ChemicalBook > CAS DataBase List > 4-Benzyloxyindole

4-Benzyloxyindole

Product Name
4-Benzyloxyindole
CAS No.
20289-26-3
Chemical Name
4-Benzyloxyindole
Synonyms
NSC 92539;4-BENZYLOXYINDOLE;4-BENZYLOXYLINDOLE;4-Benzyloxyindole>4-BENZYLOXYINDOLE 98%;4-BENZYLOXY-1H-INDOLE;4-Benzyloxyindole,99%;4-Benzyloxyindole ,98%;4-(phenylmethoxy)-1h-indole;4-(Benzyloxy)-1H-indole 98%
CBNumber
CB4319405
Molecular Formula
C15H13NO
Formula Weight
223.27
MOL File
20289-26-3.mol
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4-Benzyloxyindole Property

Melting point:
57-61 °C (lit.)
Boiling point:
364.56°C (rough estimate)
Density 
1.0707 (rough estimate)
refractive index 
1.5500 (estimate)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
pka
17.17±0.30(Predicted)
form 
Solid
color 
Beige to Brown
BRN 
183150
InChI
InChI=1S/C15H13NO/c1-2-5-12(6-3-1)11-17-15-8-4-7-14-13(15)9-10-16-14/h1-10,16H,11H2
InChIKey
LJFVSIDBFJPKLD-UHFFFAOYSA-N
SMILES
N1C2=C(C(OCC3=CC=CC=C3)=CC=C2)C=C1
CAS DataBase Reference
20289-26-3(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-37/39
WGK Germany 
3
HazardClass 
IRRITANT
HS Code 
29339990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
246212
Product name
4-Benzyloxyindole
Purity
98%
Packaging
1g
Price
$30
Updated
2023/06/20
TCI Chemical
Product number
B2811
Product name
4-Benzyloxyindole
Purity
>98.0%(GC)
Packaging
1g
Price
$77
Updated
2024/03/01
TCI Chemical
Product number
B2811
Product name
4-Benzyloxyindole
Purity
>98.0%(GC)
Packaging
5g
Price
$234
Updated
2024/03/01
Alfa Aesar
Product number
L17147
Product name
4-Benzyloxyindole, 99%
Packaging
1g
Price
$96.3
Updated
2021/12/16
Alfa Aesar
Product number
L17147
Product name
4-Benzyloxyindole, 99%
Packaging
250mg
Price
$33.1
Updated
2021/12/16
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4-Benzyloxyindole Chemical Properties,Usage,Production

Chemical Properties

Off-White Crystalline Solid with Few Darker (Brown) Particles

Uses

Indole derivative as substrate-binding; N297Q and I300V mutants of cytochrome P 450 2A6 display expansion of substrate specificity of cytochrome P 450 2A6 to oxidize substituted indoles

Uses

4-Benzyloxyindole was used in the synthesis of 4-alkyloxy-aminoalkyl indole derivatives.

Reactions

4-Benzyloxyindole was used in the synthesis of 4-alkyloxy-aminoalkyl indole derivatives.

  1. Reactant for regioselective synthesis of oxopyrrolidine analogs via iodine-catalyzed Markovnikov addition
  2. Reactant for preparation of indoles by Bartoli reductive cyclization as useful intermediates in medicinal chemistry research
  3. Reactant for synthesis of carbon-11-labeled 4-aryl-4H-chromenes as new PET agents for imaging of apoptosis in cancer
  4. Reactant for preparation of HCV inhibitors.
  5. Reactant for preparation of indol-3-yl tetramethylcyclopropyl ketones as CB2 cannabinoid receptor ligands
  6. Reactant for preparation of 4-aryl-4H-chromenes as apoptosis inducers

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 34, 1990
The Journal of Organic Chemistry, 51, p. 4294, 1986 DOI: 10.1021/jo00372a037
Tetrahedron Letters, 24, p. 4561, 1983 DOI: 10.1016/S0040-4039(00)85955-9

Synthesis

To a stirred solution of 162.2 g (0.50 mol) of (E)-6-benzyloxy-2-nitro-β-pyrrolidinostyrene in 1 L of THF and 1 L of methanol at 30°C under nitrogen is added 10 mL of Raney nickel followed by 44 mL (0.75 mol) of 85% hydrazine hydrate. Vigorous gas evolution is observed. The red color turns dark brown within 10 minutes, and the reaction temperature rises to 46°C. An additional 44 mL of 85% hydrazine hydrate is added after 30 min and again 1 hr later. The temperature is maintained between 45 and 50°C with a water bath during the reaction and for 2 hr after the last addition. The mixture is cooled to room temperature, and the catalyst is removed by filtration through a bed of Celite. The catalyst is washed several times with methylene chloride. The filtrate is evaporated, and the residue is dried by evaporating with 500 mL of toluene. The reddish residue (118.5 g), dissolved in ca. 1 L of toluene-cyclohexane (1 : 1), is applied to a column of 500 g of silica gel (70–230-mesh, Merck) prepared in the same solvent. Elution with 6.0 L of toluene–cyclohexane (1 : 1) followed by 3 L of toluene–cyclohexane (1 : 2) affords 108.3 g of white solid, which is crystallized from 150 mL of toluene and 480 mL of cyclohexane. 107.3 g (96% yield) of 4-benzyloxyindole is obtained in three crops as white prisms, mp 60–62°C.

4-Benzyloxyindole Preparation Products And Raw materials

Raw materials

Preparation Products

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4-Benzyloxyindole Suppliers

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View Lastest Price from 4-Benzyloxyindole manufacturers

Dorne Chemical Technology co. LTD
Product
4-Benzyloxyindole 20289-26-3
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
100kg
Release date
2024-05-28
Wuhan Circle Star Chem-medical Technology Co.,Ltd
Product
4-Benzyloxyindole 20289-26-3
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99
Supply Ability
1000
Release date
2024-12-25
WUHAN FORTUNA CHEMICAL CO., LTD
Product
4-Benzyloxyindole 20289-26-3
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-31

20289-26-3, 4-BenzyloxyindoleRelated Search:

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