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6-Bromoindole

6-Bromoindole structure

CAS No:
52415-29-9
Formula:
C8H6BrN
Chemical Name:
6-Bromoindole
Synonyms:
1H-Indole,6-bromo-;Indole,6-bromo-;6-Bromo-1H-indole;6-Bromoindole;1294514-42-3
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

White to brown powder

6-Bromoindole Basic Attributes

Molecular Weight：

196.04

Exact Mass：

196.04

BRN：

112711

EC Number：

-0

DSSTox ID：

DTXSID00350299

HScode：

2933990090

Characteristics

PSA：

15.8

XLogP3：

3.3

Appearance：

White to brown Powder

Density：

1.7±0.1 g/cm3

Melting Point：

94 °C

Boiling Point：

70-75°C0,01mm

Flash Point：

70-75°C/0.01mm

Refractive Index：

1.712

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36-37/39

Marks：

Hazard note：

Irritant

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

6-bromoindole

6-Bromoindole Use and Manufacturing

Methods of Manufacturing

To a solution of 4-bromo-2-nitrotoluene (7.9 g, 36.6 mmol) in dimethylformamide (73 mL) were added N, N-dimethylformamide dimethylacetal (14.5 mL, 110 mmol) and pyrrolidine (4.7 mL), and the mixture was heated at 110° C. for 90 minutes. The cooled reaction mixture was diluted with diethyl ether, and washed with water. The aqueous layer was re-extracted with diethyl ether twice, and the combined organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue obtained was dissolved in aqueous acetic acid (245 mL, 80percent), and heated to 75° C. Zinc powder (20.8 g, 318 mmol) was added to the hot solution in small portions over 2 hours. The reaction mixture was then heated at 85° C. for 3 hours and 30 minutes, cooled to room temperature and then to 0° C. The precipitate formed was removed by filtration, and the filtrate was diluted with ethyl acetate and washed with water twice. The organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure to give a brown oil. The crude product was purified by flash column chromatography (95:5 hexanes/ethyl acetate, then 90:10 hexanes/ethyl acetate) to give 6-bromoindole as a grey solid (2.61 g, 36percent): Zinc granules (30 g, 459 mmol) were added over 30 minutes to a solution of crude Intermediate 10 (25 g, 93 mmol) in acetic acid (400 mL) and water (100 mL) at 75° C., after which the mixture was stirred for an additional 1 hour. The suspension was cooled, filtered, and extracted with ethyl acetate (2.x.2 L). The combined organic extracts were washed with water (2.x.2 L), saturated NaHCO3 solution (2.x.500 mL), and brine (2.x.500 mL), dried over magnesium sulfate (MgSO4), and filtered. The solvent was removed under reduced pressure to yield a purple residue which was purified by flash column chromatography, eluting with hexanes/methylene chloride (1:1), to provide 6-bromoindole (Intermediate 11) as a blue-white powder (4.9 g, 27percent over two steps): TLC Rf (1:9 ethyl acetate/chloroform)=0.81. The proton NMR spectrum (300 MHz, CDCl3) was identical to the known compound.

Uses

6-Bromoindole is a starting material in the synthesis of various indole derivatives.

Computed Properties

Molecular Weight:196.04
XLogP3:3.3
Hydrogen Bond Donor Count:1
Exact Mass:194.96836
Monoisotopic Mass:194.96836
Topological Polar Surface Area:15.8
Heavy Atom Count:10
Complexity:126
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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