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Indole-3-acetic acid

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Name

Indole-3-acetic acid

EINECS 201-748-2
CAS No. 87-51-4 Density 1.355 g/cm3
PSA 53.09000 LogP 1.79500
Solubility Soluble in ethanol, acetone, diethyl ether. Slightly soluble in chloroform. Insoluble in water Melting Point 165-169 °C(lit.)
Formula C10H9NO2 Boiling Point 415.03 °C at 760 mmHg
Molecular Weight 175.187 Flash Point 204.803 °C
Transport Information N/A Appearance white to tan crystals
Safety 22-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 87-51-4 (Indole-3-acetic acid) Hazard Symbols IrritantXi
Synonyms

beta-Indolylacetic acid;1H-Indole-3-acetic-a-t acid (9CI);Indole-3-acetate;omega-Skatole carboxylic acid;Acetic acid, indolyl-;.alpha.-IAA;.beta.-Indole-3-acetic acid;2-(1H-indol-3-yl)acetate;alpha-IAA;GAP;meso-2,3-Butanediol-bis(iodoacetate);3-Indolylmethylcarboxylic acid;3-Iaa;3-Indolylacetic acid;beta-Indoleacetic acid;Indolyl-3-acetic acid;1H-indol-3-ylacetic acid;Heteroauxin;Indol-3-ylacetic acid;[(2R,3S)-3-(2-iodoacetyl)oxybutan-2-yl] 2-iodoacetate;[3H]-IAA;(1H-Indol-3-yl)acetic acid;.beta.-Indolylacetic acid;Hexteroauxin;Indoleacetate;2-(3-Indolyl)acetic acid 3-(Carboxymethyl)-1H-indole;3-(Carboxymethyl)indole;potassium 2-(1H-indol-3-yl)acetate;.alpha.-Indol-3-yl-acetic acid;2-(1H-Indol-3-yl)acetic acid;Indole-3-acetic-t acid;Rhizopon A;Heteroauxinhexteroauxiniaa;3-Indolebutyric acid(IBA);.beta.-Indoleacetic acid;1H-Indole-3-acetic acid (9CI);Rhizopin;3-Indole acetic acid;3-Indoleacetic acid(IAA);Indole-3- acetic acid;3-Indoleacetic Acid, Indole-3-acetic acid;indoleI-3-acetic acid;Indole-3-acetic acid (3-IAA);3-Indole propanoic acid;

Article Data 107

Indole-3-acetic acid Synthetic route

120-72-9

indole

polyglycolide

polyglycolide

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With potassium hydroxide In water at 250℃; under 34200 - 38000 Torr; for 12h;95%
392-12-1

Indole-3-pyruvic acid

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With sodium perborate In water for 48h; Ambient temperature;71%
With sodium hydroxide; dihydrogen peroxide
40432-84-6

(5-bromo-1H-indol-3-yl)-acetic acid

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With hydrogen; sodium acetate; nickel In ethanol under 2327.2 Torr; for 4h; Ambient temperature;52%
623-73-4

diazoacetic acid ethyl ester

120-72-9

indole

A

87-51-4

indole-3-acetic acid

B

indole-1,3-diyl-di-acetic acid

Conditions
ConditionsYield
With diethyl ether; copper Erhitzen des Reaktionsprodukts mit methanol. KOH;
120-72-9

indole

79-14-1

glycolic Acid

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With potassium hydroxide at 250℃;
Stage #1: indole; glycolic Acid With potassium hydroxide at 250℃; for 18h;
Stage #2: With hydrogenchloride In water at 10℃;
With hydrogenchloride; potassium hydroxide In water
2591-98-2

indole-3-acetaldehyde

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With potassium permanganate; acetone
With NAD; water; enzyme AldC from Pseudomonas syringae In aq. buffer at 25℃; pH=8.0; Enzymatic reaction;
771-51-7

indole-3-acetonitrile

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With potassium hydroxide
With potassium hydroxide
With sodium hydroxide
526-55-6

2-(3-indole)-ethanol

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With potassium permanganate; sodium carbonate
239127-19-6

ethyl 3-indolylmethyl sulfide

A

87-51-4

indole-3-acetic acid

B

879-37-8

3-indolylacetamide

Conditions
ConditionsYield
With ethanol; sodium cyanide
87-52-5

3-(Dimethylaminomethyl)indole

87-51-4

indole-3-acetic acid

Conditions
ConditionsYield
With ethanol; sodium cyanide at 200℃;
Multi-step reaction with 2 steps
1: NaCN; aqueous ethanol
2: aqueous NaOH
View Scheme
With ethanol; sodium cyanide at 200℃;

Indole-3-acetic acid Consensus Reports

Reported in EPA TSCA Inventory.

Indole-3-acetic acid Specification

The Indole-3-acetic acid, with the CAS registry number 87-51-4, is also known as 3-Indolylacetic acid. It belongs to the product categories of Indole derivative; Indoles and derivatives; Carboxylic Acids; Pyrroles & Indoles; Indole; Organic acids; API intermediates; Indoles; Auxins; Biochemistry; Plant Growth Regulators; Simple Indoles; Plant Hormones; Carboxylic Acids; Heterocycles. Its EINECS number is 201-748-2. This chemical's molecular formula is C10H9NO2 and molecular weight is 175.19. What's more, its systematic name is 1H-Indol-3-ylacetic acid. Its classification codes are: (1)Agricultural Chemical; (2)Growth Substances; (3)Growth regulator / Fertilizer; (4)Mutation data; (5)Plant growth regulators; (6)Reproductive Effect; (7)Tumor data. This chemical should be sealed and stored in a cool and dry place. It is the most common, naturally-occurring, plant hormone of the auxin class. It is the best known of the auxins, and has been the subject of extensive studies by plant physiologists.

Physical properties of Indole-3-acetic acid are: (1)ACD/LogP: 1.526; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.48; (4)ACD/LogD (pH 7.4): -1.32; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 14.45; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 53.09 Å2; (13)Index of Refraction: 1.694; (14)Molar Refractivity: 49.642 cm3; (15)Molar Volume: 129.315 cm3; (16)Polarizability: 19.68×10-24cm3; (17)Surface Tension: 66.4 dyne/cm; (18)Density: 1.355 g/cm3; (19)Flash Point: 204.803 °C; (20)Enthalpy of Vaporization: 70.436 kJ/mol; (21)Boiling Point: 415.03 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 3-indol-3-yl-2-oxo-propionic acid at the ambient temperature. This reaction will need reagent sodium perborate tetrahydrate and solvent H2O with the reaction time of 48 hours. The yield is about 71%.

Indole-3-acetic acid can be prepared by 3-indol-3-yl-2-oxo-propionic acid at the ambient temperature

Uses of Indole-3-acetic acid: it can be used to produce indol-3-yl-acetyl chloride at the temperature of 0 °C. It will need reagent PCl5 and solvent diethyl ether with the reaction time of 1 hour. The yield is about 72%.

Indole-3-acetic acid can be used to produce indol-3-yl-acetyl chloride at the temperature of 0 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. You should not breathe dust. When using it, you must avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)Cc2c1ccccc1nc2
(2)Std. InChI: InChI=1S/C10H9NO2/c12-10(13)5-7-6-11-9-4-2-1-3-8(7)9/h1-4,6,11H,5H2,(H,12,13)
(3)Std. InChIKey: SEOVTRFCIGRIMH-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
rat LD oral > 500mg/kg (500mg/kg)   National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 7, 1953.

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