Ethanone, 1-(7-broMo-1H-indol-3-yl)-
- Product Name
- Ethanone, 1-(7-broMo-1H-indol-3-yl)-
- CAS No.
- 944086-09-3
- Chemical Name
- Ethanone, 1-(7-broMo-1H-indol-3-yl)-
- Synonyms
- 3-Acetyl-7-bromoindole;3-acetyl-7-bromo-1H-indole;1-(7-BroMo-1H-indol-3-yl)ethanone;1-(7-bromo-1H-indol-3-yl)ethan-1-one;Ethanone, 1-(7-broMo-1H-indol-3-yl)-
- CBNumber
- CB12608133
- Molecular Formula
- C10H8BrNO
- Formula Weight
- 238.08
- MOL File
- 944086-09-3.mol
Ethanone, 1-(7-broMo-1H-indol-3-yl)- Property
- Melting point:
- 190-191 °C
- Boiling point:
- 389.0±22.0 °C(Predicted)
- Density
- 1.591±0.06 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Room Temperature
- pka
- 13.71±0.30(Predicted)
- Appearance
- Off-white to light brown Solid
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H332Harmful if inhaled
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- 6139AC
- Product name
- 1-(7-Bromo-1H-indol-3-yl)ethanone
- Packaging
- 100mg
- Price
- $143
- Updated
- 2021/12/16
- Product number
- 6139AC
- Product name
- 1-(7-Bromo-1H-indol-3-yl)ethanone
- Packaging
- 250mg
- Price
- $200
- Updated
- 2021/12/16
- Product number
- FB159591
- Product name
- 1-(7-Bromo-1H-indol-3-yl)ethanone
- Packaging
- 100mg
- Price
- $230
- Updated
- 2021/12/16
- Product number
- FB159591
- Product name
- 1-(7-Bromo-1H-indol-3-yl)ethanone
- Packaging
- 250mg
- Price
- $300
- Updated
- 2021/12/16
- Product number
- HCH0362083
- Product name
- 1-(7-BROMO-1H-INDOL-3-YL)ETHANONE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $495.91
- Updated
- 2021/12/16
Ethanone, 1-(7-broMo-1H-indol-3-yl)- Chemical Properties,Usage,Production
Synthesis
51417-51-7
75-36-5
944086-09-3
A typical method for the synthesis of 1-(7-bromo-1H-indol-3-yl)ethanone from 7-bromoindole and acetyl chloride (Method 3, cf. Scheme 2, TP3) is as follows: first, 7-bromoindole (442 mg, 2.25 mmol) was dissolved in anhydrous dichloromethane (10 mL) at 0 °C, and diethylaluminum chloride (Et2AlCl, 3.4 mL. 1.0 M, 3.4 mmol). The reaction mixture was stirred at 0°C for 25 minutes. Subsequently, a dichloromethane (5 mL) solution of acetyl chloride (0.24 mL, 3.36 mmol) was added dropwise and stirring was continued at 0 °C until TLC showed complete conversion of 7-bromoindole (1-3 h). Upon completion of the reaction, saturated aqueous sodium bicarbonate solution (10 mL) was added slowly, the mixture was diluted with dichloromethane (60 mL) and carefully acidified to pH 4-5 with 2 M hydrochloric acid (~10 mL) to promote phase separation. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed with saturated aqueous sodium bicarbonate and evaporated to dryness to give the acetylated crude product (496 mg, 93% yield). The crude product was dissolved in acetonitrile (10 mL), cesium carbonate (Cs2CO3, 1.55 g, 4.76 mmol) and 1-chloro-3-iodopropane (0.70 mL, 6.52 mmol) were added, and the mixture was stirred at 50 °C overnight. After completion of the reaction, the suspension was diluted with dichloromethane (70 mL), filtered and adsorbed onto diatomaceous earth. Purification by fast chromatography (eluent: heptane → heptane:ethyl acetate = 3:2) afforded the title product 1-(7-bromo-1-(3-chloropropyl)-1H-indol-3-yl)ethanone (611 mg, 86% overall yield in two steps). The structure of the product was confirmed by 1H NMR and 13C NMR.
References
[1] Patent: WO2007/79239, 2007, A2. Location in patent: Page/Page column 75-76
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 13, p. 4474 - 4489
[3] Chemical Communications, 2017, vol. 53, # 28, p. 3945 - 3948
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 12, p. 1426 - 1436
[5] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 7, p. 702 - 707
Ethanone, 1-(7-broMo-1H-indol-3-yl)- Preparation Products And Raw materials
Raw materials
Preparation Products
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