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Cas Database |
| Name |
1-Naphthaleneboronic acid |
EINECS | 604-119-4 |
| CAS No. | 13922-41-3 | Density | 1.21 g/cm3 |
| PSA | 40.46000 | LogP | 0.51960 |
| Solubility | 2.5 g/100 mL in water | Melting Point |
208-214 °C(lit.) |
| Formula | C10H9BO2 | Boiling Point | 381.9 °C at 760 mmHg |
| Molecular Weight | 171.991 | Flash Point | 184.8 °C |
| Transport Information | N/A | Appearance | Off-white to pink beige powder |
| Safety | 26-36-37/39 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| Synonyms |
NSC78936;a-Naphthaleneboronic acid;a-Naphthylboronic acid;1-Naphthylboric acid;1-Naphthaleneboronicacid (6CI,7CI,8CI);Boronic acid, 1-naphthalenyl- (9CI);(1-Naphthalenyl)boronic acid; |
Article Data | 65 |
1-Naphthaleneboronic acid Synthetic route
- 90-11-9
1-Bromonaphthalene
- 13922-41-3
1-Naphthylboronic acid
| Conditions | Yield |
|---|---|
| Stage #1: 1-Bromonaphthalene With tert.-butyl lithium In tetrahydrofuran at 78℃; for 0.75h; Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 4h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; ethyl acetate at 20℃; | 96% |
| Stage #1: 1-Bromonaphthalene With diisobutylaluminium hydride; magnesium; lithium chloride In tetrahydrofuran; toluene at 20℃; for 15h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran; toluene at 0℃; Inert atmosphere; Stage #3: With hydrogenchloride; water In tetrahydrofuran; toluene at 0℃; Inert atmosphere; | 86% |
| Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran for 2h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water | 74% |
| Conditions | Yield |
|---|---|
| Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 12h; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 0.5h; Inert atmosphere; | 84% |
| With n-butyllithium In tetrahydrofuran N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10% HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal; | |
| Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Schlenk technique; Stage #2: Trimethyl borate In tetrahydrofuran; hexane at 20℃; Schlenk technique; |
| Conditions | Yield |
|---|---|
| Stage #1: Triisopropyl borate; 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene at 20℃; for 1h; | 83% |
| With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere; | 83% |
| With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere; | 83% |
| Conditions | Yield |
|---|---|
| Stage #1: Triisopropyl borate; 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran; hexane; toluene at 20℃; for 1h; | 83% |
| Conditions | Yield |
|---|---|
| Stage #1: tri-n-propyl borate; 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane; toluene at -30 - 20℃; for 6h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene at 20℃; for 1h; | 83% |
- 67-56-1
methanol
- 131765-96-3
dicyclohexylamine borane complex
- 90-11-9
1-Bromonaphthalene
- 13922-41-3
1-Naphthylboronic acid
| Conditions | Yield |
|---|---|
| Stage #1: dicyclohexylamine borane complex; 1-Bromonaphthalene With magnesium In tetrahydrofuran at 70℃; Stage #2: methanol In tetrahydrofuran at 0℃; for 1h; Stage #3: With hydrogenchloride; water In methanol at 20℃; for 1h; | 82% |
- 67-56-1
methanol
- 55124-35-1
diisopropylamine borane
- 90-11-9
1-Bromonaphthalene
- 13922-41-3
1-Naphthylboronic acid
| Conditions | Yield |
|---|---|
| Stage #1: diisopropylamine borane With magnesium; phenylmagnesium bromide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 1-Bromonaphthalene In tetrahydrofuran at 70℃; Stage #3: methanol Further stages; | 80% |
| Conditions | Yield |
|---|---|
| Stage #1: diisopropopylaminoborane With iodine; magnesium at 25℃; Barbier Coupling Reaction; Reflux; Inert atmosphere; Stage #2: 1-Bromonaphthalene at 65℃; for 4.083h; Stage #3: With hydrogenchloride In water at 25 - 65℃; for 0.416667h; | A n/a B 79% |
- 90-11-9
1-Bromonaphthalene
- 22092-92-8
diisopropopylaminoborane
- 7732-18-5
water
- 13922-41-3
1-Naphthylboronic acid
| Conditions | Yield |
|---|---|
| Stage #1: 1-Bromonaphthalene; diisopropopylaminoborane With magnesium In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Stage #2: water With hydrogenchloride In tetrahydrofuran at 65℃; for 0.25h; Barbier Coupling Reaction; Inert atmosphere; | 79% |
| Conditions | Yield |
|---|---|
| With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate In toluene at 110 - 120℃; Inert atmosphere; | 76.3% |
1-Naphthaleneboronic acid Specification
The 1-Naphthaleneboronic acid is an organic compound with the formula C10H9BO2. The IUPAC name of this chemical is naphthalen-1-ylboronic acid. With the CAS registry number 13922-41-3, it is also named as Boronic acid, B-1-naphthalenyl-. The product's categories are Blocks; Boronic Acids; Boronic Acid Series; Naphthalene Derivatives; Heterocyclic Compounds; Naphthalene; Organoborons; B (Classes of Boron Compounds). It is off-white to pink beige powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container, kept away from light and stored in thewell-ventilated and dry place.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.82; (2)# of Rule of 5 Violations: 0; (3)#H bond acceptors: 2; (4)#H bond donors: 2; (5)#Freely Rotating Bonds: 3; (6)Polar Surface Area: 18.46 Å2; (7)Index of Refraction: 1.638; (8)Molar Refractivity: 50.84 cm3; (9)Molar Volume: 141.3 cm3; (10)Polarizability: 20.15×10-24 cm3; (11)Surface Tension: 50.4 dyne/cm; (12)Density: 1.21 g/cm3; (13)Flash Point: 184.8 °C; (14)Enthalpy of Vaporization: 66.48 kJ/mol; (15)Boiling Point: 381.9 °C at 760 mmHg; (16)Vapour Pressure: 1.63E-06 mmHg at 25°C.
Preparation of 1-Naphthaleneboronic acid: It can be obtained by tributyl-naphthalen-1-yl-stannane. This reaction needs reagents BH3, H2O and solvent tetrahydrofuran by heating. The reaction time is 4 hours. The yield is 68%.
Uses of 1-Naphthaleneboronic acid: It is used as pharmaceutical intermediate. And it can react with 4-iodo-3,5-dimethyl-isoxazole to get 4-(1-naphthyl)-3,5-dimethylisoxazole. This reaction needs reagents (PPh3)2PdCl2, NaHCO3 and solvents 1,2-dimethoxy-ethane, H2O at temperature of 80 °C. The reaction time is 18 hours. The yield is 75%.
When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.
People can use the following data to convert to the molecule structure.
1. SMILES:OB(O)c2cccc1ccccc12
2. InChI:InChI=1/C10H9BO2/c12-11(13)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,12-13H
3. InChIKey:HUMMCEUVDBVXTQ-UHFFFAOYAQ
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