Seradix
3-Indolebutyric acid
CAS: 133-32-4
Molecular Formula: C12H13NO2
Seradix - Names and Identifiers
| Name | 3-Indolebutyric acid |
| Synonyms | IBA Seradix jiffygrow Naftidrofuryl indolebutyricacid Indolebutyric acid hormexrootingpowder 3-Indolebutyvic acid 3-Indolebutyric acid indolyl-3-butyricacid Indole-3-butyric acid 3-Indole Butyric Acid 3-Indolylbutyric acid 1h-indole-3-butanoicacid Indole-3-butyric acid IBA 4-(3-Indolyl)butyric acid 4-(1H-indol-3-yl)butanoate kyselina4-indol-3-ylmaselina gamma-(3-indolyl)butyricacid gamma-(indole-3)-butyricacid 4-(3-1H-Indolyl)butyric acid gamma-(indol-3-yl)butyricacid 4-(1H-indol-3-yl)butanoic acid Indole-3-butyric acid,[4-(3-Indolyl)butyric acid] |
| CAS | 133-32-4 |
| EINECS | 205-101-5 |
| InChI | InChI=1/C12H13NO2/c14-12(15)7-3-4-9-8-13-11-6-2-1-5-10(9)11/h1-2,5-6,8,13H,3-4,7H2,(H,14,15)/p-1 |
| InChIKey | JTEDVYBZBROSJT-UHFFFAOYSA-N |
Seradix - Physico-chemical Properties
| Molecular Formula | C12H13NO2 |
| Molar Mass | 203.24 |
| Density | 1.1255 (rough estimate) |
| Melting Point | 124-125.5°C(lit.) |
| Boling Point | 341.55°C (rough estimate) |
| Flash Point | 211.8°C |
| Water Solubility | Soluble in water(0.25g/L). |
| Solubility | Soluble in ethanol, ether and acetone, almost insoluble in water and chloroform. |
| Vapor Presure | 4.9E-08mmHg at 25°C |
| Appearance | White or light yellow crystals |
| Color | Clear colorless to pale yellow |
| Merck | 14,4965 |
| BRN | 171120 |
| pKa | 4.83±0.10(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. Light sensitive. |
| Sensitive | Air Sensitive |
| Refractive Index | 1.5440 (estimate) |
| MDL | MFCD00005664 |
| Physical and Chemical Properties | Melting point 120-125°C |
| Use | Used as plant growth stimulating hormone, promote plant root growth, improve germination rate, survival rate |
Seradix - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S38 - In case of insufficient ventilation, wear suitable respiratory equipment. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S28A - |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | NL5250000 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | T |
| HS Code | 29339990 |
| Hazard Note | Irritant |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 i.p. in mice: 100 mg/kg (Anderson) |
Seradix - Reference
| Reference Show more | 1. Li Jianjun An Xiaoqin Medina Maihaiti et al. Study on Influencing Factors of 'Hotan' Rose Dormant Branch Cutting [J]. Journal of Xinjiang Agricultural University 2019 v.42;No.185(05):39-45. 2. Liu Liujiao, Liu Zhen, Wei Yan. Effects of Different Concentrations of IBA and Substrate on Rooting of Rosemary Cutting [J]. Southern Horticultural 2019 30(02):15-19. 3. Wang Chenxia, Li Yan, Chang Ruixue, et al. Effect of rare earth chelate on soil-borne pathogenic bacteria and its morphological and toxicological mechanism [J]. Chinese Journal of Rare Earth, 2020(4):532-538. 4. Zhao Lu, Zhou Xinfang, Sun Tianzun, et al. Physiological analysis of overwintering bud development of ginseng-endogenous plant hormone analysis based on HPLC-MS/MS method [J]. Journal of Northeast Normal University: Natural Science Edition 2020(1):127-135. 5. Wang Chenxia, Li Yan, Chang Ruixue, Chen Qing, Hu Lin, Cui Jianyu, Mu Kangguo. Effect of rare earth chelate on soil-borne pathogenic bacteria and its morphological and toxicological mechanism [J]. Chinese Journal of Rare Earth, 2020,38(04):532-538. 6. [IF = 3.463] Dejian Zhang et al."Root hair development of Poncirus trifoliata grow in different growth cultures and treated with 3-indolebutyric acid and ethephon." Sci Hortic-Amsterdam. 2013 Aug;160:389 7. [IF = 4.046] Yiwei Zhou et al."Effect of heterocystous nitrogen-fixing cyanobacteria against rice sheath blight and the underlying mechanism." Appl Soil Ecol. 2020 Sep;153:103580 |
Seradix - Nature
Open Data Verified Data
The Pure product was a white crystalline solid with a melting point of 123-125 °c. Insoluble in water, 20 deg C in water solubility of 0.25g/L. Soluble in benzene, soluble in other organic solvents.
