Substance
ID:717042
Names and Identifiers
IUPAC name
1H-indole
IUPAC Traditional name
indole
Synonyms
Indole吲哚
Registration numbers
Merck Index
MDL Number
Beilstein Number
CAS Number
EC Number
Properties
Safety Information
Hazard Class
6.1
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
Corrosive to metals, category 1
Skin corrosion, categories 1A,1B,1C
Serious eye damage, category 1
Hazardous to the aquatic environment
Acute hazard, category1
Chronic hazard, categories 1,2
Risk Statements
21/22-41-50
European Hazard Symbols
Nature polluting (N)
Harmful (X)RTECS
NL2450000
Packing Group
III
Safety Statements
26-36/37/39-57-60
GHS Hazard statements
H311-H302-H318-H400
Storage Warning
Light Sensitive
TSCA Listed
是
UN Number
UN2811
GHS Precautionary statements
P280-P305+P351+P338-P361-P302+P352-P405-P501A
Physical Property
Flash Point
121°C(249°F)
Melting Point
50-54°C
Density
1.220
Boiling Point
253-254°C
Product Information
Purity
99%
Molecule Details
No Data Available
Click here to submit data
Molecular Spectra
No Data Available
Click here to submit data
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).
• Treatment with EtMgI followed by ZnCl2 leads to an N-zinc derivative. This undergoes acylation at the 3-position: Tetrahedron, 46, 6061 (1990).
• 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).
• 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).
• Halogenation in the 2-position has been effected via the Li 1-carbamate and subsequent 2-lithiation: J. Org. Chem., 57, 2495 (1992):
