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Cas Database

135-61-5

135-61-5

Identification

  • Product Name:2-Naphthalenecarboxamide,3-hydroxy-N-(2-methylphenyl)-

  • CAS Number: 135-61-5

  • EINECS:205-205-0

  • Molecular Weight:277.323

  • Molecular Formula: C18H15NO2

  • HS Code:2924299090

  • Mol File:135-61-5.mol

Synonyms:2-Naphtho-o-toluidide,3-hydroxy- (7CI,8CI);2-Hydroxy-3-naphtho-o-toluidide;2-Hydroxy-3-naphthoic o-toluidide;2-Hydroxy-N-(2-methylphenyl)-3-naphthamide;3-Hydroxy-2-naphth-o-toluidide;3-Hydroxy-2'-methyl-2-naphthanilide;3-Hydroxynaphthalene-2-carboxy-o-toluidide;Acco Naf-Sol AS-D;Acco NaphtholAS-D;Amanil Naphthol AS-D;Anarthol AS-D;Anthonaphthol AS-D;Azobase Red OT;Azoic Coupling Component 18;Azotol OT;Brentosyn OTN;C.I. AzoicCoupling Component 110;C.I. Developer 21;Celcot RTO;Cibanaphthol RTO;Daito Grounder D;Diathol D;Dycosthol AS-D;HiltonaphtholAS-D;Kiwa Grounder D;Naphthol AS-D;

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Safety information and MSDS view more

  • Pictogram(s):DangerousN

  • Hazard Codes:N

  • Signal Word:Warning

  • Hazard Statement:H317 May cause an allergic skin reactionH411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
  • Product Description
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  • Purchase
  • Manufacture/Brand:TRC
  • Product Description:3-Hydroxy-2''-methyl-2-naphthanilide
  • Packaging:5g
  • Price:$ 65
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Hydroxy-2'-methyl-2-naphthanilide >97.0%(HPLC)
  • Packaging:500g
  • Price:$ 869
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Hydroxy-2'-methyl-2-naphthanilide >97.0%(HPLC)
  • Packaging:25g
  • Price:$ 69
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Hydroxy-N-o-tolylnaphthalene-2-carboxamide
  • Packaging:10 g
  • Price:$ 152
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-HYDROXY-2'-METHYL-2-NAPHTHANILIDE Aldrich
  • Packaging:1g
  • Price:$ 33.4
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  • Manufacture/Brand:Crysdot
  • Product Description:3-Hydroxy-N-(o-tolyl)-2-naphthamide 95+%
  • Packaging:1000g
  • Price:$ 446
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  • Manufacture/Brand:Chemenu
  • Product Description:3-Hydroxy-N-(o-tolyl)-2-naphthamide 95%
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  • Price:$ 417
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Naphthol AS-D
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  • Price:$ 168
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Naphthol AS-D
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  • Manufacture/Brand:Biosynth Carbosynth
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Relevant articles and documentsAll total 5 Articles be found

Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides

Kos, Jiri,Zadrazilova, Iveta,Pesko, Matus,Keltosova, Stanislava,Tengler, Jan,Gonec, Tomas,Bobal, Pavel,Kauerova, Tereza,Oravec, Michal,Kollar, Peter,Cizek, Alois,Kralova, Katarina,Jampilek, Josef

, p. 7977 - 7997 (2013)

In this study, a series of twenty-two ring-substituted 3-hydroxy- Nphenylnaphthalene- 2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 μmol/L) against S. aureus as well as methicillinresistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2- carboxamide showed higher activity (MIC = 28.4 μmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2- carboxamide expressed higher activity (MIC = 13.0 μmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.

Synthesis of Polysubstituted 2-Naphthols by Palladium-Catalyzed Intramolecular Arylation/Aromatization Cascade

Cai, Jinhui,Hu, Xu-Dong,Liu, Wen-Bo,Wang, Zhen-Kai,Yao, Fei,Zhang, Yun-Hao

, (2020/02/25)

A palladium-catalyzed intramolecular α-arylation and defluorinative aromatization strategy for the synthesis of polysubstituted 2-naphthols is reported. With ortho-bromobenzyl-substituted α-fluoroketones as the substrates and palladium acetate/triphenylphosphine as the catalyst, this method features good functional group tolerance, readily available catalyst and starting materials, and high yields. The applications of the strategy are demonstrated by the synthesis of useful building blocks, such as naphtha[2,3-b]furan, naphthol AS-D, and ligands/catalysts. (Figure presented.).

3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity

Kos, Jiri,Kapustikova, Iva,Clements, Carol,Gray, Alexander I.,Jampilek, Josef

, p. 887 - 892 (2018/02/12)

Abstract: Series of ring-substituted 3-hydroxynaphthalene-2-carboxanilides were screened for their in vitro activity against wild-type S427 (bloodstream form) of Trypanosoma brucei brucei. 3-Hydroxy-N-(3-trifluoromethylphenyl)- and 3-hydroxy-N-(4-trifluoromethylphenyl)naphthalene-2-carboxamides showed the highest biological activity (MIC?=?1.56 and 2.08?μmol/dm3, respectively). Antitrypanosomal activity was correlated with the experimentally determined lipophilicity and acid–base dissociation constants of the compounds as well as with the calculated electronic properties of individual anilide substituents expressed as Hammett’s σ parameters. The substitution in the meta- or para-position of anilide of derivatives with higher lipophilicity by an electron-withdrawing moiety is favourable for higher activity. The optimum thermodynamic pKa T value was found to be ca. 7.5. The structure–activity relationships of all compounds are discussed. Graphical abstract: [Figure not available: see fulltext.].

