indobinine
Indole-3-propionic acid
Conditions | Yield |
---|---|
With sodium hydroxide for 0.25h; Heating; | 95% |
benzyl 3-indole propionate
Indole-3-propionic acid
Conditions | Yield |
---|---|
With sodium hydroxide; water for 0.25h; Heating; | 95% |
Conditions | Yield |
---|---|
With tetraacetyl diborate In acetonitrile at 20℃; Reagent/catalyst; Solvent; | 89% |
With acetic anhydride; acetic acid at 20℃; for 168h; | 50% |
With acetic anhydride In acetic acid at 43 - 50℃; for 50 - 64h; Product distribution / selectivity; |
3-(2-carboxyethyl)-1H-indole-2-carboxylic acid
Indole-3-propionic acid
Conditions | Yield |
---|---|
at 200℃; | 85% |
at 230℃; |
3-(1-pivaloyl-1H-indol-3-yl)propanoic acid
Indole-3-propionic acid
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran; hexane at 40 - 45℃; for 2h; | 78% |
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - 45℃; for 2h; Inert atmosphere; | 78% |
methyl 3-(2-thioxo-3-indolinyl)propanoate
A
Indole-3-propionic acid
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol at 20℃; for 0.416667h; | A 35% B 32% |
Conditions | Yield |
---|---|
at 120℃; |
(3-Indolyl)bernsteinsaeure
Indole-3-propionic acid
Conditions | Yield |
---|---|
at 205℃; |
diethyl 2-((1H-indol-3-yl)methyl)malonate
Indole-3-propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide | |
Multi-step reaction with 2 steps 1: aqueous NaOH View Scheme | |
Multi-step reaction with 2 steps 1: aqueous KOH View Scheme |
4-Nitrophenyl 3-(1H-Indol-3-yl)propanoate
A
4-nitro-phenol
B
Indole-3-propionic acid
Conditions | Yield |
---|---|
With water at 37℃; Rate constant; pH 7.0 to 8.0, enhancement of the hydrolysis rate in presence of Cu2+; |
Indole-3-propionic acid
Conditions | Yield |
---|---|
With potassium hydroxide |
Indole-3-propionic acid
Conditions | Yield |
---|---|
at 190 - 230℃; |
Indole-3-propionic acid
Conditions | Yield |
---|---|
at 190 - 230℃; |
ethyl 2-((1H-indol-3-yl)methyl)-3-oxobutanoate
Indole-3-propionic acid
Conditions | Yield |
---|---|
Behandeln des Reaktionsprodukts mit alkoh. Schwefelsaeure, anschliessend mit alkoh. Kalilauge; |
Indole-3-propionic acid
Conditions | Yield |
---|---|
at 190 - 230℃; |
ethanol
A
2-deoxy-D-glucose
B
β-D-2-deoxy-glucopyranose
C
Indole-3-propionic acid
D
D-glucal
Conditions | Yield |
---|---|
With 4-methyl-morpholine; water at 65℃; Product distribution; Kinetics; Further Variations:; EtOH/H2O ratio; Hydrolysis; alcoholysis; |
5-bromo-1H-indole
Indole-3-propionic acid
Indole-3-propionic acid
Conditions | Yield |
---|---|
In acetic acid at 0 - 75℃; for 1h; Product distribution / selectivity; |
Indole-3-propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) HCl; 2.) Na2CO3 / 1.) ethanol, reflux, 72 h; 2.) diethylene glycol, reflux, 72 h 2: 85 percent / 200 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: dibutyl ether 2: aqueous NaOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: piperidine; acetic acid; benzene 2: platinum; ethanol / Hydrogenation 3: aqueous KOH View Scheme |
(3-Indolmethylen)malonsaeure-diethylester
Indole-3-propionic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: platinum; ethanol / Hydrogenation 2: aqueous KOH View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: sodium acetate; hydrazine hydrate / ethyl methyl ether View Scheme |
3-(1H-indol-3-yl)-3-oxopropanoic acid
Indole-3-propionic acid
Conditions | Yield |
---|---|
With sodium acetate; hydrazine hydrate In ethyl methyl ether |
Conditions | Yield |
---|---|
In aq. phosphate buffer at 10 - 47℃; pH=6.8; Kinetics; |
diazomethane
Indole-3-propionic acid
Methyl indole-3-propionate
Conditions | Yield |
---|---|
In diethyl ether at 20℃; for 1h; | 100% |
Indole-3-propionic acid
Conditions | Yield |
---|---|
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 24h; | 100% |
Indole-3-propionic acid
1-amino-4-[(tert-butyloxycarbonyl)amino]butane
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1-amino-4-[(tert-butyloxycarbonyl)amino]butane In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 100% |
Indole-3-propionic acid
5-tert-butoxycarbonylamino-1-aminopentane
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 5-tert-butoxycarbonylamino-1-aminopentane With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 1h; | 99% |
With [ReOCl2(1,2-bis(diphenylphosphino)ethane)]; hydrogen; potassium tetraphenylborate In tetrahydrofuran at 160℃; under 30003 Torr; for 36h; Autoclave; Inert atmosphere; | 99% |
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 1h; | 98% |
