ChemicalBook--->CAS DataBase List--->10075-52-2

10075-52-2

10075-52-2 Structure

10075-52-2 Structure
IdentificationBack Directory
[Name]

5-Bromo-1-methyl-1H-indole
[CAS]

10075-52-2
[Synonyms]

CHEMBRDG-BB 9072049
1-methyl-5-bromoindole
N-Methyl-5-bromoindole
5-BROMO-1-METHYL-INDOLE
5-Bromo-1-methy-1H-indole
5-BROMO-1-METHYL-1H-INDOLE
5-Bromo-1-methylindole 97%
1H-Indole,5-bromo-1-methyl-
5-bromo-1-methyl-1H-indole(SALTDATA: FREE)
[Molecular Formula]

C9H8BrN
[MDL Number]

MFCD00159857
[MOL File]

10075-52-2.mol
[Molecular Weight]

210.07
Chemical PropertiesBack Directory
[Melting point ]

43 °C
[Boiling point ]

300.9±15.0 °C(Predicted)
[density ]

1.47±0.1 g/cm3(Predicted)
[Fp ]

>110℃
[storage temp. ]

Sealed in dry,Room Temperature
[form ]

solid
[Appearance]

Light yellow to yellow Solid
[InChI]

InChI=1S/C9H8BrN/c1-11-5-4-7-6-8(10)2-3-9(7)11/h2-6H,1H3
[InChIKey]

SBOITLSQLQGSLO-UHFFFAOYSA-N
[SMILES]

N1(C)C2=C(C=C(Br)C=C2)C=C1
Safety DataBack Directory
[Symbol(GHS) ]


GHS05,GHS07
[Signal word ]

Danger
[Hazard statements ]

H302-H315-H318-H335
[Precautionary statements ]

P280-P301+P312+P330-P302+P352-P305+P351+P338+P310
[Hazard Codes ]

Xi,Xn
[Risk Statements ]

22-36/37/38-41-37/38
[Safety Statements ]

22-26-36/37/39-39
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HS Code ]

2933998090
Spectrum DetailBack Directory
[Spectrum Detail]

5-Bromo-1-methyl-1H-indole(10075-52-2)1HNMR
Hazard InformationBack Directory
[Synthesis]

5-Bromoindole

10075-50-0

Iodomethane

74-88-4

5-Bromo-1-methyl-1H-indole

10075-52-2

1. 5-bromo-1H-indole (2.08 g, 10.6 mmol) was dissolved in 35 mL of DMF at 0 °C. 2. Sodium hydride (60% dispersed in mineral oil, 467 mg, 11.67 mmol) was added to the above solution, keeping the reaction temperature at 0 °C. 3. After stirring for 30 min, iodomethane (663 μL, 10.6 mmol) was slowly added. 4. The reaction mixture was gradually warmed to room temperature and stirring was continued for 10 min. 5. Upon completion of the reaction, the reaction was quenched with ice water at 0 °C. The reaction was then quenched with ice water. 6. The reaction mixture was extracted with ethyl acetate (3 × appropriate amount). 7. 7. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. 8. The product was purified by fast column chromatography (eluent: 10% ethyl acetate/hexane) to give 5-bromo-1-methyl-1H-indole (2.16 g, 97% yield). 9. The product was analyzed by 1H NMR. 9. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.74 (d, J = 1.6 Hz, 1H), 7.30 (dd, J = 8.4, 2.0 Hz, 1H), 7.19 (d, J = 8.8 Hz, 1H), 7.05 (d, J = 3.2 Hz, 1H), 6.42 (d, J = 2.8 Hz, 1H), 3.78 (s, 3H), 6.42 (d, J = 2.8 Hz, 1H) 3.78 (s, 3H).

[References]

[1] Chemistry Letters, 1991, # 7, p. 1125 - 1128
[2] Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 3, p. 333 - 336
[3] Organic Letters, 2015, vol. 17, # 2, p. 254 - 257
[4] Patent: WO2016/114816, 2016, A1. Location in patent: Paragraph 0332
[5] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 12, p. 4524 - 4529
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