is recommended to wear protective gloves and eyewear when working with this chemical. In case of ingestion or inhalation, seek medical attention immediately. Proper ventilation should be ensured when using this compound to avoid the buildup of vapors. It is also important to prevent the release of 3-Thiopheneboronic acid into the environment as it may have harmful effects on aquatic life.

Applicable Fields

Organic Synthesis: 3-Thiopheneboronic acid is commonly used in organic synthesis as a building block for the preparation of various compounds. Its purpose in this field involves its ability to undergo reactions such as cross-coupling reactions, Suzuki-Miyaura reactions, and Buchwald-Hartwig reactions. The mechanism of action in organic synthesis involves the formation of new carbon-carbon or carbon-heteroatom bonds, allowing the synthesis of complex molecules.

Pharmaceuticals: This compound is also utilized in the pharmaceutical industry for the development of new drugs. Its purpose in this field involves its ability to interact with biological targets and modulate their activity. The mechanism of action in pharmaceuticals can vary depending on the specific drug being developed, but it often involves binding to specific receptors or enzymes, leading to therapeutic effects.

Storage

Conditions: Store in a cool and dry place.

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3.2 Methods of Manufacturing: General procedure: Triphenylphosphene (0.131 g, 0.5 mmol, 20 mol percent), p-iodoanisol (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added to a 50 mL round-bottomed flask equipped with a sidearm, condenser, and stir bar. This solution was then degassed by alternating vacuum and argon three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol percent) was then added under positive argon pressure. After stirring at room temperature for 15 min, diisopropylaminoborane (5 mL, 1 M solution in THF, 5 mmol) was added and the reaction mixture was degassed again by alternating vacuum and argon three times. The reaction solution was then heated to reflux. After 12 h of reflux the reaction was cooled to 0 °C and 6 mL of methanol was added through the condenser slowly (Caution: exothermic reaction with evolution of hydrogen). After 15 min of stirring all the solvent was removed under reduced pressure to yield a black solid. This solid was dissolved with sodium hydroxide (3 M, 8 mL) and subsequently washed with hexanes (3.x.10 mL). The aqueous layer was then cooled to 0 °C (ice bath) and acidified to pH <=1 with concentrated HCl, with the boronic acid usually precipitating out as a white solid. The aqueous fraction was then extracted with diethyl ether (3.x.10 mL). The organic fractions were combined, dried with magnesium sulfate and filtered. The solvent was then removed under reduced pressure yielding a white solid.Preparation of Compound 1-1After 3-bormothiophene (50 g, 306 mmol) was dissolved in THF (300 mL) and toluen (1, 200 mL), the mixture was cooled to -78 °C, and n-BuLi (150 mL, 2.5M in hexane, 367 mmol) was added thereto. After stirring the mixture for 1 hour, triisopropylborate (112 mL, 490 mmol) was added while maintaining temperature at -78 °C. The mixture was stirred for 10 minutes. Upon completion of the reaction, HA solution of 3-bromothiophene (30.67 mmol=5 g) and tri-isopropyl borate (40 mmol=8.33 g or 9 ml) in 30 ml THF was treated with n-BuLi (2.5M in hexanes, 40 mmol 16 ml) at -78° C. over a period of 20 minutes. The resulting solution was stirred at -78° C. for an hour, and was then warmed up to -20° C. slowly and quenched slowly using 2N HCl. The mixture was then warmed to room temperature, diluted with ethyl acetated and brine. The organic layer was separated, concentrated and dried in vacuo. The white crude residue was re-crystallized using hot water to give 2.25 g of pure thiophene-3-boronic acid (17.58 mmol, 57.3percent) with m.p at 126-128° C. [128-130° C. reported] (see Collis, G. E.; Burrell, A. K.; Scott, S. M.; Officer, D. L., J. Org. Chem. 2003, 68, (23), 8974-8983).General procedure: In a flask containing the appropriate potassiumorganotrifluoroborate (0.5 mmol) in distilled water(1 mL) was added montmorillonite K10 (150percent m/m). Themixture was stirred for the time indicated in Scheme 1at room temperature. After this period, the mixture wasextracted with EtOAc (3 × 10 mL) and the organic phasewas washed with water (2 × 15 mL). The organic phasewas dried over anhydrous MgSO4, filtered and the solventwas removed in vacuo to yield the corresponding boronicacids 2a-o.A. A.

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3.3 Usage: suzuki reaction 3-Thiopheneboronic acid Preparation Products And Raw materials Raw materials

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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5. Synthesis Route

6165-69-1Total: 4 Synthesis Route

872-31-1 237 Suppliers

6165-69-1 228 Suppliers

17249-80-8 93 Suppliers

6165-69-1 228 Suppliers

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6. Precursor and Product

precursor:

872-31-1

688-74-4

17249-80-8

1192-06-9

5419-55-6

product:

5347-12-6

66768-57-8

6453-99-2

2404-87-7

822-84-4

51175-71-4

3172-56-3

199659-23-9

10486-61-0

7. Computed Properties

Molecular Weight：127.952g/mol
Molecular Formula：C₄H₅BO₂S
Compound Is Canonicalized：True
XLogP3-AA：128.0103307
Monoisotopic Mass：128.0103307
Complexity：78.4
Rotatable Bond Count：1
Hydrogen Bond Donor Count：2
Hydrogen Bond Acceptor Count：3
Topological Polar Surface Area：68.7
Heavy Atom Count：：8
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADcYJgMABAAAAAAAAAAAAAAAAAASAAAAAAAAAAAAAAAAABgAAoGAQACAAACACEUACwAYAAAAiEACBCAAADAIAgCBBIiBgAAIgIIAAgAQAAAAAAAAAgAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

8.Other Information

Mesh Entry Terms: thiophene-3-boronic acid

9. Toltal 221 Suppliers View more

Hebei Yanxi Chemical Co.,Ltd

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Dayang Chem (Hangzhou) Co., Ltd.

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Jinlan Pharm-Drugs Technology Co., Limited

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Hangzhou KieRay Chem Co., Ltd.

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Hangzhou Tianye chemicals Co., Ltd

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Tel: Update Time:2024/10/22

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10. Related Questions

: What are the characteristics and applications of 3-Thiopheneboronic acid?Introduction 3-Thiopheneboronic acid, also known as 3-Thiopheneboronic Acid, has a chemical formula of C?H?BO?S and a molecular weight of 127.96. It appears as a grayish-white or white to pale yellow ..; What are the applications of 3-Thiopheneboronic Acid? 3-ThiPheneboronic Acid, as an important chemical synthetic intermediate, has extensive application value. This article will explore the specific application of 3- 噻piene boric acid for relevant rese..

11. Realated Product Infomation