708-06-5

Basic information

• Product Name: 2-hydroxynaphthalene-1-carbaldehyde
• Synonyms: 2-Hydroxy-1-phthaldehyde;TIMTEC-BB SBB003835;1-formyl-2-hydroxynaphthalene;1-Formyl-2-hydroxy-naphthalene;1-Formyl-2-naphthol;1-Hydroxy-2-naphthalenecarboxaldehyde;1-Naphthaldehyde, 2-hydroxy-;2-Hydroxy-1-naphthalaldehyde
• CAS NO: 708-06-5
• Molecular Formula: C₁₁H₈O₂
• Molecular Weight: 172.18
• EINECS: 211-902-0
• Product Categories: Naphthalene series;Intermediates of Dyes and Pigments;Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C10 to C21;Carbonyl Compounds;Building Blocks;C10-C12;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 708-06-5.mol

Chemical Properties

• Melting Point: 76-80 °C(lit.)
• Boiling Point: 192 °C27 mm Hg(lit.)
• Flash Point: 191-193°C/27mm
• Appearance: Yellow/Crystalline Moist Powder
• Density: 1.1153 (rough estimate)
• Vapor Pressure: 0.000443mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol
• PKA: 8.27±0.50(Predicted)
• Water Solubility: Soluble in water (40 g/L at 20°C).
• Sensitive: Air Sensitive
• BRN: 742777
• CAS DataBase Reference: 2-hydroxynaphthalene-1-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxynaphthalene-1-carbaldehyde(708-06-5)
• EPA Substance Registry System: 2-hydroxynaphthalene-1-carbaldehyde(708-06-5)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36-60-61-24/25-37
• RIDADR: UN 3077 9/PG 3
• WGK Germany: 2
• RTECS: QJ0300000
• TSCA: Yes
• HazardClass: 9
• Hazardous Substances Data: 708-06-5(Hazardous Substances Data)

Usage

Uses

Used in Merrified-type Synthesis:
2-Hydroxy-1-naphthaldehyde is used as a reagent in Merrified-type synthesis for the determination of free amino acid groups in polymers. Its chemical properties allow it to effectively identify and quantify these groups, which is crucial for understanding the structure and function of the polymers.

Purification Methods

Crystallise the aldehyde from EtOH (1.5mL/g), aqueous EtOH, aqueous AcOH (m 84o), EtOAc or H2O. [Russell & Lockhart Org Synth Coll Vol III 463 1955, Beilstein 8 H 143, 8 I 564, 8 II 171, 8 III 1108, 8 IV 1160.]

InChI:InChI=1/C11H8O2/c12-7-10-9-4-2-1-3-8(9)5-6-11(10)13/h1-7,13H

Upstream product

• 5419-02-3 1-dimethylaminomethyl-naphthalen-2-ol 
• 612-54-4 2-chloro-3H-indol-3-one 
• 135-19-3 β-naphthol 
• 100-97-0 hexamethylenetetramine 
• 731-90-8 N-(2-hydroxy-1-naphthalidene)aniline 
• 58132-00-6 2-(2-oxo-1,2-dihydro-naphthalen-1-ylidene)-1,2-dihydro-indol-3-one 
• 77287-34-4 formamide 
• 864131-95-3 N,N'-diphenylformamidine 
• 93-61-8 N-methyl-N-phenylformamide 
• 50-00-0 formaldehyd 
• 302-17-0 chloral hydrate 
• 74-90-8 hydrogen cyanide 
• 67-66-3 chloroform 
• 18747-04-1 2-methylnaphtho[2,1-b]furan 