Indole-3-propionic acid
pivaloyl chloride
3-(1-pivaloyl-1H-indol-3-yl)propanoic acid
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: pivaloyl chloride In tetrahydrofuran; hexane at -78 - -20℃; for 0.75h; Inert atmosphere; | 99% |
Stage #1: Indole-3-propionic acid With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.0833333h; Inert atmosphere; Stage #2: pivaloyl chloride In tetrahydrofuran; hexane at -78 - -20℃; for 0.75h; Inert atmosphere; | 99% |
With n-butyllithium In tetrahydrofuran at -78℃; | 91% |
Conditions | Yield |
---|---|
With sulfuric acid | 99% |
With sulfuric acid for 1h; Heating; | 97% |
Stage #1: methanol; Indole-3-propionic acid With sulfuric acid for 5h; Reflux; Stage #2: With sodium hydrogencarbonate In dichloromethane; water | 96% |
Conditions | Yield |
---|---|
With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 2h; Inert atmosphere; | 99% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate | 98% |
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h; | 97% |
Stage #1: Indole-3-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 23 - 25℃; for 4h; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With sulfuric acid In water at 0℃; Reflux; | 98% |
With sulfuric acid for 20h; Reflux; | 96% |
Stage #1: Indole-3-propionic acid; ethanol With sulfuric acid In water Heating / reflux; Stage #2: With water; sodium hydrogencarbonate In ethyl acetate | 95% |
Conditions | Yield |
---|---|
With methyl chloroformate | 98% |
Conditions | Yield |
---|---|
With iodine In acetonitrile at 20℃; | 98% |
With HMTAB In acetonitrile at 20℃; for 0.0666667h; | 98% |
Indole-3-propionic acid
diphenyl diselenide
3-(1H-indol-3-yl)-selenopropionic acid Se-phenyl ester
Conditions | Yield |
---|---|
With tributylphosphine In dichloromethane at 20℃; for 4h; | 98% |
Indole-3-propionic acid
N1-(1,2,3,4-tetrahydroacridin-9-yl)pentane-1,5-diamine
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 4h; Stage #2: N1-(1,2,3,4-tetrahydroacridin-9-yl)pentane-1,5-diamine In tetrahydrofuran at 20℃; for 20h; | 97% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 22℃; for 1h; Inert atmosphere; | 97% |
Indole-3-propionic acid
N,N-bis(trimethylsilyloxy)-1-propen-2-amine
Conditions | Yield |
---|---|
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h; regioselective reaction; | 97% |
Indole-3-propionic acid
N-BOC-1,2-diaminoethane
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: N-BOC-1,2-diaminoethane With triethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere; | 97% |
Indole-3-propionic acid
indole-3-propionic acid sodium salt
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 20℃; for 1h; | 96.05% |
With sodium hydroxide In ethanol for 2h; Reflux; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1.5h; Stage #2: With ammonia In tetrahydrofuran at 20℃; for 2.5h; | 96% |
Stage #1: Indole-3-propionic acid With triethylamine; methyl chloroformate In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With ammonia In tetrahydrofuran at 0℃; for 1h; | 95% |
With ammonia; triethylamine; diethyl dicarbonate In tetrahydrofuran at 20℃; for 16h; | 84% |
Conditions | Yield |
---|---|
With HMTAB In acetonitrile at 20℃; for 0.1h; | 96% |
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid; 2,4-Dimethoxybenzylamine With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.5h; Stage #2: With Lawessons reagent In 1,2-dimethoxyethane at 80℃; for 2h; | 96% |
Indole-3-propionic acid
4-tert-Butylaniline
N-(4-tert-butylphenyl)-3-(1H-indol-3-yl)propanamide
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-tert-Butylaniline In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane Condensation; | 95% |
With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine In dichloromethane at 0 - 20℃; coupling; | 95% |
Indole-3-propionic acid
methyl iodide
N-methyl-3-(indol-3-yl)propionic acid
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid; methyl iodide With potassium hydroxide In acetone at 20℃; for 4h; Stage #2: With potassium hydroxide In water for 2h; Heating; Further stages.; | 95% |
Stage #1: Indole-3-propionic acid; methyl iodide With potassium hydroxide In acetone at 0 - 25℃; Stage #2: With potassium hydroxide In water at 2℃; Reflux; Stage #3: With hydrogenchloride In water | 86% |
With sodium hydride In tetrahydrofuran for 16h; Inert atmosphere; | |
Stage #1: Indole-3-propionic acid; methyl iodide With potassium hydroxide In acetone at 0 - 20℃; for 4h; Stage #2: With potassium hydroxide In water for 2h; Reflux; |
