4-Hydroxy-1H-indole-3-carbaldehyde | 4-Hydroxyindole-3-carboxaldehyde | Indoles

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Quality Control of 4-Hydroxy-1H-indole-3-carbaldehyde Purity: 95% SDS Specification

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NMR

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Product Details of 4-Hydroxy-1H-indole-3-carbaldehyde

CAS No. :	81779-27-3
Formula :	C₉H₇NO₂
M.W :	161.16
SMILES Code :	OC1=C2C(=CC=C1)[NH]C=C2C=O
Synonyms :	4-Hydroxyindole-3-carboxaldehyde
MDL No. :	MFCD05864721
InChI Key :	QLBZIZLLMNWTHG-UHFFFAOYSA-N
Pubchem ID :	9815282

Safety of 4-Hydroxy-1H-indole-3-carbaldehyde

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of 4-Hydroxy-1H-indole-3-carbaldehyde

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 81779-27-3 ]

[ 81779-27-3 ] Synthesis Path-Downstream 1~35

1
[ 72527-73-2 ]
[ 81779-27-3 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

2
[ 141692-10-6 ]
[ 81779-27-3 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

3
[ 81779-27-3 ]
[ 106-95-6 ]
[ 109523-70-8 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

4
[ 81779-27-3 ]
[ 106-89-8 ]
[ 109523-75-3 ]
[ 109523-76-4 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

5
[ 81779-27-3 ]
[ 74-88-4 ]
[ 109523-69-5 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

6
[ 487-89-8 ]
[ 81779-27-3 ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

7
[ 81779-27-3 ]
4-Hydroxy-7-nitro-1H-indole-3-carbaldehyde [ No CAS ]
[ 183621-60-5 ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

8
[ 7042-71-9 ]
[ 81779-27-3 ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

9
[ 24424-99-5 ]
[ 81779-27-3 ]
[ 404888-00-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With dmap; In acetonitrile; at 0℃; for 3h;	EXAMPLE 2 OF REFERENCE 3-Formyl-4-hydroxyindole-1-carboxylic Acid tert-butyl Ester (2-1) (R7=R11=H) A mixture of the 3-formyl-4-hydroxyindole (1-1) 323 mg, di-tert-butyldicarbonate 458 mg, dimethylaminopyridine 12.5 mg and acetonitrile 25 ml was stirred under cooling in ice for 3 h.The solvent was removed under reduced pressure and the residue obtained was recrystallized from acetone-isopropyl ether to give the titled compound as pale yellow crystals, m.p. 159-161 C.(dec.), 389 mg.Yield 74%. 1H-NMR(CDCl3): 1.71 (9H, s), 6.84 (1H, dd, J=8.1, 0.9 Hz), 7.31 (1H, t, J=8.1 Hz), 7.61 (1H, dd, J=8.1, 0.9 Hz), 8.25 (1H, s), 9.76 (1H, d, J=0.6 Hz), 10.13 (1H, s).

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.
[2]Patent: US2003/236295,2003,A1 .Location in patent: Page 9.

10
[ 81779-27-3 ]
5-bromo-4-hydroxyindole-3-carbaldehyde [ No CAS ]
[ 404887-98-5 ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

11
[ 81779-27-3 ]
5-bromo-4-hydroxyindole-3-carbaldehyde [ No CAS ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

12
[ 81779-27-3 ]
[ 404888-04-6 ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

13
[ 81779-27-3 ]
[ 404888-02-4 ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

14
[ 81779-27-3 ]
4-benzyloxy-5-bromoindole-3-acetonitrile [ No CAS ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

15
[ 81779-27-3 ]
4-benzyloxy-1-tert-butoxycarbonylindole-3-carbaldehyde [ No CAS ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

16
[ 81779-27-3 ]
1-benzyl-4-benzyloxy-7-bromindole-3-carbaldehyde [ No CAS ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

17
[ 81779-27-3 ]
[ 404888-03-5 ]

References: [1]Chemical and pharmaceutical bulletin,2002,vol. 50,p. 92 - 99.

