| Identification | More | [Name]
3-Dimethylaminophenylboronic acid | [CAS]
178752-79-9 | [Synonyms]
3-(DIMETHYLAMINO)BENZENEBORONIC ACID
3-(DIMETHYLAMINO)PHENYLBORONIC ACID
3-DIMETHYLAMINOPHENYLBORONIC ACID HCL
3-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID
AKOS BRN-0450
3-(Dimethylamino)Phenylboronic
3-Dimethylaminophenylboronic acid hydrochloride | [Molecular Formula]
C8H12BNO2 | [MDL Number]
MFCD04112542 | [Molecular Weight]
165 | [MOL File]
178752-79-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Solid | [Melting point ]
191-193°C | [Boiling point ]
344.0±44.0 °C(Predicted) | [density ]
1.12±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
8.54±0.10(Predicted) | [color ]
Pale Green to Pale Grey | [InChI]
InChI=1S/C8H12BNO2/c1-10(2)8-5-3-4-7(6-8)9(11)12/h3-6,11-12H,1-2H3 | [InChIKey]
YZQQHZXHCXAJAV-UHFFFAOYSA-N | [SMILES]
B(C1=CC=CC(N(C)C)=C1)(O)O | [CAS DataBase Reference]
178752-79-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 3335 | [WGK Germany ]
3 | [HazardClass ]
IRRITANT | [HS Code ]
29319090 |
| Hazard Information | Back Directory | [Chemical Properties]
Solid | [Uses]
Reactant involved in synthesis of different protein effector including:
- Modulators of survival motor neuron protein
- Glucokinase activators
- Aryl ethers for use as Bacillus anthracis enoyl-ACP reductase inhibitors
Reactant involved in synthesis of:
- Thiourea-functionalized paracyclophanes
- Low-background fluorescent imaging agents for nitric oxide
Reactant to undergo regioselective iodination and bromination | [General Description]
May contain varying amounts of anhydride | [Synthesis]
The general procedure for the synthesis of 3-(N,N-dimethylamino)phenylboronic acid from 3-bromo-N,N-dimethylaniline was as follows: 3-bromo-N,N-dimethylaniline (500 mg, 2.50 mmol) was dissolved in tetrahydrofuran (THF, 8 mL) and the solution was cooled to -78 °C. At -78 °C, n-butyllithium (1.6 M in hexane, 1.56 mL, 3.75 mmol) was slowly added dropwise, and after the drop was completed, the reaction mixture continued to be stirred for 5 min by maintaining this temperature. Subsequently, trimethyl borate (1.11 mL, 10.0 mmol) was added and stirred at -78 °C for 1 h, followed by a slow warming to -20 °C over 20 min. 2 M hydrochloric acid (3 mL) was added and after stirring for 5 min, the reaction mixture was neutralized with saturated sodium bicarbonate (NaHCO3) solution. The mixture was extracted with ethyl acetate (3 × 10 mL), the organic phases were combined, and the crude product was concentrated under reduced pressure. Purification by silica gel fast column chromatography with acetone/dichloromethane (1:1, v/v) as eluent gave the target product 3-(N,N-dimethylamino)phenylboronic acid (251 mg, 61% yield). | [References]
[1] Patent: US2006/270686, 2006, A1. Location in patent: Page/Page column 26
[2] Patent: WO2008/8059, 2008, A1. Location in patent: Page/Page column 68
[3] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673
[4] Organic Letters, 2012, vol. 14, # 18, p. 4814 - 4817,4 |
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