3-Thiopheneboronic acid
- Product Name
- 3-Thiopheneboronic acid
- CAS No.
- 6165-69-1
- Chemical Name
- 3-Thiopheneboronic acid
- Synonyms
- THIOPHEN-3-YLBORONIC ACID;THIOPHENE-3-BORONIC ACID;AKOS BRN-0047;3-thienoborate;3-Boronothiophene;RARECHEM AH PB 0232;TIMTEC-BB SBB004244;3-Thiopheneboronica;3-ThiopheneBoricAcid;3-THIENYLBORONIC ACID
- CBNumber
- CB2755805
- Molecular Formula
- C4H5BO2S
- Formula Weight
- 127.96
- MOL File
- 6165-69-1.mol
3-Thiopheneboronic acid Property
- Melting point:
- 164-169 °C (lit.)
- Boiling point:
- 287.9±32.0 °C(Predicted)
- Density
- 1.32±0.1 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- pka
- 8.25±0.10(Predicted)
- form
- Powder
- color
- Almost white to grayish
- BRN
- 113573
- InChI
- InChI=1S/C4H5BO2S/c6-5(7)4-1-2-8-3-4/h1-3,6-7H
- InChIKey
- QNMBSXGYAQZCTN-UHFFFAOYSA-N
- SMILES
- C1SC=CC=1B(O)O
- CAS DataBase Reference
- 6165-69-1(CAS DataBase Reference)
Safety
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26-37/39-36
- WGK Germany
- 3
- Hazard Note
- Irritant
- HazardClass
- IRRITANT, IRRITANT-HARMFUL, KEEP COLD
- HS Code
- 29339900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 436844
- Product name
- 3-Thienylboronic acid
- Purity
- ≥95.0%
- Packaging
- 1g
- Price
- $37.5
- Updated
- 2025/07/31
- Product number
- 436844
- Product name
- 3-Thienylboronic acid
- Purity
- ≥95.0%
- Packaging
- 5g
- Price
- $60.73
- Updated
- 2025/07/31
- Product number
- T1975
- Product name
- 3-Thiopheneboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 1g
- Price
- $27
- Updated
- 2025/07/31
- Product number
- T1975
- Product name
- 3-Thiopheneboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $77
- Updated
- 2025/07/31
- Product number
- T344640
- Product name
- 3-ThiopheneboronicAcid
- Packaging
- 10g
- Price
- $635
- Updated
- 2021/12/16
3-Thiopheneboronic acid Chemical Properties,Usage,Production
Chemical Properties
white to light yellow crystal powder
Uses
suzuki reaction
Uses
3-Thiopheneboronic Acid is used in the synthesis of porphyrins as inhibitiors of telomerase. It is also used to prepare 1,4-disubstituted imidazoles as potential antibacterial agents.
Synthesis
872-31-1
6165-69-1
General procedure for the synthesis of 3-thiophene boronic acid from 3-bromothiophene: Triphenylphosphine (0.131 g, 0.5 mmol, 20 mol%), p-iodoiodobenzene (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added sequentially to a 50 mL round-bottomed flask (equipped with a side arm, a condenser, and a stir bar). The reaction system was degassed by alternating vacuum and argon filling three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol%) was added under positive argon pressure. After stirring for 15 minutes at room temperature, diisopropylaminoborane (5 mL, 1 M THF solution, 5 mmol) was added and the reaction mixture was again degassed by alternating vacuum and argon filling three times. The reaction solution was heated to reflux and kept at reflux for 12 hours. Upon completion of the reaction, the reaction solution was cooled to 0 °C and 6 mL of methanol was slowly added (note: this is an exothermic reaction, which releases hydrogen). After stirring for 15 minutes, all solvent was removed by distillation under reduced pressure to give a black solid. The solid was dissolved in 3M sodium hydroxide solution (8 mL) and subsequently washed with hexane (3 x 10 mL). The aqueous layer was cooled to 0°C (ice bath) and acidified with concentrated hydrochloric acid to pH ≤ 1, at which point 3-thiopheneboronic acid precipitated as a white solid. The aqueous layer was extracted with ether (3 x 10 mL), the organic phases were combined, dried with magnesium sulfate and filtered. Finally, the solvent was removed by distillation under reduced pressure to obtain 3-thiopheneboronic acid in white solid form.
References
[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 224 - 239
[2] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[3] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[4] Patent: US6342610, 2002, B2. Location in patent: Page column 77
[5] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
3-Thiopheneboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 3-Thiopheneboronic acid manufacturers
- Product
- 3-Thiopheneboronic acid 6165-69-1
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-09-27
- Product
- 3-Thiopheneboronic acid 6165-69-1
- Price
- US $1.00/KG
- Min. Order
- 1G
- Purity
- 98%
- Supply Ability
- 1000KG
- Release date
- 2018-08-10