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120-72-9

Basic Information
CAS No.: 120-72-9
Name: Indole
Molecular Structure:
Molecular Structure of 120-72-9 (Indole)
Formula: C8H7N
Molecular Weight: 117.16
Synonyms: 2,3-Benzopyrrole;1-Benzo(b)pyrrole;1H-indole;1-Azaindene;Benzopyrrole;2, 3-Benzopyrrole;Indole 99%min;Indole perfume;Indole industrial;Indole Crystal;1-Benzazole;2,3-Benzopyrole;Ketole;Benzo[b]pyrrole;3-benzopyrrole; 1H-indole;
EINECS: 204-420-7
Density: 1.22 g/cm3
Melting Point: 51-54 °C(lit.)
Boiling Point: 253 °C at 760 mmHg
Flash Point: 107.839 °C
Solubility: methanol: 0.1 g/mL, clear
Appearance: white crystals with an unpleasant odour
Hazard Symbols: HarmfulXn,DangerousN,ToxicT
Risk Codes: 21/22-37/38-41-50/53-36-39/23/24/25-23/24/25
Safety: 26-36/37/39-60-61-45-36/37
Transport Information: UN 2811 6.1/PG 3
PSA: 15.79000
LogP: 2.16790
Synthetic route
13618-91-2

4,5,6,7-tetrahydroindole

120-72-9

indole

Conditions
ConditionsYield
With hydrogen; palladium/alumina at 370℃;100%
With hydrogen; palladium/alumina at 350 - 370℃; Product distribution; other palladium catalysts;100%
With hydrogen sulfide; palladium/alumina In toluene at 350℃; for 0.5h;100%
496-15-1

1-indoline

120-72-9

indole

Conditions
ConditionsYield
tris(triphenylphosphine)ruthenium(II) chloride In toluene for 6h; Rate constant; Mechanism; Heating;100%
With C21H32Cl4N2Ru In toluene for 6h; Reagent/catalyst; Heating;100%
With tert.-butylhydroperoxide; iron(III) chloride; C42H40Cu2N8 In water; acetonitrile at 60℃; for 16h;100%
15121-84-3

2-nitro-benzeneethanol

120-72-9

indole

Conditions
ConditionsYield
Pd-C100%
With C28H28ClNO2Ru; oxygen; potassium carbonate In isopropyl alcohol at 130℃; for 6h; Reagent/catalyst;92%
With hydrogen In o-xylene under 760.051 Torr; for 12h; Reflux;68%
5339-85-5

2-aminophenethyl alcohol

120-72-9

indole

Conditions
ConditionsYield
100%
100%
With C21H28I3IrN6Pd; potassium hydroxide In toluene at 110℃; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique;99%
31271-90-6

1-(p-toluenesulfonyl)-1H-indole

120-72-9

indole

Conditions
ConditionsYield
With methanol; magnesium for 0.333333h; sonication: 35 kHz, 120-240 W;100%
With naphthalene; tetraethylammonium bromide In N,N-dimethyl-formamide at 0℃; Inert atmosphere; Electrolysis;97%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Mechanism; Reagent/catalyst; Solvent; Inert atmosphere; Sealed tube; Irradiation;96%
116548-00-6

N-<2-(Trimethylsilylethynyl)phenyl>methanesulfonamide

120-72-9

indole

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h; Heating;100%
40899-71-6

1-benzenesulfonylindole

120-72-9

indole

Conditions
ConditionsYield
With magnesium; lithium tert-butoxide In tetrahydrofuran at 20℃; for 12h; Product distribution; Further Variations:; Reagents;100%
With formic acid; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; Irradiation;91%
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; Darkness; Schlenk technique;91%
42185-27-3

2-(cyanomethyl)cyclohexanone

7440-06-4

platinum

120-72-9

indole

Conditions
ConditionsYield
With hydrogen100%

1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indole

120-72-9

indole

Conditions
ConditionsYield
With titanium(IV) isopropylate; chloro-trimethyl-silane; magnesium In tetrahydrofuran at 50℃; for 12h; Inert atmosphere;100%
70957-04-9

N-pivaloyl indole

120-72-9

indole

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - 45℃; for 2h; Inert atmosphere;100%
610-66-2

2-nitro-benzeneacetonitrile

120-72-9

indole

Conditions
ConditionsYield
With hydrogen In methanol at 20℃; under 760.051 Torr; for 12h;99%
With sodium tetrahydroborate In methanol at 50℃; for 24h; chemoselective reaction;93%
With hydrogen at 20℃; under 760.051 Torr; for 36h; Time; Schlenk technique;68%
496-15-1

1-indoline

A

120-72-9

indole

B

4a-(2,3-Dihydro-indol-1-yl)-5-ethyl-3,7,8,10-tetramethyl-5,10-dihydro-4aH-benzo[g]pteridine-2,4-dione

