| Identification | More | [Name]
3,4-METHYLENEDIOXYPHENYLBORONIC ACID | [CAS]
94839-07-3 | [Synonyms]
1,3-BENZODIOXOL-5-YLBORONIC ACID
3,4-METHYLENEDIOXYBENZENEBORONIC ACID
3,4-METHYLENEDIOXYPHENYLBORONIC ACID
BENZO[D][1,3]DIOXOL-5-YLBORONIC ACID
RARECHEM AH PB 0145
TIMTEC-BB SBB003898
1,3-Benzodioxole-5-boronic acid
3,4-Methylenedioxyphenylboroni
3,4-Methylenedioxyphenylboronic acid ,98%
3,4-(Methylenedioxy)phenylboronic Acid (contains varying amounts of Anhydride) | [EINECS(EC#)]
672-307-3 | [Molecular Formula]
C7H7BO4 | [MDL Number]
MFCD01009695 | [Molecular Weight]
165.94 | [MOL File]
94839-07-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White powder | [Melting point ]
224-229 °C(lit.)
| [Boiling point ]
347.3±52.0 °C(Predicted) | [density ]
1.42±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [form ]
Powder | [pka]
8.48±0.20(Predicted) | [color ]
White to off-white | [Detection Methods]
HPLC | [BRN ]
5523347 | [InChI]
InChI=1S/C7H7BO4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3,9-10H,4H2 | [InChIKey]
CMHPUBKZZPSUIQ-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C2OCOC2=C1)(O)O | [CAS DataBase Reference]
94839-07-3(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 . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [Chemical Properties]
3,4-METHYLENEDIOXYPHENYLBORONIC ACID is white powder
| [Uses]
Reactant involved in:• ;Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids1• ;Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scafford2• ;Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides3,4• ;Oxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivatives5• ;Intramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine6 | [Uses]
suzuki reaction | [Synthesis]
General procedure for the synthesis of benzo[d][1,3]dioxol-5-ylboronic acid from 4-bromo-1,2-methylenedioxybenzene and triisopropyl borate: In a 100 mL three-necked round-bottomed flask under nitrogen protection, 5-bromobenzo[d][1,3]dioxolene (2 g, 9.95 mmol, 1.00 eq.) and THF (20 mL) were added, and the flask was cooled to -78 °C. Butyl lithium (BuLi, 5.6 mL, 1.40 eq.) was slowly added dropwise, followed by triisopropyl borate (1.96 g, 14.00 mmol). The reaction mixture was stirred at -78 °C for 1 hour and then slowly warmed to room temperature and continued stirring for 4 hours. Upon completion of the reaction, the reaction was quenched with 10 mL of water and acidified with sulfuric acid (4.9 g, 50.00 mmol, 5.00 equiv). The mixture was heated to reflux overnight. After cooling, it was extracted with ethyl acetate (3 x 50 mL), the organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with ethyl acetate (3 x 3 mL) to give 0.5 g (30% yield) of benzo[d][1,3]dioxol-5-ylboronic acid as a white solid. | [References]
[1] Patent: US2014/128392, 2014, A1. Location in patent: Paragraph 0311; 0312 |
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