2-Hydroxy-1-naphthaldehyde

Base Information

• Chemical Name: 2-Hydroxy-1-naphthaldehyde
• CAS No.: 708-06-5
• Molecular Formula: C11H8O2
• Molecular Weight: 172.183
• Hs Code.: 29124990
• European Community (EC) Number: 211-902-0
• NSC Number: 2104
• UNII: PP9CFN7QNL
• DSSTox Substance ID: DTXSID9061041
• Nikkaji Number: J40.507H
• Wikidata: Q63398130
• ChEMBL ID: CHEMBL3265255
• Mol file: 708-06-5.mol

Synonyms:2-hydroxy-1-naphthaldehyde

Chemical Property of 2-Hydroxy-1-naphthaldehyde

Chemical Property:

• Appearance/Colour: yellow-beige-brown powder
• Vapor Pressure: 0.000443mmHg at 25°C
• Melting Point: 76-80 °C(lit.)
• Refractive Index: 1.719
• Boiling Point: 305.8 °C at 760 mmHg
• PKA: 8.27±0.50(Predicted)
• Flash Point: 134.3 °C
• PSA: 37.30000
• Density: 1.288 g/cm³
• LogP: 2.35790
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Methanol
• Water Solubility.: Soluble in water (40 g/L at 20°C).
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 172.052429494
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

1-Formylnaphthalen-2-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36-60-61-24/25-37

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Benzaldehydes
• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2C=O)O
• General Description: 2-Hydroxy-1-naphthaldehyde is a key precursor in the synthesis of chiral Schiff base catalysts, which are employed in asymmetric Henry reactions to produce enantioenriched β-nitro alcohols with high enantiomeric excess (up to 91%) and moderate to good yields. Its reactivity with chiral amino alcohols forms effective catalysts, demonstrating its utility in enantioselective organic transformations.

Technology Process of 2-Hydroxy-1-naphthaldehyde

There total 72 articles about 2-Hydroxy-1-naphthaldehyde 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: 97.0%

C20H20O3 → 2-hydroxynaphthalene-1-carbaldehyde (708-06-5)

Guidance literature:

With silica-OSO₃H; silica gel; In toluene; at 60 - 70 ℃; for 1h;

DOI:10.3390/71000751

Reference yield: 92.0%

2-methoxy-1-naphthaldehyde (5392-12-1) → 2-hydroxynaphthalene-1-carbaldehyde (708-06-5)

Guidance literature:

With aluminium trichloride; In dichloromethane; at 20 ℃; for 1h;

Reference yield: 92.0%

C16H14O4 (954374-79-9) + p-toluidine (106-49-0,12221-03-3) → C33H33NO7 + 2-hydroxynaphthalene-1-carbaldehyde (708-06-5)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jo7013593

upstream raw materials:

1-dimethylaminomethyl-naphthalen-2-ol

2-chloro-3H-indol-3-one

β-naphthol

hexamethylenetetramine

Downstream raw materials:

5-(2-hydroxy-[1]naphthylmethylene)-2-thioxo-thiazolidin-4-one

(E)-N'-((2-hydroxynaphthalen-1-yl)methylene)picolinohydrazide

(E)-N'-((2-hydroxynaphthalen-1-yl)methylene)nicotinohydrazide

(E)-N'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide

Refernces

Asymmetric henry reaction catalyzed by chiral schiff base

10.1134/S1070428013060080

The research investigates the use of chiral Schiff bases as catalysts in the asymmetric Henry reaction. The purpose is to develop efficient catalysts for the addition of nitroalkanes to aldehydes, aiming to achieve high enantiomeric excess (ee) and yields. The study synthesizes four chiral Schiff bases (Ia–Id) from chiral amino alcohols (IIa–IId) and 2-hydroxynaphthalene-1-carbaldehyde. These Schiff bases are then used to catalyze the reaction of nitroalkanes with aldehydes under ambient conditions. The optimal conditions identified include using Schiff base Id and Cu(OAc)2·2H2O as catalysts, butan-1-ol as solvent, and an excess of nitromethane. Under these conditions, various aldehydes were tested, yielding products with moderate to good yields and high ee values, up to 91%. The study concludes that the chiral Schiff bases, particularly Id, are effective catalysts for the asymmetric Henry reaction, providing a promising approach for synthesizing enantioenriched ?-nitro alcohols.