5-Acetylsalicylamide Struktur

5-Acetylsalicylamid

Bezeichnung:5-Acetylsalicylamid

CAS-Nr40187-51-7

Englisch Name:5-Acetylsalicylamide

CBNumberCB1472008

SummenformelC9H9NO3

Molgewicht179.17

MOL-Datei40187-51-7.mol

Synonyma

5-Acetylsalicylamid

5-Acetylsalicylamid physikalisch-chemischer Eigenschaften

Schmelzpunkt	220-222 °C(lit.)
Siedepunkt	311.69°C (rough estimate)
Dichte	1.2822 (rough estimate)
Brechungsindex	1.5600 (estimate)
storage temp.	Sealed in dry,Room Temperature
Löslichkeit	DMSO (Slightly), Methanol (Slightly)
Aggregatzustand	Solid
pka	6.57±0.18(Predicted)
Farbe	White to Light Brown
InChI	InChI=1S/C9H9NO3/c1-5(11)6-2-3-8(12)7(4-6)9(10)13/h2-4,12H,1H3,(H2,10,13)
InChIKey	LWAQTCWTCCNHJR-UHFFFAOYSA-N
SMILES	C(N)(=O)C1=CC(C(C)=O)=CC=C1O
CAS Datenbank	40187-51-7(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-36/37/38-22
S-Sätze:	26-36-37/39
WGK Germany	3
RTECS-Nr.	CU8702280
HS Code	2924.29.7790

Gefahreninformationscode (GHS)

5-Acetylsalicylamide 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.
R22:Gesundheitsschädlich beim Verschlucken.
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.
S37/39:Bei der Arbeit geeignete Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
cream to beige powder
Verwenden
5-Acetylsalicylamide is used as a reagent in the synthesis of Phosphotyrosine(P365000) peptidomimetic prodrugs, compounds that have similar structure to small protein-like chains in order to mimic peptide activities. 5-Acetylsalicylamide is also used as a reagent to prepare 4-aminopiperidine ureas, compounds that act as human β3 adrenergic receptor agonists.
Synthese

75-36-5

65-45-2

40187-51-7

1) Preparation of NaCl-AlCl3 low melting point mixed molten salt system: assemble a mechanical stirrer, condenser tube (connected to the tail gas HCl absorption device), 0~200°C thermometer and constant pressure dropping funnel in a 100 ml three-neck flask. The device was placed in a constant temperature oil bath. Quickly weigh 0.0648 mol (~8.64 g) of anhydrous aluminum chloride and 0.0648 mol (~3.79 g) of sodium chloride into the flask, turn on the mechanical stirring, and heat to 140°C until the solids are completely melted and the temperature is stable. Note: After about 25 minutes, the anhydrous aluminum chloride and sodium chloride should be in a molten state. 2) With stirring, weigh 0.036 mol (about 5.00 g) of salicylamide into a flask that has been heated to 140°C and allowed to melt, keeping the temperature in the flask stable. 3) Weigh 0.0432 mol (about 3.39 g) of acetyl chloride and add it slowly dropwise through a constant pressure dropping funnel into the reaction system for about 10 minutes. The reaction temperature was maintained at 140 °C and continued for 0.5 h to ensure complete reaction. The reaction was carried out in a NaCl-AlCl3 low melting point mixed molten salt system. 4) Immediately after completion of the reaction, 60 mL of acidic solution (consisting of 1 mL of concentrated hydrochloric acid and 59 mL of ice-water mixture) was added slowly (uniformly over about 5 min) to the system, at which time a yellowish solid was produced. After adding the acidic solution, continue stirring at room temperature for 30 minutes until no more yellowish solids are generated to obtain the suspension. 5) The suspension was filtered, the light yellow solid was collected, washed three times (5 mL each time) with hot water at 80°C, and then dried at 80°C for 5 hours to obtain the crude product. 6) The crude product was dissolved in 20 mL of ethanol and heated to reflux temperature to dissolve it completely. Subsequently, recrystallization was carried out in an ice bath, and the precipitated crystals were filtered and dried at 80 °C for 5 h. The final product was 5-acetyl-2-hydroxybenzamide as a white solid (purity ≥98.1%) in 92.2% yield.
Einzelnachweise
[1] Heterocyclic Communications, 2013, vol. 19, # 1, p. 23 - 28
[2] Patent: CN104557604, 2017, B. Location in patent: Paragraph 0039; 0040; 0041; 0042; 0043-0057; 0068-0075
[3] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1952, vol. 234, p. 1058

5-Acetylsalicylamide Upstream-Materialien And Downstream Produkte

5-Acetylsalicylamid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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