Benzaldehyde
General
Other names	Phenylmethanal Benzenecarboxaldehyde Benzoic aldehyde Benzene carbaldehyde (IUPAC Formal)
Molecular formula	C7H6O
SMILES	c1ccccc1C=O
Molar mass	106.13 g/mol
Appearance	colorless liquid
CAS number	[100-52-7]
Properties
Density and phase	1.0415 g/ml, liquid
Solubility in water	Slightly soluble (0.6 wt at 20 °C)
Solubility in ethanol	Miscible
Melting point	−26 °C
Boiling point	178.1 °C
Viscosity	1.4 cP at 25 °C
Thermodynamic data
Standard enthalpy of formation ΔfH°liquid	−86.8 kJ/mol
Standard enthalpy of combustion ΔcH°liquid	−3525.1 kJ/mol
Standard molar entropy S°liquid	? J.K−1.mol−1
Hazards
MSDS	J. T. Baker
EU classification	Harmful (Xn)
R-phrases	R22
S-phrases	(S2), S24
Flash Point	63 C (Closed Cap)
NFPA 704	Image File history File links Benzaldehyde. ... Image File history File links Size of this preview: 569 × 599 pixelsFull resolution (1100 × 1158 pixel, file size: 198 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Benzaldehyde ... This article does not cite its references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... “HOH” redirects here. ... Ethanol, also known as ethyl alcohol, drinking alcohol or grain alcohol, is a flammable, colorless, slightly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... Viscosity is a measure of the resistance of a fluid to deform under shear stress. ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... The standard enthalpy of formation or standard heat of formation of a compound is the change of enthalpy that accompanies the formation of 1 mole of a substance in its standard state from its constituent elements in their standard states (the most stable form of the element at 1 atmosphere... Standard enthalpy of Combustion is the Enthalpy change when one mole of a substance is totally combusted in oxygen, and is measured at 298K and 1 atmospheric pressure. ... In chemistry, the standard molar entropy is the entropy content of one mole of substance, under conditions of standard temperature and pressure. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... 2 2 0
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Regulatory data	Flash point, RTECS number, etc.
Related compounds
Related aldehydes	anisaldehyde vanillin
Related compounds	Benzyl alcohol Benzoic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR Spectroscopy) is the subset of spectroscopy that deals with the IR region of the EM spectrum. ... It has been suggested that NMR Data Processing be merged into this article or section. ... Mass spectrometry (also known as mass spectroscopy (deprecated)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... An aldehyde. ... Anisaldehyde, or anisic aldehyde or 4-methoxybenzaldehyde, is an organic compound that consists of a benzene ring substituted with an aldehyde and a methoxy group. ... Vanillin, methyl vanillin, or 4-hydroxy-3-methoxybenzaldehyde, is an organic compound with the molecular formula C8H8O3. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ... Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ...

Benzaldehyde (C₆H₅CHO) is a chemical compound consisting of a benzene ring with an aldehyde substituent. It is the simplest representative of the aromatic aldehydes and one of the most industrially used members of this family of compounds. At room temperature it is a colorless liquid with a characteristic and pleasant almond-like odor: benzaldehyde is an important component of the scent of almonds, hence its typical odor. It is the primary component of bitter almond oil extract, and can be extracted from a number of other natural sources in which it occurs, such as apricot, cherry, and laurel leaves, peach seeds and, in a glycoside combined form (amygdalin), in certain nuts and kernels. Currently benzaldehyde is primarily made from toluene by a number of different processes. Benzene, also known as benzol, is an organic chemical compound with the formula C6H6. ... An aldehyde. ... In chemistry, an aromatic molecule is one in which electrons are free to cycle around circular arrangements of atoms, which are alternately singly and doubly bonded to one another. ... Block quote |}Insert non-formatted text hereInsert non-formatted text here-- For other uses, see Almond (disambiguation). ... Binomial name Prunus armeniaca L. For other uses, see Apricot (disambiguation). ... “Cherry tree” redirects here. ... Binomial name Laurus nobilis L. The Bay Laurel (Laurus nobilis, Lauraceae), also known as True Laurel, Sweet Bay, Grecian Laurel, or just Laurel, is an evergreen tree or large shrub reaching 10–18 m tall, native to the Mediterranean region. ... In the armed forces, leave is permission to be away from ones unit for a period of time. ... Binomial name Prunus persica (L.) Batsch Percentages are relative to US recommendations for adults. ... A ripe red jalapeño cut open to show the seeds For other uses, see Seed (disambiguation). ... A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ... Chemical structure of Amygdalin Amygdalin (from Greek: , almond), C20H27NO11, is a glycoside isolated from bitter almonds by H. E. Robiquet and A. F. Boutron-Charlard in 1830, and subsequently investigated by Liebig and Wöhler, and others. ... Hazelnuts from the Common Hazel Chestnut A nut can be either a seed or a fruit. ... A ripe red jalapeño cut open to show the seeds For other uses, see Seed (disambiguation). ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ...

