1-Naphthylacetic acid

Base Information

• Chemical Name: 1-Naphthylacetic acid
• CAS No.: 86-87-3
• Deprecated CAS: 61913-11-9,69072-67-9,267410-73-1,267410-73-1
• Molecular Formula: C12H10O2
• Molecular Weight: 186.21
• Hs Code.: 2916.39 Oral rat LD50: 1000 mg/kg
• European Community (EC) Number: 201-705-8
• NSC Number: 15772
• UNII: 33T7G7757C
• DSSTox Substance ID: DTXSID8020915
• Nikkaji Number: J4.267F
• Wikipedia: 1-Naphthaleneacetic_acid
• Wikidata: Q161660
• Metabolomics Workbench ID: 45700
• ChEMBL ID: CHEMBL428495
• Mol file: 86-87-3.mol

Synonyms:1-naphthaleneacetic acid;1-naphthaleneacetic acid, ammonium salt;1-naphthaleneacetic acid, potassium salt;1-naphthaleneacetic acid, sodium salt;1-naphthylacetic acid;2-(1-naphthyl)acetic acid;2-(alpha-naphthyl)ethanoic acid;2-(naphthalen-1-yl)acetic acid;alpha-naphthaleneacetic acid;Galle-Donau;potassium 1-naphthaleneacetate;sodium 1-naphthaleneacetate

Chemical Property of 1-Naphthylacetic acid

Chemical Property:

• Appearance/Colour: white to off white crystals
• Vapor Pressure: 3.13E-06mmHg at 25°C
• Melting Point: 126-133.5 oC
• Refractive Index: 1.6010 (estimate)
• Boiling Point: 373.207 °C at 760 mmHg
• PKA: 4.30±0.30(Predicted)
• Flash Point: 270.1 °C
• PSA: 37.30000
• Density: 1.263 g/cm3
• LogP: 2.46690
• Storage Temp.: 2-8°C
• Solubility.: acetone: 50 mg/mL, clear
• Water Solubility.: Slightly soluble in water, ethanol, acetone, chloroform and ether.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 186.068079557
• Heavy Atom Count: 14
• Complexity: 212

Purity/Quality:

99% ^*data from raw suppliers

1-Naphthaleneacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn,C
• Hazard Codes: Xi,Xn,C
• 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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2CC(=O)O
• 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
• Uses: Inducing rooting of plant cuttings, spraying apple trees to prevent early drop, fruit thinner. 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, 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.

Technology Process of 1-Naphthylacetic acid

There total 90 articles about 1-Naphthylacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

carbon dioxide (124-38-9,18923-20-1) → naphth-1-yl acetic acid (86-87-3)

Guidance literature:

1-naphthylmethyl halide; With lithium chloride; zinc;

carbon dioxide; With lithium chloride; In N,N-dimethyl-formamide; at 50 ℃; for 24h; under 760.051 Torr;

With hydrogenchloride; water; In N,N-dimethyl-formamide;

DOI:10.1021/ol900528h

Reference yield: 99.0%

2-naphthaleneethanol (773-99-9) → naphth-1-yl acetic acid (86-87-3)

Guidance literature:

With periodic acid; tripropylammonium fluorochromate (VI); In acetonitrile; at 0 ℃;

DOI:10.1016/j.jfluchem.2005.07.012

Reference yield: 96.7%

naphthalene (91-20-3,71998-51-1,72931-45-4) + chloroacetic acid (79-11-8) → naphth-1-yl acetic acid (86-87-3)

Guidance literature:

at 200 ℃; Molecular sieve; Large scale;

upstream raw materials:

naphthalen-1-ylacetonitrile

ethyl 2-(1-naphthyl)acetate

diethyl ether

methylammonium carbonate

Downstream raw materials:

2,6-Dimethyl-4-((E)-2-naphthalen-1-yl-vinyl)-phenol

N-Methyl-2-naphthalen-1-yl-N-((1S,2R)-2-pyrrolidin-1-yl-cyclohexyl)-acetamide

4-Benzyloxy-7-methyl-2-naphthalen-1-ylmethyl-1H-benzoimidazole

2-(naphthalen-1-yl)acetic anhydride

Refernces

• 1、 Sousa Da Silva, Eliana,Sarakha, Mohamed,Burrows, Hugh D.,Wong-Wah-Chung, Pascal. "Decatungstate anion as an efficient photocatalytic species for the transformation of the pesticide 2-(1-naphthyl)acetamide in aqueous solution". . p. 61 - 73. Retrieved 2017.
• 2、 Southwick et al.. "-". . p. 754. Retrieved 1954.
• 3、 -. "Preparation method of naphthalene ring C marked α .". Paragraph 0046-0047; 0052-0057; 0062-0067; 0072-0075. . Retrieved 2021/10/05.
• 4、 Siddiki,Rashed, Md. Nurnobi,Touchy, Abeda Sultana,Jamil, Md. A. R.,Jing, Yuan,Toyao, Takashi,Maeno, Zen,Shimizu, Ken-Ichi. "Hydrolysis of amides to carboxylic acids catalyzed by Nb2O5". . p. 1949 - 1960. Retrieved 2021/03/26.