3-Carboxy-5-nitrophenylboronic acid

Bezeichnung:3-Carboxy-5-nitrophenylboronic acid

CAS-Nr101084-81-5

Englisch Name:3-Carboxy-5-nitrophenylboronic acid

CBNumberCB1431069

SummenformelC7H6BNO6

Molgewicht210.94

MOL-Datei101084-81-5.mol

3-Carboxy-5-nitrophenylboronic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	229°C(lit.)
Siedepunkt	502.6±60.0 °C(Predicted)
Dichte	1.62±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Sealed in dry,Room Temperature
Aggregatzustand	powder to crystal
pka	3.49±0.10(Predicted)
Farbe	White to Light yellow
InChI	1S/C7H6BNO6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3,12-13H,(H,10,11)
InChIKey	WNIFCLWDGNHGMX-UHFFFAOYSA-N
SMILES	OB(O)c1cc(cc(c1)[N+]([O-])=O)C(O)=O
CAS Datenbank	101084-81-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xi,Xn
R-Sätze:	20/21/22-36/37/38
S-Sätze:	26-36
WGK Germany	3
HazardClass	IRRITANT
HS Code	29319090
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

3-Carboxy-5-nitrophenylboronic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
White solid
Verwenden
Reactant for:
- Copper-catalyzed chlorination
- Parallel solid-phase synthesis of azabicyclooctylidenemethylbenzamides as μ- and d-opioid agonists
Used for:
- Immobilization of glucose oxidase and acetylcholinesterase on boronic acid-activated silica surfaces
Verwenden
suzuki reaction
Synthese

25487-66-5

101084-81-5

The general procedure for the synthesis of 3-carboxy-5-nitrophenylboronic acid from 3-carboxyphenylboronic acid is as follows: first, 7.5 g of 3-carboxyphenylboronic acid (45.2 mmol) was mixed with 25 ml of concentrated sulphuric acid, and 25 ml of fuming nitric acid was slowly added under rapid stirring conditions while cooling using an ice water bath. The reaction mixture was stirred for 15 min, then the ice water bath was removed and the reaction continued to be stirred for 15 min. Subsequently, the reaction solution was poured into ice water to produce a precipitate, which was filtered and then the precipitate was washed with ice water for 5 times, and finally 6.01 g of 3-nitro-5-carboxyphenylboronic acid as a white solid was obtained by aqueous recrystallization in 63.0% yield. Next, 1.50 g of 3-carboxy-5-nitrophenylboronic acid (7.1 mmol) was dissolved in 20 ml of methanol, and 2 g of 10% Pd/C catalyst was added in a 50 ml three-necked flask for a catalytic hydrogenolysis reaction for 6 hours. After completion of the reaction, the Pd/C catalyst was removed by filtration and the filtrate was evaporated to dryness to give 1.25 g of 3-amino-5-carboxyphenylboronic acid as a white powdery solid in 97.1% yield.
Einzelnachweise
[1] Patent: CN103497211, 2016, B. Location in patent: Paragraph 0190
[2] Organic Preparations and Procedures International, 1991, vol. 23, # 6, p. 729 - 734
[3] Journal of the American Chemical Society, 1959, vol. 81, p. 3017
[4] Arkiv foer Kemi, 1957, vol. 10, p. 497,503

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3-Carboxy-5-nitrophenylboronic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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