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	{{chembox		{{Chembox
			|Watchedfields = changed
	| verifiedrevid = 413884824
			|verifiedrevid = 443414932
	| Name = Benzaldehyde
	| ImageFileL1 = Benzaldehyde.png		|Name = Benzaldehyde
			|ImageFileL1 = Benzaldehyde.png
			|ImageNameL1 = Skeletal (structural) formula
	| ImageSizeL1 = 100px
			|ImageClassL1 = skin-invert
	| ImageNameL1 = Benzaldehyde
	| ImageFileR1 = Benzaldehyde-3D-balls-B.png		|ImageFileR1 = Benzaldehyde-3D-balls-B.png
			|ImageNameR1 = Ball-and-stick model
	| ImageSizeR1 = 125px
			|PIN = Benzaldehyde<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 908 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
	| ImageNameR1 = Benzaldehyde
			|OtherNames = Benzenecarboxaldehyde<br />Phenylmethanal<br />Benzoic aldehyde
	| IUAPCName = Benzaldehyde
			|IUPACName = Benzenecarbaldehyde
	| OtherNames = Phenylmethanal<br/>Benzenecarboxaldehyde<br/>Benzoic aldehyde
	| Section1 = {{Chembox Identifiers		|Section1 = {{Chembox Identifiers
	| UNII_Ref = {{fdacite|correct|FDA}}		|UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = TA269SD04T		|UNII = TA269SD04T
	| KEGG_Ref = {{keggcite|correct|kegg}}		|KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = D02314		|KEGG = D02314
	| InChI = 1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H		|InChI = 1/C6H5CHO/c8-6-7-4-2-1-3-5-7/h1-6H
	| PubChem = 240		|PubChem = 240
	| InChIKey = HUMNYLRZRPPJDN-UHFFFAOYAE		|InChIKey = HUMNYLRZRPPJDN-UHFFFAOYAE
	| SMILES1 = c1ccc(cc1)C=O		|SMILES1 = c1ccc(cc1)C=O
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 15972		|ChEMBL = 15972
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H		|StdInChI = 1S/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = HUMNYLRZRPPJDN-UHFFFAOYSA-N		|StdInChIKey = HUMNYLRZRPPJDN-UHFFFAOYSA-N
	| CASNo = 100-52-7		|CASNo = 100-52-7
	| CASNo_Ref = {{cascite|correct|CAS}}		|CASNo_Ref = {{cascite|correct|CAS}}
	| EC-number = 202-860-4		|EC_number = 202-860-4
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 235		|ChemSpiderID = 235
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 17169
	| SMILES = O=Cc1ccccc1		|ChEBI = 17169
			|SMILES = O=Cc1ccccc1
			|RTECS = CU437500
	}}
			|UNNumber = 1990
	| Section2 = {{Chembox Properties
	| C=7|H=6|O=1
	| Appearance = colorless liquid
	| Density = 1.0415 g/ml, liquid
	| Solubility = 0.6 g/100 ml (20 °C)
	| MeltingPt = &minus;26 °C
	| BoilingPt = 178.1 °C
	| Viscosity = 1.4 ] (25 °C)
	}}
	| Section4 = {{Chembox Thermochemistry
	| DeltaHf = &minus;36.8 kJ/mol
	| DeltaHc = &minus;3525.1 kJ/mol
	| Entropy =
	}}
	| Section7 = {{Chembox Hazards
	| EUClass = Harmful ('''Xn''')
	| RPhrases = {{R22}}
	| SPhrases = {{S2}}, {{S24}}
	| FlashPt = 63 °C
	| NFPA-H = 2
	| NFPA-F = 2
	| NFPA-R =
	| ExternalMSDS =
	}}
	| Section8 = {{Chembox Related
	| OtherCpds = ]<br />]
	}}
	}}		}}
			|Section2 = {{Chembox Properties
			|C=7 | H=6 | O=1
			|Appearance = colorless liquid <br> strongly refractive
			|Odor = almond-like
			|Density = 1.044 g/mL, liquid
			|Solubility = 6.95 g/L (25&nbsp;°C)<ref>{{cite web | url=http://gestis-en.itrust.de/nxt/gateway.dll?f=templates$fn=default.htm$vid=gestiseng:sdbeng | title=GESTIS Substance database | publisher=Institute for Occupational Safety and Health of the German Social Accident Insurance | access-date=21 August 2012 | archive-date=3 March 2016 | archive-url=https://web.archive.org/web/20160303201005/http://gestis-en.itrust.de/nxt/gateway.dll?f=templates$fn=default.htm$vid=gestiseng:sdbeng | url-status=dead }}</ref>
