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120-72-9 - Indole, 99% - A14427 - Alfa Aesar

A14427 Indole, 99%

Número CAS
120-72-9
Nombre Alternativo

Tamaño Precio ($) Cantidad Disponibilidad
50g 31,00
250g 116,00
1000g 388,00
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Indole, 99%

MDL
MFCD00005607
EINECS
204-420-7

Propiedades químicas

Fórmula
C8H7N
Peso molecular
117.15
Punto de fusión
50-54°
Punto de ebullición
253-254°
Punto de inflamabilidad
121°(249°F)
Densidad
1.220
Sensibilidad
Light Sensitive
Solubilidad
Soluble in methanol and water.

Aplicaciones

Indole is used in the preparation of gramine, which is obtained by Mannich reaction dimethylamine and formaldehyde. It is used as a starting material for the preparation of oxindole and indole-3-carboxaldehyde. In Diels-Alder reaction, it acts as dienophile and reacts with 2-aminofuran to get strychnine. It is the active component of jasmine oil, neroli oil and orange-blossom oil used in the perfume industry. Further, it is involved in the preparation of synthetic jasmine oil.

Notas

Light and air sensitive. Store in a cool place. Incompatible with strong oxidizing agents, iron and iron salts. Keep the container tightly closed in a dry and well-ventilated place.

Referencias documentales

Lithiation of N-protected indoles usually occurs at the 2-position, e.g. benzenesulfonation of the 1-lithio derivative, 2-lithiation with LDA and treatment with pyridine-3,4-dicarboxylic anhydride. This sequence has been reported in a synthetic route to ellipticene and olivacine: J. Org. Chem., 57, 5891 (1992).

Regioselective synthesis of 3-substituted indoles has been described using a sequence of N-silylation, 3-bromination of the 1-TBDMS detivative with NBS, 3-lithiation, treatment with an electrophile to introduce the 3-substituent, and desilylation with TBAF. Good overall yields are obtained for a range of electrophiles: J. Org. Chem., 59, 10 (1994); Org. Synth. Coll., 9, 417 (1998).

Treatment with EtMgI followed by ZnCl2 leads to an N-zinc derivative. This undergoes acylation at the 3-position: Tetrahedron, 46, 6061 (1990).

Halogenation in the 2-position has been effected via the Li 1-carbamate and subsequent 2-lithiation: J. Org. Chem., 57, 2495 (1992):

Treatment of the carbamate with Tri-n-butyl­tin chloride, A10746, followed by Stille coupling enables synthesis of 2-aryl- and 2-vinylindoles: J. Org. Chem., 60, 6218 (1995).

Johnston, A. J.; Zhang, Y. R.; Busch, S.; Pardo, L. C.; Imberti, S.; McLain, S. E. Amphipathic Solvation of Indole: Implications for the Role of Tryptophan in Membrane Proteins. J. Phys. Chem. B 2015, 119 (19), 5979-5987.

Yang, P.; Pang, M.; Shen, W.; Li, M.; He, R. Vibronic analysis of the 1Lb ? S0 transitions of indole and 3-methylindole: The influence of anharmonic, Duschinsky, and Herzberg-Teller contributions. J. Mol. Spectrosc. 2015, 313, 40-48.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H302-H311-H318

Harmful if swallowed. Toxic in contact with skin. Causes serious eye damage.

Indicaciones de precaución: P280-P305+P351+P338-P310a-P301+P312a-P405-P501a

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Merck
14,4963
Beilstein
107693
Clase de peligro
6.1
Grupo de embalaje
III
Código de tarifa arancelaria unificado
2933.99
TSCA
Yes
RTECS
NL2450000

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