Conditions
ConditionsYield
With air; FlEt+·ClO4- In acetonitrile at 36℃; for 1080h; Title compound not separated from byproducts;A 548 % Spectr.
B 99%
75400-67-8

indole-1-carboxylic acid tert-butyl ester

120-72-9

indole

Conditions
ConditionsYield
With 2,2,2-trifluoroethanol at 150℃; for 0.25h; Product distribution / selectivity; Microwave irradiation;99%
With water at 100℃; for 4h;99%
With 2,2,2-trifluoroethanol at 150℃; for 0.25h; Product distribution / selectivity; Microwave irradiation;99%
771-50-6

1H-indole-3-carboxylic acid

120-72-9

indole

Conditions
ConditionsYield
With potassium carbonate In ethanol at 140℃; Reagent/catalyst; Solvent; Temperature; Schlenk technique;99%
With [Rh(OH)(cod)]2; 1,3-bis-(diphenylphosphino)propane; water; sodium hydroxide In toluene at 100℃; for 24h; Inert atmosphere;85%
With potassium phosphate; L-Aspartic acid; [(cinnamyl)PdCl]2 In tetrahydrofuran at 100℃; for 24h;78%
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Chemistry

Molecular Structure:

Molecular Formula: C8H7N
Molecular Weight: 117.1479
IUPAC Name: 1H-Indole
Synonyms of Indole (CAS NO.120-72-9): 1-Azaindene ; 1-Benzazole ; 1-Benzo(b)pyrrole ; 1H-Indole ; 2,3-Benzopyrole ; 2,3-Benzopyrrole ; AI3-01540 ; Benzopyrrole ; CCRIS 4421 ; Caswell No. 498B ; EINECS 204-420-7 ; EPA Pesticide Chemical Code 025000 ; FEMA No. 2593 ; HSDB 599 ; INDOLE ; Indol [German] ; Indole (natural) ; Ketole ; NSC 1964 ; UNII-8724FJW4M5
CAS NO: 120-72-9
Classification Code: Skin / Eye Irritant ; Tumor data 
Density: 1.22g/cm3
Melting Point: 51-54oC
Boiling Point: 253-254oC
Flash Point: 136oC
Solubility: 2.80 g/L (25oC)
Appearance: white crystals with an unpleasant odour
Mol File: 120-72-9.mol
storage temp.: 2-8oC
Sensitive: Light Sensitive
BRN:107693

History

  Indole (CAS NO.120-72-9) can be used to produce isatin and oxindole. Oxindole was  reduced  to indole using zinc dust by Adolf von Baeyer In 1866. Then in 1869, Adolf von Baeyer give a formula for indole.Until the end of the 19th century,one kind of indole derivatives was important dyestuffs. Later, In the 1930s, people found that the indole nucleus is present in many important alkaloids.  It plays an important role in today research work.

Uses

  Indole (CAS NO.120-72-9) is used in Natural jasmine oil. Natural jasmine oil is used in the perfume industry which contains about 2.5% of indole. Besides,Indole is used in the manufacture of synthetic jasmine oil.

Production

Method of synthesis of Indole (CAS NO.120-72-9): Leimgruber-Batcho indole synthesis; Fischer indole synthesis; Bartoli indole synthesis; Bischler-M?hlau indole synthesis; Fukuyama indole synthesis; Gassman indole synthesis; Hemetsberger indole synthesis; Larock indole synthesis; Madelung synthesis; Nenitzescu indole synthesis; Reissert indole synthesis; Baeyer-Emmerling indole synthesis

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 117mg/kg (117mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 94, Pg. 1620, 1974.
mouse LD50 subcutaneous 225mg/kg (225mg/kg)   Klinische Wochenscrift. Vol. 35, Pg. 504, 1957.
mouse LDLo oral 1070mg/kg (1070mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 14, Pg. 111, 1985.
rabbit LD50 skin 790mg/kg (790mg/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat LD50 oral 1gm/kg (1000mg/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

A poison by intraperitoneal and subcutaneous routes. Moderately toxic by ingestion and skin contact. A severe eye irritant. Questionable carcinogen with experimental carcinogenic and tumorigenic data. When heated to decomposition it emits toxic fumes of NOx.
Safty informations about Indole (CAS NO.120-72-9):
Hazard Codes: XiIrritant,NDangerous,TToxic
Risk Statements:21/22-37/38-41-50/53-36-39-23/24/25 
R21/22: Harmful in contact with skin and if swallowed. 
R37/38: Irritating to respiratory system and skin. 
R41: Risk of serious damage to the eyes. 
R50/53: Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R36: Irritating to eyes. 
R39: Danger of very serious irreversible effects. 
R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements:26-36/37/39-60-61-45 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S60: This material and its container must be disposed of as hazardous waste. 
S61: Avoid release to the environment. Refer to special instructions / safety data sheets. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 1
RIDADR: UN 2811 6.1/PG 3
RTECS: NL2450000
F: 8-13
HazardClass: 9
PackingGroup: III