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Indole, 99%, Thermo Scientific Chemicals
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Catalog number A14427.0B
also known as A14427-0B
Price (USD)/ Each
463.65
Online exclusive
515.00 Save 51.35 (10%)
-
Quantity:
1000 g
Price (USD)/ Each
463.65
Online exclusive
515.00 Save 51.35 (10%)
Indole, 99%, Thermo Scientific Chemicals
Catalog numberA14427.0B
Price (USD)/ Each
463.65
Online exclusive
515.00 Save 51.35 (10%)
-
Chemical Identifiers
CAS120-72-9
IUPAC Name1H-indole
Molecular FormulaC8H7N
InChI KeySIKJAQJRHWYJAI-UHFFFAOYSA-N
SMILESN1C=CC2=CC=CC=C12
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Specifications
Specification Sheet
Specification SheetFormCrystals or powder or crystalline powder or flakes
Appearance (Color)White to pale cream
Assay (GC)≥98.5% (non-U.S. specification)
CommentSpecification differs for U.S. and non-U.S. material where indicated
Water Content (Karl Fischer Titration)≤1% (non-U.S. specification)
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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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Soluble in methanol and water.
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.
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.
Solubility
Soluble in methanol and water.
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.
RUO – Research Use Only
General 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-butyl tin 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.