Production

Benzaldehyde can be obtained by many processes. Currently liquid phase chlorination or oxidation of toluene are among the most used processes. There is also a number of discontinued applications such as partial oxidation of benzyl alcohol, alkali treating of benzal chloride and reaction between benzene and carbon monoxide. General Name, Symbol, Number chlorine, Cl, 17 Series halogens Group, Period, Block 17 (VIIA), 3, p Density, Hardness 3. ... Illustration of a redox reaction Redox (shorthand for oxidation/reduction reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ... In chemistry, an alkali (from Arabic: al-qalyالقلوي, القالي ) is a basic, ionic salt of an alkali metal or alkali earth metal element. ... Benzoyl chloride, also known as benzenecarbonyl chloride, is a colourless, fuming liquid, C6H5COCl, with an irritating odour. ... Carbon monoxide, with the chemical formula CO, is a colorless, odorless, and tasteless gas. ...

Reactions

On oxidation, benzaldehyde is converted into unpleasant smelling benzoic acid. Benzyl alcohol can be formed from benzaldehyde by means of hydrogenation or by treating the compound with alcoholic potassium hydroxide thus undergoing a simultaneous oxidation and reduction which result in the production of potassium benzoate and benzyl alcohol. Reaction of benzaldehyde with anhydrous sodium acetate and acetic anhydride yields cinnamic acid, while alcoholic potassium cyanide can be used to catalyze the condensation of benzaldehyde to benzoin. Benzoic acid, C7H6O2 (or C6H5COOH), is a colorless crystalline solid and the simplest aromatic carboxylic acid. ... Benzyl alcohol, also known as phenylmethanol, is a clear, colorless liquid with a mild pleasant aromatic odor. ... Hydrogenation is a class of chemical reactions in which the net result is an addition of hydrogen. ... The chemical compound potassium hydroxide, (KOH) sometimes known as caustic potash, potassa, potash lye, and potassium hydrate, is a metallic base. ... Illustration of a redox reaction Redox (shorthand for oxidation/reduction reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... Potassium benzoate, the potassium salt of benzoic acid, is a food preservative that inhibits the growth of mold, yeast and some bacteria. ... Sodium acetate, (also rarely, sodium ethanoate) is the sodium salt of acetic acid. ... Acetic anhydride, also known as ethanoic anhydride, is one of the simplest of acid anhydrides. ... Cinnamic acid Cinnamic acid has the formula C6H5CHCHCOOH and is an odorless white crystalline acid, which is slightly soluble in water. ... Potassium cyanide or KCN is the potassium salt of hydrogen cyanide or hydrocyanic acid. ... In chemistry and biology, catalysis is the acceleration (increase in rate) of a chemical reaction by means of a substance, called a catalyst, that is itself not consumed by the overall reaction. ... Benzoin is also used to describe benzoin resin, which does not contain the benzoin described on this page. ...

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Benzaldehyde can also undergo disproportionation in concentrated alkali (Cannizzaro's reaction): one molecule of the aldehyde is reduced to the corresponding alcohol and another molecule is simultaneously oxidized to the salt of a carboxylic acid. The speed of this reaction depends on the substituents present in the aromatic ring. Disproportionation is a concept in chemistry and is a redox reaction where a reactant is both oxidised and reduced in the same chemical reaction. ... The Cannizzaro reaction named after Stanislao Cannizzaro is a chemical reaction that involves the base-induced disproportionation of an aldehyde lacking a hydrogen atom in the alpha position. ... Structure of a carboxylic acid The 3D structure of the carboxyl group A space-filling model of the carboxyl group Carboxylic acids are organic acids characterized by the presence of a carboxyl group, which has the formula -C(=O)OH, usually written -COOH or -CO2H. [1] Carboxylic acids are Bronsted...

