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90-02-8

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90-02-8 Usage

Description

Salicylaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4CHO-2-OH. Along with 3-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde. It is a colorless or pale yellow liquid with a bitter almond odor and a burning taste. It is soluble in alcohol, benzene, and ether, and very slightly soluble in water. Salicylaldehyde is found in shrubs of the genus Spiraea and is usually produced from phenol by the action of chloroform in the presence of an alkali base. It is used in the production of coumarin, saligenin, and salicylaldoxime (an important analytical reagent), and also in analytical chemistry—for example, to detect hydrazine. Besides, salicylaldehyde is a key precursor to various chelating agents and a flavouring ingredient.

Chemical Properties

Salicylaldehyde is a colourless to yellow oily liquid with a pungent, irritating, bitter, almond-like odor similar to benzaldehyde, acetophenone and nitrobenzene, but with phenolic notes. It has a nut-like, coumarin flavor at low levels. slightly soluble in water, soluble in ethanol and ether. It turns purple in case of ferric chloride.

Occurrence

Occurs frequently in nature; in the flowers of Spirea ulmaria and other Spireae, in the roots of Crepis foetida L., in the fruits of Pinus avium, in the rind of Rauqolfia caffra, in the leaves of Ceanothus velutinus and in the essential oil of Cinnamomum cassia and of tobacco leaves. Also reported found in grapes, tomato, baked potato, cinnamon bark, cassia leaf, peppermint oil, pennyroyal oil, parmesan cheese, butter, milk powder, roasted chicken, beer, rum, Japanese whiskey, sherry, coffee, tea, soybean, mushroom, buckwheat, Bourbon vanilla, Chinese quince, Muscat grape, vanilla and mastic gum oil.

Uses

Salicylaldehyde, is used as flavor and fragrance components. Salicylaldehyde is also a common highly-functionalized arene, that can be used as a precursor in the synthesis of other chemicals.

Preparation

Salicylaldehyde is synthesized from phenol, chloroform, and alkali according to the Reimer–Tiemman method, which was developed in 1876. starting material for the manufacture of coumarin.

Definition

ChEBI: Salicylaldehyde is a hydroxybenzaldehyde carrying a hydroxy substituent at position 2. It has a role as a nematicide and a plant metabolite.

Taste threshold values

Taste characteristics at 20 ppm: spicy, medicinal and astringent

Synthesis Reference(s)

Synthetic Communications, 24, p. 1757, 1994 DOI: 10.1080/00397919408010181

General Description

Liquid; colorless or pale yellow; bitter almond odor. Sinks and mixes slowly in water.

Reactivity Profile

Salicylaldehyde is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation.

Health Hazard

Salicylaldehyde is a skin irritant; 500 mg/daycaused moderate irritation to rabbit skin. Itcan have injurious effects on fertility. Studieson rats indicate that subcutaneous administrationof salicylaldehyde in a high doseof >400 mg/kg can produce developmentalabnormalities, fetal death, and postimplantationmortality.The toxicity of this compound, however,is low. No toxic symptoms were noted.LD50 value, oral (rats): 520 mg/kgLD50 value, skin (rats): 600 mg/kg.

Fire Hazard

Combustible. Can react with oxidizing materials.

Purification Methods

It is precipitated as the bisulfite addition compound by pouring the aldehyde slowly and with stirring into a 25% solution of NaHSO3 in 30% EtOH, then standing for 30minutes. The precipitate, after filtering at the pump, and washing with EtOH, is decomposed with aqueous 10% NaHCO3, and the aldehyde is extracted into diethyl ether, dried with Na2SO4 or MgSO4, and distilled, under reduced pressure. Alternatively, salicylaldehyde is precipitated as its Cu complex by adding it to warm, saturated aqueous Cu(OAc)2, shaking and standing in ice. The precipitate is filtered off, washed with EtOH, then Et2O, and decomposed with 10% H2SO4; the aldehyde is extracted into Et2O, dried and vacuum distilled. It was also purified by dry column chromatography on Kieselgel G [Nishiya et al. J Am Chem Soc 108 3880 1986]. The acetyl derivative has m 38-39o (from pet ether or EtOH) and b 142o/18mm, 253o/atm. [Beilstein 8 IV 176.] The oxime, [94-67-7] M 137.1, crystallises CHCl3/pet ether (b 40-60o) with m 57o [Beilstein 8 IV 203.]

Waste Disposal

Salicylaldehyde is burned in a chemicalincinerator equipped with an afterburner andscrubber.

