4-(Indol-3-yl)buttersäure

Bezeichnung:4-(Indol-3-yl)buttersäure

CAS-Nr133-32-4

Englisch Name:Indole-3-butyric acid

CBNumberCB3286999

SummenformelC12H13NO2

Molgewicht203.24

MOL-Datei133-32-4.mol

Synonyma

4-(Indol-3-yl)buttersure

4-(Indol-3-yl)buttersäure

4-(Indol-3-yl)buttersäure physikalisch-chemischer Eigenschaften

Schmelzpunkt	124-125.5 °C(lit.)
Siedepunkt	341.55°C (rough estimate)
Dichte	1.1255 (rough estimate)
chüttdichte	360kg/m3
Brechungsindex	1.5440 (estimate)
storage temp.	2-8°C
Löslichkeit	DMF: 25 mg/mL; DMSO: 25 mg/mL; Ethanol: 25 mg/mL; PBS (pH 7.2): 0.1 mg/mL
pka	4.83±0.10(Predicted)
Aggregatzustand	Liquid
Farbe	Clear colorless to pale yellow
Wasserlöslichkeit	Soluble in water(0.25g/L).
Sensitive	Air Sensitive
Merck	14,4965
BRN	171120
Stabilität	Stable. Incompatible with strong oxidizing agents. Light sensitive.
InChIKey	JTEDVYBZBROSJT-UHFFFAOYSA-N
LogP	2.300
CAS Datenbank	133-32-4(CAS DataBase Reference)
EPA chemische Informationen	Indole-3-butyric acid (133-32-4)

Sicherheit

Kennzeichnung gefährlicher	T,Xi
R-Sätze:	25-36/37/38
S-Sätze:	26-36-45-38-36/37/39-28A
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	NL5250000
F	8-10-23
Hazard Note	Irritant
TSCA	T
HazardClass	6.1
PackingGroup	III
HS Code	29339990
Giftige Stoffe Daten	133-32-4(Hazardous Substances Data)
Toxizität	LD50 i.p. in mice: 100 mg/kg (Anderson)

Gefahreninformationscode (GHS)

Indole-3-butyric acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
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.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
S38:Bei unzureichender Belüftung Atemschutzgerät anlegen.
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
Chemische Eigenschaften
Indole-3-butyric acid (IBA) is a white to light yellow powder or crystalline solid with a slight characteristic odor. It is practically insoluble in chloroform, but is soluble in alcohol, ether and acetone. The solubility of IBA in water is 250 mg L-1 (EPA, 2010).
Verwenden
Used to stimulate root formation of plant clippings. Suitable for plant cell culture tested.
Verwenden
Indole-3-butyric acid is auxin-family plant hormone (phytohormone). IBA is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.
Definition
ChEBI: Indole-3-butyric acid is a indol-3-yl carboxylic acid that is butanoic acid carrying a 1H-indol-3-yl substituent at position 1. It has a role as a plant hormone, a plant metabolite and an auxin. It derives from a butyric acid. It is a conjugate acid of an indole-3-butyrate.
Allgemeine Beschreibung
Indole-3-butyric acid is a plant hormone in the auxin family and is widely used in agriculture since it induces rooting in various plants species such as mung bean (Vigna radiata?L.) cuttings.
Biochem/physiol Actions
Indole-3-butyric acid (IBA) is a naturally occurring phytohormone auxin (plant growth regulator). It promotes root formation in cuttings but does not affect ethylene levels. IBA might be a precursor for indole-3-acetic acid (IAA) through β oxidation pathway. IBA is present in plant species like Zea mays, Pisum sativum and Arabidopsis. IBA is more potent than IAA for inducing root formation.
Synthese

96-48-0

120-72-9

133-32-4

Indole (11.7 g), γ-butyrolactone (11.2 g), tetrahydronaphthalene (58.5 g), polyethylene glycol (loading 17% of hydrazine) and Na-NaOH/γ-Al2O3 (loading 5% of hydrazine) were added sequentially to the reactor. A stirrer was activated and the reaction was stirred for 30 min at room temperature to mix the reactants homogeneously. Subsequently, the reaction system was heated to 210 °C for reflux reaction. After 5 hours of reaction, the heating was stopped and the solid catalyst was removed by filtration. The filtrate was cooled, the organic layer was separated and acidified with hydrochloric acid to obtain an off-white solid. After filtration, washing with water and drying, 3-indolebutyric acid (18.2 g) was obtained. The above reaction conditions were repeated using the recovered catalyst to catalyze the reaction of indole and γ-butyrolactone to give 3-indolebutyric acid (17.7 g).
läuterung methode
Recrystallise the acid from H2O. It is soluble in EtOH, Et2O and Me2CO but insoluble in CHCl3. [Bowman & Islip Chem Ind London 154 1971, Jackson & Manske J Am Chem Soc 52 5029 1930, Albaum & Kaiser Am J Bot 24 420 1937.] It has also been recrystallised from EtOH/water [James & Ware J Phys Chem 89 5450 1985]. Its UV has 278 and 320nm in isoPrOH [Elvidge Quart J Pharm Pharmacol 13 219 1940].max The methyl ester has m 73-74o (from *C6H6/pet ether) and b 230o/6mm [Bullock & Hand J Am Chem Soc 78 5854 1951]. [Beilstein 22 III/IV 1128, 22/3 V 140.]
Einzelnachweise
[1] Patent: CN108440371, 2018, A. Location in patent: Paragraph 0027-0028; 0029; 0031-0032; 0035-0036; 0039-0040

Indole-3-butyric acid Upstream-Materialien And Downstream Produkte

4-(Indol-3-yl)buttersäure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

133-32-4, Indole-3-butyric acid Verwandte Suche:

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