Uses

While it is commonly employed as a commercial food flavourant (almond flavour) or industrial solvent, benzaldehyde is used chiefly in the synthesis of other organic compounds, ranging from pharmaceuticals to plastic additives. It is also an important intermediate for the processing of perfume and flavouring compounds and in the preparation of certain aniline dyes. This article is about flavor, the sensory impression. ... Block quote |}Insert non-formatted text hereInsert non-formatted text here-- For other uses, see Almond (disambiguation). ... A solvent is a liquid that dissolves a solid, liquid, or gaseous solute, resulting in a solution. ... Aniline, phenylamine or aminobenzene (C6H5NH2) is an organic chemical compound which is a primary aromatic amine consisting of a benzene ring and an amino group. ... Look up dye in Wiktionary, the free dictionary. ...

The synthesis of mandelic acid starts from benzaldehyde: Mandelic acid, also called phenylglycollic acid, (C8H8O3) (C6H5•CH(OH)•OOH), is an isomer of cresotinic acid and oxymethylbenzoic acid. ...

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First hydrocyanic acid is added to benzaldehyde and the resulting mandelic acid nitrile is subsequently hydrolysed to a racemic mixture of mandelic acid. (The scheme above depicts only one of the two formed enantiomers). Hydrogen cyanide is a chemical compound with chemical formula H-C≡N. A solution of hydrogen cyanide in water is called hydrocyanic acid or prussic acid. ... A nitrile is any organic compound which has a -C≡N functional group. ... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecules. ... Mandelic acid, also called phenylglycollic acid, (C8H8O3) (C6H5•CH(OH)•OOH), is an isomer of cresotinic acid and oxymethylbenzoic acid. ... In chemistry, enantiomers are stereoisomers that are mirror images of each other. ...

Glaciologists LaChapelle and Stillman reported in 1966 that benzaldeyde and N-heptaldehyde inhibit the recrystallization of snow and therefore the formation of depth hoar. This treatment may prevent avalanches caused by unstable depth hoar layers. However, the chemicals are not in widespread use because they damage vegetation and contaminate water supplies.^{[citation needed]} Please wikify (format) this article or section as suggested in the Guide to layout and the Manual of Style. ...

Biology

Image File history File links Size of this preview: 800 × 275 pixelsFull resolution (1082 × 372 pixel, file size: 7 KB, MIME type: image/png) I created the picture myself and converted it to png I, the creator of this work, hereby release it into the public domain. ...

Almonds, apricots, apples and cherry kernels, contain significant amounts of amygdalin. This glycoside breaks up under enzyme catalysis into benzaldehyde, hydrocyanic acid and two molecules of glucose. Block quote |}Insert non-formatted text hereInsert non-formatted text here-- For other uses, see Almond (disambiguation). ... Binomial name Prunus armeniaca L. For other uses, see Apricot (disambiguation). ... This article is about the satellite APPLE. For the fruit apple, see Apple. ... “Cherry tree” redirects here. ... This is a disambiguation page — a navigational aid which lists other pages that might otherwise share the same title. ... Chemical structure of Amygdalin Amygdalin (from Greek: , almond), C20H27NO11, is a glycoside isolated from bitter almonds by H. E. Robiquet and A. F. Boutron-Charlard in 1830, and subsequently investigated by Liebig and Wöhler, and others. ... A glycoside is a molecule where a sugar group is bonded through its anomeric carbon to a nonsugar group by either an oxygen or a nitrogen atom. ... Hydrogen cyanide is a chemical compound with chemical formula H-C≡N. A solution of hydrogen cyanide in water is called hydrocyanic acid or prussic acid. ... Glucose (Glc), a monosaccharide (or simple sugar), is the most important carbohydrate in biology. ...

External links

• International Chemical Safety Card 0102
• European Chemicals Bureau
• Benzaldehyde description at ChemicalLand21.com

• Links to external chemical sources