| Identification | More | [Name]
4-(Hydroxymethyl)phenylboronic acid | [CAS]
59016-93-2 | [Synonyms]
4-(HYDROXYMETHYL)BENZENEBORONIC ACID
4-(HYDROXYMETHYL)PHENYLBORONIC ACID
AKOS BRN-0115
RARECHEM AH PB 0190
4-(Hydroxymethyl)Phenylboronic
(4-Boronophenyl)methanol
4-Boronobenzyl alcohol
4-(Hydroxymethyl)phenylboronic Acid (contains varying amounts of Anhydride)
4-(Hydroxymethyl pPhenylboronic Acid
4-(Hydroxylmethyl)phenylboronic acid | [Molecular Formula]
C7H9BO3 | [MDL Number]
MFCD00792672 | [Molecular Weight]
151.96 | [MOL File]
59016-93-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Off-white Cryst | [Melting point ]
251-256 °C (lit.) | [Boiling point ]
362.0±44.0 °C(Predicted) | [density ]
1.25±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator (+4°C) | [form ]
Crystalline Powder | [pka]
8.53±0.10(Predicted) | [color ]
White to slightly yellow | [PH]
4.5 (10g/l, H2O) | [Water Solubility ]
25 g/L | [BRN ]
2831413 | [InChI]
InChI=1S/C7H9BO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,9-11H,5H2 | [InChIKey]
PZRPBPMLSSNFOM-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C(CO)C=C1)(O)O | [CAS DataBase Reference]
59016-93-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white Cryst | [Uses]
Reactant involved in the synthesis of biologically active compounds including:
- Imidazo[4,5-b]pyrazin-2-ones for use as mTOR kinase inhibitors
- Human immunodificiency virus protease inhibitors with activity against resistant viruses
Reactant involved in:
- Suzuki coupling reactions
- Copper-catalyzed transformation from arylboronic acids in water
Involved in the synthesis of polyurethane containing spindle-type chromophores | [Uses]
suzuki reaction | [Synthesis]
Sodium borohydride (0.38 g, 11 mmol) was added to a solution of (4-formylphenyl)boronic acid (1.5 g, 11 mmol) in methanol (40 mL) in batches at 0 °C, keeping the temperature at 0 °C and stirring the reaction mixture for 1 hour. Upon completion of the reaction, the mixture was concentrated under reduced pressure to remove the solvent to give the crude product. The crude product was dissolved in water, cooled to 0-5 °C, and the pH was adjusted to 5 by slowly adding 5% aqueous acetic acid.The precipitated solid was collected by diafiltration and washed with cold water, and dried to give 4-hydroxymethylphenylboronic acid (1.2 g, 80% yield). The product was characterized by 1H NMR (400 MHz, CD3OD): δ 7.72 (d, J=7.2 Hz, 2H), 7.59 (d, J=7.6 Hz, 2H), 7.35-7.30 (m, 2H), 4.60 (s, 2H); Mass Spectrometry (ES+): m/z 542.15,544.35 [M+H]; LCMS retention time: tR = 2.42 min. | [References]
[1] Patent: WO2015/81280, 2015, A1. Location in patent: Paragraph 00689; 00698; 00699
[2] Patent: US5827887, 1998, A
[3] Dyes and Pigments, 2012, vol. 92, # 3, p. 982 - 987
[4] Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5781 - 5788
[5] Patent: US6576789, 2003, B1 |
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