Indole

Iupac Name：1H-indole

Molecular Weight：117.14788

Modify Date.: 2023-02-17 03:49

Introduction: Indole, also called Benzopyrrole, an aromatic heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. This off flavour occurs in beer due to contaminant coliform bacteria during the primary fermentation stage of beer brewing. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.Indoles are important precursors for other substances made within the human body and are, therefore, researched and used in lifeclass and medical applications. The compound was officially discovered in 1866 by a scientist working with the properties of zinc dust who reduced oxindole from the zinc dust into an indole. After the discovery, indoles became important constituents of the textile industry, and as more research was conducted, the larger role that indoles played within the human body system was realized. The indolic nucleus in substances like tryptophan and auxin has led to a better understanding of their mechanism within the body. View more+

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1. Names and Identifiers

1.1 Name: Indole
1.2 Synonyms: 1-Azaindene 1-Benzazole 1H-Benzo[b]pyrrole 1H-Indole 1H-Indole - 3H-indole (1:1) 1H-Indole (9CI) 1H-Indole, compd. with 3H-indole (1:1) 2,3-Benzopyrole 2,3-Benzopyrrole 2,3-Benzopyrrole,OrBenzazole,Indole 3H-indole benzazole BENZO(B)PYRROLE Benzo[b]pyrrole Benzopyrrole EINECS 204-420-7 FEMA 2593 Indol Indole (8CI) INDOLE CRYSTALLINE GR indole hydrochloride indole, 14C-labeled Indole-15N IndoleGr Ketole MFCD00005607 NSC 1964 T56 BMJ UNII-8724FJW4M5

1.3 CAS No.: 120-72-9

1.4 CID: 798

1.5 EINECS(EC#): 204-420-7

1.6 Molecular Formula: C8H7N (isomer)

1.7 Inchi: InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

1.8 InChkey: SIKJAQJRHWYJAI-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C=CN2

1.10 Isomers Smiles: C1=CC=C2C(=C1)C=CN2

2. Properties

2.1 Density: 1.22

2.1 Melting point: 51-54℃

2.1 Boiling point: 253-254℃

2.1 Refractive index: 1.68

2.1 Flash Point: 136℃

2.1 Precise Quality: 117.05800

2.1 PSA: 15.79000

2.1 logP: 2.16790

2.1 Solubility: methanol: 0.1?g/mL, clear

2.2 Appearance: white crystals with an unpleasant odour

2.3 Atmospheric OH Rate Constant: 1.54e-10 cm3/molecule*sec

2.4 Storage: Light Sensitive. Ambient temperatures.

2.5 Chemical Properties: Indole has an unpleasant odor at high concentration, odor becomes floral at higher dilutions

2.6 Physical Properties: Colorless to yellow scales with an unpleasant odor. Turns red on exposure to light and air. Odorthreshold of 0.14 ppm was reported by Buttery et al. (1988).

2.7 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

2.8 Heat of Combustion: 3.650 kJ/kg at 25 deg C

2.9 Odor: ALMOST FLORAL ODOR WHEN HIGHLY PURIFIED, OTHERWISE EXHIBITS CHARACTERISTIC ODOR OF FECES

2.10 Odor Threshold: 0.0003ppm

2.11 PH: 5.9 (1000g/l, H2O, 20℃)

2.12 pKa: 3.17 (quoted, Sangster, 1989)

2.13 Water Solubility: 2.80 g/L (25 oC)

2.14 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

2.15 Stability: Stable, but may be light or air sensitive. Incompatible with strong oxidizing agents, iron and iron salts.

2.16 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Environmental Fate: Biological. In 9% anaerobic municipal sludge, indole degraded to 1,3-dihydro-2H-indol-2-one(oxindole), which degraded to methane and carbon dioxide (Berry et al., 1987). Heukelekian andRand (1955) reported a 5-d BOD value of 1.70 g/g which is 65.4% of the ThOD value of 2.48 g/g.Chemical/Physical. The aqueous chlorination of indole by hypochlorite/hypochlorous acid,chlorine dioxide, and chloramines produced oxindole, isatin, and possibly 3-chloroindole (Lin andCarlson, 1984).

