| Identification | More | [Name]
6-Bromo-1H-indole | [CAS]
52415-29-9 | [Synonyms]
6-BROMO-1H-INDOLE
6-BROMOINDOLE
BROMOINDOLE-6
bromoindole
6-Bromoindole,98%
bromoindole 6-Bromoindole
6-BROMOINDOLE 98% | [EINECS(EC#)]
610-835-8 | [Molecular Formula]
C8H6BrN | [MDL Number]
MFCD00238550 | [Molecular Weight]
196.04 | [MOL File]
52415-29-9.mol |
| Chemical Properties | Back Directory | [Appearance]
White to brown powder | [Melting point ]
92-96 °C (lit.) | [Boiling point ]
70-75°C 0,01mm | [density ]
1.660±0.06 g/cm3(Predicted) | [Fp ]
70-75°C/0.01mm | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Powder | [pka]
16.07±0.30(Predicted) | [color ]
White to brown | [Sensitive ]
Air & Light Sensitive | [BRN ]
112711 | [InChI]
InChI=1S/C8H6BrN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H | [InChIKey]
MAWGHOPSCKCTPA-UHFFFAOYSA-N | [SMILES]
N1C2=C(C=CC(Br)=C2)C=C1 | [CAS DataBase Reference]
52415-29-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29339900 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
4-Bromo-2-nitrotoluene-->EthenaMine, 2-(4-broMo-2-nitrophenyl)-N,N-diMethyl--->N,N-Dimethylformamide dimethyl acetal-->N,N-Dimethylformamide-->Pyrrolidine-->Acetic acid-->ZINC | [Preparation Products]
6-Bromoindole-3-carboxaldehyde-->7-bromoquinoline-4-carboxylic acid-->AKOS B006681-->Indole-6-boronic acid-->Indole-6-boronic acid pinacol ester-->3H-Indol-3-one, 6-bromo-2-(6-bromo-1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,2-dihydro--->Indole-->6-Bromoisatin-->3-IODO-6-BROMO INDOLE-->6-Bromo-3-(1-methyl-1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole-->1H-INDOLE-3-ACETIC ACID, 6-BROMO-α-OXO--->6-Bromo-1-(tert-butyldimethylsilyl)indole |
| Hazard Information | Back Directory | [Chemical Properties]
White to brown powder | [Uses]
6-Bromoindole is a starting material in the synthesis of various indole derivatives. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 49, p. 249, 1984 DOI: 10.1021/jo00176a007 | [General Description]
6-Bromoindole is an indole derivative. It undergoes palladium-catalyzed reaction with 2-(4-fluorophenyl)ethylpiperazine to afford the carbonylation products. | [Synthesis]
Step A: Under nitrogen protection, 4-bromo-2-nitrotoluene (7.9 g, 36.6 mmol) was dissolved in anhydrous N,N-dimethylformamide (73 mL), and N,N-dimethylformamide dimethyl acetal (14.5 mL, 110 mmol) and pyrrolidine (4.7 mL) were added sequentially. The reaction mixture was heated and stirred in an oil bath at 110 °C for 90 min. After completion of the reaction, the mixture was cooled to room temperature, diluted with ether (200 mL), and washed with deionized water (3 × 100 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was dissolved in 80% aqueous acetic acid (245 mL) and heated to 75 °C. Under stirring, zinc powder (20.8 g, 318 mmol) was added in batches for 2 hours. After addition, the reaction mixture was warmed to 85 °C and stirring was continued for 3.5 hours. After completion of the reaction, the mixture was cooled to room temperature and then to 0 °C in an ice bath and filtered to remove insoluble matter. The filtrate was diluted with ethyl acetate (200 mL) and washed with deionized water (2 × 100 mL). The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give a brown oily crude product. The crude product was purified by fast column chromatography with the eluent being a mixed solvent of hexane/ethyl acetate in the order of 95:5 and 90:10 to give 6-bromoindole as a gray solid (2.61 g, 36% yield). The structure of the product was confirmed by 1H NMR (500 MHz, CDCl3): δ 8.14 (br s, 1H), 7.53 (s, 1H), 7.49 (d, J = 8.4 Hz, 1H), 7.21 (dd, J = 8.4, 1.7 Hz, 1H), 7.17-7.15 (m, 1H), 6.53-6.51 (m, 1H). | [References]
[1] Journal of Organic Chemistry, 2004, vol. 69, # 20, p. 6812 - 6820
[2] RSC Advances, 2014, vol. 4, # 9, p. 4672 - 4675
[3] Patent: US2006/52378, 2006, A1. Location in patent: Page/Page column 154
[4] Tetrahedron, 1999, vol. 55, # 4, p. 935 - 942
[5] Patent: US2011/46370, 2011, A1. Location in patent: Page/Page column 10 |
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