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

A14427 Indole, 99%

CAS Number
120-72-9
Synonyms

Size Price ($) Quantity Availability
50g 30.90
250g 118.45
1000g 348.94
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Indole, 99%

MDL
MFCD00005607
EINECS
204-420-7

Chemical Properties

Formula
C8H7N
Formula Weight
117.15
Melting point
50-54°
Boiling Point
253-254°
Flash Point
121°(249°F)
Density
1.220
Sensitivity
Light Sensitive
Solubility
Soluble in methanol and water.

Applications

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.

Notes

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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H311-H302-H318-H400

Toxic in contact with skin. Harmful if swallowed. Causes serious eye damage. Very toxic to aquatic life.

Precautionary Statements: P273-P280-P305+P351+P338-P361-P310-P301+P312-P312-P363-P405-P501a

Avoid release to the environment. 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. Remove/Take off immediately all contaminated clothing. Immediately call a POISON CENTER or doctor/physician. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,4963
Beilstein
107693
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2933.99
TSCA
Yes
RTECS
NL2450000

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