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86-87-3

Basic Information
CAS No.: 86-87-3
Name: 1-Naphthalene acetic acid
Article Data: 96
Molecular Structure:
Molecular Structure of 86-87-3 (1-Naphthalene acetic acid)
Formula: C12H10O2
Molecular Weight: 186.21
Synonyms: 1-NAA;1-Naphthylacetic acid;2-(1-Naphthyl)acetic acid;2-(Naphthalen-1-yl)aceticacid;2-(a-Naphthyl)ethanoic acid;ANU;Agronaa;Alman;Biokor;Celmone;Etifix;Fruitofix;Fruitone N;Germon;N 10;N40;NAA;NSC 15772;Naftal;Nafusaku;Naphthalen-1-ylacetic acid;Naphthaleneacetic acid;Naphthylacetic acid;Phyomone;Planofix;Planofixe;Pomoxon;Raizon 05;Rasin;Rhizopon B;Rhodofix;Stimolante 66f;Tre-hold;Vardhak;a-NAA;a-Naphthaleneacetic acid;a-Naphthylacetic acid;
EINECS: 201-705-8
Density: 1.263 g/cm3
Melting Point: 126-133.5 oC
Boiling Point: 373.207 °C at 760 mmHg
Flash Point: 270.1 °C
Solubility: Soluble in diethyl ether, acetone, chloroform and acetic acid. Slightly soluble in cold water and ethanol
Appearance: white to off white crystals
Hazard Symbols: IrritantXi,HarmfulXn,CorrosiveC
Risk Codes: 36/37/38-22-68-41-34
Safety: 26-24/25-22-23-45-36/37/39-27
PSA: 37.30000
LogP: 2.46690
Synthetic route
124-38-9

carbon dioxide

1-naphthylmethyl halide

1-naphthylmethyl halide

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
Stage #1: 1-naphthylmethyl halide With lithium chloride; zinc
Stage #2: carbon dioxide With lithium chloride In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; for 24h;
Stage #3: With hydrogenchloride; water In N,N-dimethyl-formamide
100%
773-99-9

2-naphthaleneethanol

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃;99%
With periodic acid; pyridinium chlorochromate In acetonitrile97%
91-20-3

naphthalene

79-11-8

chloroacetic acid

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
at 200℃; Molecular sieve; Large scale;96.7%
at 165℃; dann auf 180-185grad;
With iron; potassium bromide at 220℃;
91668-57-4

α-(N-Methylanilino)-β-(1-naphthyl)acrylonitrile

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 3h; Heating;96%
86803-54-5

(Z)-α-(N-Methylanilino)-β-(1-naphthyl)acrylonitrile

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran for 3h; Heating;96%

4-((tert-butyldimethylsilyl)oxy)benzyl 2-(naphthalen-1-yl)acetate

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 0.0833333h; Reagent/catalyst;94%
2876-78-0

methyl 1-naphthylacetate

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With high-silica Hβ-75 zeolite In water at 130℃; for 24h;93%
With potassium carbonate; thiophenol In 1-methyl-pyrrolidin-2-one at 190℃; for 0.166667h; Substitution;90%
With potassium fluoride; thiophenol In various solvent(s) at 190℃; for 0.166667h;80%
119670-67-6

Naphthalen-1-yl-acetic acid 2-oxo-2-phenyl-ethyl ester

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With sodium hydrogen telluride In N,N-dimethyl-formamide for 0.333333h; Ambient temperature;93%
2122-70-5

ethyl 2-(1-naphthyl)acetate

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With water; sodium hydroxide In 1,4-dioxane at 60℃; for 2h; pH=10 - 14;92%
With sodium hydroxide
132-75-2

naphthalen-1-ylacetonitrile

86-87-3

naphth-1-yl acetic acid

Conditions
ConditionsYield
With potassium phosphate buffer at 30℃; for 96h; Rhodococcus sp. AJ270 cells;91.3%
Stage #1: naphthalen-1-ylacetonitrile With sodium hydroxide In water for 3h; Reflux;
Stage #2: With hydrogenchloride In water pH=2; Time;
74.8%
With sulfuric acid; acetic acid
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    Product Name: 1-Naphthaleneacetic acid CAS: 86-87-3 MF: C12H10O2 MW: 186.21 EINECS: 201-705-8 Mol File: 86-87-3.mol 1-Naphthaleneacetic acid Structure 1-Naphthaleneacetic acid Chemical Properties Melting point 141-143 °C(l

