1-Naphthaleneacetic acid CAS 86-87-3
Introduction：Basic information about 1-Naphthaleneacetic acid CAS 86-87-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
1-Naphthaleneacetic acid Basic information
| Product Name: | 1-Naphthaleneacetic acid |
| Synonyms: | NAA, α-Naphthalene acetic acid;ALFA-NAPHTHALENEACETIC ACID 99%;α-naphthaleneacetic acid free acid;A-NAPHTHYLACETIC ACID:1-NAPHTHYLACETIC ACID;1-naphthaleneacetic acid, α-Naphthalene acetic acid, NAA;1-Naphthylaceticacid,96%;1-Naphthalene acetic acid;1-Naphthaleneacetic acid |
| CAS: | 86-87-3 |
| MF: | C12H10O2 |
| MW: | 186.21 |
| EINECS: | 201-705-8 |
| Product Categories: | Pesticide intermediates;Plant growth regulator, intermediates;plantgrowth;Auxins;Biochemistry;Plant Growth Regulators;Plant Hormones;PLANT GROWTH REGULATOR;Naphthalene series;Plant growth hormone;plant regulator;Naphthalene derivatives;Organics;Organic acids |
| Mol File: | 86-87-3.mol |
1-Naphthaleneacetic acid Chemical Properties
| Melting point | 141-143 °C(lit.) |
| Boiling point | 280.69°C (rough estimate) |
| density | 1.1032 (rough estimate) |
| bulk density | 240kg/m3 |
| refractive index | 1.6010 (estimate) |
| Fp | >100°C |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | acetone: 50 mg/mL, clear |
| form | crystalline |
| pka | 4.30±0.30(Predicted) |
| color | light yellow |
| Odor | Odorless |
| PH | 3.0 (0.6g/l, H2O, 25℃) |
| Water Solubility | Slightly soluble in water, ethanol, acetone, chloroform and ether. |
| Merck | 14,6371 |
| BRN | 1308415 |
| Stability: | Hygroscopic |
| Major Application | agriculture environmental |
| Cosmetics Ingredients Functions | SKIN CONDITIONING |
| InChI | 1S/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14) |
| InChIKey | PRPINYUDVPFIRX-UHFFFAOYSA-N |
| SMILES | OC(=O)Cc1cccc2ccccc12 |
| LogP | 2.240 |
| CAS DataBase Reference | 86-87-3(CAS DataBase Reference) |
| NIST Chemistry Reference | 1-Naphthaleneacetic acid(86-87-3) |
| EPA Substance Registry System | 1-Naphthaleneacetic acid (86-87-3) |
Safety Information
| Hazard Codes | Xi,Xn,C |
| Risk Statements | 36/37/38-22-68-41-37/38-34 |
| Safety Statements | 26-36-24/25-36/39-22-23-45-36/37/39-27 |
| WGK Germany | 3 |
| RTECS | QJ0876000 |
| TSCA | TSCA listed |
| HazardClass | IRRITANT |
| HS Code | 29163900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 3 Eye Dam. 1 Skin Irrit. 2 STOT SE 3 |
| Hazardous Substances Data | 86-87-3(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 1000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Description | 1-naphthaleneacetic acid (NAA), also known as α-naphthaleneacetic acid, belongs to a class of organic compounds of naphthalenes, which contain a naphthalene moiety of two fused benzene rings. NAA is a synthetic auxin plant hormone. It is used as a plant growth regulator to control preharvest fruit drop, flower induction and fruit thinning in various crops such as apples, potatoes, olives, and citrus fruits. It is used as a rooting agent and used for the vegetative propagation of plants from stem and leaf cutting. It is also used for plant tissue culture and as herbicide. Applied as a dust or spray it delays dissolution of the abscission layer, retarding the fruit drop. The effect of NAA on plant growth is greatly dependent on the time of admission and concentration. When used after four weeks, NAA stimulates shoot growth, while full-time use limits growth. When used in a 4-week pulse, adventitious root growth is greatly increased. |
| Chemical Properties | White needle crystal or crystalline powder, odorless. Slightly soluble in cold water and ethanol, easily soluble in hot water, acetone, ether, chloroform, benzene, acetic acid and alkali solution. |
| Uses | 1-Naphthaleneacetic acid is widely employed in agriculture as a synthetic plant hormone in the auxin family or a plant growth regulator, which can find applications in tissue culture. Inducing rooting of plant cuttings, spraying apple trees to prevent early drop, fruit thinner. 1-Naphthaleneacetic acid has been used: to modify MS media for the initiation of callus as a supplement in solid K3 medium for the selection of transformants in the preparation of culture medium like V-KM medium and Cg medium |
| Application | 1-Naphthaleneacetic acid (NAA) is a synthetic phytohormone auxin that is added to cell culture media such as Murashige & Skoog media and Chu′s N6 media. |