Downstream Products

• 268736-98-7 5-(2-hydroxy-[1]naphthylmethylene)-2-thioxo-thiazolidin-4-one 
• 15017-25-1 (E)-N'-((2-hydroxynaphthalen-1-yl)methylene)picolinohydrazide 
• 15017-29-5 (E)-N'-((2-hydroxynaphthalen-1-yl)methylene)nicotinohydrazide 
• 796-42-9 (E)-N'-((2-hydroxynaphthalen-1-yl)methylene)isonicotinohydrazide 
• 1592-43-4 1,3,3-trimethylspiro[indoline-2,3'-[3H]naphtho[2,1-b]pyran] 
• 15900-11-5 (5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-4-ylidene)-methane 
• 135-19-3 β-naphthol 
• 64468-29-7 2-(N-Phenylcarboxamido)-3(H)-oxonaphtho<2,1-b>pyran 
• 64468-31-1 N-(4-Methylphenyl)-3-oxo-3H-naphtho<2,1-b>pyran-2-carboxamid 
• 894-96-2 1-(((4-hydroxyphenyl)imino)methyl)naphthalen-2-ol 
• 727-80-0 3-acetylbenzo[f]coumarin 
• 29101-37-9 2-hydroxynaphthalene-1-carbaldehydene-1-naphthylamine 
• 4852-81-7 2-benzoyl-3H-benzo[f]chromen-3-one 
• 6638-21-7 1-[(4-methylphenylimino)methyl]-2-naphthol 

Relevant articles and documents

Pyrophosphate selective fluorescent chemosensors: Cascade recognition of nuclear stain mimicking DAPI

A new zinc(ii) complex with a condensed hydroxynaphthyl pyridine (SPHN) as the coordinated ligand has been synthesized for the selective recognition of pyrophosphate (PPi) over other anions including phosphate in a mixed aqueous solution. The fluorescence enhancement of SPHN in association with Zn 2+ ions is quenched in the presence of intracellular pyrophosphate. This phenomenon is utilized in the construction of a logic gate. The binding of SPHN with Zn2+ and its displacement by PPi have been established by photophysical investigation and supported by the DFT level of studies. The development of blue fluorescence in the {SPNH-Zn} complex upon binding of zinc with SPHN is shown to be useful as a nucleus marker in a cell similar to the commercially available staining compound, DAPI (diamino-2-phenylindole). This journal is the Partner Organisations 2014.

FRET based selective and ratiometric 'naked-eye' detection of CN - in aqueous solution on fluorescein-Zn-naphthalene ensemble platform

We have developed a FRET-based ratiometric fluorescent probe for the detection of CN- using a fluorescein-Zn-naphthalene ensemble (NFH·Zn2+). The sensing mechanism was ascribed by displacement approach. The chemosensor exhibits high selectivity and sensibility for CN -. The speculation was supported by fluorescence emission spectra, UV-vis spectrum, 1H NMR titration experiments, and mass spectra. The interconversion of probe NFH and NFH·Zn2+ via the complexation/decomplexation by the modulation of Zn2+/CN- mimics INHIBIT gate. In addition, it also shows an excellent performance in 'dip stick' method.

Rapid detection of hydrazine in a naphthol-fused chromenyl loop and its effectiveness in human lung cancer cells: Tuning remarkable selectivity via the reaction altered pathway supported by theoretical studies

Our designed and synthesized chemosensor naphthalene based chromenyl derivative (NAC) [1-(3-hydroxy-3 methyl-3H-benzo[f]chromen-2-yl) ethanone] has been used for fast (2H4 by a new way via the chromenyl ring opening followed by the pyrazole ring formation giving a strong blue fluorescence. The DFT study and the real application in different water samples along with the dipstick method in low cost devices have also been performed here. Human lung cancer cells (NCI-H460) have been used for hydrazinolysis of the NAC in vivo system for detection by the appearance of blue fluorescence and also for the MTT assay showing its remarkable cancer sensitivity. This journal is

Recognition of Mg2+ and Zn2+ based on a naphthalene-based fluorescent probe by regulating solvents

In this study, a naphthalene schiff-base which serves as a dual analyte chemosensor and quantifies Mg2+ and Zn2+ has been synthesized. The sensor shows "off-on" fluorescent response toward Mg2+ in acetonitrile while the detection of the sensor could be switched for Zn2+ by regulating solvents from acetonitrile to a mixture of ethanol-water (v/v, 4:1). Both of the sensing mechanisms are attributed to the formation of 1:1 ligand-metal complexes which inhibit photo-induced electron transfer (PET) process. More importantly, the reversibility of the recognition processes of HL is performed by adding a bonding agent Na2EDTA.

Synthesis of 2-hydroxy-1-naphthaldehyde under conditions of heterogeneous catalysis

A procedure was developed for synthesis of 2-hydroxy-1-naphthaldehyde by Reimer-Tiemann fluorination of 2-naphthol under conditions of heterogeneous catalysis.

