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135-19-3

Basic Information
CAS No.: 135-19-3
Name: 2-Naphthalenol
Article Data: 645
Molecular Structure:
Molecular Structure of 135-19-3 (2-Naphthalenol)
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: HarmfulXn,DangerousN
Risk Codes: 20/22-50
Safety: 24/25-61
Transport Information: UN 3077 9/PG 3
PSA: 20.23000
LogP: 2.54540
Synthetic route
1523-11-1

naphthalen-2-yl acetate

135-19-3

β-naphthol

Conditions
ConditionsYield
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%
91902-97-5

ethyl (naphthalene-2-yl)carbonate

135-19-3

β-naphthol

Conditions
ConditionsYield
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%
93-44-7

2-naphthyl benzoate

137-07-5

2-amino-benzenethiol

A

883-93-2

2-Phenylbenzothiazole

B

135-19-3

β-naphthol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 0.75h; Hydrolysis; cyclization; debenzoylation;A n/a
B 100%
1503-86-2

2-naphthyl pivalate

137-07-5

2-amino-benzenethiol

A

17626-88-9

2-(tert-butyl)benzo[d]thiazole

B

135-19-3

β-naphthol

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; potassium carbonate at 100℃; for 2h; Hydrolysis; cyclization;A n/a
B 100%
93-44-7

2-naphthyl benzoate

135-19-3

β-naphthol

Conditions
ConditionsYield
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;
15231-91-1

6-bromo-naphthalen-2-ol

135-19-3

β-naphthol

Conditions
ConditionsYield
With triethylamine In isopropyl alcohol UV-irradiation;100%
30784-04-4

2-naphthyl tetrahydro-2H-pyran-2-yl ether

135-19-3

β-naphthol

Conditions
ConditionsYield
poly(4-vinylpyridinium) p-toluenesulfonate In tetrahydrofuran; ethanol at 75℃; for 20h; Hydrolysis;99%
silica-supported prop-1-ylsulfonic acid In methanol99.4%
With methanol; zirconium(IV) chloride at 20℃; for 6h;96%
580-13-2

2-bromonaphthalene

135-19-3

β-naphthol

Conditions
ConditionsYield
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%
3698-15-5

2-(allyloxy)naphthalene

135-19-3

β-naphthol

Conditions
ConditionsYield
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%

135-19-3

β-naphthol

Conditions
ConditionsYield
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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    Product Name: 2-Naphthol CAS: 135-19-3 MF: C10H8O MW: 144.17 Mol File: 135-19-3.mol 2-Naphthol Structure 2-Naphthol Chemical Properties Melting point 120-122 °C(lit.) Boiling point 285-286 °C(lit.) density 1,28 g/

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Uses

 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.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

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.