90-02-8

Basic information

• Product Name: Salicylaldehyde
• Synonyms: 2-HYDROXYBENZALDEHYDE FOR SYNTHESIS;Salicylaldehyde reagent grade, 98%;Salicylaldehyde redist., >=99.0% (GC);Salicylaldehyde, Standard for GC,>=99.5%(GC);o-Hydroxybenzaldehyde 2-Hydroxybenzaldehyde;FEMA 3004;2-FORMYLPHENOL;2-HYDROXYBENZALDEHYDE
• CAS NO: 90-02-8
• Molecular Formula: C₇H₆O₂
• Molecular Weight: 122.12
• EINECS: 201-961-0
• Product Categories: P-S;Volatiles/ Semivolatiles;Aromatic Aldehydes & Derivatives (substituted);Amino Group Labeling Reagents for HPLC;Analytical Chemistry;HPLC Labeling Reagents;UV Detection (HPLC Labeling Reagents);Aldehydes;Alpha Sort;Analytical Standards;Analytical/Chromatography;Building Blocks;C7;Carbonyl Compounds;Chemical Synthesis;Chromatography;Environmental Standards;Organic Building Blocks
• Mol File: 90-02-8.mol
• Article Data: 419

Chemical Properties

• Melting Point: 1-2 °C(lit.)
• Boiling Point: 197 °C(lit.)
• Flash Point: 170 °F
• Appearance: Clear yellow/Liquid
• Density: 1.146 g/mL at 25 °C(lit.)
• Vapor Density: 4.2 (vs air)
• Vapor Pressure: 1 mm Hg ( 33 °C)
• Refractive Index: n20/D 1.573(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 4.9g/l
• PKA: 8.37(at 25℃)
• Water Solubility: slightly soluble
• Sensitive: Air & Light Sensitive
• Stability: Stable. Combustible. Incompatible with strong bases, strong reducing agents, strong acids, strong oxidizing agents.
• Merck: 14,8326
• BRN: 471388
• CAS DataBase Reference: Salicylaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: Salicylaldehyde(90-02-8)
• EPA Substance Registry System: Salicylaldehyde(90-02-8)

Safety Data

• Hazard Codes: Xn,N
• Statements: 21/22-36/38-68-36/37/38-20/21/22-51-36-51/53-22
• Safety Statements: 26-36/37-36/37/39-36-61-64-29/35
• RIDADR: 3082
• WGK Germany: 2
• RTECS: VN5250000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 6.1(b)
• PackingGroup: II
• Hazardous Substances Data: 90-02-8(Hazardous Substances Data)

Usage

Uses

Used in Flavor and Fragrance Industry:
Salicylaldehyde is used as a flavor and fragrance component due to its spicy, medicinal, and astringent taste characteristics at 20 ppm. It is a key precursor to various chelating agents and a flavoring ingredient.
Used in Chemical Synthesis:
Salicylaldehyde is a common highly-functionalized arene, which can be used as a precursor in the synthesis of other chemicals, such as coumarin, saligenin, and salicylaldoxime (an important analytical reagent).
Used in Analytical Chemistry:
Salicylaldehyde is used in analytical chemistry for detecting hydrazine.
Used in Pharmaceutical Industry:
Salicylaldehyde has a role as a nematicide and a plant metabolite, making it a promising candidate for various pharmaceutical applications.
Occurrence:
Salicylaldehyde occurs frequently in nature and can be found in various plants, fruits, and essential oils, such as the flowers of Spirea ulmaria, the roots of Crepis foetida L., the fruits of Pinus avium, the rind of Rauwolfia caffra, the leaves of Ceanothus velutinus, and the essential oil of Cinnamomum cassia and tobacco leaves. It is also reported to be 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.
General Description:
Salicylaldehyde is a liquid that is colorless or pale yellow with a bitter almond odor. It sinks and mixes slowly in water.

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.

Synthesis Reference(s)

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

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

InChI:InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H

Upstream product

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• 13486-92-5 4-(3-oxo-3-phenyl-propionimidoyl)-morpholine 
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Relevant articles and documents

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

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