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HCID 6862Erstellt: 26. Oktober 2026

1-Naphthaleneacetic Acid

Aids017630 · Aids-017630

https://huagongshe.com/de/chemical/6862

Molekülstruktur von 1-Naphthaleneacetic Acid

Identifikatoren & physikalische Daten

CAS No.26445-01-2
SummenformelC12H10O2
Durchschnittliche Molmasse186,21 g/mol
Monoisotopische Masse186,06807956 g/mol
SMILESO=C(O)Cc1cccc2ccccc12
InChIKeyPRPINYUDVPFIRX-UHFFFAOYSA-N
PubChem CID6862
ChEMBLCHEMBL428495
ChEBICHEBI:32918
EC No.201-705-8
DTXSIDDTXSID8020915

Chemische & physikalische Eigenschaften

XLogP2,7
Polarare Oberfläche (TPSA)37,3
H-Brücken-Donoren1
H-Brücken-Akzeptoren2
Frei drehbare Bindungen2
Schwere Atome14
Formalladung0
Komplexität212
ArzneimittelPharmaceuticals -> Listed in ZINC15
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
PestizideAttractantsActive substance -> EU Pesticides database: ApprovedPesticides -> Plant Growth RegulatorsEnvironmental transformation -> Pesticides (parent, predecessor)
LogP (Verteilungskoeffizient)log Kow = 2.24
GeruchOdorless
Color/FormNeedles from waterWhite crystalsColorless crystals
LöslichkeitSlightly soluble in ethanol, trifluoroacetic acidsoluble in benzene and acetic acidvery soluble in ethyl ether, acetone, and chloroform.10.6 mg/l in carbon tetrachloride @ 26 °C55 mg/l in xylene at 26 °CAbout 30 parts in alcoholVery sol in isopropanolIn water, 420 mg/l @ 20 °C
Endocrine DisruptorsPotential endocrine disrupting compound
SiedepunktDecomposes
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Schmelzpunkt134.5-135.5 °CMelting point of 125-128 °C /Technical grade/134.5 - 135.5 °C
Dampfdruck0.0000159 [mmHg]

