2-Thiopheneboronic acid
- Product Name
- 2-Thiopheneboronic acid
- CAS No.
- 6165-68-0
- Chemical Name
- 2-Thiopheneboronic acid
- Synonyms
- THIOPHEN-2-YLBORONIC ACID;THIOPHENE-2-BORONIC ACID;2-THIENYLBORONIC ACID;2-thiophenylboric acid;AKOS BRN-0022;BUTTPARK 98\04-23;2-Boronothiophene;Thienylboronic aci;RARECHEM AH PB 0243;TIMTEC-BB SBB004243
- CBNumber
- CB6273875
- Molecular Formula
- C4H5BO2S
- Formula Weight
- 127.96
- MOL File
- 6165-68-0.mol
2-Thiopheneboronic acid Property
- Melting point:
- 138-140 °C (lit.)
- Boiling point:
- 287.9±32.0 °C(Predicted)
- Density
- 1.32±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- Soluble in methanol.
- pka
- 8.41±0.53(Predicted)
- form
- Powder
- color
- Off-white to beige
- BRN
- 112375
- Stability:
- store cold
- InChI
- InChI=1S/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H
- InChIKey
- ARYHTUPFQTUBBG-UHFFFAOYSA-N
- SMILES
- C1(B(O)O)SC=CC=1
- CAS DataBase Reference
- 6165-68-0(CAS DataBase Reference)
Safety
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26-36/37-37/39-36
- WGK Germany
- 3
- Hazard Note
- Harmful/Irritant/Keep Cold
- 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
- 436836
- Product name
- 2-Thienylboronic acid
- Purity
- ≥95.0%
- Packaging
- 1g
- Price
- $50.4
- Updated
- 2025/07/31
- Product number
- 436836
- Product name
- 2-Thienylboronic acid
- Purity
- ≥95.0%
- Packaging
- 5g
- Price
- $82.8
- Updated
- 2025/07/31
- Product number
- T1772
- Product name
- 2-Thiopheneboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 1g
- Price
- $23
- Updated
- 2025/07/31
- Product number
- T1772
- Product name
- 2-Thiopheneboronic Acid (contains varying amounts of Anhydride)
- Packaging
- 5g
- Price
- $71
- Updated
- 2025/07/31
- Product number
- 05-1040
- Product name
- 2-Thiopheneboronic acid, min. 97%
- Packaging
- 5g
- Price
- $85
- Updated
- 2024/03/01
2-Thiopheneboronic acid Chemical Properties,Usage,Production
Chemical Properties
white to light yellow crystal powder
Uses
suzuki reaction
Uses
2-Thienylboronic Acid is a reagent used for palladium-catalyzed Suzuki-Miyaura cross-couplings. It is also used in preparation of photophysical properties of oxygen-containing polycyclic aromatic triptycenes.
Uses
2-Thiopheneboronic acid can be used as reagent used for Palladium-catalyzed Suzuki-Miyaura cross-couplings; Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide ;Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer; Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters.
Synthesis
1003-09-4
6165-68-0
General procedure for the synthesis of 2-thiophene boronic acid from 2-bromothiophene: Triphenylphosphine (0.131 g, 0.5 mmol, 20 mol%), p-iodoanisole (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, condenser, and stirring bar). The reaction system was degassed three times by alternating vacuum and argon displacement. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol%) was added under positive argon pressure. After stirring at room temperature for 15 minutes, diisopropylaminoborane (5 mL, 1 M THF solution, 5 mmol) was added and again degassed three times by alternating vacuum and argon displacement. The reaction mixture was heated to reflux and kept at reflux for 12 hours. Upon completion of the reaction, the mixture was cooled to 0°C and 6 mL of methanol was slowly added (note: this process is exothermic and accompanied by hydrogen release). After stirring for 15 minutes, all solvent was removed by distillation under reduced pressure to give a black solid. The solid was dissolved with 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 2-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 2-thiopheneboronic acid as a white solid.
References
[1] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583
[2] Arkiv foer Kemi, 1957, vol. 11, p. 373,379, 380
[3] New Journal of Chemistry, 2002, vol. 26, # 4, p. 373 - 375
[4] Patent: EP674635, 2001, B1
2-Thiopheneboronic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2-Thiopheneboronic acid manufacturers
- Product
- 2-Thiopheneboronic acid 6165-68-0
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 1ton
- Release date
- 2022-10-09
- Product
- 2-Thiopheneboronic acid 6165-68-0
- Price
- US $8.00-6.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-04-23
- Product
- 2-Thiopheneboronic acid 6165-68-0
- Price
- US $1.00/KG
- Min. Order
- 1G
- Purity
- 98%
- Supply Ability
- 1000KG
- Release date
- 2018-08-10