Fluorescent substrates for potential use in enzyme-linked immunosorbent assay of membrane-bound nucleic acids

Fujita, Satoshi,Momiyama, Masayoshi,Kondo, Yasumitsu,Kagiyama, Naoto,Hori, Samuel H.,Toru, Takeshi

, p. 1347 - 1353 (2007/10/02)

A number of phosphorylated fluorochromes were synthesized and tested for the alkaline phosphatase-linked fluorescence assay of membrane-bound nucleic acids. 3-Hydroxy-N-2′-biphenyl-2-naphthalenecarboxamide phosphate ester (HBNP) was found to be the most suitable for the assay. Nonfluorescent HBNP is hydrolyzed by phospholipase bound to the probe DNA to the highly fluorescent 3-hydroxy-N,2′-biphenyl-2-naphthalenecarboxamide (HBN). HBN is insoluble enough in aqueous medium to precipitate on the nylon membrane. Spots containing as little as 5 fg of λ DNA can be successfully detected on the membrane with HBNP.

Process for the preparation of pure, aromatic o-hydroxy-carboxylic acid aryl amides

-

, (2008/06/13)

Process for the preparation of pure aromatic o-hydroxy-carboxylic acid aryl amides by condensing an aromatic o-hydroxy-carboxylic acid with an aryl amine in the presence of phosphorus chlorides in an organic solvent or diluent, which process comprises treating the reaction mixture or the reaction product with 1 to 25 %, calculated on the weight of the reaction product, of an aliphatic amino-polycarboxylic acid as chelate forming agent. It is not necessary to purify the products, because they are obtained in such a pure form that they can be used directly as coupling components for azo pigments.

Process route upstream and downstream products

Process route

<i>o</i>-toluidine
95-53-4

o-toluidine

3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
With phosphorus trichloride; In chlorobenzene; at 100 - 130 ℃; for 0.75h; Microwave irradiation;
74%
With chlorobenzene; anschliessend Erhitzen mit Phosphor(III)-chlorid;
With phosphorus trichloride; Multistep reaction; 1) xylene, 80 deg C, 10 min; 2) xylene, reflux, 2 h;
With phosphorus trichloride; In chlorobenzene; Microwave irradiation; Heating;
With thionyl chloride;
With phosphorus trichloride;
3-Hydroxy-2-naphthoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
o-toluidine; With triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
117.2 mg
nitrilotriacetic acid
139-13-9,80751-51-5

nitrilotriacetic acid

<i>o</i>-toluidine
95-53-4

o-toluidine

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
With sodium carbonate; In anhydrous phosphorus trichloride; water;
3-hydroxy-2-naphthoic acid methyl ester
883-99-8

3-hydroxy-2-naphthoic acid methyl ester

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: water; sodium hydroxide / ethanol / 6 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere
2.2: 12 h / 20 °C / Inert atmosphere
With oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In ethanol; dichloromethane;
3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
With chlorobenzene; phosphorus trichloride; anschliessend Erhitzen mit o-Toluidin;
3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

2-tolyl isothiocyanate
614-69-7

2-tolyl isothiocyanate

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
at 220 ℃;
naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
<i>o</i>-toluidine
95-53-4

o-toluidine

3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
With phosphorus trichloride; In chlorobenzene; at 100 - 130 ℃; for 0.75h; Microwave irradiation;
74%
With chlorobenzene; anschliessend Erhitzen mit Phosphor(III)-chlorid;
With phosphorus trichloride; Multistep reaction; 1) xylene, 80 deg C, 10 min; 2) xylene, reflux, 2 h;
With phosphorus trichloride; In chlorobenzene; Microwave irradiation; Heating;
With thionyl chloride;
With phosphorus trichloride;
3-Hydroxy-2-naphthoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
o-toluidine; With triethylamine; In dichloromethane; at 20 ℃; for 12h; Inert atmosphere;
117.2 mg
nitrilotriacetic acid
139-13-9,80751-51-5

nitrilotriacetic acid

<i>o</i>-toluidine
95-53-4

o-toluidine

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
With sodium carbonate; In anhydrous phosphorus trichloride; water;
3-hydroxy-2-naphthoic acid methyl ester
883-99-8

3-hydroxy-2-naphthoic acid methyl ester

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: water; sodium hydroxide / ethanol / 6 h / 20 °C / Inert atmosphere
2.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 0 - 20 °C / Inert atmosphere
2.2: 12 h / 20 °C / Inert atmosphere
With oxalyl dichloride; water; N,N-dimethyl-formamide; sodium hydroxide; In ethanol; dichloromethane;
3-Hydroxy-2-naphthoic acid
92-70-6

3-Hydroxy-2-naphthoic acid

naphthol ASD
135-61-5

naphthol ASD

Conditions
Conditions Yield
With chlorobenzene; phosphorus trichloride; anschliessend Erhitzen mit o-Toluidin;

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