Methyl-3,5-dihydroxybenzoat

Bezeichnung:Methyl-3,5-dihydroxybenzoat

CAS-Nr2150-44-9

Englisch Name:Methyl 3,5-dihydroxybenzoate

CBNumberCB8192187

SummenformelC8H8O4

Molgewicht168.15

MOL-Datei2150-44-9.mol

Synonyma

Methyl-3,5-dihydroxybenzoat

Methyl-3,5-dihydroxybenzoat physikalisch-chemischer Eigenschaften

Schmelzpunkt	167-170 °C (lit.)
Siedepunkt	257.07°C (rough estimate)
Dichte	1.3037 (rough estimate)
Brechungsindex	1.5090 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	Acetone (Slightly), Methanol (Slightly)
pka	8.63±0.10(Predicted)
Aggregatzustand	Fine Crystalline Powder
Farbe	Slightly yellow to beige
Wasserlöslichkeit	Slightly soluble in water.
BRN	2091651
InChI	InChI=1S/C8H8O4/c1-12-8(11)5-2-6(9)4-7(10)3-5/h2-4,9-10H,1H3
InChIKey	RNVFYQUEEMZKLR-UHFFFAOYSA-N
SMILES	C(OC)(=O)C1=CC(O)=CC(O)=C1
CAS Datenbank	2150-44-9(CAS DataBase Reference)
EPA chemische Informationen	Benzoic acid, 3,5-dihydroxy-, methyl ester (2150-44-9)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38
S-Sätze:	26-37/39-24/25
WGK Germany	3
Hazard Note	Irritant
TSCA	TSCA listed
HS Code	29182900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

Methyl 3,5-dihydroxybenzoate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
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.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
slightly yellow to beige fine crystalline powder
Verwenden
The methyl ester of 3,5-Dihydroxybenzoic Acid (D451700) with potential antifeedant activity for pine weevil, Hylobius abietis.
Verwenden
Methyl 3,5-dihydroxybenzoate was used in the synthesis of cored dendrimers. It was also used in the preparation of bis(5-carbomethoxy-1,3-phenylene)-32-crown-10, a semi-rigid 32-membered ring diester crown ether.
Allgemeine Beschreibung
Ribonucleotide reductase inhibiton and antiumor activity of methyl 3,5-dihydroxybenzoate has been studied.
Synthese

67-56-1

99-10-5

2150-44-9

Methyl 3,5-dihydroxybenzoate was synthesized from methanol and 3,5-dihydroxybenzoic acid using the method described by Brouwer et al. The method was adapted for the metathesis synthesis of amino acid-based dendritic polymers, aiming at obtaining dendritic macromolecules with alkyne groups on the surface for 1,3-dipolar cycloaddition ("click") reactions with amino acid/peptide-derived azides. This was done as follows: first, 3,5-dihydroxymethylbenzoate (21.4 g, 130 mmol) was dissolved in anhydrous DMF (250 mL), followed by the addition of anhydrous K2CO3 (45 g, 330 mmol, 2.5 eq.). A toluene solution of propargyl bromide (35 mL, 314 mmol, 2.5 eq.) was added slowly and dropwise to this suspension. The reaction mixture was stirred continuously for 48 hours at room temperature. Upon completion of the reaction, DMF was removed by evaporation and the residue was redissolved in EtOAc (400 mL). The organic phase was washed sequentially with H2O (3 × 100 mL), KHSO4 (3 × 100 mL) and brine (3 × 100 mL), after which it was dried with Na2SO4 and evaporated under vacuum. The residue was recrystallized by EtOAc/hexane to afford the target product 1 as off-white crystals in 81% yield (25.2 g). The product was characterized by thin layer chromatography (TLC) and nuclear magnetic resonance (NMR): Rf (EtOAc/hexane 4:1 v/v): 0.76; Rf (DMC/MeOH 98:2 v/v): 0.87; Rf (CHCl3/MeOH/AcOH 95:20:3 v/v): 0.83; 1H-NMR (CDCl3) δ 2.55 (t, J=2.47Hz, 2H), 3.91 (s, 3H), 4.72 (d, J=2.47Hz, 4H), 6.81 (t, J=2.20Hz, 1H), 7.29 (d, J=2.20Hz, 2H); 13C-NMR (CDCl3) δ 52.4, 56.0, 76.0, 77.9, 107.5, 108.8, 132.0, 157.8, 158.4; elemental analysis results: C14H12O4, calculated value C 68.83, H 4.95, measured value C 68.76, H 4.95.
Einzelnachweise
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 2825 - 2829
[2] Chemistry Letters, 1999, # 11, p. 1193 - 1194
[3] Chemical Communications, 2005, # 36, p. 4581 - 4583
[4] Patent: EP1733742, 2006, A1. Location in patent: Page/Page column 5-6; 12
[5] Journal of the American Chemical Society, 2007, vol. 129, # 10, p. 2774 - 2776

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