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Indole(CAS No. 120-72-9)

Indole C8H7N (cas 120-72-9) Molecular Structure

120-72-9 Structure

Identification and Related Records

【Name】
Indole
【CAS Registry number】
120-72-9
【Synonyms】
2,3-Benzopyrrole
1-Benzazole
1-Azaindene
Indol
2,3-Benzopyrole
Benzopyrrole
Ketole
1H-Benzo[b]pyrrole
Indole, (1-Benzazole)
1H-Indole
【EINECS(EC#)】
204-420-7
【Molecular Formula】
C8H7N (Products with the same molecular formula)
【Molecular Weight】
117.15
【Inchi】
InChI=1/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H
【InChIKey】
SIKJAQJRHWYJAI-UHFFFAOYSA-N
【Canonical SMILES】
C1=CC=C2C(=C1)C=CN2
【MOL File】
120-72-9.mol

Chemical and Physical Properties

【Appearance】
white crystals with an unpleasant odour
【Density】
1.22
【Melting Point】
51-54℃
【Boiling Point】
253-254℃
【Vapour】
0.0298mmHg at 25°C
【Refractive Index】
1.68
【Flash Point】
136℃
【Water】
2.80 g/L (25℃)
【Solubilities】
2.80 g/L (25 oC)
【Color/Form】
LEAFLETS (WATER, PETROLEUM), CRYSTALS (ETHER)
Colorless to yellowish scales, turning red on exposure to light and air.
WHITE CRYSTALLINE SOLID
Colorless, shiny flakes
【Stability】
Stable, but may be light or air sensitive. Incompatible with strong oxidizing agents, iron and iron salts.
【HS Code】
2933990090
【Storage temp】
2-8°C
【Spectral properties】
MAX ABSORPTION (ALCOHOL): 218 NM (LOG E= 4.44); 271 NM (LOG E= 3.79); 287 NM (LOG E= 3.66)
SADTLER REF NUMBER: 4586 (IR, PRISM)
Intense mass spectral peaks: 117 m/z (100%), 90 m/z (33%), 89 m/z (21%), 118 m/z (9%)
IR: 415 (Sadtler Research Laboratories IR Grating Collection)
UV: 1269 (Sadtler Research Laboratories Spectral Collection)
NMR: 473 (Sadtler Research Laboratories Spectral Collection)
MASS: 442 (Atlas of Mass Spectral Data, John Wiley & Sons, New York)
Intense mass spectral peaks: 63 m/z
【Computed Properties】
Molecular Weight:117.14788 [g/mol]
Molecular Formula:C8H7N
XLogP3:2.1
H-Bond Donor:1
H-Bond Acceptor:0
Rotatable Bond Count:0
Exact Mass:117.057849
MonoIsotopic Mass:117.057849
Topological Polar Surface Area:15.8
Heavy Atom Count:9
Formal Charge:0
Complexity:101
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:0
Conformer Sampling RMSD:0.4
CID Conformer Count:1

Safety and Handling

【Hazard Codes】
Xn:Harmful
【Risk Statements】
R21/22;R36
【Safety Statements 】
S26;S36/37/39
【HazardClass】
9
【Safety】

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

【PackingGroup 】
III
【Sensitive】
Light Sensitive
【Transport】
UN 2811 6.1/PG 3
【Formulations/Preparations】
FOUND IN NEROLI OIL IN TRACE QUANTITIES /approx 0.1%/
CONSTITUTES 2.5% OF JASMINE OIL
Technical, CP, FCC
【Octanol/Water Partition Coefficient】
Log P= 2.14
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

PREPN FROM O-FORMOTOLUIDE: TYSON, ORG SYN COLL VOL III, 479 (1955); BY DEHYDROCYCLIZING ORTHO ALKYL ANILINES: ERNER ET AL, US PATENT 2,953,575 (1960 TO HOUDRY PROCESS); FROM N-(2-TOLYL)-N'-METHYL-N'-PHENYLFORMAMIDINE: LORENZ ET AL, J ORG CHEM 30, 2531 (1965).
OBTAINED FROM 240-260 DEG C FRACTION FROM COAL TAR: WEISSGERBER, CHEMISCHE BERICHTE 43, 3520 (1910); FROM FECES: BERGEIM, J BIOL CHEM 32, 17 (1917).
CAN BE PREPARED ALSO BY REDN OF INDOXYL, INDOXYL CARBOXYLIC ACID, OR INDIGO.
INDOLE IS PRODUCED BY CONDENSING ANILINE WITH BENZOIN IN THE PRESENCE OF ZINC CHLORIDE
In coal tar distillation, the indole is concentrated in a biphenyl-indole fraction which boils between 245 and 255 deg C. Following extraction of phenols and bases, the indole is isolated from this fraction and separated from the other major component, biphenyl... by melting with potassium hydroxide to give the potassium salt of indole, by azeotropic distillation with diethylene glycol, or by extraction with selective solvents. The crude indole can then be purified by crystallization from aliphatic hydrocarbon solvents.
Indole is also synthesized in technical quantities. Methods used include Madelung synthesis of formyltoluidine (from o-toluidine and formic acid), followed by cyclization, dehydrogenating cyclization of 2-ethylaniline, cyclocondensation of aniline and ethylene glycol in the liquid or gas phase, and cyclization of 2-(2-nitrophenyl)ethanol.
U.S. Exports

(1986) ND
U.S. Imports

(1984) 9.92X10+6 g
U.S. Production

(1986) ND

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(3), and a measured Koc of 187 from a synthetic soil with 0-2% added humic acid(4), indicate that indole will have moderate mobility in soil(SRC). Volatilization of indole should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 5.3X10-7 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(5) and water solubility(6). Indole is expected to readily biodegrade under both aerobic and anaerobic conditions in soil(SRC). Indole, added to Chernozem soil at 1 and 10 g/kg soil, was completely biodegraded in 19 and 135 days, respectively(7). Indole was completely biodegraded by suspensions of an organic soil (Carlisle muck) under methanogenic and denitrifying conditions within 67 and 144 days, respectively; oxindole was reported as a metabolite of this process(8).
AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow(2) and a recommended regression-derived equation(1), and a measured Koc value of 187(3) indicate that indole may adsorb to suspended solids and sediment in water(SRC). Indole is not expected to volatilize from water surfaces(1,SRC) based on an estimated Henry's Law constant of 5.3X10-7 atm-cu m/mole(SRC), calculated from experimental values for vapor pressure(4) and water solubility(5). According to a classification scheme(6), an estimated BCF value of 25(1,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Indole is expected to readily biodegrade under both aerobic and anaerobic conditions in water(SRC). At 10 deg C, aerobic groundwater containing a mixture of aromatic compounds completely biodegraded indole in 310 hours, including an acclimation period of 130 hours(7). Complete metabolism of indole by methanogenic sediments from the shore, edge, and bottom of Buffalo Run stream, PA, occurred within 33 days; oxindole was formed during this process(8). Indole was completely biodegraded under denitrifying conditions in 7 days using a sewage inoculum(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), indole, which has a measured vapor pressure of 0.0122 mm Hg at 25 deg C(2), will exist solely as a vapor in the ambient atmosphere. Vapor-phase indole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals, nitrate radicals, and ozone(SRC); the half-lives for these reactions in air are estimated to be about 2 to 3 hours,

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