1H-indole

• ChemBase ID: 4103
• Molecular Formular: C8H7N
• Molecular Mass: 117.14788
• Monoisotopic Mass: 117.05784923
• SMILES: c1ccc2[nH]ccc2c1
• Canonical SMILES: c1ccc2c(c1)[nH]cc2
• InChI: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
• InChIKey: SIKJAQJRHWYJAI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H-indole; indole
• IUPAC Traditional name: indole; @indole
• Synonyms: 2,3-Benzopyrrole; 1H-Indole; Indole; 2,3-Benzopyrrole, ketole; 1-benzazole; 1H-Benzo[b]pyrrole; Indole; 1H-Indole, 1-Azaindene; Benzo[b]pyrrole; Ketole; NSC 1964; 2,3-苯并吡咯; 吲哚

Database IDs

• CAS Number: 120-72-9
• EC Number: 204-420-7
• MDL Number: MFCD00005607
• Beilstein Number: 107693
• Merck Index: 144963
• PubChem SID: 24874767; 24896037; 160967536; 24856309; 24867930; 24901173; 46508707
• PubChem CID: 798
• CHEBI ID: 16881
• CHEMBL: 15844
• Chemspider ID: 776
• FEMA ID: 2593
• KEGG ID: C00463
• Unique Ingredient Identifier: 8724FJW4M5
• Wikipedia Title: Indole
• Council of Europe Number: 560
• Flavis Number: 14.007

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.437037
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 2.072008
• LogD (pH = 7.4): 2.072008
• Log P: 2.072008
• Molar Refractivity: 37.1445 cm^3
• Polarizability: 15.66808 Å^3
• Polar Surface Area: 15.79 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.29
• LOG S: -1.34
• Solubility (Water): 5.31e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.19 g/100 ml (20 °C); Soluble in hot water; Chloroform; Methanol; methanol: soluble0.1 g/mL, clear
• Apperance: Off-White Solid; White solid
• Melting Point: 47-52°C; 50-53 °C; 50-54°C; 51-54 °C(lit.); 52–54 °C; 52-54°C; 52-54°C
• Boiling Point: 253-254 °C(lit.); 253-254°C; 253-254°C; 253–254°C (526 K)
• Flash Point: 121 °C; 121°C; 121°C(249°F); 249.8 °F
• Density: 1.1747 g/cm^3, solid; 1.22; 1.220
• pKa: 16.2; (21.0 in DMSO)
• pKb: 17.6
• Organoleptic: butter; cheese; chocolate; grape; honey; jasmine; musty; fatty; floral; vanilla; vegetable; earthy; fishy; wine-like; animal

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• Storage Warning: Light Sensitive; Toxic/Corrosive/Harmful/Irritant/Air Sensitive/Light Sensitive/Stench/Keep Cold/Store under Argon
• RTECS: NL2450000
• European Hazard Symbols: Nature polluting (N); X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 1
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 21/22-37/38-41-50/53; 21/22-41-50; R:22-27-36/37/38
• Safety Statements: 26-36/37/39-57-60; 26-36/37/39-60-61; R R: 21/22-37/38-41-50/53; S: 26-36/37/39-60-61; S:25-26-36/37/39
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H311-H315-H318-H335-H400; H311-H302-H318-H400
• GHS Precautionary statements: P261-P273-P280-P305 + P351 + P338-P312; P280-P305+P351+P338-P361-P302+P352-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Regulation Compliance: FCC; FDA 21 CFR (172.515)

Pharmacology Properties

• Allergens: no known allergens

Product Information

• Purity: ≥98.5% (GC); ≥99%; 95+%; 98%; 99%
• Grade: analytical standard; Kosher; NI; puriss.
• Packaging: ampule of 1000 mg
• Empirical Formula (Hill Notation): C8H7N

DETAILS

MP Biomedicals - 02102036

Crystalline

DrugBank - DB04532

Drug information: experimental

Sigma Aldrich - W259306

Biochem/physiol Actions
Taste at 0.3-2 ppm
Other Notes
Natural occurrence: Burley tobacco, butter, coffee, dried bonito, egg, fish, malt, rum, tea, and wine.
Packaging
1 kg in glass bottle
1 sample in glass bottle
10, 25 kg in poly drum
100 g in glass bottle

Sigma Aldrich - I3408

Packaging
25, 100, 500 g in glass bottle

Sigma Aldrich - 269077

Packaging
100 g in glass bottle

Toronto Research Chemicals - I577320

Can be used in perfumes and in the synthesis of tryptophan.

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).