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| CAS No.: | 135-19-3 |
|---|---|
| Name: | 2-Naphthalenol |
| Molecular Structure: | |
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| Formula: | C10H8O |
| Molecular Weight: | 144.173 |
| Synonyms: | 2-Naphthol(8CI);2-Hydroxynaphthalene;Azogen Developer A;Betanaphthol;C.I. 37500;C.I. Developer 5;Developer AMS;Developer BN;Isonaphthol;NSC 2044;Naphthol B;b-Hydroxynaphthalene;b-Naphthol;b-Naphthyl alcohol; |
| EINECS: | 205-182-7 |
| Density: | 1.182 g/cm3 |
| Melting Point: | 120-122 °C(lit.) |
| Boiling Point: | 285.499 °C at 760 mmHg |
| Flash Point: | 144.002 °C |
| Solubility: | Very slightly soluble in water: 1 g/L (20 °C) |
| Appearance: | broken white shiny flakes or white powder |
| Hazard Symbols: |
 Xn, N
|
| Risk Codes: | 20/22-50 |
| Safety: | 24/25-61 |
| Transport Information: | UN 3077 9/PG 3 |
| PSA: | 20.23000 |
| LogP: | 2.54540 |
| Conditions | Yield |
|---|---|
| With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 5h; Hydrolysis; deacetylation; | 100% |
| With sodium hydrogen telluride; acetic acid In ethanol for 0.5h; Heating; | 98% |
| With 2,2-dibutyl-1,3,2-dioxastannane; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 0.5h; | 98% |
ethyl (naphthalene-2-yl)carbonate
β-naphthol
| Conditions | Yield |
|---|---|
| With sodium hydrogen telluride In ethanol for 0.5h; Quantum yield; Heating; buffer: deoxygen. acetic acid; | 100% |
| With potassium tert-butylate; hydrogen; C16H18BrCoINO2 In dibutyl ether at 160℃; under 45004.5 Torr; for 20h; Sealed tube; Autoclave; | 75% |
2-naphthyl benzoate
2-amino-benzenethiol
A
2-Phenylbenzothiazole
B
β-naphthol
| Conditions | Yield |
|---|---|
| With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.75h; Hydrolysis; cyclization; debenzoylation; | A n/a B 100% |
2-naphthyl pivalate
2-amino-benzenethiol
A
2-(tert-butyl)benzo[d]thiazole
B
β-naphthol
| Conditions | Yield |
|---|---|
| With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 2h; Hydrolysis; cyclization; | A n/a B 100% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In 1-methyl-pyrrolidin-2-one for 0.5h; Heating; | 100% |
| With potassium fluoride; thiophenol In 1-methyl-pyrrolidin-2-one for 0.5h; Heating; | 92% |
| With HEPES buffer; human liver microsomal carboxylesterase 1 In dimethyl sulfoxide pH=7.4; Enzyme kinetics; Further Variations:; Reagents; |
6-bromo-naphthalen-2-ol
β-naphthol
| Conditions | Yield |
|---|---|
| With triethylamine In isopropyl alcohol UV-irradiation; | 100% |
2-naphthyl tetrahydro-2H-pyran-2-yl ether
β-naphthol
| Conditions | Yield |
|---|---|
| poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 20h; Hydrolysis; | 99% |
| silica-supported prop-1-ylsulfonic acid In methanol | 99.4% |
| With methanol; zirconium(IV) chloride at 20℃; for 6h; | 96% |
| Conditions | Yield |
|---|---|
| With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry; | 99% |
| With copper(l) iodide; potassium hydroxide In water at 120℃; for 12h; Inert atmosphere; | 96% |
| With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 92% |
| Conditions | Yield |
|---|---|
| With chloro-trimethyl-silane; Ti(OiPr)[{(O-2,4-Me2C6H2)-6-CH2}3N]; magnesium In tetrahydrofuran at 40 - 50℃; for 12h; Inert atmosphere; regioselective reaction; | 99% |
| With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0333333h; | 98% |
| With chloro-trimethyl-silane; sodium cyanoborohydride In acetonitrile at 20℃; for 0.25h; ether cleavage; | 98% |
β-naphthol
| Conditions | Yield |
|---|---|
| With bismuth(lll) trifluoromethanesulfonate In methanol at 20℃; for 0.0333333h; | 99% |
| montmorillonite K-10 for 0.0833333h; Solid phase reaction; desilylation; microwave irradiation; | 98% |
| With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.15h; Green chemistry; | 98% |
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2-Naphthol (CAS NO.135-19-3) is an intermediate of naphthalene acid which is a plant growth regulator.
