Indole

• Catalog No.: A14427
• CAS Number: 120-72-9
• M. F.: C8H7N
• M. W.: 117.14788
• Purity: 99%

SYNONYMS

• Title: 吲哚
• IUPAC name: 1H-indole
• IUPAC Traditional name: indole

DATABASE IDS

• MDL Number: MFCD00005607
• Merck Index: 144963
• EC Number: 204-420-7
• Beilstein Number: 107693
• CAS Number: 120-72-9

PROPERTIES

• GHS Hazard statements: H311-H302-H318-H400
• European Hazard Symbols: X
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P280-P305+P351+P338-P361-P302+P352-P405-P501A
• Risk Statements: 21/22-41-50
• RTECS: NL2450000
• Safety Statements: 26-36/37/39-57-60
• Storage Warning: Light Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN2811
• Packing Group: III
• Purity: 99%
• Boiling Point: 253-254°C
• Density: 1.220
• Flash Point: 121°C(249°F)
• Melting Point: 50-54°C

REFERENCES

• 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).
• 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).
• Halogenation in the 2-position has been effected via the Li 1-carbamate and subsequent 2-lithiation: J. Org. Chem., 57, 2495 (1992):
  
• Treatment with EtMgI followed by ZnCl₂ leads to an N-zinc derivative. This undergoes acylation at the 3-position: Tetrahedron, 46, 6061 (1990).