			| MeltingPtC = -57.12<ref>{{citation | author=Haynes, William M. | title=CRC Handbook of Chemistry and Physics | edition=95th | publisher=CRC press | year=2014 | pages=3–34|isbn=9781482208689| title-link=CRC Handbook of Chemistry and Physics }}</ref>
			|BoilingPtC = 178.1
			|Viscosity = 1.321 ] (25&nbsp;°C)
			|RefractIndex = 1.5456
			|MagSus = -60.78·10<sup>−6</sup> cm<sup>3</sup>/mol
			<!--| LogP = 1.48 -->
			|LogP = 1.64<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/100-52-7_946834.html|title=Benzaldehyde_msds}}</ref>
			}}
			|Section4 = {{Chembox Thermochemistry
			|DeltaHf = −36.8 kJ/mol
			|DeltaHc = −3525.1 kJ/mol
			}}
			|Section7 = {{Chembox Hazards
			|GHSPictograms = {{GHS07}}
			|GHSSignalWord = Warning
			|HPhrases = {{H-phrases|302}}
			|PPhrases = {{P-phrases|264|270|301+312|330|501}}
			|FlashPtC = 64
			|AutoignitionPtC = 192
			|ExploLimits = 1.4–8.5%
			|NFPA-H = 2
			|NFPA-F = 2
			|NFPA-R = 0
			|ExternalSDS =
			|LD50 = 1300 mg/kg (rat, oral)
			}}
			|Section8 = {{Chembox Related
			|OtherCompounds = ]<br />]<br/>]
			}}
			}}
			'''Benzaldehyde''' (C<sub>6</sub>H<sub>5</sub>CHO) is an ] consisting of a ] ring with a ] substituent. It is among the simplest ] ]s and one of the most industrially useful.
			It is a colorless liquid with a characteristic ]-like ], and is commonly used in ]-flavored ].<ref>{{Cite journal |last=Loch |first=Christine |last2=Reusch |first2=Helmut |last3=Ruge |first3=Ingrid |last4=Godelmann |first4=Rolf |last5=Pflaum |first5=Tabea |last6=Kuballa |first6=Thomas |last7=Schumacher |first7=Sandra |last8=Lachenmeier |first8=Dirk W. |date=2016 |title=Benzaldehyde in cherry flavour as a precursor of benzene formation in beverages |journal=Food Chemistry |volume=206 |pages=74–77 |doi=10.1016/j.foodchem.2016.03.034 |pmid=27041300}}</ref> A component of ] oil, benzaldehyde can be extracted from a number of other natural sources.<ref name=Ullmann/> Synthetic benzaldehyde is the flavoring agent in imitation almond extract, which is used to flavor cakes and other baked goods.<ref>{{Cite book|title = The Cook's Illustrated Baking Book|url = https://books.google.com/books?id=doZKCgAAQBAJ&pg=PT2457|publisher = America's Test Kitchen|date = 2013|isbn = 9781936493784}}</ref>
			==History==
			Benzaldehyde was first extracted in 1803 by the French pharmacist Martrès. His experiments focused on elucidating the nature of ], the poisonous compound found in ], the fruit of '']''.<ref>In 1803 C. Martrès published a manuscript on the oil of bitter 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 until an extract was published in 1819: Martrès ''fils'' (1819) ''Journal de Pharmacie'', vol. 5, pages 289–296.</ref> Further work on the oil by ] and Antoine Boutron Charlard, two French chemists, produced benzaldehyde.<ref>''Nouvelles expériences sur les amandes amères et sur l'huile volatile qu'elles fournissent'' Robiquet, Boutron-Charlard, Annales de chimie et de physique, 44 (1830), 352–382,</ref> In 1832, ] and ] first synthesized benzaldehyde.<ref>{{cite journal|author=Wöhler, Friedrich and Liebig, Justus von |year=1832|url=https://books.google.com/books?id=z-VAAAAAYAAJ&pg=249 |title=Untersuchungen über das Radikal der Benzoesäure|trans-title=Investigations of the radical of benzoic acid|journal=Annalen der Pharmacie|volume= 3|issue=3| pages= 249–282|doi=10.1002/jlac.18320030302|hdl=2027/hvd.hxdg3f|hdl-access=free}}</ref>
	'''Benzaldehyde''' (C<sub>6</sub>H<sub>5</sub>CHO) is an ] consisting of a ] ring with a ] substituent. It is the simplest ] ] and one of the most industrially useful. This colorless liquid has a characteristic pleasant ]-like ]. In fact, benzaldehyde is the primary component of bitter almond oil and can be extracted from a number of other natural sources.<ref>http://www.freepatentsonline.com/1416128.pdf, United States Patent 1416128 - Process of treating nut kernels to produce food ingredients.</ref>
