86-87-3 Usage
Description
1-naphthaleneacetic acid (NAA, also named 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.
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.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.1-Naphthaleneacetic acid has been used:to modify MS media for the initiation of callusas a supplement in solid K3 medium for the selection of transformantsin the preparation of culture medium like V-KM medium and Cg medium
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.
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
Chemical Properties
Different sources of media describe the Chemical Properties of 86-87-3 differently. You can refer to the following data:
1. 1-Naphthalene acetic acid is Light yellow crystals
2. 1-Naphthaleneacetic acid is a white crystalline solid, needles, powder, or colorless liquid. Odorless.
Uses
Different sources of media describe the Uses of 86-87-3 differently. You can refer to the following data:
1. Inducing rooting of plant cuttings, spraying
apple trees to prevent early drop, fruit thinner.
2. 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.
3. 1-Naphthaleneacetic Acid, is widely used in agriculture for various purposes. It is a synthetic plant hormone in the auxin family and is an ingredient in many commercial plant rooting horticultural products.
Definition
1-Naphthaleneacetic acid is a naphthylacetic acid substituted by a carboxymethyl group at position 1.
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.
Hazard
Skin irritant.
Agricultural Uses
Plant growth regulator: An agent 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 (pending). Registered for use in
the 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 and
1-Naphthaleneacetamide); STAFAST?; STIK?; STOPDROP
?; TEKKAM?; TIPOFF?; TRANSPLANTONE?
(component, with 1-Naphthaleneacetamide); TREHOLD
?; VARDHAK?
Safety Profile
Poison by
intraperitoneal route. Moderately toxic by
ingestion. Mutation data reported. A skin,
mucous membrane, and severe eye irritant.
Can cause depression. A pesticide, When heated to decomposition it emits acrid
smoke 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, strong
bases, strong acids, oxoacids, epoxides, chlorates nitrates, ammonia, aliphatic amines, alkanolamines, isocyanates,
alkylene oxides, epichlorohydrin. Compounds of the carboxyl
group react with all bases, both inorganic and
organic (i.e., amines) releasing substantial heat, water and a
salt that may be harmful. Incompatible with arsenic compounds
(releases hydrogen cyanide gas), diazo compounds,
dithiocarbamates, isocyanates, mercaptans, nitrides, and
sulfides (releasing heat, toxic, and possibly flammable
gases), thiosulfates and dithionites (releasing hydrogen sulfate
and oxides of sulfur).
Waste Disposal
Incineration. In accordance
with 40CFR165, follow recommendations for the disposal
of pesticides and pesticide containers.
Check Digit Verification of cas no
The CAS Registry Mumber 86-87-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 86-87:
(4*8)+(3*6)+(2*8)+(1*7)=73
73 % 10 = 3
So 86-87-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H10O2/c13-12(14)8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7H,8H2,(H,13,14)/p-1
86-87-3Relevant articles and documents
-
Wolthuis,E.,Vander Jagt,D.L.
, p. 963 - 964 (1964)
-
-
Ogata,Ishiguro
, p. 4302 (1950)
-
Radical chemistry of glucosamine naphthalene acetic acid and naphthalene acetic acid: A pulse radiolysis study
Shibin, Naduvilpurakkal B.,Sreekanth, Radhakrishnan,Aravind, Usha K.,Afsal Mohammed, Kadavilpparampu M.,Chandrashekhar, Narayana V.,Joseph, Jayan,Sarkar, Sisir K.,Naik, Devidas B.,Aravindakumar, Charuvila T.
, p. 478 - 483 (2014)
Free radical-induced oxidation reactions of glucosamine naphthalene acetic acid (GNaa) and naphthalene acetic acid (Naa) have been studied using pulse radiolysis. GNaa was synthesized by covalently attaching Naa on glucosamine. Hydroxyl adduct (from the reaction of hydroxyl radicals (?OH) at the naphthalene ring) was identified as the major transient intermediate (suggesting that the ?OH reaction is on the naphthalene ring) and is characterized by its absorption maxima of 340 and 400 nm. Both GNaa and Naa undergo similar reaction pattern. The bimolecular rate constants determined for the reactions are 4.8 × 109 and 8.9 × 109 dm3 mol-1 s-1 for GNaa and Naa respectively. The mechanism of reaction of ?OH with GNaa was further confirmed using steady-state method. Radical cation of GNaa was detected as an intermediate during the reaction of sulfate radical (SO4 ?-) with GNaa (k2 = 4.52 × 109 dm3 mol-1 s-1). This radical cation transforms to a ?OH adduct at higher pH. The radical cation of GNaa is comparatively long lived, and a cyclic transition state by neighboring group participation accounts for its stability. The oxy radical anion (O ?-) reacts with GNaa (k2 = 1.12 × 10 9 dm3 mol-1 s-1) mainly by one-electron transfer mechanism. The reduction potential values of Naa and GNaa were determined using cyclic voltammetric technique, and these are 1.39 V versus NHE for Naa and 1.60 V versus NHE for GNaa.
Desulfonylative Electrocarboxylation with Carbon Dioxide
Zhong, Jun-Song,Yang, Zi-Xin,Ding, Cheng-Lin,Huang, Ya-Feng,Zhao, Yi,Yan, Hong,Ye, Ke-Yin
supporting information, p. 16162 - 16170 (2021/09/02)
Electrocarboxylation of organic halides is one of the most investigated electrochemical approaches for converting thermodynamically inert carbon dioxide (CO2) into value-added carboxylic acids. By converting organic halides into their sulfone derivatives, we have developed a highly efficient electrochemical desulfonylative carboxylation protocol. Such a strategy takes advantage of CO2as the abundant C1 building block for the facile preparation of multifunctionalized carboxylic acids, including the nonsteroidal anti-inflammatory drug ibuprofen, under mild reaction conditions.
Naphthylacetic acid preparation method
-
Paragraph 0037; 0041-0046; 0047; 0051-0056; 0057; 0061-0067, (2020/03/12)
The invention discloses a naphthylacetic acid preparation method, which comprises: naphthylacetic acid is prepared by using 1-chloromethylnaphthalene as a starting raw material, using cuprous iodide as a catalyst, using potassium ferrocyanide as a cyanide source and adding triethyl benzyl ammonium chloride as a phase transfer catalyst into a reaction system. According to the invention, traditionalpotassium cyanide or sodium cyanide is replaced with potassium ferrocyanide as the cyanide source, so the safety threat of potassium cyanide or sodium cyanide to operators in a production process isavoided, and environment pollution caused by highly toxic substances is reduced; and the preparation method has advantages of simple post-treatment, low energy consumption and few three-waste.