References

https://en.wikipedia.org/wiki/Salicylaldehyde https://pubchem.ncbi.nlm.nih.gov/compound/salicylaldehyde#section=Top http://www.wisegeek.com/what-is-salicylaldehyde.htm https://www.merriam-webster.com/medical/salicylaldehyde http://encyclopedia2.thefreedictionary.com/Salicylaldehyde

Check Digit Verification of cas no

The CAS Registry Mumber 90-02-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 90-02:
(4*9)+(3*0)+(2*0)+(1*2)=38
38 % 10 = 8
So 90-02-8 is a valid CAS Registry Number.
InChI:InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H

90-02-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (A13833)  Salicylaldehyde, 99%   

  • 90-02-8

  • 100g

  • 193.0CNY

  • Detail
  • Alfa Aesar

  • (A13833)  Salicylaldehyde, 99%   

  • 90-02-8

  • 500g

  • 544.0CNY

  • Detail
  • Alfa Aesar

  • (A13833)  Salicylaldehyde, 99%   

  • 90-02-8

  • 2500g

  • 2538.0CNY

  • Detail
  • Sigma-Aldrich

  • (03273)  Salicylaldehyde  analytical standard

  • 90-02-8

  • 03273-1ML-F

  • 255.06CNY

  • Detail
  • Sigma-Aldrich

  • (03273)  Salicylaldehyde  analytical standard

  • 90-02-8

  • 03273-5ML-F

  • 993.33CNY

  • Detail

90-02-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name salicylaldehyde

1.2 Other means of identification

Product number -
Other names salicyaldehyde

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:90-02-8 SDS

90-02-8Relevant articles and documents

Acceleration Effect of Fe(II), Co(II), Ni(II) and Cu(II) on the Hydrolysis Rate of Ortho or Para-Hydroxy Schiff Bases

El-Taher

, p. 815 - 820 (1998)

The kinetics of hydrolysis of ortho- or para-hydroxybenzylidene-4-benzidine Schiff bases have been examined in the pH range 1.70-11.90, in aqueous media containing 20wt% dioxane, at 20°C. In basic media, pH > 8.47, a slight increase in the hydrolysis reaction rate of the Schiff bases is observed. In such basic media, the rate-controlling step is the attack of hydroxide ion on the ionized Schiff base. Below pH 6.82, the rate-determining step is ascribed to be the attack of water molecules on the protonated substrate. The effects of Fe(II), Co(II), Ni(II) and Cu(II) ions on the hydrolysis reaction rate of the Schiff bases have been studied and discussed on the basis of formation of a monocyclic chelate rings. The various thermodynamic parameters have also been evaluated and discussed.

One-step construction of a novel AIE probe based on diaminomaleonitrile and its application in double-detection of hypochlorites and formaldehyde gas

Wen, Xiaoye,Yan, Li,Fan, Zhefeng

, p. 8155 - 8165 (2021)

As the environmental residues of formaldehyde and hypochlorites are very harmful to human health, a new simple and efficient aggregation-induced emission probe based on diaminomaleonitrile was designed and applied in the independent detection of hypochlorites and formaldehyde. The probe shows high selectivity and anti-interference ability against other potential competitive substances. ClO- promotes the oxidized splitting of CN in the probe, and induces evident color changes visible to the naked eye together with quenched fluorescence. The detection of ClO- by this probe was fast, sensitive, and visible to the naked eye. The detection limit of the probe to ClO- in the range of 0.70-20 μM is 18 nM. Through the condensation mechanism and with amine as the binding site of formaldehyde, the exposed amino group in the probe structure responds sensitively and efficiently to formaldehyde. The probe can effectively monitor 0.50-25 μM formaldehyde in aqueous solutions, with a detection limit as low as 42 nM. A portable solid sensor-a formaldehyde detection plate was built by directly covering the probe on a thin-layer chromatography plate. Thereby, formaldehyde gas can be effectively and sensitively detected, which offers a clue for developing solid-state formaldehyde-detection plates. The high experimental recovery rates prove that this new probe is highly promising in hypochlorite detection in the real water environment.

Spectroscopic studies of the interaction of aspirin and its important metabolite, salicylate ion, with DNA, A·T and G·C rich sequences

Bathaie,Nikfarjam,Rahmanpour,Moosavi-Movahedi

, p. 1077 - 1083 (2010)

Among different biological effects of acetylsalicylic acid (ASA), its anticancer property is controversial. Since ASA hydrolyzes rapidly to salicylic acid (SA), especially in the blood, interaction of both ASA and SA (as the small molecules) with ctDNA, oligo(dA·dT)15 and oligo(dG·dC)15, as a possible mechanism of their action, is investigated here. The results show that the rate of ASA hydrolysis in the absence and presence of ctDNA is similar. The spectrophotometric results indicate that both ASA and SA cooperatively bind to ctDNA. The binding constants (K) are (1.7 ± 0.7) × 103 M-1 and (6.7 ± 0.2) × 103 M-1 for ASA and SA, respectively. Both ligands quench the fluorescence emission of ethidium bromide (Et)-ctDNA complex. The Scatchard plots indicate the non-displacement based quenching (non-intercalative binding). The circular dichroism (CD) spectra of ASA- or SA-ctDsNA complexes show the minor distortion of ctDNA structure, with no characteristic peaks for intercalation of ligands. Tm of ctDNA is decreased up to 3 °C upon ASA binding. The CD results also indicate more distortions on oligo(dG·dC)15 structure due to the binding of both ASA and SA in comparison with oligo(dA·dT)15. All data indicate the more affinity for SA binding with DNA minor groove in comparison with ASA which has more hydrophobic character.