3.2 Purification Methods: It can be further purified by sublimation in a vacuum or by zone melting. The picrate forms orange crystals from EtOH and has m 175o. [Beilstein 20 II 196, 20 III/IV 3176, 20/7 V 5.] Indole Preparation Products And Raw materials Preparation Products

3.3 Usage: (1) According to the GB 27 60-96 , indole can be used as flavouring agent and mainly used for preparing the essence of cheese, citrus, coffee, nuts, grape, strawberry, raspberry, chocolate, assorted fruit, jasmine and lily etc. (2) It can be used as the reagent for the determination of nitrite, can also used in the manufacture of perfume and medicine.(3) It can be used as the raw material of perfume, pharmaceuticals and plant growth hormone.(4) Indole is the intermediate for the indole acetic acid and indole butyric acid.The indole acetic acid and indole butyric are plant growth regulator.(5) It can be widely used in the manufacture of the essences of jasmine, lilac, orange blossom, gardenia, honeysuckle, lotus, narcissus, ylang, orchid and prynne etc. It is usually combined with the methyl indole to imitate the artificial civet. The extremely few of the indole can be used in chocolate, raspberry, strawberry, bitter orange, coffee, nuts, cheese, grapes and fruit and other fruity essential oil.(6) Indole is mainly used as spices, dyes, amino acids and the raw materials of pesticide. Indole itself is a spice commonly used in producing the essences of jasmine, lilac, lotus flowers, orchids and other flower flavor. The usage is generally in a few thousandths.(7) It can be used for verifying the gold, potassium and nitrite and manufacturing jasmine-type fragrance. It can also be used in pharmaceutical industry.

4. Safety and Handling

4.1 Symbol: GHS05, GHS06, GHS09

4.1 Hazard Codes: Xn

4.1 Signal Word: Danger

4.1 Risk Statements: R21/22;R36

4.1 Safety Statements: S26;S36/37/39

4.1 Packing Group: III

4.1 Octanol/Water Partition Coefficient: Log P= 2.14

4.2 Fire Hazard: Noncombustible solid.

4.3 Hazard Class: 9

4.3 Hazard Declaration: H302-H311-H315-H318-H335-H400

4.3 DisposalMethods: 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.

4.4 RIDADR: UN 2811 6.1/PG 3

4.4 Caution Statement: P261-P273-P280-P305 + P351 + P338-P312

4.4 Formulations/Preparations: FOUND IN NEROLI OIL IN TRACE QUANTITIES /approx 0.1%/
CONSTITUTES 2.5% OF JASMINE OIL
Technical, CP, FCC

4.5 WGK Germany: 1

4.5 RTECS: NL2450000

4.5 Report: Reported in EPA TSCA Inventory.

4.6 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: Xi,N,T
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

4.7 Sensitive: Light Sensitive

4.8 Toxicity

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.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H311 Toxic in contact with skin
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P361+P364 Take off immediately all contaminated clothing and wash it before reuse.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 400 MHz in CDCl3

1H NMR : parameter in acetone

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

120-72-9Total: 63 Synthesis Route

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Literatures:
Chemische Berichte, , vol. 21, p. 1930 Gazzetta Chimica Italiana, , vol. 18, p. 387 Chemische Berichte, , vol. 21, p. 673
Yield: null

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120-72-9 339 Suppliers

10500-57-9 178 Suppliers

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Literatures:
European Journal of Organic Chemistry, , # 14 p. 3011 - 3016
Yield: null