| Preparation | Industrially, 1-naphthaleneacetic acid is prepared by condensation reaction of naphthalene and chloroacetic acid in the presence of catalyst potassium chloride or aluminum powder. |
| Definition | ChEBI: 1-naphthaleneacetic acid is a naphthylacetic acid substituted by a carboxymethyl group at position 1. It has a role as a synthetic auxin. It is a conjugate acid of a 1-naphthaleneacetate. |
| General Description | 1-Naphthaleneacetic acid is widely employed in agriculture as a synthetic plant hormone in the auxin family or a plant growth regulator, which can find applications in tissue culture. It is used for the vegetative propagation of plants from stem and leaf cutting, abscission promoter and substrate for auxin inducers of specific plant enzymes. Further, it stimulates root formation in cuttings of woody and herbaceous plants. It is also used to prevent premature flower and fruit drop. It is also employed to control regrowth of tree sprouts after trimminguse. In addition to this, it is used in ornaments and serves as an ingredient in many commercial plant rooting horticultural products. |
| Hazard | Skin irritant. |
| Agricultural Uses | Plant growth regulator: An agent for thinning fruit sets in apples, pears, olivesand some citrus. Induces root formation on cuttingsand transplants. Inhibits fruit drops. Not currently registeredin EU countries (pending). Registered for use inthe U.S. and Canada. |
| Trade name | AGRONAA®; ALCO® NAA; ALPHASPRA®; AMCOTONE® APPL-SET®; CELMONE®;DESTRUXOL®; DIP’N GROW®; FRUITONE®;GOLDENGRO®; HORMEX®; KLINGTITE®; LIQUISTIK®; NAA 800®; NAFUSAKU®; NIAGARASTIK®; NU-TONE®; PARMONE®; PHYMONE®;PIMACOL-SOL®; PLANOFIX®; PLUCKER®;PRIMACOL®; RHIZOPON B ROOTING POWDER;ROOTONE® (component, with Indole-3-butyric acid and1-Naphthaleneacetamide); STAFAST®; STIK®; STOPDROP®; TEKKAM®; TIPOFF®; TRANSPLANTONE®(component, with 1-Naphthaleneacetamide); TREHOLD®; VARDHAK® |
| Biochem/physiol Actions | 1-Naphthaleneacetic acid is one of the synthetic auxins, used in plant propagation. It can induce the formation of lateral and adventitious roots. |
| Safety Profile | Poison byintraperitoneal route. Moderately toxic byingestion. Mutation data reported. A skin,mucous membrane, and severe eye irritant.Can cause depression. A pesticide, When heated to decomposition it emits acridsmoke and irritating fumes. |
| Potential Exposure | 1-Naphthaleneacetic acid is a carboxylic acid plant growth regulator used for thinning fruit sets in apples, pears, olives, and some citrus. Induces root formation on cuttings and transplants. Inhibits fruit drops. Not currently registered in EU countries (may be pending). |
| Shipping | UN1759 Corrosive solids, n.o.s., Hazard Class:8; Labels: 8-Corrosive material, Technical Name Required. |
| Purification Methods | Crystallise the acid from EtOH or water. [Beilstein 9 H 666, 9 IV 2424.] |
| Incompatibilities | Incompatible with oxidizers (chlorates,nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions.Keep away from alkaline materials, strongbases, strong acids, oxoacids, epoxides, chlorates nitrates, ammonia, aliphatic amines, alkanolamines, isocyanates,alkylene oxides, epichlorohydrin. Compounds of the carboxylgroup react with all bases, both inorganic andorganic (i.e., amines) releasing substantial heat, water and asalt that may be harmful. Incompatible with arsenic compounds(releases hydrogen cyanide gas), diazo compounds,dithiocarbamates, isocyanates, mercaptans, nitrides, andsulfides (releasing heat, toxic, and possibly flammablegases), thiosulfates and dithionites (releasing hydrogen sulfateand oxides of sulfur). |
| Waste Disposal | Incineration. In accordancewith 40CFR165, follow recommendations for the disposalof pesticides and pesticide containers. |
| References | [1] https://en.wikipedia.org/wiki/1-Naphthaleneacetic_acid [2] http://pmep.cce.cornell.edu/profiles/herb-growthreg/naa-rimsulfuron/naa/herb-prof-naa.html |
1-Naphthaleneacetic acid Preparation Products And Raw materials
| Raw materials | Chloroacetic acid-->Aluminum-->Naphthalene-->Potassium Acetate-->Manganese triacetate dihydrate-->2-Naphthylacetonitrile |
| Preparation Products | Naphazoline hydrochloride-->Naphazoline nitrate-->2-Naphthylacetic acid-->Methyl naphthalene-1-acetate-->1-NAPHTHALENEACETAMIDE-->N-(2-AMINOETHYL)-2-(1-NAPHTHYL)ACETAMIDE-->1-(2-CHLOROETHYL)NAPHTHALENE-->1,2-BIS(1-NAPHTHYL)ETHANE-->Naphazoline-->1-NAPHTHALENEACETHYDRAZIDE-->1-Acenaphthenone-->1-ACENAPHTHENOL |
