Benzaldehyde

Benzaldehyde (C6H5CHO) is an organic compound consisting of a

benzene ring with a formyl substituent. It is among the simplest aromatic
aldehydes and one of the most industrially useful.

Benzaldehyde

Names

IUPAC name
Benzenecarbaldehyde
Preferred IUPAC name
Benzaldehyde[1]

Other names
Benzenecarboxaldehyde
Phenylmethanal
Benzoic aldehyde

Identifiers

CAS Number 100-52-7 (https://

commonchemistry
.[Link]/detail?cas
_rn=100-52-7)

3D model (JSmol) Interactive image (

[Link]
[Link]/jmol/jm
[Link]?model=O%
3DCc1ccccc1)
 Interactive image (
[Link]
[Link]/jmol/jm
[Link]?model=c1c
cc%28cc1%29C%
3DO)
ChEBI CHEBI:17169 (http
s://[Link]/
chebi/[Link]
?chebiId=17169)

ChEMBL ChEMBL15972 (ht

tps://[Link].u
k/chembl/explore/
compound/ChEM
BL15972)

ChemSpider 235 ([Link]

[Link]/C
 [Link]/C

hemical-Structure.
[Link])
ECHA InfoCard 100.002.601 (http
s://[Link]
/substance-inform
ation/-/substancei
nfo/100.002.601)

EC Number 202-860-4

KEGG D02314 ([Link]

[Link]/entry/
D02314)

PubChem CID 240 ([Link]

[Link]
v/compound/240
)

RTECS number CU437500

UNII TA269SD04T (htt

UNII TA269SD04T (htt
ps://[Link].g
ov/uniisearch/srs/u
nii/TA269SD04T
)

UN number 1990
CompTox DTXSID8039241 (
Dashboard (EPA)
[Link]
[Link]/dashboard/c
hemical/details/DT
XSID8039241)

InChI [show]

SMILES [show]

Properties

Chemical formula C 7H 6O

Molar mass 106.124 g·mol−1

Appearance colorless liquid

Appearance colorless liquid
strongly refractive

Odor almond-like

Density 1.044 g/mL, liquid

Melting point −57.12[2] °C

(−70.82 °F;
216.03 K)

Boiling point 178.1 °C

(352.6 °F;
451.2 K)

Solubility in water 6.95 g/L (25 °C)[3]

log P 1.64[4]
Magnetic −60.78·10−6
susceptibility (χ)
cm3/mol
Refractive index 1.5456
(nD)

Viscosity 1.321 cP (25 °C)

Viscosity 1.321 cP (25 °C)

Thermochemistry
Std enthalpy of −36.8 kJ/mol
formation
(ΔfH⦵298)
Std enthalpy of −3525.1 kJ/mol
combustion
(ΔcH⦵298)
Hazards

GHS labelling:

Pictograms

Signal word Warning

Hazard H302
statements
Precautionary P264, P270,
statements
P301+P312,
P330, P501

NFPA 704
NFPA 704 2
2 0
(fire diamond)

Flash point 64 °C (147 °F;

337 K)

Autoignition 192 °C (378 °F;

temperature
465 K)

Explosive limits 1.4–8.5%

Lethal dose or concentration (LD, LC):

LD50 (median 1300 mg/kg (rat,
dose) oral)

Safety data sheet J. T. Baker ([Link]

(SDS) [Link]/msds/
mf/baker/baker/file
s/[Link])

Related compounds
Related Benzyl alcohol
 Related Benzyl alcohol
compounds
Benzoic acid
Benzaldehyde
oxime
Except where otherwise noted, data are
given for materials in their standard
state (at 25 °C [77 °F], 100 kPa).
verify ([Link]
[Link]?title=Special:ComparePages&re
v1=443414932&page2=Benzaldehyd
e) (what is ?)
Infobox references

It is a colorless liquid with a characteristic almond-like odor, and is

commonly used in cherry-flavored sodas.[5] A component of bitter almond
oil, benzaldehyde can be extracted from a number of other natural
sources.[6] Synthetic benzaldehyde is the flavoring agent in imitation
almond extract, which is used to flavor cakes and other baked goods.[7]

History
Benzaldehyde was first extracted in 1803 by the French pharmacist
Martrès. His experiments focused on elucidating the nature of amygdalin,
the poisonous compound found in bitter almonds, the fruit of Prunus
dulcis.[8] Further work on the oil by Pierre Robiquet and Antoine Boutron
Charlard, two French chemists, produced benzaldehyde.[9] In 1832,
Friedrich Wöhler and Justus von Liebig first synthesized benzaldehyde.[10]

Production
Benzaldehyde can be produced from both petroleum-based chemicals or
plant-derived chemicals. Synthetic benzaldehyde is primarily produced
using liquid phase chlorination and oxidation of toluene. Numerous other
methods have been developed, such as the partial oxidation of benzyl
alcohol, alkali hydrolysis of benzal chloride, and the carbonylation of
benzene (the Gatterman-Koch reaction).[6]