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 0.9% (1 of 112) of reports.DangerH302 (97.3%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 112 reports by companies from 25 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische InformationenChemical: 1-Naphthaleneacetic acidCommission Regulation (EC) No 33/2008Napthalene Acetates is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)2008/941/EC, Reg. (EU) 2023/2592, Reg. (EU) No 2019/291, Reg. (EU) No 540/2011, Reg. (EU) No 787/20111-Naphthylacetic acid: Does not have an individual approval but may be used under an appropriate group standard
BrandpotenzialNONFLAMMABLE
GefahrenübersichtA skin and mucous membrane irritantA severe eye irritantHigh-dose animal studies: reduce food intake, decreased hemoglobin, increased liver enzymes[HSDB] The naphthalene acetates are metabolized in the body and excreted as glycine and glucoronic acid conjugates within 48 hours of exposureThe most common effect seen in high-dose animal studies is a reduction in body weight1-naphthaleneacetic acid derivatives covered in the RED are the acetamide (CAS # 86-86-2), potassium salt (CAS # 15165-79-4), ammonium salt (CAS # 25545-89-5), sodium salt (CAS # 61-31-4), and ethyl ester (CAS # 2122-70-5)[Reference #1]The major hazards encountered in the use and handling of 1-naphthaleneacetic acid stem from its toxicologic properties. Toxic primarily via inhalation and dermal contact. Exposure to this odorless, white, crystalline substance (or colorless solution) may occur from its production or application as a herbicide and plant growth regulator. Effects from exposure include nasal, skin, and eye irritation. Wear gloves when handling this substance. This nonflammable, noncorrosive material should be stored in a cool, dry, dark area (to prevent the possibility of ultraviolet degradation). Before implementing land disposal of waste 1-naphthaleneacetic acid, consult with environmental regulatory agencies for guidance.
FIFRA-AnforderungenAs the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. 1-Naphthaleneacetic acid is found on List A, which contains most food use pesticides and consists of the 194 chemical cases (or 350 individual active ingredients) for which EPA issued registration standards prior to FIFRA '88. Case No: 0379Pesticide type: growth regulatorRegistration Standard Date: 08/31/81Case Status: OPP is reviewing data from the pesticide's producers regarding its human health and/or environmental effects, or OPP is determining the pesticide's eligibility for reregistration and developing the RED document.Active ingredient (AI): 1-naphthaleneacetic acidData Call-in (DCI) Date(s): 09/11/90AI Status: The producers of the pesticide have made commitments to conduct the studies and pay the fees required for reregistration, and are meeting those commitments in a timely manner..Tolerances are established for residues of the plant growth regulator 1-naphthaleneacetic acid in or on the following raw agricultural commodities: applecherry, sweetoliveorange, sweetpearpineaple (from the application of the sodium salt to the growing crop)quinceand tangerine.
Hazard Classes and CategoriesAcute Tox. 4 (97.3%)
Skin, Eye, and Respiratory IrritationsA skin, mucous membrane, and severe eye irritant.Dusts may cause nasal irritation.
Hazardous Reactivities and IncompatibilitiesSolutions of the heavy-metal salts of other acids form sparingly-soluble salts of 1-naphthylacetic acid.
Lagerbedingungen...Store in cool, dry, dark place.
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.
Preventive MeasuresSRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.Do not get on skin or in eyes. ... Do not spray in strong sunlightpreferably spray in late afternoon, evening, or at dusk.
Allowable TolerancesTolerances are established for residues of the plant growth regulator 1-naphthaleneacetic acid in or on the following raw agricultural commodities: apple, 1 ppmcherry, sweet, 0.1 ppmolive, 0.1ppm (negligible residues)orange, sweet, 0.1 ppmpear, 1 ppmpineaple (from the application of the sodium salt to the growing crop), 0.05 ppmquince, 1 ppmand tangerine, 0.1 ppm.
Personal Protective Equipment (PPE)Wear rubber gloves.
WechselwirkungenThe inhibition of wheat coleoptile extension growth by concn of NC 9634 at about 260 muM was completely overcome by 50 uM naphthaleneacetic acid (NAA). Extension growth of intact apple shoots was inhibited by NAA, which was lethal at about 6.25X10-4 M. NC 9634 applied in combination with NAA reduced this growth inhibiting effect and prevented death of shoots sprayed with high auxin concn.
ÖkotoxizitätswerteLC50 Mallard duck (8 days) >10,000 mg/kgLC50 Bobwhite quail (8 days) >10,000 mg/kgLC50 Rainbow trout 57 mg active ingredient /L / 96 hr /Conditions of bioassay not specified/LC50 Bluegill sunfish 82 mg active ingredient/L/96 hr /Conditions of bioassay not specified/
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.24(2) and a regression-derived equation(3), indicates that 1-naphthaleneacetic acid is expected to have moderate mobility in soil(SRC). The pKa of 1-naphthaleneacetic acid is 4.23(4), indicating that this compound will exist as an anion in the environment and anions typically have greater mobility in soils than do neutral species(5). Volatilization of 1-naphthaleneacetic acid from moist soil surfaces is not expected to be an important fate process(SRC) because anions do not volatilize. 1-Naphthaleneacetic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.6X10-5 mm Hg(SRC), determined from a fragment constant method(6). 1-Naphthaleneacetic acid has a reported half-life in soil of 10 days, attributed to microbial degradation(7).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.24(2) and a regression-derived equation(3), indicates that 1-naphthaleneacetic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected based upon a pKa of 1-naphthaleneacetic acid of 4.23(4), indicating that this compound will primarily exist in the dissociated form in the environment and anions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts(5). According to a classification scheme(6), a BCF range of 0.5-4.2(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation is not expected to be a fast environmental fate process in water based upon a 0% theoretical BOD using activated sludge and the MITI test(7). Photolysis may be an important environmental fate process as indicated by the detection of photolysis products 1-naphthoic and phthalic acids following exposure of an aqueous solution of 1-naphthaleneacetic acid to sunlight(8,9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-naphthaleneacetic acid, which has an estimated vapor pressure of 1.6X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1-naphthaleneacetic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 10 hrs(SRC), calculated from its rate constant of 3.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1-naphthaleneacetic acid may be removed from the air by wet and dry deposition(SRC). Photolysis may be an important environmental fate process in the atmosphere as indicated by the detection of photolysis products 1-naphthoic and phthalic acids during analysis of a sunlight exposed aqueous solution of 1-naphthaleneacetic acid(4,5).
Lebensmitteluntersuchungswerte1-Naphthaleneacetic acid was detected in 1 of 2,363 domestic apple samples collected between October 1, 1985 and September 30, 1991, analyzed as part of the EPA Total Diet Study(1). The maximum residue measured was 0.02 ppm(1).
Unerwünschte WirkungenOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Ökotoxizitätsauszüge/OTHER TERRESTRIAL SPECIES/ Nontoxic to bees
Plant Concentrations1-Naphthaleneacetic acid was shown to be readily absorbed in tomato fruit cuticles(1). Lipophilic in nature, 1-naphthaleneacetic acid applied as a spray concn of 1 g/l to maize, rape, strawberry, and sugar beet resulted in plant uptake rates of 26, 98, 96, and 61% of amount applied, respectively, after 24 hrsplants characterized by waxy leaves exhibited more rapid uptake(2). Use of a surfactant (NP8, nonylphenol) decreased the rate of absorption to 17, 15, 35, and 13%, respectively(2).
Acute Toxicity LinkChemical: POTASSIUM NAPHTHALENEACETATE
Soil Adsorption/MobilityThe Koc of 1-naphthaleneacetic acid is estimated as 390(SRC), using a log Kow of 2.24(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1-naphthaleneacetic acid is expected to have moderate mobility in soil. The pKa of 1-naphthaleneacetic acid is 4.23(4), indicating that this compound will primarily exist in the dissociated form in the environment and anions generally have greater mobility than their neutral counterparts(5).
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Dusts may cause nasal irritation./HUMAN EXPOSURE STUDIES/ A skin, mucous membrane, and severe eye irritant.
Artificial Pollution Sources1-Naphthaleneacetic acid's production may result in its release to the environment through various waste streamsit's use as a plant growth regulator(1) will result in its direct release to the environment(SRC).
Environmental BiodegradationAEROBIC: 1-Naphthaleneacetic acid, present at 30 mg/l, reached 0% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 100 mg/l and the Japanese MITI test(1). 1-Naphthaleneacetic acid has a reported half-life in soil of 10 days, attributed to microbial degradation(2).