3D Mol Similar

6-Bromo-1H-indole

Iupac Name：6-bromo-1H-indole

CAS No.: 52415-29-9

Molecular Weight：196.04394

Modify Date.: 2022-11-23 23:19

Introduction: 6-Bromoindole is a starting material in the synthesis of various indole derivatives. View more+

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1. Names and Identifiers

1.1 Name: 6-Bromo-1H-indole
1.2 Synonyms: 1H-Indole, 6-bromo- 6-BROMO-1H-INDOLE 6-Bromoindole 6-Bromoindole in stock Factory bromoindole bromoindole 6-Bromoindole BROMOINDOLE-6 EOS-60560 Indole, 6-bromo-

1.3 CAS No.: 52415-29-9

1.4 CID: 676493

1.5 EINECS(EC#): 000-000-0

1.6 Molecular Formula: C8H6BrN (isomer)

1.7 Inchi: InChI=1S/C8H6BrN/c9-7-2-1-6-3-4-10-8(6)5-7/h1-5,10H

1.8 InChkey: MAWGHOPSCKCTPA-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC2=C1C=CN2)Br

1.10 Isomers Smiles: C1=CC(=CC2=C1C=CN2)Br

2. Properties

2.1 Density: 1.66

2.1 Melting point: 89-91℃

2.1 Boiling point: 316.9 °C at 760 mmHg

2.1 Refractive index: 1.711

2.1 Flash Point: 316.9 °C at 760 mmHg

2.1 Precise Quality: 194.96800

2.1 PSA: 15.79000

2.1 logP: 2.93040

2.1 Appearance: White to brown Powder

2.2 Storage: Air Sensitive. Light Sensitive. Ambient temperatures.

2.3 Chemical Properties: White to brown powder

2.4 Color/Form: Yellow to Brown Solid

2.5 pKa: 16.07±0.30(Predicted)

3. Use and Manufacturing

3.1 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.

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

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H315-H319-H335

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P261-P305 + P351 + P338

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

52415-29-9Total: 15 Synthesis Route

875-51-4 152 Suppliers

52415-29-9 212 Suppliers

Literatures:
Sakamoto, Takao; Kondo, Yoshinori; Iwashita, Shigeki; Yamanaka, Hiroshi Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 5 p. 1823 - 1828
Yield: null

103-88-8 79 Suppliers

52415-29-9 212 Suppliers

Literatures:
Sakamoto, Takao; Kondo, Yoshinori; Iwashita, Shigeki; Yamanaka, Hiroshi Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 5 p. 1823 - 1828
Yield: null

881-50-5 16 Suppliers

52415-29-9 212 Suppliers

Literatures:
Sakamoto, Takao; Kondo, Yoshinori; Iwashita, Shigeki; Yamanaka, Hiroshi Chemical & Pharmaceutical Bulletin, 1987 , vol. 35, # 5 p. 1823 - 1828
Yield: null

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7. Precursor and Product

precursor:

112671-42-8

61293-29-6

112671-48-4

16732-65-3

103-88-8

875-51-4

108061-73-0

112671-54-2

5318-27-4

63839-24-7

881-50-5

99474-21-2

64085-52-5

78508-22-2

View all

product :

93862-70-5

884507-19-1

106851-31-4

224434-83-7

57916-08-2

145951-26-4

63839-24-7

189265-99-4

679794-03-7

642494-36-8

147621-18-9

17826-04-9

372077-73-1

868656-97-7

88704-40-9

301856-44-0

115666-46-1

1196-70-9

101774-27-0

115666-47-2

1217500-59-8

1204-32-6

125872-95-9

885271-72-7

View all

8. Other Information

8.0 Mesh Entry Terms: 6-bromoindole

9. Computational chemical data

Molecular Weight: 196.04394g/mol
Molecular Formula: C₈H₆BrN
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 194.96836
Monoisotopic Mass: 194.96836
Complexity: 126
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 15.8
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYByAAAAEAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAFgB8AAAHABQAAABrAjBHgQ8wPLJkACgAzRnRACCgCAxAiQI2aA4ZLgIIOLAkZGEIAhgkADIyhcQgIAOAgAAAAECAAAEAAAAAgQAAAAAAAAAAA==

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2-(4-Cyano-1H-indol-3-yl)acetic acid