2-Naphthol is used as a feed preservative and analytical reagent.
2-Naphthol is an important organic raw material and dyes intermediate, for the manufacture of Tobias acid, butyric acid, β-naphthol-3-carboxylic acid, and used to manufacture antioxidant, Antioxidant DNP, and other antioxidant, organic pigments and fungicides.
Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.
The 2-Naphthol, with the CAS registry number 135-19-3,is also known as 2-Hydroxynaphthalene; 2-Naphthalenol; beta-Hydroxynaphthalene. It belongs to the product categories of Organic Building Blocks;Oxygen Compounds;Particles and Stains.Its EINECS number is 205-182-7. This chemical's molecular formula is C10H8O and molecular weight is 144.17. What's more,Its systematic name is 2-Naphthalenol.It is a white or off-white powder with a slight which is stable, Combustible,dust may form explosive mixture with air,incompatible with strong oxidizing agents,phenol.It is an important organic raw material and dyes intermediate, for the manufacture of Tobias acid, butyric acid, β-naphthol-3-carboxylic acid, and used to manufacture antioxidant, Antioxidant DNP, and other antioxidant, organic pigments and fungicides.
Physical properties about 2-Naphthol are:
(1)ACD/LogP: 2.724; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.72; (4)ACD/LogD (pH 7.4): 2.72; (5)ACD/BCF (pH 5.5): 69.26; (6)ACD/BCF (pH 7.4): 68.80; (7)ACD/KOC (pH 5.5): 722.79; (8)ACD/KOC (pH 7.4): 718.00; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.678; (13)Molar Refractivity: 45.977 cm3; (14)Molar Volume: 121.979 cm3; (15)Surface Tension: 51.0940017700195 dyne/cm; (16)Density: 1.182 g/cm3; (17)Flash Point: 144.002 °C; (18)Enthalpy of Vaporization: 54.56 kJ/mol; (19)Boiling Point: 285.499 °C at 760 mmHg; (20)Vapour Pressure: 0.0020000000949949 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES:c1ccc2cc(ccc2c1)O;
(2)Std. InChI:InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H;
(3)Std. InChIKey:JWAZRIHNYRIHIV-UHFFFAOYSA-N.
The toxicity data of 2-Naphthol are as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| cat | LDLo | oral | 100mg/kg (100mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
| guinea pig | LD50 | oral | 1335mg/kg (1335mg/kg) | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(9), Pg. 22, 1965. | |
| guinea pig | LDLo | subcutaneous | 2670mg/kg (2670mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 186, Pg. 195, 1937. |
| mouse | LD50 | intraperitoneal | 97500mg/kg (97500mg/kg) | European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 13, Pg. 381, 1978. | |
| mouse | LDLo | oral | 100mg/kg (100mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
| mouse | LDLo | subcutaneous | 100mg/kg (100mg/kg) | Zeitschrift fuer Hygiene und Infektionskrankheiten. Vol. 64, Pg. 113, 1909. | |
| rabbit | LD50 | skin | > 10gm/kg (10000mg/kg) | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 26-4/1973, | |
| rabbit | LDLo | oral | 3800mg/kg (3800mg/kg) | Yakkyoku. Pharmacy. Vol. 31, Pg. 1499, 1980. | |
| rabbit | LDLo | subcutaneous | 3gm/kg (3000mg/kg) | "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1289, 1935. | |
| rabbit | LDLo | unreported | 3800mg/kg (3800mg/kg) | Yakkyoku. Pharmacy. Vol. 32, Pg. 605, 1981. | |
| rat | LC50 | inhalation | > 770mg/m3/1H (770mg/m3) | GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS | BIOFAX Industrial Bio-Test Laboratories, Inc., Data Sheets. Vol. 26-4/1973, |
| rat | LD50 | oral | 1960mg/kg (1960mg/kg) | Gigiena Truda i Professional'naya Patologiya v Estonskoi SSR. Labor Hygiene and Occupational Pathology in the Estonian SSR. Vol. 8, Pg. 145, 1972. | |
| rat | LDLo | subcutaneous | 2940mg/kg (2940mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SLEEP BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 186, Pg. 195, 1937. |