18
[ 81779-27-3 ]
[ 135531-93-0 ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

19
[ 81779-27-3 ]
[ 183621-63-8 ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

20
[ 81779-27-3 ]
1,4-dihydroxy-5-nitroindole [ No CAS ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

21
[ 81779-27-3 ]
[ 183621-62-7 ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

22
[ 81779-27-3 ]
4-Acetoxy-1-acetyl-5-nitro-1H-indole-3-carboxylic acid [ No CAS ]

References: [1]Heterocycles,1996,vol. 43,p. 1855 - 1858.

23
[ 81779-27-3 ]
[ 109523-71-9 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

24
[ 81779-27-3 ]
[ 109523-74-2 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

25
[ 81779-27-3 ]
[ 109523-77-5 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

26
[ 81779-27-3 ]
[ 109523-78-6 ]

References: [1]Heterocycles,1986,vol. 24,p. 3065 - 3069.

27
[ 2380-94-1 ]
[ 68-12-2 ]
[ 81779-27-3 ]

Yield	Reaction Conditions	Operation in experiment
82%		EXAMPLE 1 OF REFERENCE 4-Hydroxyindole-3-carbaldehyde (1-1) (R7=R11=H) phosphorous oxychloride 7.35 ml was added dropwise to dry dimethylformamide 15 ml under cooling in ice-methanol bath and the mixture was stirred for 15 min.Then, a solution of the 4-hydroxyindole 5.0 g in dry dimethylformamide 10 ml was added dropwise to the mixture under cooling in ice and the mixture was stirred for 2 h at room temperature.water was added under cooling in ice to the mixture, which was made alkaline with a 30% aqueous sodium hydroxide solution and was stirred for 15 min.Then, the mixture was acidified to PH 4 with 5N-HCl and the precipitate was collected by filtration, washed with water and dried to give the titled compound 4.99 g as crude crystalline materials.Yield 82%.Crude crystalline materials are recrystallized from methanol to give yellow crystals m.p. 190-193 C. 1H-NMR(DMSO-d6): 6.54 (1H, dd, J=8.1, 0.9 Hz), 6.95 (1H, dd, J=8.1, 0.9 Hz), 7.13 (1H, t, J=8.1 Hz), 8.37 (1H, s), 9.64 (1H, s), 10.54 (1H, br s), 12.35 (1H, br s).

References: [1]Patent: US2003/236295,2003,A1 .Location in patent: Page 9.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 3 4-Hydroxy-3-formylindole 17.2 g. 4-Benzyloxy-3-formylindole (see Can. J. Chem., 42, 514/1964) are dissolved in 700 ml. methanol, 5 ml. triethylamine are added thereto and the reaction mixture is mixed with 3 g. 10% palladium-active charcoal and hydrogenated at ambient temperature and 1 bar hydrogen pressure. After removal of the catalyst, the reaction mixture is evaporated to give 11 g. (98% of theory) 4-hydroxy-3-formylindole; m.p. 196-200 C.

29
[ 2380-94-1 ]
[ 81779-27-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; trichlorophosphate; In N-methyl-acetamide; water;	4-Hydroxyindole-3-carbaldehyde(1-1) (R7=R11=H) Phosphorous oxychloride 7.35 ml was added dropwise to dry dimethylformamide 15 ml under cooling in ice-methanol bath and the mixture was stirred for 15 min. Then, a solution of the 4-hydroxyindole 5.0 g in dry dimethylformamide 10 ml was added dropwise to the mixture under cooling in ice and the mixture was stirred for 2 h at room temperature. Water was added under cooling in ice to the mixture, which was made alkaline with a 30% aqueous sodium hydroxide solution and was stirred for 15 min. Then, the mixture was acidified to pH 4 with 5N-HCl and the precipitate was collected by filtration, washed with water and dried to give the titled compound 4.99 g as crude crystalline materials. Yield 82%. Crude crystalline materials are recrystallized from methanol to give yellow crystals m.p. 190-193 ØC. 1H-NMR(DMSO-d6): 6.54 (1H, dd, J = 8.1, 0.9 Hz), 6.95 (1H, dd, J = 8.1, 0.9 Hz), 7.13 (1H, t, J = 8.1 Hz), 8.37 (1H, s), 9.64 (1H, s), 10.54 (1H, br s), 12.35 (1H, br s).

References: [1]Patent: EP1325909,2003,A1 .

