1H-Indole-3-carboxaldehyde,6-bromo-
- CAS Number:17826-04-9
- Molecular Formula:C9H6 Br N O
- Molecular Weight:224.057
- Mol File:17826-04-9.mol
Synonyms:Indole-3-carboxaldehyde,6-bromo- (8CI); 3-Formyl-6-bromo-1H-indole; 6-Bromo-1H-indole-3-carboxaldehyde;6-Bromoindole-3-carbaldehyde; 6-Bromoindole-3-carboxaldehyde
Physicochemical Properties
- Melting Point:202-203 ºC
- Boiling Point:395.6°Cat760mmHg
- Density:1.727g/cm3
- Solubility:N/A
- Flash Point:193°C
- Vapor Density:N/A
- Refractive Index:N/A
- Sensitive:N/A
- Storage Temp.:N/A
- Appearance/Colour:N/A

1H-Indole-3-carboxaldehyde,6-bromo- Safety information and MSDS
·Hazard identification:
Pictogram(s) | ![]() |
---|---|
Signal word | Warning |
Hazard statement(s) | H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
Precautionary statement(s) | |
Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. 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 | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/…if you feel unwell. P330 Rinse mouth. 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/…if 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 ... |
·Composition/information on ingredients:
Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
---|---|---|---|---|
6-bromo-1H-indole-3-carbaldehyde | 6-bromo-1H-indole-3-carbaldehyde | 17826-04-9 | none | 100% |
·First-aid measures:
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
·Fire-fighting measures:
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
1H-Indole-3-carboxaldehyde,6-bromo- Relevant articles
All total 2 Articles be found
Structure-activity relationship for bromoindole carbaldehydes: Effects on the sea urchin embryo cell cycle
Moubax, Isabelle,Bontemps-Subielos, Nathalie,Banaigs, Bernard,Combaut, Georges,Huitorel, Philippe,Girard, Jean-Pierre,Pesando, Danielle
, p. 589 - 596 (2007/10/03)
Natural derivatives of indole-3-carbaldehyde were isolated from the tropical marine ascidian Stomoza murrayi. A series of 13 derivatives, three natural and 10 synthetic (brominated and N-methylated), were examined for their effects on cell division of sea urchin eggs. These derivatives were shown to inhibit the first mitotic cycle in a concentration-dependent manner. By comparing the IC50 values with the structure of the various molecules, we were able to determine that bromination increased the cytotoxicity of the compound with a maximum occurring when bromine was added to carbon number 2, while addition of N-methylation was shown to markedly reduce the cytotoxicity of these same compounds brominated at carbon 2 only. Biological activity of this family of compounds has been characterized, via detailed study of addition of the most active derivative, 2,5,6-tribromoindole-3-carbaldehyde, on macromolecule synthesis and cytoskeleton reorganization during the first mitotic cycle of fertilized sea urchin eggs. Fluorescence localization of chromatin and microtubules revealed that 2,5,6-tribromoindole-3-carbaldehyde allowed pronuclei migration and fusion but prevented the condensation of chromatin, nuclear envelope breakdown, and bipolar mitotic spindle assembly, inducing an arrest of sea urchin embryogenesis at the beginning of mitosis. It is postulated here that this phenotype is likely to be due to a strong inhibition of DNA replication and protein synthesis.
6-bromoindole-3-carbaldehyde, from an Acinetobacter Sp. Bacterium associated with the ascidian Stomozoa murrayi
Olguin-Uribe,Abou-Mansour,Boulander,Debard,Francisco,Combaut
, p. 2507 - 2521 (2007/10/03)
The ascidian Stomozoa murrayi from Caribbean coral reefs is not overgrown by macroepibionts. Chemical extraction of this organism gave 6-bromoindole-3-carbaldehyde (1) and its debromo analog (2). These two compounds, previously obtained from several marine organisms, were also extracted from an Acinetobacter sp. bacterium isolated from the surface of S. murrayi. Compound 1 exhibits in vitro settlement inhibition of barnacle larvae, moderate antibacterial properties, but not antialgal or fish-feeding deterrent activities. Its potential role in contributing to the reduced fouling in S. murrayi is proposed.
1H-Indole-3-carboxaldehyde,6-bromo- Synthetic route And Reaction conditions
- 487-89-8,1228547-52-1
Indole-3-carboxaldehyde
- 877-03-2
5-bromo-1H-indole-3-carboxaldehyde
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

Conditions | Yield |
---|---|
Withbromine;
acetic acid; |
- 487-89-8,1228547-52-1
Indole-3-carboxaldehyde
- 877-03-2
5-bromo-1H-indole-3-carboxaldehyde
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde
- 17900-95-7
5,6-dibromo-1H-indole-3-carboxaldehyde