Last Update：2024-01-02 23:10:35
Seradix - Preparation Method
Open Data Verified Data
obtained by condensation of indole with Y-Butyrolactone at the reflux temperature of tetralin. Or by indole and Grignard reagent and a chloro propionitrile reaction, prepared 3 a nitrile indole, and then by NaOH hydrolysis and hydrochloric acid reaction.
Last Update：2022-01-01 09:27:34
Seradix - Introduction
Slightly special smell. Soluble in ethanol, ether, benzene, DMSO, petroleum ether and acetone, almost insoluble in water and chloroform. Toxic, half lethal dose (mice, oral) 100mg/kg. It's irritating. Solubility in water: 250 mg/l (20 c).
Last Update：2022-10-16 17:13:25
Seradix - Use
Open Data Verified Data
is a broad-spectrum indole plant growth regulator, is a good rooting agent, can promote the rooting of herbaceous and Woody ornamental plants.
Last Update：2022-01-01 09:27:35
Seradix - Safety
Open Data Verified Data
mice were injected intraperitoneally with LD50:100mg/kg.
Last Update：2022-01-01 09:27:35
Seradix - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Plant growth regulator | Plant growth regulator is artificially synthesized with physiological activity, similar to plant hormones and can regulate plant physiological processes and control plant growth and Reproduction of organic compounds, indolebutyric acid (IBA) and naphthaleneacetic acid (NAA) are two commonly used plant growth regulators for cuttings and rooting, among them, indolebutyric acid has the best effect, because it operates less in plants and is easy to remain near the use site. In addition, if a root-promoting growth regulator is mixed with another substance that is beneficial to the role of the growth regulator, it can show synergy or additive effect, which may make plants that are difficult to root get more satisfactory results. Indolebutyric acid has a strong rooting effect, but the adventitious roots produced are thin and long, while the root-promoting effect of naphthaleneacetic acid (NAA) is that the roots are small and thick. Therefore, a mixture of the two can often obtain better results. In 1928, F.W.Went first isolated this chemical messenger that caused coleoptile bending and named it auxin. In 1934, F.Kogl et al. determined it to be indole acetic acid. Therefore, it is customary to use indole acetic acid as a synonym for auxin. Soon after recognizing that indole acetic acid has a growth-regulating effect, scientists discovered that indole propionic acid (IPA) and indole butyric acid (IBA) also have physiological effects similar to auxin. Later, it was discovered that naphthalene acetic acid (NAA), 2, 4-dichlorophenoxyacetic acid (2,4-D), 2,4, 6-trichlorobenzoic acid and 4-amino -3,5, 6-trichloropyridine carboxylic acids and some of their derivatives (including salts, esters, amides, such as sodium naphthalene acetate, 2,4-D butyl ester, naphthaleneacetamide, etc.), all have auxin activity. 3-indole butyric acid is not easy to be oxidized in plants, and its conductivity is poor. It has a physiological effect similar to indole acetic acid, which can act on the cell division and cell growth of plants, but it is not as obvious as indole acetic acid. It is mainly used to promote the rooting of cuttings and effectively promote the cell division of the cambium. Maintain the efficacy for a long time, form more adventitious roots and slender, and the effect of mixed application with naphthaleneacetic acid is better. 3-indole butyric acid can be used for cuttings and cuttings of chrysanthemum and other ornamental plants to promote rooting at a concentration of 0.5~1.0mg/L, but should not be used in leaves of plants. Degradation and metabolism: soil can degrade rapidly. |