	== Production ==		== Production ==
	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 ] and ] of ] are the main routes. Numerous other methods have been developed, such as the partial oxidation of ], ] hydrolysis of ], and the ] of benzene.<ref>Friedrich Brühne and Elaine Wright “Benzaldehyde” in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a03_463}}</ref>		As of 1999, 7000 ]s of synthetic and 100 tonnes of natural benzaldehyde were produced annually.<ref name=":2">{{Cite book|url=https://books.google.com/books?id=85yUennC-pUC&pg=PA87|title=Innovation in food engineering : new techniques and products|date=2010|publisher=CRC Press|others=Passos, Maria Laura., Ribeiro, Claudio P.|isbn=9781420086072|location=Boca Raton, Florida|pages=87|oclc=500683261}}</ref> Liquid phase ] and ] of ] are the main routes. Numerous other methods have been developed, such as the partial ] of ], ] hydrolysis of ], and the ] of benzene (the ]).<ref name=Ullmann>Brühne, Friedrich and Wright, Elaine (2002) "Benzaldehyde" in ''Ullmann's Encyclopedia of Industrial Chemistry''. Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a03_463}}</ref>
	Benzaldehyde can be synthesized from ] obtained from the oil of ] by refluxing in ]/] solution between 90°C and 150°C with a ] (most commonly ] or ]) for 5 to 80 hours<ref>http://www.patentstorm.us/patents/pdfs/patent_id/4617419.html, Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor, Charles Wienes, Middletown; Alan O. Pittet, Atlantic Highlands, both of N.J.</ref>, followed by distillation of the formed benzaldehyde. This reaction also yields ].		A significant quantity of natural benzaldehyde is produced from ] obtained from ] by the retro-]:<ref name=":2" /> the cinnamaldehyde is heated in an ]/]ic solution between 90&nbsp;°C and 150&nbsp;°C with a ] (most commonly ] or ]) for 5 to 80 hours,<ref>Wienes, Charles and Pittet, Alan O. (1985) {{US Patent|4617419}} Process for preparing natural benzaldehyde and acetaldehyde, natural benzaldehyde and acetaldehyde compositions, products produced thereby and organoleptic utilities therefor.</ref> followed by distillation of the formed benzaldehyde. This reaction also yields ]. The ] of benzaldehyde obtained in this way is controversial.<ref name=":2" />
	==Occurrence==		==Occurrence==
			Benzaldehyde and similar chemicals occur naturally in many foods. Most of the benzaldehyde that people eat is from natural plant foods, such as ].<ref name=":0">{{Cite journal|title = The FEMA GRAS assessment of benzyl derivatives used as flavor ingredients|journal = Food and Chemical Toxicology|date = 2005-08-01|pmid = 15950815|pages = 1207–1240|volume = 43|issue = 8|doi = 10.1016/j.fct.2004.11.014|first1 = T. B.|last1 = Adams|first2 = S. M.|last2 = Cohen|first3 = J.|last3 = Doull|first4 = V. J.|last4 = Feron|first5 = J. I.|last5 = Goodman|first6 = L. J.|last6 = Marnett|first7 = I. C.|last7 = Munro|first8 = P. S.|last8 = Portoghese|first9 = R. L.|last9 = Smith}}</ref>
	Glaciologists LaChapelle and Stillman reported in 1967 that benzaldehyde and N-heptaldehyde inhibit the recrystallization of snow and therefore the formation of ]. 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.{{Fact|date=February 2007}}
	]s, ]s, ]s and ] ], contain significant amounts of ]. This ] breaks up under enzyme catalysis into benzaldehyde, ] and two molecules of ]:		Almonds, ]s, ]s, and ] ] contain significant amounts of ]. This ] breaks up under enzyme catalysis into benzaldehyde, ] and two equivalents of ].