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Specification

The 1-Naphthalene acetic acid, with the CAS registry number 86-87-3, is also known as Naphthalene-1-acetic acid. It belongs to the product categories of Naphthalene derivatives; Organics; Organic acids; Auxins; Biochemistry; Plant Growth Regulators; Plant Hormones. Its EINECS number is 201-705-8. This chemical's molecular formula is C12H10O2 and molecular weight is 186.21. What's more, its systematic name is 1-Naphthylacetic acid. Its classification codes are: (1)Agricultural Chemical; (2)Growth regulator / Fertilizer; (3)Herbicide; (4)Mutation data; (5)Skin / Eye Irritant. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from fire and moisture. This chemical is a synthetic plant hormone in the auxin family and is an ingredient in many commercial plant rooting horticultural products. It is a rooting agent and used for the vegetative propagation of plants from stem and leaf cutting. It is also used for plant tissue culture.

Physical properties of 1-Naphthalene acetic acid are: (1)ACD/LogP: 2.529; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.30; (4)ACD/LogD (pH 7.4): -0.49; (5)ACD/BCF (pH 5.5): 2.91; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 33.41; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 37.3 Å2; (13)Index of Refraction: 1.652; (14)Molar Refractivity: 55.209 cm3; (15)Molar Volume: 150.992 cm3; (16)Polarizability: 21.887×10-24cm3; (17)Surface Tension: 54.1 dyne/cm; (18)Density: 1.233 g/cm3; (19)Flash Point: 270.097 °C; (20)Enthalpy of Vaporization: 65.454 kJ/mol; (21)Boiling Point: 373.207 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by naphthalen-1-yl-acetonitrile at the temperature of 30 °C. This reaction will need reagent potassium phosphate buffer with the reaction time of 96 hours. The yield is about 91.3%.

1-Naphthalene acetic acid can be prepared by naphthalen-1-yl-acetonitrile at the temperature of 30 °C

Uses of 1-Naphthalene acetic acid: it can be used to produce 2-[1]naphthyl-3-phenyl-acrylic acid at the temperature of 120 °C. It will need reagents Ac2O, Et3N with the reaction time of 24 hours. The yield is about 90%.

1-Naphthalene acetic acid can be used to produce 2-[1]naphthyl-3-phenyl-acrylic acid at the temperature of 120 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful if swallowed. It is irritating to eyes, respiratory system and skin. This substance can cause burns. It has a risk of serious damage to eyes and a possible risk of irreversible effects. In case of contact with eyes, you should rinse immediately with plenty of water and seek medicl advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection and you must avoid contact with skin and eyes. You should not breathe dust. After using it, you must take off immediately all contaminated clothing. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)Cc2cccc1ccccc12
(2)Std. InChI: 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)
(3)Std. InChIKey: PRPINYUDVPFIRX-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 609mg/kg (609mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 15, Pg. 443, 1968.
mouse LD50 oral 743mg/kg (743mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 14, Pg. 132, 1967.
mouse LD50 subcutaneous 733mg/kg (733mg/kg)   Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 15, Pg. 443, 1968.
rabbit LD50 skin > 5gm/kg (5000mg/kg)   Pesticide Manual. Vol. 9, Pg. 607, 1991.
rat LC50 inhalation > 207gm/m3 (207000mg/m3)   Pesticide & Toxic Chemical News. Vol. 9, Pg. 10, 1980.
rat LD50 intraperitoneal 100mg/kg (100mg/kg)   Pesticide & Toxic Chemical News. Vol. 9, Pg. 10, 1980.
rat LD50 oral 1gm/kg (1000mg/kg)   "Wirksubstanzen der Pflanzenschutz und Schadlingsbekampfungsmittel," Perkow, W., Berlin, Verlag Paul Parey, 1971-1976Vol. -, Pg. -, 1971/1976.