9-Anthraceneboronic acid
- Iupac Name：anthracen-9-ylboronic acid
- CAS No.: 100622-34-2
- Molecular Weight：222.05
- Modify Date.: 2022-11-22 21:28
- Introduction:
suzuki reaction
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1. Names and Identifiers
- 1.1 Name
- 9-Anthraceneboronic acid
- 1.2 Synonyms
9-Anthracenylboronic 9-Anthracenylboronic acid, 9-Anthrylboronic acid 9-Anthracenylboronic acid 9-Anthrylboronic acid 9-Anthrylboronicacid 9-Boronoanthracene Anthracen-9-ylboronic acid ANTHRACENE-9-BORONIC ACID Boronic acid, B-9-anthracenyl- Boronic acid,B-9-anthracenyl- MFCD03425925
- 1.3 CAS No.
- 100622-34-2
- 1.4 CID
- 15510213
- 1.5 EINECS(EC#)
- 626-419-4
- 1.6 Molecular Formula
- C14H11BO2 (isomer)
- 1.7 Inchi
- InChI=1S/C14H11BO2/c16-15(17)14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9,16-17H
- 1.8 InChkey
- VHHDLIWHHXBLBK-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- B(C1=C2C=CC=CC2=CC3=CC=CC=C13)(O)O
- 1.10 Isomers Smiles
- B(C1=C2C=CC=CC2=CC3=CC=CC=C13)(O)O
2. Properties
- 2.1 Density
- 1.26
- 2.1 Melting point
- 203-250℃
- 2.1 Boiling point
- 479.5°Cat760mmHg
- 2.1 Refractive index
- 1.709
- 2.1 Flash Point
- 243.8°C
- 2.1 Precise Quality
- 222.08500
- 2.1 PSA
- 40.46000
- 2.1 logP
- 1.67280
- 2.1 Appearance
- White to tan Crystalline Solid
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- Tan solid
- 2.4 Color/Form
- White to tan
- 2.5 pKa
- 8.53±0.30(Predicted)
- 2.6 StorageTemp
- Keep in dark place,Sealed in dry,Room Temperature
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- 9-bromoanthracence (10.0 g, 38.9 mmol) was dissolvedin anhydrous THF solution (500 mL) and stirred at ?78C. Then, 1.6 M n-BuLi (29.3 mL, 46.7 mmol) was added. Triethyl borate (9.3 mL, 54.5 mmol) was added to the reaction after30 min. After the reaction was finished, the solution was acidified with 2 N HCl solutionat room temperature and extracted with ethyl acetate and water. The organic layer wasdried with anhydrous MgSO4 and filtered. The solution was evaporated. The residue wasredissolved in hexane and added to ethyl acetate. The precipitate was filtered and washedwith hexane to obtain a beige compound (7.70 g, 89percent). 1H-NMR (300 MHz, CDCl3):δ(ppm) = 8.47 (s, 1H), 8.14 (d, J = 9.2 Hz, 2H), 8.04 (d, J = 9.8 Hz, 2H), 7.53–7.44 (m, 4H), 5.07 (s, 2H).9-Bromoanthracene 38.6 g was dissolved in dehydrated toluene 80 ml and dehydrated THF (tetrahydrofuran) 160 ml, and the solution was cooled to -40°C. (i) As shown in Reaction Scheme 3 9-Bromoanthracene (10 g, 38.9 mmol) was added to a solution of Placed in a 3-neck round bottom flask and 300 mL of anhydrous THF under nitrogen. 2M n-BuLi (24.0 mL, 46.7 mmol) was slowly added while maintaining the temperature at -78 dege C. In the middle of the reaction, TLC was taken under the condition of EA: hexane = 1: 10, and the progress of the reaction was examined. After the spot of the reaction disappeared, triethyl borate (9.50 mL, 54.5 mmol) was added to -78 deg. The progress of the reaction was examined by taking TLC under the conditions of EA: hexane = 1: 10. After the reaction was completed, HCl (7.20 mL, 85.6 mmol) was added at room temperature, EA and H2O. A small amount of H2O in the EA layer was removed with MgSO4. After the MgSO4 was filtered off, the product in the EA layer was evaporated. The product was dissolved in a small amount of THF and reprecipitated with hexane, followed by filtration to obtain 7.55 g (yield 87percent) of Compound 6 as an orange solid.Compound 42d.; Step a: Preparation of 9-anthracene boronic acid; A solution of 9-bromoanthracene (1 g, 3.9 mmol) and triisopropylborate (1.35 ml, 5.85 mmol) in absolute THF (30 ml) was cooled down to -78°C and stirred under argon. roe-BuLi (2.9 ml, 1.6 M in hexanes, 4.68 mmol) was then added dropwise over one hour and it was stirred at -78° C for one hour.
- 3.2 Purification Methods
- Crystallise the boronic acid from dilute HCl (m 180-184o). The disodium salt has m 209-213o. [Beilstein 16 IV 1679.] 9-Anthraceneboronic acidSupplier
- 3.3 Usage
- suzuki reaction
4. Safety and Handling
- 4.1 Symbol
- GHS06
- 4.1 Hazard Codes
- T
- 4.1 Signal Word
- Danger
- 4.1 Risk Statements
- R25
- 4.1 Safety Statements
- S45
- 4.1 Packing Group
- Ⅲ
- 4.1 Hazard Class
- IRRITANT
- 4.1 Hazard Declaration
- H301
- 4.1 RIDADR
- UN 2811
- 4.1 Caution Statement
- P301 + P310
- 4.1 WGK Germany
- 3
- 4.1 Safety
-
Hazard Codes: T.gif)
Risk Statements:
25: Toxic if swallowed
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
- 4.2 Specification
-
9-Anthraceneboronic acid (100622-34-2) is boron compounds and electronic Chemicals.And 9-Anthraceneboronic acid (100622-34-2) also can be called for boronic acid, B-9-anthracenyl- and Anthracen-9-ylboronic acid .
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Danger |
| Hazard statement(s) | H301 Toxic if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. |
| Storage | P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
100622-34-2Total: 8 Synthesis Route
8. Other Information
- 8.0 BRN
- 3301031
- 8.1 Chemical Properties
- Tan solid
- 8.2 Uses
- suzuki reaction
- 8.3 Purification Methods
- Crystallise the boronic acid from dilute HCl (m 180-184o). The disodium salt has m 209-213o. [Beilstein 16 IV 1679.]
9. Computational chemical data
- Molecular Weight: 222.05g/mol
- Molecular Formula: C14H11BO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 222.0852098
- Monoisotopic Mass: 222.0852098
- Complexity: 247
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 40.5
- Heavy Atom Count: 17
- 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: AAADccJwMAAAAAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAADBVAAoGAAACAAADACAGAAwAMAAAACAAiBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAgMAOwAACAAAQAACAAAQAACAAAAAAAAAAAA==
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