Benzaldehyde

Title: Benzaldehyde
CAS Registry Number: 100-52-7
Additional Names: Benzoic aldehyde; artificial essential oil of almond
Molecular Formula: C7H6O
Molecular Weight: 106.12
Percent Composition: C 79.23%, H 5.70%, O 15.08%
Literature References: Occurs in kernels of bitter almonds; made synthetically from benzal chloride and lime or by oxidation of toluene. Laboratory prepn from benzal chloride: A. I. Vogel, Practical Organic Chemistry (Longmans, London, 3rd ed., 1959) p 693; Gattermann-Wieland, Praxis des Organischen Chemikers (de Gruyter, Berlin, 40th ed., 1961) p 184. Toxicity data: P. M. Jenner et al., Food Cosmet. Toxicol. 2, 327 (1964). Review: A. E. Williams in Kirk-Othmer Encyclopedia of Chemical Technology vol. 3 (Wiley-Interscience, New York, 3rd ed., 1978) pp 736-743.
Properties: Strongly refractive liquid, becoming yellowish on keeping; characteristic odor of volatile oil of almond; burning aromatic taste. Oxidizes in air to benzoic acid; volatile with steam. d415 1.050; 1.043 at 25°. bp 179°. mp -56.5°. Flash pt 62°C. nD20 1.5456. Sol in 350 parts water; miscible with alcohol, ether, oils. It reduces ammoniacal AgNO3, but not Fehling's soln. Keep tightly closed and protected from light. LD50 in rats, guinea pigs (mg/kg): 1300, 1000 orally (Jenner).
Melting point: mp -56.5°
Boiling point: bp 179°
Flash point: Flash pt 62°C
Index of refraction: nD20 1.5456
Density: d415 1.050; 1.043 at 25°
Toxicity data: LD50 in rats, guinea pigs (mg/kg): 1300, 1000 orally (Jenner)
NOTE: Benzaldehyde FFC designates a grade of benzaldehyde free from chlorine.
CAUTION: Narcotic in high concns. May cause contact dermatitis.
Use: Manufacture of dyes, perfumery, cinnamic and mandelic acids, as solvent; in flavors.
Benzalkonium Chloride Benzamide Benzanilide Benzanthrone Benzarone

Benzaldehyde
Skeletal (structural) formula Ball-and-stick model
Identifiers
CAS number 100-52-7 YesY
PubChem 240
ChemSpider 235 YesY
UNII TA269SD04T YesY
EC-number 202-860-4
KEGG D02314 YesY
ChEBI CHEBI:17169 YesY
ChEMBL CHEMBL15972 YesY
RTECS number CU437500
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C7H6O
Molar mass 106.12 g mol−1
Appearance colorless or yellowish liquid
strongly refractive
Odor almond-like
Density 1.0415 g/ml, liquid
Melting point −26 °C; −15 °F; 247 K
Boiling point 178.1 °C; 352.6 °F; 451.2 K
Solubility in water .695 g/100 mL
Solubility soluble in liquid ammonia
log P 1.48
Acidity (pKa) 14.90
Refractive index (nD) 1.5456
Viscosity 1.321 cP (25 °C)
Thermochemistry
Std enthalpy of
formation ΔfHo298
−36.8 kJ/mol
Std enthalpy of
combustion ΔcHo298
−3525.1 kJ/mol
Hazards
MSDS J. T. Baker
EU classification Harmful (Xn)
R-phrases R22
S-phrases (S2), S24
NFPA 704
NFPA 704.svg
2
3
1
Flash point 64 °C; 147 °F; 337 K
Autoignition temperature 192 °C; 378 °F; 465 K
Explosive limits 1.4-8.5%
LD50 1300 mk/kg (rat, oral)
Related compounds
Related compounds Benzyl alcohol
Benzoic acid
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 pleasant almond-like odor. In fact, benzaldehyde is the primary component of bitter almond oil and can be extracted from a number of other natural sources.[1] Benzaldehyde was first extracted from bitter almonds in 1803 by the French pharmacist Martrès.[2] In 1832 German chemists Friedrich Wöhler and Justus von Liebig first synthesized benzaldehyde.[3]