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5-Methoxyindole

CAS：1006-94-6
MW:147.177
MF：C9H9NO

5-Methoxyindole, with the chemical formula C9H9NO and CAS registry number 1006-94-6, is a compound known for its presence in various natural products and pharmaceuticals. This white to off-white crystalline powder is characterized by its methoxy functional group attached to the indole ring. It is commonly used as a building block in the synthesis of indole derivatives and as a precursor for the preparation of tryptamines and other biologically active compounds. 5-Methoxyindole has been studied for its potential therapeutic applications, including its role as an antioxidant, anti-inflammatory, and anticancer agent. It has also been investigated for its effects on the central nervous system and its potential use in the treatment of neurological disorders. Further research is ongoing to explore the full range of its biological activities and potential applications in medicine.

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
NMR Spectrum
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: 5-Methoxyindole

1.2 Synonyms: 1H-Indole, 5-methoxy-; 5-MeO-indole; 5-Methoxy indole; 5-Methoxy-1H-indole; 5-methoxy-1H-indole(SALTDATA: FREE); 5-methoxy-2,3-dihydro-1H-indole; 5-methoxy-indol; 5-methoxy-indole; 5-METHOXYINDOLE (5MeOI); 5-METHOXYINDOLE REPANIDAL; 5-MethoxyindoleF; 5-Methoxylindole; 5-OMe-indole; EINECS 213-745-3; Femedol; methoxy-5indole; Methoxyindole; MFCD00005674; NSC 521752;

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1.3 CAS No.: 1006-94-6

1.4 CID: 13872

1.5 EINECS: 213-745-3

1.6 Molecular Formula: C9H9NO

1.7 Inchi: InChI=1S/C9H9NO/c1-11-8-2-3-9-7(6-8)4-5-10-9/h2-6,10H,1H3

1.8 InChkey: DWAQDRSOVMLGRQ-UHFFFAOYSA-N

1.9 Canonical Smiles: COC1=CC2=C(C=C1)NC=C2

1.10 Isomers Smiles: COC1=CC2=C(C=C1)NC=C2

2. Properties

2.1 Appearance: White solid.

2.2 Storage: Keep Cold. Light Sensitive.

2.3 Chemical Properties: white to light brownish crystalline powder

2.4 Color/Form: Yellow to Brown Solid

2.5 pKa: 16.70±0.30(Predicted)

2.6 Water Solubility: insoluble

2.7 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.8 StorageTemp: Keep in dark place,Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Description

5-Methoxyindole, with the chemical formula C9H9NO2, has the CAS number 1006-94-6. It appears as a white to off-white crystalline powder with a slight odor. The basic structure of 5-Methoxyindole consists of a benzene ring fused with a pyrrole ring, with a methoxy group attached to the benzene ring. This compound is sparingly soluble in water. Safety information regarding 5-Methoxyindole is not available.

Applicable Fields

Pharmaceuticals: 5-Methoxyindole is used in the pharmaceutical industry for various purposes. Its mechanism of action in this field may involve its ability to interact with specific receptors or enzymes, leading to desired therapeutic effects. However, specific information about its mechanism of action in pharmaceuticals is not available.

Storage

Conditions: Store in a cool and dry place.

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3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 32 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 2 of 32 companies. For more detailed information, please visit ECHA C&L website

Of the 6 notification(s) provided by 30 of 32 companies with hazard statement code(s):

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (96.67%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

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3.3 Purification Methods: Crystallise 5-methoxyindole from cyclohexane pet ether or pet ether/Et2O. [Saito & Kikugawa J Heterocycl Chem 16 1325 1979, Beilstein 21 III/IV 765, 21/3 V 18.] 5-Methoxyindole Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Sensitive: Light Sensitive

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL9500000

CHEMICAL NAME :: Indole, 5-methoxy-

CAS REGISTRY NUMBER :: 1006-94-6

LAST UPDATED :: 199109

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H9-N-O

MOLECULAR WEIGHT :: 147.19

WISWESSER LINE NOTATION :: T56 BMJ GO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 370 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: EJMCA5 European Journal of Medicinal Chemistry--Chimie Therapeutique. (Editions Scientifiques Elsevier, 29 rue Buffon, F-75005, Paris, France) V.9- 1974- Volume(issue)/page/year: 9,453,1974

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. 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

Predict 1H proton NMR

IR : CCl4 solution

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

1006-94-6Total: 64 Synthesis Route

120-72-9 341 Suppliers

1006-94-6 332 Suppliers

100-17-4

1006-94-6 332 Suppliers

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8. Precursor and Product

precursor:

4770-33-6

4284-48-4

1930-89-8

4382-54-1

591-31-1

120-72-9

104-94-9

1215-59-4

1006-94-6

product:

608-07-1

712-09-4

5883-96-5

2521-13-3

3671-01-0

7699-18-5

2009-03-2

73-31-4

6705-03-9

1953-54-4

9. Computed Properties

Molecular Weight：147.177g/mol
Molecular Formula：C₉H₉NO
Compound Is Canonicalized：True
XLogP3-AA：147.068413911
Monoisotopic Mass：147.068413911
Complexity：138
Rotatable Bond Count：1
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：1
Topological Polar Surface Area：25
Heavy Atom Count：：11
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：AAADccByIAAAAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHgAQAAAADAzBngY+xvLJlACgAzRnRACCiCAxIiAI2aA+bJgMJuLEsZuEMChk0BHI6Aew0LIOAEABAAACAAAAgAIAAAQAAAAAAAAAAA==

10.Other Information

BRN: 116722

Chemical Properties: white to light brownish crystalline powder

Uses: 5-Methoxyindole (cas# 1006-94-6) is a compound useful in organic synthesis.

Synthesis Reference(s): Journal of Heterocyclic Chemistry, 26, p. 1405, 1989 DOI: 10.1002/jhet.5570260533
The Journal of Organic Chemistry, 58, p. 5558, 1993 DOI: 10.1021/jo00072a052
Tetrahedron Letters, 27, p. 837, 1986 DOI: 10.1016/S0040-4039(00)84114-3

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Purification Methods: Crystallise 5-methoxyindole from cyclohexane pet ether or pet ether/Et2O. [Saito & Kikugawa J Heterocycl Chem 16 1325 1979, Beilstein 21 III/IV 765, 21/3 V 18.]

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12. Related Questions

: What are the four traditional synthesis methods of 5-methoxyindole? In the field of organic synthesis, 5- Armo-oxygen is an important compound that has attracted much attention due to its extensive biological activity. This article will introduce four traditional syn..; How is 5-Methoxyindole synthesized?Introduction 5-Methoxyindole is an important pharmaceutical intermediate and an important raw material for the production of drugs for the prevention and treatment of cardiovascular diseases, neurolog..

13. Realated Product Infomation