7-Benzyloxyindole
- Iupac Name：7-phenylmethoxy-1H-indole
- CAS No.: 20289-27-4
- Molecular Weight：223.275
- Modify Date.: 2022-11-29 10:42
- Introduction: Indole analogue as inhibitor 7-BenzyloxyindoleSupplier
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1. Names and Identifiers
- 1.1 Name
- 7-Benzyloxyindole
- 1.2 Synonyms
1H-Indole,7-(phenylMethoxy)- 7-(Phenylmethoxy)-1H-indole 7-(PHENYLMETHOXY)INDOLE 7-benzyloxyindolecrystalline NSC 92526
- 1.3 CAS No.
- 20289-27-4
- 1.4 CID
- 260798
- 1.5 Molecular Formula
- C15H13NO (isomer)
- 1.6 Inchi
- InChI=1S/C15H13NO/c1-2-5-12(6-3-1)11-17-14-8-4-7-13-9-10-16-15(13)14/h1-10,16H,11H2
- 1.7 InChkey
- DIGZMTAFOACVBW-UHFFFAOYSA-N
- 1.8 Canonical Smiles
- C1=CC=C(C=C1)COC2=CC=CC3=C2NC=C3
- 1.9 Isomers Smiles
- C1=CC=C(C=C1)COC2=CC=CC3=C2NC=C3
2. Properties
- 2.1 Density
- 1.196
- 2.1 Melting point
- 70-74℃
- 2.1 Boiling point
- 411.6 °C at 760 mmHg
- 2.1 Refractive index
- 1.669
- 2.1 Flash Point
- 148.9 °C
- 2.1 Precise Quality
- 223.10000
- 2.1 PSA
- 25.02000
- 2.1 logP
- 3.74690
- 2.1 Appearance
- Off-white crystalline powder
- 2.2 Storage
-
-20℃
- 2.3 Chemical Properties
- Pale-Yellow Solid
- 2.4 Color/Form
- Powder
- 2.5 pKa
- 16.36±0.30(Predicted)
- 2.6 StorageTemp
- Keep in dark place,Inert atmosphere,Room temperature
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- A mixture of Intermediate 30 (31.8 g, 130 mmol), pyrrolidine (11.0 mL, 130 mmol), and N, N-dimethylformamide dimethyl acetal (52 mL, 392 mmol) in anhydrous N, N-dimethylformamide (100 mL) was heated at 110° C. under a nitrogen blanket for 3 hours. The cooled mixture was diluted with water (1.5 L), extracted with ether (2.x.500 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to afford the intermediate enamine as a dark red oil, which was immediately used in the next step without purification. [0238] A solution of the enamine fin methanol (150 mL) and acetic acid (5 mL) was treated with a catalytic amount of 10percent palladium on carbon (2 g, 10percent wet), and the resulting mixture was stirred under a hydrogen atmosphere (50 psi) at room temperature for 2 hours. The palladium catalyst was removed by vacuum filtration through MgSO4 (10 g), and the filtrate was concentrated under reduced pressure to provide a dark brown residue. The residue was purified by flash column chromatography, eluting with ethyl acetate/chloroform (1:19), to provide Intermediate 31 as an off-white solid (3.82 g, 21percent over three steps): TLC Rf (4:1 hexanes/ethyl acetate)=0.61; 1H NMR (300 MHz, DMSO-d6): δ 11.18 (s, 1H), 7.56 (d, J=7.2 Hz, 2H), 7.43-7.38 (m, 3H), 7.35 (s, 1H), 7.23 (d, J=2.9 Hz, 1H), 6.88 (t, J=7.6 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 6.39 (t, J=2.5 Hz, 1H), 2-5.26 (s, 2H) ppm.
- 3.2 Usage
- Indole analogue as inhibitor 7-BenzyloxyindoleSupplier
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Safety Statements
- 24/25
- 4.1 Hazard Class
- IRRITANT
- 4.1 Hazard Declaration
- H315
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
- 4.1 WGK Germany
- 3
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
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 |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. |
| 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. |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
6. Synthesis Route
20289-27-4Total: 9 Synthesis Route
8. Other Information
- 8.0 Storage Conditions
- A mixture of Intermediate 30 (31.8 g, 130 mmol), pyrrolidine (11.0 mL, 130 mmol), and N, N-dimethylformamide dimethyl acetal (52 mL, 392 mmol) in anhydrous N, N-dimethylformamide (100 mL) was heated at 110° C. under a nitrogen blanket for 3 hours. The cooled mixture was diluted with water (1.5 L), extracted with ether (2.x.500 mL), dried over Na2SO4, and filtered. The solvent was removed under reduced pressure to afford the intermediate enamine as a dark red oil, which was immediately used in the next step without purification. [0238] A solution of the enamine fin methanol (150 mL) and acetic acid (5 mL) was treated with a catalytic amount of 10percent palladium on carbon (2 g, 10percent wet), and the resulting mixture was stirred under a hydrogen atmosphere (50 psi) at room temperature for 2 hours. The palladium catalyst was removed by vacuum filtration through MgSO4 (10 g), and the filtrate was concentrated under reduced pressure to provide a dark brown residue. The residue was purified by flash column chromatography, eluting with ethyl acetate/chloroform (1:19), to provide Intermediate 31 as an off-white solid (3.82 g, 21percent over three steps): TLC Rf (4:1 hexanes/ethyl acetate)=0.61; 1H NMR (300 MHz, DMSO-d6): δ 11.18 (s, 1H), 7.56 (d, J=7.2 Hz, 2H), 7.43-7.38 (m, 3H), 7.35 (s, 1H), 7.23 (d, J=2.9 Hz, 1H), 6.88 (t, J=7.6 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 6.39 (t, J=2.5 Hz, 1H), 2-5.26 (s, 2H) ppm.
9. Computational chemical data
- Molecular Weight: 223.275g/mol
- Molecular Formula: C15H13NO
- Compound Is Canonicalized: True
- XLogP3-AA: 3.5
- Exact Mass: 223.099714038
- Monoisotopic Mass: 223.099714038
- Complexity: 237
- Rotatable Bond Count: 3
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 1
- Topological Polar Surface Area: 25
- Heavy Atom Count: 17
- 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: AAADccByIAAAAAAAAAAAAAAAAAAAAWAAAAAwYAAAAAAAAFgB9AAAHgAQAAAADAzhngY8xvLJlACgAzRnRASCiCAxYiAI2aA/bJgOJuLEsZuHOCjk0BHY6AeQ0LAOAAABAAACEAAAAAIAAAQgAAAAAAAAAA==
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