			{{Biochem reaction subunit/top}}
			{{Biochem reaction subunit|compound=Amygdalin|image=Amygdalin_structure.svg|class=skin-invert-image|imagesize=180px}}
			{{Biochem reaction subunit|direction=forward|for_subst=2 {{H2O-nl}}|for_prod=]}}
			{{Biochem reaction subunit|compound=benzaldehyde|image=benzaldehyde.png|class=skin-invert-image|imagesize=50px}}
			{{Biochem reaction subunit|compound=glucose|n=2|image=Alpha-D-glucose-2D-skeletal-hexagon.png|class=skin-invert-image}}
			{{Biochem reaction subunit/end}}
			Benzaldehyde contributes to the scent of ] (''Pleurotus ostreatus'').<ref name="OysterAlde">{{cite journal | doi = 10.1021/jf960876i | title = Volatile Compounds Secreted by the Oyster Mushroom (''Pleurotus ostreatus'') and Their Antibacterial Activities | year = 1997 | last1 = Beltran-Garcia | first1 = Miguel J. | last2 = Estarron-Espinosa | first2 = Mirna | last3 = Ogura | first3 = Tetsuya | journal = Journal of Agricultural and Food Chemistry | volume = 45 | pages = 4049 | issue = 10}}</ref>
	:]
	== Reactions ==		== Reactions ==
	On oxidation, benzaldehyde is converted into the odorless ], which is a common impurity in laboratory samples. ] can be formed from benzaldehyde by means of ]. Reaction of benzaldehyde with anhydrous ] and ] yields ], while alcoholic ] can be used to ] the condensation of benzaldehyde to ]. Benzaldehyde undergoes ] upon treatment with concentrated alkali (]): one molecule of the aldehyde is reduced to the corresponding alcohol and another molecule is simultaneously oxidized to ].		Benzaldehyde is easily oxidized to ] in air at room temperature,<ref>{{cite journal |last1=Sankar |first1=Meenakshisundaram |title=The benzaldehyde oxidation paradox explained by the interception of peroxy radical by benzyl alcohol |journal=Nature Communications |volume=5 |pages=3332 |url=https://www.nature.com/articles/ncomms4332.pdf?origin=ppub|pmid=24567108 |year=2014 |doi=10.1038/ncomms4332 |bibcode=2014NatCo...5.3332S |doi-access=free}}</ref> 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 ]. ] can be formed from benzaldehyde by means of ]. Reaction of benzaldehyde with anhydrous ] and ] yields ], while alcoholic ] can be used to ] the condensation of benzaldehyde to ]. Benzaldehyde undergoes ] upon treatment with concentrated alkali (]): one molecule of the aldehyde is reduced to the ] and another molecule is simultaneously oxidized to ].
	:]		:]
			With diols, including many sugars, benzaldehyde condenses to form ]s.
	== Uses ==		== Uses ==
			Benzaldehyde is commonly employed to confer ] flavor to foods and scented products, including e-cigarette liquids. It is sometimes used in cosmetics products.<ref name=":1">{{Cite journal|title = Final report on the safety assessment of benzaldehyde|journal = International Journal of Toxicology|date = 2006-01-01|pmid = 16835129|pages = 11–27|volume = 25|doi = 10.1080/10915810600716612|first = Alan|last = Andersen| issue=Suppl 1 |s2cid = 32177208|doi-access = free}}</ref>
	It is commonly employed to confer ] flavor. Benzaldehyde is used chiefly as a precursor to other organic compounds, ranging from pharmaceuticals to plastic additives. The ] ] ] is prepared from benzaldehyde and ]. It is a precursor to certain ] dyes as well. Via ]s, benzaldehyde is converted into derivatives of ] and ]. The synthesis of ] starts from benzaldehyde:
			In industrial settings, benzaldehyde is used chiefly as a precursor to other organic compounds, ranging from pharmaceuticals to plastic additives. The ] ] is prepared from benzaldehyde and ]. Benzaldehyde is also a precursor to certain ] dyes. Via ]s, benzaldehyde is converted into derivatives of ] and ]. The synthesis of ] starts with the addition of ] to benzaldehyde:
	:]
			:]
	First ] is added to benzaldehyde, and the resulting ] is subsequently ] to ]. (The scheme above depicts only one of the two formed ]s).
