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Benzaldehyde

Benzaldehyde
Skeletal (structural) formula
Ball-and-stick model
Names
Preferred IUPAC name
Benzaldehyde
Systematic IUPAC name
Benzenecarbaldehyde
Other names
Benzenecarboxaldehyde
Phenylmethanal
Benzoic aldehyde
Identifiers
100-52-7 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:17169 YesY
ChEMBL ChEMBL15972 YesY
ChemSpider 235 YesY
ECHA InfoCard 100.002.601
EC Number 202-860-4
KEGG D02314 YesY
PubChem 240
RTECS number CU437500
UNII TA269SD04T YesY
Properties
C7H6O
Molar mass 106.12 g·mol−1
Appearance colorless or yellowish liquid
strongly refractive
Odor almond-like
Density 1.044 g/mL, liquid
Melting point −57.12 °C (−70.82 °F; 216.03 K)
Boiling point 178.1 °C (352.6 °F; 451.2 K)
0.3 g/100 mL (20 °C)
Solubility soluble in liquid ammonia
Solubility .695 g/100 mL
log P 1.48
-60.78·10−6 cm3/mol
1.5456
Viscosity 1.321 cP (25 °C)
Thermochemistry
−36.8 kJ/mol
−3525.1 kJ/mol
Hazards
Safety data sheet J. T. Baker
Harmful Xn
R-phrases R22
S-phrases (S2), S24
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 64 °C (147 °F; 337 K)
192 °C (378 °F; 465 K)
Explosive limits 1.4-8.5%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
1300 mg/kg (rat, oral)
Related compounds
Related compounds
Benzyl alcohol
Benzoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is the simplest aromatic aldehyde and one of the most industrially useful.

This colorless liquid has a characteristic almond-like odor. Benzaldehyde is the primary component of bitter almond oil and can be extracted from a number of other natural sources. Synthetic benzaldehyde is the flavoring agent in imitation almond extract, which is used to flavor cakes and other baked goods.

Benzaldehyde was first extracted from bitter almonds in 1803 by the French pharmacist Martrès. In 1832 German chemists Friedrich Wöhler and Justus von Liebig first synthesized benzaldehyde.

Benzaldehyde can be obtained by many processes. In the 1980s, an estimated 18 million kilograms were produced annually in Japan, Europe, and North America, a level that can be assumed to continue. Currently liquid phase chlorination and oxidation of toluene are the main routes. Numerous other methods have been developed, such as the partial oxidation of benzyl alcohol, alkali hydrolysis of benzal chloride, and the carbonylation of benzene.

Benzaldehyde can be synthesized from cinnamaldehyde obtained from the oil of cinnamon by refluxing in aqueous/alcoholic solution between 90 °C and 150 °C with a base (most commonly sodium carbonate or bicarbonate) for 5 to 80 hours, followed by distillation of the formed benzaldehyde. This reaction also yields acetaldehyde.


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Wikipedia

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