| Identification | More | [Name]
2-Naphthoxyacetic acid | [CAS]
120-23-0 | [Synonyms]
2-NAPHTHOXYACETIC ACID
(2-NAPHTHYLOXY)ACETIC ACID
AKOS B000128
AKOS BBB/203
BETA-NAPHTHOXYACETIC ACID
(B-NAPHTHOXY)ACETIC ACID
BNOA
(NAPHTHALEN-2-YLOXY)ACETIC ACID
O-(2-NAPHTHYL)GLYCOLIC ACID
TIMTEC-BB SBB003523
(2-Naphthalenyloxy)acetic acid
(2-naphthalenyloxy)-aceticaci
(2-naphthalenyloxy)-Aceticacid
(2-Naphthloxy)acetic acid
(2-naphthoxy)ethanoicacid
(2-naphthyloxy)-aceticaci
(beta-Naphthalenyloxy)acetic acid
(beta-naphthalenyloxy)aceticacid
(b-Naphthalenyloxy)acetic acid
(b-Naphthyloxy)acetic acid | [EINECS(EC#)]
204-380-0 | [Molecular Formula]
C12H10O3 | [MDL Number]
MFCD00004066 | [Molecular Weight]
202.21 | [MOL File]
120-23-0.mol |
| Chemical Properties | Back Directory | [Appearance]
Gray crystals | [Melting point ]
151-154 °C(lit.) | [Boiling point ]
300.32°C (rough estimate) | [density ]
1.1868 (rough estimate) | [refractive index ]
1.5440 (estimate) | [storage temp. ]
Store at 0-5°C | [solubility ]
Soluble in DMSO | [form ]
crystalline
| [pka]
3.18±0.30(Predicted) | [color ]
gray
| [Water Solubility ]
Soluble in alcohol, ether, acetic acid and dimethyl sulfoxide. Slightly soluble in water. | [Merck ]
14,6397 | [BRN ]
1074148 | [Henry's Law Constant]
3.5×105 mol/(m3Pa) at 25℃, Ebert et al. (2023) | [InChI]
1S/C12H10O3/c13-12(14)8-15-11-6-5-9-3-1-2-4-10(9)7-11/h1-7H,8H2,(H,13,14) | [InChIKey]
RZCJYMOBWVJQGV-UHFFFAOYSA-N | [SMILES]
OC(=O)COc1ccc2ccccc2c1 | [LogP]
2.530 | [CAS DataBase Reference]
120-23-0(CAS DataBase Reference) | [NIST Chemistry Reference]
Acetic acid, (2-naphthyloxy)-(120-23-0) | [EPA Substance Registry System]
120-23-0(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H302 | [Precautionary statements ]
P301+P312+P330 | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
AI9659000
| [TSCA ]
Yes | [HazardClass ]
IRRITANT | [HS Code ]
29189900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral | [Toxicity]
LD50 orally in Rabbit: 500 mg/kg |
| Hazard Information | Back Directory | [Description]
2-naphthyloxyacetic acid is a plant hormone used to encourage fruit set. It is moderately soluble in water and is not volatile. It is not considered to be environmentally persistent but does have potential to leach to groundwater. It has a moderate to low toxicity to most biodiversity. 2-naphthyloxyacetic acid has a moderate oral mammalian toxicity and is a recognised irritant. | [Chemical Properties]
2-Naphthoxyacetic acid is Gray crystals
| [Uses]
2-Naphthoxyacetic acid has been used as a component for embryo cell suspension maintenance medium. It has been used as a medium component for inducing somatic embryogenesis in grapevine. | [Uses]
2-Naphthoxyacetic Acid is a derivative of Naphthalene (N345600) and considered to be a phytohormone belonging to the class of auxins. | [Uses]
2-Naphthoxyacetic acid is a phytohormone used as a plant growth regulator on tomatoes and strawberries.
| [Definition]
ChEBI: 2-naphthyloxyacetic acid is a naphthyloxyacetic acid. | [Production Methods]
2-Naphthyloxyacetic acid is commercially synthesised by a process that involves a nucleophilic substitution reaction, where 2-naphthol is treated with chloroacetic acid (or sodium chloroacetate) in the presence of a base such as sodium hydroxide. This facilitates the formation of an ether bond between the naphthol and acetic acid moieties, yielding the active compound 2-naphthyloxyacetic acid. The reaction is typically carried out in aqueous or alcoholic media under reflux, followed by acidification and crystallisation to purify the product. | [General Description]
2-Naphthoxyacetic acid is a plant growth hormone having structure related to auxin and is majorly used to regulate growth of tomatoes, apple and grapes. | [Biochem/physiol Actions]
2-Naphthoxyacetic acid promotes seed germination and early flowering in tomatoes. 2-naphthoxyacetic acid effectively improves fruit size and color. However, it is also regarded slightly hazardous and may contribute to mutagenesis. | [Mechanism of action]
Absorbed by leaves and roots | [storage]
Store at -20°C | [Purification Methods]
Crystallise the acid from hot water or *benzene. [Beilstein 6 IV 4274.] | [Pesticide Type]
Plant Growth Regulator; Herbicide |
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