			The resulting ] is ] to ]. (The scheme above depicts only one of the two formed ]s).
			===Niche uses===
			Benzaldehyde is used as a ].<ref>{{Cite book|title = Why Do Bees Buzz?: Why Do Bees Buzz? Fascinating Answers to Questions about Bees|url = https://books.google.com/books?id=xzQ4NWlIrHwC&pg=PA177|publisher = Rutgers University Press|date = 2010-02-09|isbn = 9780813549200|language = en|first1 = Elizabeth|last1 = Evans|first2 = Carol|last2 = Butler|pages = 177–178}}</ref> 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.<ref>{{Cite book|title = Storey's Guide to Keeping Honey Bees: Honey Production, Pollination, Bee Health|url = https://books.google.com/books?id=cos5WSDNKrEC&pg=PA167|publisher = Storey Publishing|date = 2010-01-01|isbn = 9781603425506|language = en|first1 = Malcolm T.|last1 = Sanford|first2 = Richard E.|last2 = Bonney|page = 167}}</ref> The ] can then remove the ]s from the bee hive with less risk to both bees and beekeeper.
			Benzaldehyde reacts with ] in the presence of a catalyst to produce ], a precursor to ] and other chemicals.<ref>{{cite web |url=https://erowid.org/archive/rhodium/chemistry/phenyl-2-nitropropene.html |title=Synthesis of Phenyl-2-Nitropropene |author=<!--Not stated--> |website=Erowid |access-date=October 7, 2023}}</ref>
			== Safety ==
			As used in food, cosmetics, pharmaceuticals, and soap, benzaldehyde is "generally regarded as safe" (]) by the ]<ref>{{citation | author=Friedrich Brühne | author2=Elaine Wright | contribution=Benzaldehyde | title=Ullmann's Encyclopedia of Industrial Chemistry | edition=7th | publisher=Wiley | year=2007 | page=11| title-link=Ullmann's Encyclopedia of Industrial Chemistry }}</ref> and ].<ref name=":0" /> This status was reaffirmed after a review in 2005.<ref name=":0" /> It is accepted in the European Union as a flavoring agent.<ref name=":1" /> Toxicology studies indicate that it is safe and non-carcinogenic in the concentrations used for foods and cosmetics,<ref name=":1" /> and may even have ] (anti-cancer) properties.<ref name=":1" />
			For a 70&nbsp;kg human, the lethal dose is estimated at 50 ml.<ref name="Ullmann" /> An ] of 15&nbsp;mg/day has been identified for benzaldehyde by the ].<ref>{{Cite web|url=https://cfpub.epa.gov/ncea/risk/recordisplay.cfm?deid=41551 |title=Health and Environmental Effects Profile for Benzaldehyde |last=Assessment|first=US EPA National Center for Environmental|website=cfpub.epa.gov|access-date=2017-09-16}}</ref> Benzaldehyde does not accumulate in human tissues.<ref name=":1" /> It is metabolized and then excreted in urine.<ref name=":1" />
	== References ==		== References ==
			{{reflist}}
	<references/>
	== External links ==		== External links ==
			{{Commons category|Benzaldehyde}}
	*{{ICSC|0102|02}}		*{{ICSC|0102|02}}
	*{{SIDS|name=benzaldehyde|id=100527}}		*{{SIDS|name=benzaldehyde| id=100527}}
	*		*
			*
			*
			{{Authority control}}
			{{Use dmy dates|date=March 2018}}
	]		]
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