1-Naphthol

Base Information

• Chemical Name: 1-Naphthol
• CAS No.: 90-15-3
• Deprecated CAS: 50356-21-3
• Molecular Formula: C10H8O
• Molecular Weight: 144.173
• Hs Code.: 2907.15
• European Community (EC) Number: 201-969-4,215-322-9
• NSC Number: 9586
• UNII: 2A71EAQ389
• DSSTox Substance ID: DTXSID6021793
• Nikkaji Number: J3.911J
• Wikipedia: 1-Naphthol
• Wikidata: Q408876
• Metabolomics Workbench ID: 41859
• ChEMBL ID: CHEMBL122617
• Mol file: 90-15-3.mol

Synonyms:1-hydroxynaphthalene;1-naphthol;1-naphthol, 1-(14)C-labeled;1-naphthol, 2-(13)C-labeled;1-naphthol, ion(1+);1-naphthol, lithium salt;1-naphthol, potassium salt;1-naphthol, sodium salt;alpha-naphthol

Chemical Property of 1-Naphthol

Chemical Property:

• Appearance/Colour: pale grey to brown solid
• Vapor Pressure: 1 mm Hg ( 94 °C)
• Melting Point: 94-96 °C(lit.)
• Refractive Index: 1.6224
• Boiling Point: 288 °C at 760 mmHg
• PKA: 9.34(at 25℃)
• Flash Point: 144 °C
• PSA: 20.23000
• Density: 1.181 g/cm³
• LogP: 2.54540
• Storage Temp.: Store in dark!
• Sensitive.: Air & Light Sensitive
• Solubility.: Soluble in benzene, chloroform, ether and ethanol.
• Water Solubility.: 436.7mg/L(25 oC)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 144.057514874
• Heavy Atom Count: 11
• Complexity: 133

Purity/Quality:

99% ^*data from raw suppliers

1-Naphthol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,N
• Statements: 21/22-37/38-41-51/53
• Safety Statements: 22-26-37/39-2-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthols
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2O
• Description: 1-Naphthol, or α-naphthol, is a fluorescent organic compound with the formula C10H7OH. It is a white solid. It is an isomer of 2-naphthol differing by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol, with the hydroxyl group being more reactive than in the phenols. Both isomers are soluble in simple alcohols, ethers, and chloroform. They are precursors to a variety of useful compounds. Naphthols (both 1 and 2 isomers) are used as biomarkers for livestock and humans exposed to polycyclic aromatic hydrocarbons.α-naphtol, combined with epichlorhydrine and sodium hydroxide to form alpha-naphtyl glycidyl ether, caused sensitization in one of three workers in a chemical plant.
• Uses: 1-Naphthol is used as a precursor in the manufacturing of various azo dyes and pharmaceuticals such as nadolol. It is used as biomarkers. It is used in analytical chemistry as Molisch's reagent (1-naphthol dissolved in ethanol) for checking the presence of carbohydrates. It plays an essential role with sodium hypobromite to detect the presence of arginine in proteins, which is called as Sakaguchi test.

Technology Process of 1-Naphthol

There total 458 articles about 1-Naphthol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

α-naphthyl benzoate (607-55-6) + N-butylamine (109-73-9,85404-21-3) → α-naphthol (90-15-3) + N-butylbenzamide (2782-40-3)

Guidance literature:

With hydrogenchloride; In benzene; for 2.5h; Ambient temperature;

Reference yield: 77.0%

1-Naphthylboronic acid (13922-41-3) → α-naphthol (90-15-3) + 1-amino-naphthalene (134-32-7)

Guidance literature:

With ammonium hydroxide; potassium nitrate; In water; at 20 ℃; for 4h; chemoselective reaction; Electrochemical reaction;

DOI:10.1021/jo400981f

Reference yield: 67.0%

naphthalen-1-yl naphthalene-2-carboxylate (88639-89-8) → α-naphthol (90-15-3) + naphthalene-2-carboxylate (93-09-4)

Guidance literature:

With boron trifluoride diethyl etherate; bromocatecholborane; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(00)99059-2

upstream raw materials:

furan

diethyl ether

lithium piperidide

chlorobenzene

Downstream raw materials:

3-(naphthalene-1-yloxy)propane-1-ol

2-piperidinomethylene-1-naphthol

2-(α-Morpholino-2-nitro-benzyl)-[1]naphthol

N,N-di(naphth-1-yl)amine

Refernces

• 1、 Kirby, Anthony J.,Percy, Jonathan M.. "EXCEPTIONAL REACTIVITY OF THE AROMATIC RING IN 8-SUBSTITUTED 1-NAPHTHOL DERIVATIVES. READY REDUCTION TO TETRALINS.". . p. 6911 - 6920. Retrieved 1988.
• 2、 Dusart,Bardy. "-". . p. 1051. Retrieved 1872.
• 3、 Srinivasulu,Srinivas,Reddy,Mukkanti,Buchireddy. "A validated stability indicating rapid LC method for duloxetine HCl". . p. 10 - 13. Retrieved 2009.
• 4、 Sogorb, Miguel A.,Vilanova, Eugenio. "Serum albumins and detoxication of anti-cholinesterase agents". . p. 325 - 329. Retrieved 2010.
• 5、 Chen, Zhifeng,Chen, Jie,Ma, Nana,Zhou, Haifeng,Cong, Zhiqi. "Selective hydroxylation of naphthalene using the H2O2-dependent engineered P450BM3 driven by dual-functional small molecules". . p. 831 - 836. Retrieved 2018.
• 6、 Li, Sifeng,Xu, Jianbin,Fan, Baomin,Lu, Zhiwu,Zeng, Chaoyuan,Bian, Zhaoxiang,Zhou, Yongyun,Wang, Jun. "Palladium/zinc co-catalyzed syn-stereoselectively asymmetric ring-opening reaction of oxabenzonorbornadienes with phenols". . p. 9003 - 9007. Retrieved 2015.
• 7、 Hawthorne. "-". . p. 1001. Retrieved 1957.
• 8、 -. "PREPARING METHODE FOR NAPHTHOL". Paragraph 0032-0048. . Retrieved 2021/01/28.
• 9、 -. "Aryl phenol compound as well as synthesis method and application thereof". Paragraph 0173-0176. . Retrieved 2021/05/12.