3D Mol Similar

3-Thiopheneboronic acid

: Iupac Name：thiophen-3-ylboronic acid; CAS No.: 6165-69-1; Molecular Weight：127.952; Modify Date.: 2022-11-29 02:16; Introduction: suzuki reaction 3-Thiopheneboronic acid Preparation Products And Raw materials Raw materials View more+

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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; View all

1.3 CAS No.: 6165-69-1

1.4 CID: 581760

1.5 Molecular Formula: C4H5BO2S (isomer)

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

1.7 InChIkey: 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 Density: 1.32

2.1 Melting point: 162-167℃

2.1 Boiling point: 287.9 °C at 760 mmHg

2.1 Refractive index: 1.562

2.1 Flash Point: 127.9 °C

2.1 Precise Quality: 128.01000

2.1 PSA: 68.70000

2.1 logP: -0.57210

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 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.; View all

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

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Declaration: H302-H315-H319-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 WGK Germany: 3

5. 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

View all

6. Synthesis Route

6165-69-1Total: 4 Synthesis Route

872-31-1 235 Suppliers

6165-69-1 230 Suppliers

Literatures:
Denton, Travis T.; Zhang, Xiaodong; Cashman, John R. Journal of Medicinal Chemistry, 2005 , vol. 48, # 1 p. 224 - 239
Yield: ~90%

17249-80-8 93 Suppliers

6165-69-1 230 Suppliers

Literatures:
Organic Letters, , vol. 14, # 18 p. 4814 - 4817,4
Yield: null

872-31-1 235 Suppliers

5419-55-6 85 Suppliers

6165-69-1 230 Suppliers

Literatures:
Syracuse University Patent: US2009/281290 A1, 2009 ; Location in patent: Page/Page column 5 ;
Yield: ~56%

View all

7. Precursor and Product

precursor:

872-31-1

688-74-4

17249-80-8

5419-55-6

1192-06-9

product :

5347-12-6

66768-57-8

17595-86-7

6453-99-2

29886-67-7

96919-48-1

2404-87-7

20608-79-1

26453-81-6

16939-06-3

199659-23-9

20608-89-3

16718-11-9

31926-67-7

214360-70-0

822-84-4

51175-71-4

16378-06-6

27921-48-8

View all

8. Other Information

8.0 Mesh Entry Terms: thiophene-3-boronic acid

9. Computational chemical data

Molecular Weight: 127.952g/mol
Molecular Formula: C₄H₅BO₂S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 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==

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thiophen-3-yl-3-ylboronic acid