Natural benzaldehyde is produced from cinnamaldehyde obtained from

cassia oil by the retro-aldol reaction:[11] the cinnamaldehyde is heated in
an aqueous/alcoholic solution between 90 °C and 150 °C with a base
(most commonly sodium carbonate or bicarbonate) for 5 to 80 hours,[12]
followed by distillation of the formed benzaldehyde. This reaction also
yields acetaldehyde. The natural status of benzaldehyde obtained in this
way is controversial.[11]

Occurrence
Benzaldehyde and similar chemicals occur naturally in many foods. Most
of the benzaldehyde that people eat is from natural plant foods, such as
almonds.[13]
Almonds, apricot seeds, apple seeds, and cherry seed contain significant
amounts of amygdalin. This glycoside breaks up under enzyme catalysis
into benzaldehyde, hydrogen cyanide and two equivalents of glucose.

Amygdalin benzaldehyde 2 × glucose

2 HC
H2O N 2×

Benzaldehyde contributes to the scent of oyster mushrooms (Pleurotus

ostreatus).[14]

Reactions
Benzaldehyde is easily oxidized to benzoic acid in air at room
temperature,[15] causing a common impurity in laboratory samples. Since
the boiling point of benzoic acid is much higher than that of benzaldehyde,
it may be purified by distillation. Benzyl alcohol can be formed from
benzaldehyde by means of hydrogenation. 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. Benzaldehyde undergoes
disproportionation upon treatment with concentrated alkali (Cannizzaro
reaction): one molecule of the aldehyde is reduced to the benzyl alcohol
and another molecule is simultaneously oxidized to benzoic acid.
With diols, including many sugars, benzaldehyde condenses to form
benzylidene acetals.

Uses
Benzaldehyde is commonly employed to confer almond flavor to foods and
scented products, including e-cigarette liquids. It is sometimes used in
cosmetics products.[16]

In industrial settings, benzaldehyde is used chiefly as a precursor to other

organic compounds, ranging from pharmaceuticals to plastic additives.
The aniline dye malachite green is prepared from benzaldehyde and
dimethylaniline. Benzaldehyde is also a precursor to certain acridine dyes.
Via aldol condensations, benzaldehyde is converted into derivatives of
cinnamaldehyde and styrene. The synthesis of mandelic acid starts with
the addition of hydrocyanic acid to benzaldehyde:

The resulting cyanohydrin is hydrolysed to mandelic acid. (The scheme

above depicts only one of the two formed enantiomers).

Niche uses
Benzaldehyde is used as a bee repellent.[17] A small amount of
benzaldehyde solution is placed on a fume board near the honeycombs.
The bees then move away from the honey combs to avoid the fumes.[18]
The beekeeper can then remove the honey frames from the bee hive with
less risk to both bees and beekeeper.

Benzaldehyde reacts with nitroethane in the presence of a catalyst to

produce phenyl-2-nitropropene, a precursor to amphetamine and other
chemicals.[19]

Safety
As used in food, cosmetics, pharmaceuticals, and soap, benzaldehyde is
"generally regarded as safe" (GRAS) by the US FDA[20] and FEMA.[13] This
status was reaffirmed after a review in 2005.[13] It is accepted in the
European Union as a flavoring agent.[16] Toxicology studies indicate that it
is safe and non-carcinogenic in the concentrations used for foods and
cosmetics,[16] and may even have anti-carcinogenic (anti-cancer)
properties.[16]

For a 70 kg human, the lethal dose is estimated at 50 ml.[6] An acceptable

daily intake of 15 mg/day has been identified for benzaldehyde by the
United States Environmental Protection Agency.[21] Benzaldehyde does
not accumulate in human tissues.[16] It is metabolized [by what?] and then
excreted in urine.[16]