Conditions | Yield |
---|---|
13% 9% 3% |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: AcOH 2: LiAH4 / tetrahydrofuran 3: methanol |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde
- 354538-27-5
6-bromo-1-tosyl-3-vinyl-1H-indole

Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C Withn-butyllithium;
potassium carbonate;Intetrahydrofuran;
hexane;
butanone;2.2: Wittig olefination; |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C 3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C 4.1: 94 percent / imidazole / CH2Cl2 / 12.5 h / 0 - 20 °C 5.1: 87 percent / Ph3P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C 6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: LiAlH4 / tetrahydrofuran / 1 h / 0 °C With1H-imidazole;
AD-mix-α;
lithium aluminium tetrahydride;
n-butyllithium;
diphenylphosphoranyl azide;
tetrabutyl ammonium fluoride;
potassium carbonate;
triphenylphosphine;
diethylazodicarboxylate;Intetrahydrofuran;
hexane;
dichloromethane;
water;
toluene;
butanone;
tert-butyl alcohol;2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation; |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde
- 354538-26-4
(S)-1-(N-tosyl-6-bromoindol-3-yl)-1,2-ethanediol

Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C 3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C WithAD-mix-α;
n-butyllithium;
potassium carbonate;Intetrahydrofuran;
hexane;
water;
butanone;
tert-butyl alcohol;2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation; |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde
- 1026187-62-1
2-azido-1-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethylamine

Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C 3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C 4.1: 94 percent / imidazole / CH2Cl2 / 12.5 h / 0 - 20 °C 5.1: 87 percent / Ph3P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C 6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: LiAlH4 / tetrahydrofuran / 1 h / 0 °C 8.1: Et3N / CH2Cl2 / 4 h / 0 °C 9.1: 335 mg / Et3N; DMAP / CH2Cl2 / 5 h / 20 °C 10.1: 88 percent / NaN3 / dimethylformamide / 12 h / 80 °C 11.1: CF3CO2H / CH2Cl2 / 20 °C With1H-imidazole;
dmap;
AD-mix-α;
lithium aluminium tetrahydride;
n-butyllithium;
sodium azide;
diphenylphosphoranyl azide;
tetrabutyl ammonium fluoride;
potassium carbonate;
triethylamine;
triphenylphosphine;
trifluoroacetic acid;
diethylazodicarboxylate;Intetrahydrofuran;
hexane;
dichloromethane;
water;
N,N-dimethyl-formamide;
toluene;
butanone;
tert-butyl alcohol;2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation; |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C 3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C 4.1: 94 percent / imidazole / CH2Cl2 / 12.5 h / 0 - 20 °C 5.1: 87 percent / Ph3P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C 6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: LiAlH4 / tetrahydrofuran / 1 h / 0 °C With1H-imidazole;
AD-mix-α;
lithium aluminium tetrahydride;
n-butyllithium;
diphenylphosphoranyl azide;
tetrabutyl ammonium fluoride;
potassium carbonate;
triphenylphosphine;
diethylazodicarboxylate;Intetrahydrofuran;
hexane;
dichloromethane;
water;
toluene;
butanone;
tert-butyl alcohol;2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation; |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde
- 354538-34-4
(R)-2-azido-2-(N-tosyl-6-bromoindol-3-yl)-1-ethanol

Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C 3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C 4.1: 94 percent / imidazole / CH2Cl2 / 12.5 h / 0 - 20 °C 5.1: 87 percent / Ph3P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C 6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C With1H-imidazole;
AD-mix-α;
n-butyllithium;
diphenylphosphoranyl azide;
tetrabutyl ammonium fluoride;
potassium carbonate;
triphenylphosphine;
diethylazodicarboxylate;Intetrahydrofuran;
hexane;
dichloromethane;
water;
toluene;
butanone;
tert-butyl alcohol;2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation; |
- 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 100 percent / K2CO3 / butan-2-one / 3 h / Heating 2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C 2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C 3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C 4.1: 94 percent / imidazole / CH2Cl2 / 12.5 h / 0 - 20 °C 5.1: 87 percent / Ph3P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C 6.1: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C 7.1: LiAlH4 / tetrahydrofuran / 1 h / 0 °C 8.1: Et3N / CH2Cl2 / 4 h / 0 °C With1H-imidazole;
AD-mix-α;
lithium aluminium tetrahydride;
n-butyllithium;
diphenylphosphoranyl azide;
tetrabutyl ammonium fluoride;
potassium carbonate;
triethylamine;
triphenylphosphine;
diethylazodicarboxylate;Intetrahydrofuran;
hexane;
dichloromethane;
water;
toluene;
butanone;
tert-butyl alcohol;2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation; |
1H-Indole-3-carboxaldehyde,6-bromo- Raw materials
1H-Indole-3-carboxaldehyde,6-bromo- Target Products
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Country :
China (Mainland)(82)
United Kingdom(2)
United States(2)
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