635-46-1 185 Suppliers

91-22-5 119 Suppliers

120-72-9 339 Suppliers

Literatures:
Chemische Berichte, , vol. 16, p. 735
Yield: null

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8. Other Information

8.0 Merck: 14,4963

8.1 BRN: 107693

8.2 description: Indole, also called Benzopyrrole, an aromatic heterocyclic organic compound occurring in some flower oils, such as jasmine and orange blossom, in coal tar, and in fecal matter. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. It can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. This off flavour occurs in beer due to contaminant coliform bacteria during the primary fermentation stage of beer brewing. At very low concentrations, however, it has a flowery smell, and is a constituent of many flower scents (such as orange blossoms) and perfumes. Natural jasmine oil, used in the perfume industry, contains around 2.5% of indole. Indole also occurs in coal tar. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine.
Indoles are important precursors for other substances made within the human body and are, therefore, researched and used in lifestyle and medical applications. The compound was officially discovered in 1866 by a scientist working with the properties of zinc dust who reduced oxindole from the zinc dust into an indole. After the discovery, indoles became important constituents of the textile industry, and as more research was conducted, the larger role that indoles played within the human body system was realized. The indolic nucleus in substances like tryptophan and auxin has led to a better understanding of their mechanism within the body.

8.3 Content analysis: Press GT-10-4 gas chromatography method for the determination with polar column.
Using the polar column method in GT-10-4 gas chromatography to determine the content of indole.

8.4 Control of Bacterial Processes: As an intercellular signal molecule in both gram-positive and gram-negative bacteria, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, resistance to drugs, biofilm formation, and virulence. Indole has been shown to control a number of bacterial processes such as spore formation, plasmid stability, drug resistance, biofilm formation, and virulence. Indole may have anticarcinogenic activity.

8.5 Usage: Indole is used in the preparation of gramine, which is obtained by Mannich reaction dimethylamine and formaldehyde. It is used as a starting material for the preparation of oxindole and indole-3-carboxaldehyde. In Diels-Alder reaction, it acts as dienophile and reacts with 2-aminofuran to get strychnine. It is the active component of jasmine oil, neroli oil and orange-blossom oil used in the perfume industry. Further, it is involved in the preparation of synthetic jasmine oil.

9. Computational chemical data

Molecular Weight: 117.14788g/mol
Molecular Formula: C₈H₇N
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 117.057849228
Monoisotopic Mass: 117.057849228
Complexity: 101
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 15.8
Heavy Atom Count: 9
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYByAAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHAAQAAAADAjBHgQ8wPLJkACgAzRnRACCgCAxAiAI2aA4ZJgIIOLAkZGEIAhgkADIyAcQgIAOAAAAAAACAAAAAAAAAAQAAAAAAAAAAA==

10. Question & Answer

Electrophilic substitution of an indole as opposed to benzofuran and benzothiophene Jul 01 2021
Regioselectivity in electrophilic aromatic substitution of benzofuran and indole This response as to the regioselectivity of the electrophilic aromatic substitution of indole left me with a few more questions than it did answers. In figure 3b, does the pi bond in the bottom half of the benzene on t...
N,N-Dimethyl-2-(indol-3-yl)glyoxylamide from indole Jun 30 2021
I would like to know how to obtain the following molecule, whose technical name should be something like N,N-dimethylindol-3-ylglyoxylamide (let's call it DMIG for short) One of the constraints being that I'd like to limit myself to compounds that are relatively easy/cheap (and, of course, legal) t...
Which atoms in indole possess the greatest amount of electron density? Jun 29 2021
Presumably the amine acts as an electron donor, but that would suggest extra electron density of the adjacent carbons, making them more shield, which isn't seen in the results in the image below. Specifically I'm wondering what causes the carbon with a chemical shift of 111 ppm to be less deshielde...
Fischer indole synthesis: significance of choice of acid catalyst Jun 24 2021
Lately, as a matter of interest, I have been studying sigmatropic rearrangements. I came across the Fischer indole synthesis, whose Wikipedia article states: The Fischer indole synthesis is a chemical reaction that produces the aromatic heterocycle indole from a (substituted) phenylhydrazine and an...

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