References

1. Nomenclature of Organic
Chemistry : IUPAC
 Chemistry : IUPAC
Recommendations and
Preferred Names 2013 (Blue
Book). Cambridge: The Royal
Society of Chemistry. 2014.
p. 908.
doi:10.1039/9781849733069
-FP001 ([Link]
9%2F9781849733069-FP00
1) . ISBN 978-0-85404-182-
4.
2. Haynes, William M. (2014),
CRC Handbook of Chemistry
and Physics (95th ed.), CRC
press, pp. 3–34,
ISBN 9781482208689
3. "GESTIS Substance database"
3. "GESTIS Substance database"
([Link]
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-[Link]/nxt/[Link]?f=
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estiseng:sdbeng) on 3 March
2016. Retrieved 21 August
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4. "Benzaldehyde_msds" (https://
4. "Benzaldehyde_msds" (https://
[Link]/en/cas/10
0-52-7_946834.html) .
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Helmut; Ruge, Ingrid;
Godelmann, Rolf; Pflaum,
Tabea; Kuballa, Thomas;
Schumacher, Sandra;
Lachenmeier, Dirk W. (2016).
"Benzaldehyde in cherry
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 &pg=PT2457) . America's Test
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almonds: "Recherches sur la
nature et le siège de
l'amertume et de l'odeur des
amandes amères" (Research
on the nature and location of
the bitterness and the smell of
bitter almonds). However, the
memoir was largely ignored
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 p://[Link]/ark:/12148/bp
t6k78139n/[Link]
) Journal de Pharmacie, vol. 5,
pages 289–296.
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amandes amères et sur l'huile
volatile qu'elles fournissent
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physique, 44 (1830), 352–
382,
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Justus von (1832).
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Radikal der Benzoesäure" (http
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 s://[Link]/books?i
d=z-VAAAAAYAAJ&pg=249)
[Investigations of the radical of
benzoic acid]. Annalen der
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doi:10.1002/jlac.1832003030
2 ([Link]
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hdl:2027/hvd.hxdg3f ([Link]
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dg3f) .
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Maria Laura., Ribeiro, Claudio
 Maria Laura., Ribeiro, Claudio
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Alan O. (1985) U.S. patent
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[Link]/patent/US4617419)
Process for preparing natural
benzaldehyde and
acetaldehyde, natural
benzaldehyde and
acetaldehyde compositions,
products produced thereby
 products produced thereby
and organoleptic utilities
therefor.
13. Adams, T. B.; Cohen, S. M.;
Doull, J.; Feron, V. J.;
Goodman, J. I.; Marnett, L. J.;
Munro, I. C.; Portoghese, P. S.;
Smith, R. L. (1 August 2005).
"The FEMA GRAS assessment
of benzyl derivatives used as
flavor ingredients". Food and
Chemical Toxicology. 43 (8):
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doi:10.1016/[Link].2004.11.014 (
[Link]
.2004.11.014) .
PMID 15950815 ([Link]
 PMID 15950815 ([Link]
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).
14. Beltran-Garcia, Miguel J.;
Estarron-Espinosa, Mirna;
Ogura, Tetsuya (1997).
"Volatile Compounds Secreted
by the Oyster Mushroom
(Pleurotus ostreatus) and Their
Antibacterial Activities".
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Food Chemistry. 45 (10):
4049. doi:10.1021/jf960876i (
[Link]
60876i) .
15. Sankar, Meenakshisundaram
(2014). "The benzaldehyde
 (2014). "The benzaldehyde
oxidation paradox explained by
the interception of peroxy
radical by benzyl alcohol" (http
s://[Link]/articles/n
[Link]?
origin=ppub) (PDF). Nature
Communications. 5: 3332.
Bibcode:2014NatCo...5.3332S
([Link]
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/24567108) .
16. Andersen, Alan (1 January
16. Andersen, Alan (1 January
2006). "Final report on the
safety assessment of
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10.1080%2F1091581060071
6612) . International Journal of
Toxicology. 25 (Suppl 1):
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612 ([Link]
2F10915810600716612) .
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17. Evans, Elizabeth; Butler, Carol
17. Evans, Elizabeth; Butler, Carol
(9 February 2010). Why Do
Bees Buzz?: Why Do Bees
Buzz? Fascinating Answers to
Questions about Bees (https://
[Link]/books?id=x
zQ4NWlIrHwC&pg=PA177) .
Rutgers University Press.
pp. 177–178.
ISBN 9780813549200.
18. Sanford, Malcolm T.; Bonney,
Richard E. (1 January 2010).
Storey's Guide to Keeping
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Health ([Link]
om/books?id=cos5WSDNKrEC
 om/books?id=cos5WSDNKrEC
&pg=PA167) . Storey
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ISBN 9781603425506.
19. "Synthesis of Phenyl-2-
Nitropropene" ([Link]
rg/archive/rhodium/chemistry/
[Link]) .
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2023.
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21. Assessment, US EPA National
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"Health and Environmental
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[Link]/ncea/risk/recordisplay.
cfm?deid=41551) .
[Link]. Retrieved
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External links

International Chemical Safety

Card 0102 ([Link]
n/icsc/[Link]?p_lang=
en&p_card_id=0102&p_version=
2)
SIDS Initial Assessment Report for
benzaldehyde ([Link]
.org/documents/sids/sids/100527.
pdf) from the Organisation for
Economic Co-operation and
Development (OECD) Archived (ht
tps://[Link]/web/201810
09042751/[Link]
/documents/sids/sids/[Link]
)
Benzaldehyde description at
[Link] ([Link]
[Link]/20121209073221/http://
[Link]/arokorh
 i/specialtychem/perchem/BENZAL
[Link])
ChemSub Online: Benzaldéhyde. (
[Link]
r/[Link])
Carcinogenicity Potency Project (h
ttp://[Link]/cpdb/che
mpages/[Link])

Retrieved from
"[Link]
title=Benzaldehyde&oldid=1286269847"
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