Indole-3-propionic acid
1-benzoyl-2-isopropylhydrazine
N'-(3-(1H-indol-3-yl)propanoyl)-N'-isopropylbenzohydrazide
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 12h; | 95% |
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 12h; |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; | 94% |
Stage #1: Indole-3-propionic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.333333h; Inert atmosphere; Stage #2: Methyl 3-aminobenzoate In N,N-dimethyl-formamide at 50℃; for 4.5h; Inert atmosphere; |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile for 8h; Heating; | 94% |
With potassium carbonate In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; N,N-dimethyl-formamide | |
With potassium carbonate In acetonitrile at 20℃; for 3h; |
Indole-3-propionic acid
1,2,3,4-tetrahydronorharman-1-one
Conditions | Yield |
---|---|
Stage #1: Indole-3-propionic acid With dimethylphosphoryl azide; triethylamine In toluene at 90℃; for 1.5h; Curtius Rearrangement; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In toluene at 0 - 20℃; for 16h; Curtius Rearrangement; Inert atmosphere; | 94% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 15h; Inert atmosphere; | 94% |
The 3-Indolepropionic acid, with the CAS registry number830-96-6, has the IUPAC name of 3-(1H-indol-3-yl)propanoic acid. For being a kind of pale yellow to yellow crystalline powder, it is slightly soluble in water, ethanol, diethyl ether, acetone, benzene, chloroform and soluble in hot water while insoluble in cold water. It has a variety of product categories which include blocks; Carboxes; IndolesOxindoles; indole derivative; Indoles and derivatives; IndoleDerivative; Auxins; Biochemistry; Plant Growth Regulators; Simple Indoles. As to its usage, it is usually applied as the plants grow stimulin.
The physical properties of this chemical are as follows: (1)ACD/LogP: 1.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1; (4)ACD/LogD (pH 7.4): -0.79; (5)ACD/BCF (pH 5.5): 2.22; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 37.32; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 31.23; (13)Index of Refraction: 1.666; (14)Molar Refractivity: 54.27 cm3; (15)Molar Volume: 145.8 cm3; (16)Polarizability: 21.51×10-24 cm3; (17)Surface Tension: 61.8 dyne/cm; (18)Density: 1.297 g/cm3; (19)Flash Point: 206.4 °C; (20)Enthalpy of Vaporization: 70.75 kJ/mol; (21)Boiling Point: 417.6 °C at 760 mmHg; (22)Vapour Pressure: 1.01E-07 mmHg at 25°C; (23)Exact Mass: 189.078979; (24)MonoIsotopic Mass: 189.078979; (25)Topological Polar Surface Area: 53.1; (26)Heavy Atom Count: 14; (27)Complexity: 217.
The production method of this chemical: BAPNA have the diazotization reaction with sodium nitrite in the acidic condition, and then react with ethyl cyclopentanone-2-carboxylate to produce α-oxoethyldioic acid phenylhydrazone; Secondly, phenylhydrazone dissolve in the alcohol solution containing 20% sulfuric acid and have the reflux reaction for 4 hours to produce indole-2-carboxylic acid-3-propanoic acid; Thirdly heat it to 225-230℃ for half an hour till its reation finishs, and then dissolve the reactant into the boiling water and filter it after adding active carbon; Next concentrate the colatuie and crystallize and then go through the recrystallization with hot water to obtain this chemical.
When you are dealing with this chemical, you should be much more cautious. For being among the irritant chemicals, it is irritating to eyes, respiratory system and skin and may cause inflammation to the skin or other mucous membranes. For anther thing, it is highly flammable and its vapours may cause drowsiness and dizziness.
Therefore, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection and then avoid contacting with skin and eyes. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. When store it, keep the container tightly closed, away from sources of ignition - No smoking. Besides, do not breathe dust.
Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
(2)InChI: InChI=1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14)
(3)InChIKey: GOLXRNDWAUTYKT-UHFFFAOYSA-N
Below are the toxicity information of this chemical:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LDLo | intraperitoneal | 100mg/kg (100mg/kg) | LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA LUNGS, THORAX, OR RESPIRATION: DYSPNEA | Proceedings of the Society for Experimental Biology and Medicine. Vol. 34, Pg. 138, 1936. |
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