Relay recognition of F- and a nerve-agent mimic diethyl cyano-phosphonate in mixed aqueous media: Discrimination of diethyl cyanophosphonate and diethyl chlorophosphate by cyclization induced fluorescence enhancement

Anion to nerve agent simulant detection by relay recognition has been designed and realized for the first time with sequence specificity (F- → DCNP) via a fluorescence "off-on-on" mechanism. The discrimination of DCNP and DCP via a CIFE (cyclization induced fluorescence enhancement) mechanism has also been demonstrated here. Test strips based on the sensors with F- and DCNP are fabricated, which can act as convenient and efficient nerve agent and F- test kits. The origin of the sequence specificity of different fluorescence recognition was revealed through single X-ray crystal and NMR analysis.

Single chemosensor for highly selective colorimetric and fluorometric dual sensing of Cu(II) as well as 'NIRF' to acetate ion

A novel fluorescent probe for the copper(II) ion in mixed aqueous media, based on fluorescence quenching mechanism with noticeable color change from light to dark yellow, was designed and synthesized. It also exhibited high selectivity for acetate in acetonitrile over other common anions in the near infrared region (NIR) accompanied with exciting color changes from light yellow to pink. Hence sensor 1 ascertains its dual chemosensing ability toward Cu(II) and acetate ions as evidenced by competitive experiments.

Novel strategy of constructing fluorescent probe for MAO-B via cascade reaction and its application in imaging MAO-B in human astrocyte

To detect monoamine oxidase B (MAO-B), the level of which is one of the most important indicators of neurodegenerative diseases such as Parkinson's disease, a new type of cascade reaction based on the formation of coumarin was applied in this research. After the reaction with MAO-B, the protecting group of hydroxyl group in probes (DEAN-MA and DEAB-MA) was removed, and the fluorescence intensity significantly increased (λem = 456 nm) as the structure of coumarin was formed subsequently. The probes showed excellent sensitivity and selectivity to MAO-B. The detection limit of DEAN-MA and DEAB-MA were 0.6 ng/mL and 0.2 ng/mL, respectively. We succeeded in detecting MAO-B in vitro and imaging it in human astrocyte (U87).

Nanoarchitecture self-assembly and photochromic studies of 2,2-diarylnaphthopyrans

The synthesis and photochromic properties of novel 2,2-diarylnaphthopyrans were described. Significantly, the nanostructured architecture through two-component self-assembly of a photochromic naphthopyran and an asymmetric biphenyl was determined by X-ray diffraction. The structure motifs of nanocavities were formed by Cl?O interactions and Ar-H?Cl hydrogen bonds among the photochromic naphthopyran molecules. It was further shown by TEM that the dimensions of cavity structures were up to nanometer level, which provides the potential to capture useful nanoscale entities and control photochromism in organic materials.

Hydrazinopyrimidine derived novel Al3+ chemosensor: Molecular logic gate and biological applications

Cost-effective and highly sensitive biocompatible probes for the detection of Al3+ have tremendously important practical applications. Herein, we report for the first time, the hydrazinopyrimidine based Al3+ chemosensor L (1-[(4,6-dimethyl-pyrimidin-2-yl)-hydrazonomethyl]-naphthalen-2-ol) prepared by the condensation of 2-hydroxy-1-naphthaldehyde and 4,6-dimethyl-2-hydrazino-pyrimidine. Our as-synthesized chemosensor L (Φ = 0.0066) shows ～15 fold fluorescence enhancement in the presence of Al3+ (Φ = 0.0955, Ka = 1.9 × 104 M-1) via chelation enhanced fluorescence (CHEF), excited state intramolecular proton transfer (ESIPT), and inhibited photo-induced electron transfer (PET) phenomena. The limit of detection (LOD) and limit of quantification (LOQ) were estimated to be 2.78 μM and 9.27 μM, respectively. Furthermore, for the first time, a hydrazino pyrimidine based 'INHIBIT' molecular logic gate for Al3+ was successfully developed using the fluorescence properties of L. The experimental sensing mechanisms of L for Al3+ were corroborated by theoretical calculations. Biocompatibility and good water-solubility properties of a pyrimidine moiety of L inspired us to investigate Al3+ imaging in human embryonic kidney cell lines, HEK293, and the results for practical applications are highly promising.