30
[ 1346151-06-1 ]
[ 81779-27-3 ]
[ 1346151-07-2 ]

Yield	Reaction Conditions	Operation in experiment
64%	With piperidine; In methanol; at 60℃; for 2h;	(b) Step 2 A solution of tert-butyl 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazine-1-carboxylate (0.056 g, 0.016 mmol) in methanol (2.0 mL) was added with <strong>[81779-27-3]4-hydroxy-1H-indole-3-carboxaldehyde</strong> (0.026 g, 0.016 mmol). Then, the mixture was added with 5 drops of piperidine, and then the mixture was stirred at 60C for 2 hours. The solvent was evaporated under reduced pressure, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain tert-butyl (Z)-4-({6-hydroxy-2-[(4-hydroxy-1H-indol-3-yl)methylene]-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazine-1-carboxylate (0.050 g, 64%). 1H NMR (300 MHz, DMSO-d6) delta 1.38 (s, 9H), 2.53 (m, 4H), 3.38 (m, 4H), 3.88 (s, 2H), 6.55 (d, J = 7.3 Hz, 1H), 6.72 (d, J = 8.1 Hz, 1H), 6.91-7.04 (m, 2H), 7.52 (d, J = 8.1 Hz, 1H), 7.69 (s, 1H), 8.06 (d, J = 2.9 Hz, 1H), 11.87 (s, 1H).

References: [1]Patent: EP2565192,2013,A1 .Location in patent: Paragraph 0197.

31
[ 81779-27-3 ]
N-(2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)hydrazinecarboxylic acid tert-butyl ester [ No CAS ]

References: [1]Patent: US2003/236295,2003,A1 .
[2]Patent: US2003/236295,2003,A1 .
[3]Patent: US2003/236295,2003,A1 .

32
[ 81779-27-3 ]
(2-Benzenesulfonyl-1-iodo-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-yl)dimethylamine [ No CAS ]

References: [1]Patent: US2003/236295,2003,A1 .
[2]Patent: US2003/236295,2003,A1 .
[3]Patent: US2003/236295,2003,A1 .

33
[ 81779-27-3 ]
[ 405891-56-7 ]

References: [1]Patent: US2003/236295,2003,A1 .
[2]Patent: US2003/236295,2003,A1 .
[3]Patent: US2003/236295,2003,A1 .

34
[ 81779-27-3 ]
dimethyl-(2,7,8,9-tetrahydro-6-oxa-2-azabenzo[c,d]azulen-8-yl)amine [ No CAS ]

References: [1]Patent: US2003/236295,2003,A1 .
[2]Patent: US2003/236295,2003,A1 .
[3]Patent: US2003/236295,2003,A1 .

35
[ 81779-27-3 ]
2,7-dihydro-6-oxa-2-azabenzo[c,d]azulene-8-carboxylic acid [ No CAS ]

References: [1]Patent: US2003/236295,2003,A1 .
[2]Patent: US2003/236295,2003,A1 .
[3]Patent: US2003/236295,2003,A1 .

Historical Records

Technical Information

• Appel Reaction • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chugaev Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Corey-Kim Oxidation • Dess-Martin Oxidation • Fischer Indole Synthesis • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Jones Oxidation • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • Martin's Sulfurane Dehydrating Reagent • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mitsunobu Reaction • Moffatt Oxidation • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Alcohols by DMSO • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Alcohols • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Alcohols • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Ritter Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Sharpless Olefin Synthesis • Stetter Reaction • Stobbe Condensation • Swern Oxidation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Precautionary Statements-General
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
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P233	Keep container tightly closed.
P234	Keep only in original container.
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P285	In case of inadequate ventilation wear respiratory protection.
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P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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P391	Collect spillage. Hazardous to the aquatic environment
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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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P370 + P378	In case of fire:
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Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
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P422
P402 + P404	Store in a dry place. Store in a closed container.
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P411 + P235	Keep cool.
Disposal
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 81779-27-3

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CAS No.: 81779-27-3

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Product Details of 4-Hydroxy-1H-indole-3-carbaldehyde

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Application In Synthesis of 4-Hydroxy-1H-indole-3-carbaldehyde

[ 81779-27-3 ] Synthesis Path-Downstream 1~35

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