| Preparation method | The laboratory obtained indole butyric acid by heating and refluxing the mixture of indole, potassium hydroxide, polyoxalic acid and dried tetralin with γ-butyrolactone. The reaction formula is as follows: Indole, potassium hydroxide, polyoxalic acid and dried tetralin are added to the reactor. After the mixture is stirred at room temperature for half an hour, γ-butyrolactone is added. Then heat reflux for 4 hours. The moisture in the reaction system is removed by the water separator. After cooling, all the solids are dissolved with water, and the organic layer is acidified with hydrochloric acid to precipitate a large amount of off-white solids. Suction filtration, water washing, drying to obtain crude indole butyric acid, the crude yield is 92.6%. After recrystallization with ethanol water, the white scaly crystal is 3-indolebutyric acid with a melting point of 121.5~123 ℃. Reference material: Editor-in-Chief Wang Daquan. Fine Chemical Production Process Diagram, Part II. Beijing: Chemical Industry Press. 1999. Page 260-261. |
| analysis method | 1. product analysis: in anhydrous ethanol, it was determined by ultraviolet spectrophotometry at 281nm (ACF Chemiefarma method). 2. Residue analysis: chloroform is used for extraction from acidic medium, methanol solution is oscillated with petroleum ether (40~60 ℃), and then ultraviolet detection (ACF Chemiefarma method) is carried out by high performance liquid chromatography. It can also refer to the residue analysis method of indole acetic acid. First, it is derived into methyl ester or trimethyl silane, and then analyzed by gas chromatography. |
| toxicity | low toxicity to humans and animals. Acute oral LD505000mg/kg in rats and 1760 mg/kg in mice. Carp LC50180mg/L(48h). Low toxicity to bees. |
| use | plant growth regulator, treated with 0.001% ~ 0.0001% liquid medicine, can promote the cutting rooting of many trees and flowers, and is of great significance to the mass propagation of saplings and flowers. It cannot be used for plant leaves when used. Plant hormone (rooting agent). Indolebutyric acid (IBA) is a broad-spectrum indole plant growth regulator, which is a good rooting agent and can promote the rooting of herbaceous and woody ornamental plant cuttings. It can also be used for fruit setting of melons and fruits to improve fruit setting rate. plant hormones; pharmaceutical intermediates used as plant growth stimulating hormone to promote the growth of plant taproots and improve the germination rate and survival rate |
| Production method | Preparation method 1 is obtained by condensation of indole and γ-butyrolactone at the reflux temperature of tetrahydronaphthalene. The operation method is as follows: 1.17g indole, 1.4g potassium hydroxide, 0.2g phase transfer catalyst polyethylene glycol and dried tetrahydronaphthalene 3mL are mixed, stirred for 30min at room temperature, 1.12g γ-butyrolactone is added, and refluxed for 4h at more than 200 ℃. The moisture in the reaction system is removed by the water separator. After cooling, the solids are completely dissolved with 15mL of water, and a large amount of off-white solids are precipitated by acidification with hydrochloric acid in the separated organic layer. Filter by suction, wash with water and dry to obtain 1.88g of product, and the yield of crude product is 92.6%. This method has the advantages of mild reaction conditions, simple operation and high yield. The second preparation method is to produce 3-butyronitrile indole by reacting indole with Grignard reagent and α-chloropropiononitrile, which is then hydrolyzed by NaOH and reacted with hydrochloric acid. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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View History
Seradix
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1,2,3,6-tetrahydro-N-(2,2,6,6-tetramethyl-4-piperidyl)-3,6-methanophthalimide
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1,2,3,6-tetrahydro-N-(2,2,6,6-tetramethyl-4-piperidyl)-3,6-methanophthalimide
ethyl 5-{benzoyl[(4-ethylphenyl)sulfonyl]amino}-2-methyl-1-benzofuran-3-carboxylate
154106-92-0
3,5-dimethoxypyridine-4-carbaldehyde
5-Amino-3-β-D-ribofuranosylimidazo[4,5-d][1,3]oxazin-7(3H)-one
(R)-4,4,4-trifluorobutan-2-amine
2231-49-4
4,5-dimethyl-2-{[(5-nitro-2-thienyl)methylene]amino}-3-thiophenecarboxamide