The antineoplastic action of o-substituted [1,2-bis(4-hydroxyphenyl)-ethylenediamine]dichloroplatinum (II) complexes and their methylethers

Karl,Schoenenberger

, p. 405 - 410 (1988)

-

A DFT and experimental study of the spectroscopic and hydrolytic degradation behaviour of some benzylideneanilines

Nelson, Peter N.,Robertson, Tahjna I.

, (2021/10/12)

The spectroscopic and hydrolytic degradation behaviour of some N-benzylideneanilines are investigated experimentally and theoretically via high quality density function theoretical (DFT) modelling techniques. Their absorption and vibrational spectra, accurately predicted by DFT calculations, are highly dependent on the nature of the substituents on the aromatic rings, hence, though some of their spectroscopic features are similar, energetic differences exist due to differences in their electronic structures. Whereas the o-hydroxy aniline derived adducts undergo hydrolysis via two pathways, the most energetically economical of which is initiated by a fast enthalpy driven hydration, over a conservative free energy (ΔG?) barrier of 53 kJ mol?1, prior to the rate limiting entropy controlled lysis step which occurs via a conservative barrier of ca.132 kJ mol?1, all other compounds hydrolyse via a slower two-step pathway, limited by the hydration step. Barriers heights for both pathways are controlled primarily by the structure and hence, stability of the transition states, all of which are cyclic for both pathways.

Magneto-structural properties and reliability of (Mn/Ni/Zn) substituted cobalt-copper ferrite heterogeneous catalyst for selective and efficient oxidation of aryl alcohols

Dhabbe, Rohant,Gaikwad, Pratapsingh,Kakade, Bhalchandra,Kamble, Prakash,Kurane, Rajnikant,Parase, Haridas,Sabale, Sandip

, (2021/09/28)

Herein, M2+ substituted CoCuFe2O4 (M2+ = Mn, Zn, Ni) ferrites have been synthesized using the sol-gel auto combustion method. The structural, morphological and magnetic studies confirm the phase formation of pure magnetic cubic spinel MCoCuFe2O4 (M2+ = Mn, Zn, Ni) ferrites. The substitution with Mn, Ni and Zn does not show large variation in binding energies obtained from XPS of Cu (2p) that specifies identical copper concentration (Cu0.5) and substitution of only cobalt (Co2+) in Mn-F, Ni-F and Zn-F catalysts. Interestingly, MCoCuFe2O4 magnetic catalysts were explored for selective oxidation of a series of substituted benzyl alcohols. Catalyst Mn-F showed 93% conversion of benzyl alcohol while, Ni-F showed 95% conversion of 4-nitrobenzyl alcohol. Whereas, the catalyst Zn-F was showed 96% conversion for 4-methoxybenzyl alcohol. Additionally the results also indicate an efficient separation and recovery of the magnetic catalysts after four successive reuses without any considerable loss in its catalytic activity.

Cu-Mn Bimetallic Complex Immobilized on Magnetic NPs as an Efficient Catalyst for Domino One-Pot Preparation of Benzimidazole and Biginelli Reactions from Alcohols

Nasseri, Mohammad Ali,Rezazadeh, Zinat,Kazemnejadi, Milad,Allahresani, Ali

, p. 1049 - 1067 (2020/09/11)

An efficient magnetically recyclable bimetallic catalyst by anchoring copper and manganese complexes on the Fe3O4 NPs was prepared and named as Fe3O4@Cu-Mn. It was founded as a powerful catalyst for the domino one-pot oxidative benzimidazole and Biginelli reactions from benzyl alcohols as a green protocol in the presence of air, under solvent-free and mild conditions. Fe3O4@Cu-Mn NPs were well characterized by FT-IR, XRD, FE-SEM, TEM, VSM, TGA, EDX, DLS, and ICP analyses. The optimum range of parameters such as time, temperature, amount of catalyst, and solvent were investigated for the domino one-pot benzimidazole and Biginelli reactions to find the optimum reaction conditions. The catalyst was compatible with a variety of benzyl alcohols, which provides favorable products with good to high yields for all of derivatives. Hot filtration and Hg poisoning tests from the nanocatalyst revealed the stability, low metal leaching and heterogeneous nature of the catalyst. To prove the synergistic and cooperative effect of the catalytic system, the various homologues of the catalyst were prepared and then applied to a model reaction separately. Finally, the catalyst could be filtered from the reaction mixture simply, and reused for five consecutive cycles with a minimum loss in catalytic activity and performance. Graphic Abstract: A new magnetically recyclable Cu/Mn bimetallic catalyst has been developed for domino one-pot oxidation-condensation of benzimidazole and Biginelli reactions from alcohols. [Figure not available: see fulltext.]

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