3-Tolylboronic acid
- Iupac Name：(3-methylphenyl)boronic acid
- CAS No.: 17933-03-8
- Molecular Weight：135.957
- Modify Date.: 2022-11-25 01:01
- Introduction: suzuki reaction 3-Tolylboronic acid Preparation Products And Raw materials Preparation Products
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1. Names and Identifiers
- 1.1 Name
- 3-Tolylboronic acid
- 1.2 Synonyms
3-Methylbenzeneboronic acid 3-Methylbenzeneboronic Acid (contains varying amounts of Anhydride) 3-Methylphenylboronic acid 3-Methylphenylboronic Acid (contains varying amounts of Anhydride) B-(3-Methylphenyl)boronic acid Boronic acid, (3-methylphenyl)- Boronic acid, B-(3-methylphenyl)- m-Boronotoluene m-Methylbenzeneboronic acid m-Methylborophenylic acid m-Methylphenylboronic acid m-Tolueneboronic acid m-Tolylboronic acid m-Tolylboronic Acid (contains varying amounts of Anhydride) m-Tolyldihydroxyborane
- 1.3 CAS No.
- 17933-03-8
- 1.4 CID
- 2733950
- 1.5 EINECS(EC#)
- 605-855-9
- 1.6 Molecular Formula
- C7H9BO2 (isomer)
- 1.7 Inchi
- InChI=1S/C7H9BO2/c1-6-3-2-4-7(5-6)8(9)10/h2-5,9-10H,1H3
- 1.8 InChkey
- BJQCPCFFYBKRLM-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- B(C1=CC(=CC=C1)C)(O)O
- 1.10 Isomers Smiles
- B(C1=CC(=CC=C1)C)(O)O
2. Properties
- 2.1 Density
- 1.1
- 2.1 Melting point
- 160-162℃
- 2.1 Boiling point
- 290.4 °C at 760 mmHg
- 2.1 Refractive index
- 1.527
- 2.1 Flash Point
- 129.4 °C
- 2.1 Precise Quality
- 136.07000
- 2.1 PSA
- 40.46000
- 2.1 logP
- -0.32520
- 2.1 Appearance
- Beige Powder and Chunks
- 2.2 Storage
- Ambient temperatures.
- 2.3 Chemical Properties
- Off-white Cryst
- 2.4 Color/Form
- Beige
- 2.5 pKa
- 8.63±0.10(Predicted)
- 2.6 Stability
- Stable under normal temperatures and pressures.
- 2.7 StorageTemp
- 0-6°C
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- The reaction flask was charged with 0.10 mol (0.1 eq) m-bromotoluene, 1.1 mol (1.1 eq) magnesium turnings, a few grains of simple iodine, 800 ml THF, stirred, and warmed to reflux. When Grignard initiated, 0.90 mol (0.9 eq) of m-bromotoluene was continuously added dropwise under the reflux condition, and the reaction of refluxing and keeping warm was completed. The reaction time is reached and the temperature is reduced to -50.0°C. 2.2 mol (2.2 eq) of trimethyl borate was added dropwise, and the reaction was incubated until the reaction of the raw materials was complete, and the temperature was raised and water was added. Hydrochloric acid was added dropwise, the pH was adjusted to 1-2, the reaction was incubated, the reaction time was reached, rotary evaporation, suction drying, and beating and purification were performed to obtain 0.90 mol of 3-methylphenylboronic acid as a white solid, 0.03percent of water, and a purity of 98.86percent. The yield was 90.0percent.General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H
- 3.2 Usage
- suzuki reaction 3-Tolylboronic acid Preparation Products And Raw materials Preparation Products
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 Class
- IRRITANT
- 4.1 Hazard Declaration
- 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
- 4.1 RTECS
- ED7788888
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
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) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. 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 | 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
7. Synthesis Route
17933-03-8Total: 13 Synthesis Route
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Yield: null
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9. Other Information
- 9.0 Storage Conditions
- The reaction flask was charged with 0.10 mol (0.1 eq) m-bromotoluene, 1.1 mol (1.1 eq) magnesium turnings, a few grains of simple iodine, 800 ml THF, stirred, and warmed to reflux. When Grignard initiated, 0.90 mol (0.9 eq) of m-bromotoluene was continuously added dropwise under the reflux condition, and the reaction of refluxing and keeping warm was completed. The reaction time is reached and the temperature is reduced to -50.0°C. 2.2 mol (2.2 eq) of trimethyl borate was added dropwise, and the reaction was incubated until the reaction of the raw materials was complete, and the temperature was raised and water was added. Hydrochloric acid was added dropwise, the pH was adjusted to 1-2, the reaction was incubated, the reaction time was reached, rotary evaporation, suction drying, and beating and purification were performed to obtain 0.90 mol of 3-methylphenylboronic acid as a white solid, 0.03percent of water, and a purity of 98.86percent. The yield was 90.0percent.General procedure: To a solution in THF (4 mL) of DIPAB (863 mg, 7.5 mmol) and Mg (182 mg, 7.5 mmol) were added a PhMgBr 1M THF solution (375 μL, 375μmol) at room temperature. After 10 min, 30 mL of anhydrous THF were added followed by the arylbromide (5 mmol). The reaction mixture was cooled down to 0 °C and quenched slowly with 7 mL of MeOH. After 1h, volatile were removed under reduced pressure and the resulting solid was dissolved in 1N HCl/MeOH (7/3). After 1h at room temperature, 100 mL of AcOEt were added, the organic phase was washed with 1N HCl (30 mL) and brine (3×30 mL). Organic phases were concentrated under reduced pressure yielding a solid which was recrystallized from H
- 9.1 Usage
- Suzuki coupling reactions
- 9.2 BRN
- 2935968
- 9.3 Chemical Properties
- Off-white Cryst
- 9.4 Uses
- suzuki reaction
10. Computational chemical data
- Molecular Weight: 135.957g/mol
- Molecular Formula: C7H9BO2
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 136.0695597
- Monoisotopic Mass: 136.0695597
- Complexity: 106
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 40.5
- Heavy Atom Count: 10
- 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: AAADccJgMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAoGAAACAAADACAGAAyAIAAAACAAiBCAAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAgAAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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12. Realated Product Infomation
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