Crotonaldehyde

{{chembox

|Verifiedfields = changed

|Watchedfields = changed

|verifiedrevid = 460108375

|Reference=Merck Index, 11th Edition, 2599

|ImageFile = Crotonaldehyde.svg

|ImageAlt = Skeletal formula of crotonaldehyde

|ImageSize = 180px

|ImageFile1 = Crotonaldehyde-3D-balls.png

|ImageAlt1 = Ball-and-stick model of (Z)-crotonaldehyde

|IUPACName = (2E)-but-2-enal

|OtherNames = Crotonaldehyde
Crotonic aldehyde
β-Methacrolein
β-Methyl acrolein
2-butenal
Propylene aldehyde

|Section1={{Chembox Identifiers

|IUPHAR_ligand = 6288

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 394562

|InChIKey = MLUCVPSAIODCQM-NSCUHMNNBQ

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = MLUCVPSAIODCQM-NSCUHMNNSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 4170-30-3

|CASNo_Comment = (E/Z)

|CASNo1_Ref = {{cascite|correct|CAS}}

|CASNo1 = 123-73-9

|CASNo1_Comment = (E)

|CASNo2_Ref = {{cascite|correct|CAS}}

|CASNo2 = 15798-64-8

|CASNo2_Comment = (Z)

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 9G72074TUW

|UNII_Comment = (E/Z)

|UNII1_Ref = {{fdacite|correct|FDA}}

|UNII1 = 6PUW625907

|UNII1_Comment = (E)

|UNII2_Ref = {{fdacite|correct|FDA}}

|UNII2 = RB9WCA91QT

|UNII2_Comment = (Z)

|UNNumber = 1143

|EINECS = 204-647-1

|PubChem = 447466

|ChEMBL_Ref = {{ebicite|correct|EBI}}

|ChEMBL = 1086445

|DrugBank_Ref = {{drugbankcite|correct|drugbank}}

|DrugBank = DB04381

|SMILES = O=C/C=C/C

|InChI = 1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+

|RTECS =GP9499000

|ChEBI_Ref = {{ebicite|correct|EBI}}

|ChEBI = 41607

|KEGG_Ref = {{keggcite|changed|kegg}}

|KEGG = C19377

}}

|Section2={{Chembox Properties

|C=4 | H=6 | O=1

|Appearance = colourless liquid

|Odor = pungent, suffocating odor

|Density = 0.846 g/cm³

|MeltingPtC = -76.5

|BoilingPtC = 104.0

|Solubility = 18% (20 °C)

|SolubleOther = very soluble in ethanol, ethyl ether, acetone
soluble in chloroform
miscible in benzene

|RefractIndex = 1.4362

|VaporPressure = 19 mmHg (20 °C)

}}

|Section3={{Chembox Hazards

|NFPA-H = 4

|NFPA-F = 3

|NFPA-R = 2

|NFPA-S = -

|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS06}}{{GHS07}}{{GHS08}}{{GHS09}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|225|301|310|311|315|318|330|335|341|373|400}}

|PPhrases = {{P-phrases|201|202|210|233|240|241|242|243|260|261|262|264|270|271|273|280|281|284|301+310|302+350|302+352|303+361+353|304+340|305+351+338|308+313|310|312|314|320|321|322|330|332+313|361|362|363|370+378|391|403+233|403+235|405|501}}

|FlashPtC = 13

|AutoignitionPtC = 207

|ExploLimits = 2.1–15.5%

|PEL = TWA 2 ppm (6 mg/m³){{PGCH|0157}}

|IDLH = 50 ppm

|REL = TWA 2 ppm (6 mg/m³)

|LC50 = 600 ppm (rat, 30 min)
1375 ppm (rat, 30 min)
519 ppm (mouse, 2 hr)
1500 ppm (rat, 30 min){{IDLH|123739|Crotonaldehyde}}

|LCLo = 400 ppm (rat, 1 hr)

}}

|Section4={{Chembox Related

|OtherFunction_label = alkenals

|OtherFunction = Acrolein

cis-3-hexenal

(E,E)-2,4-Decadienal

|OtherCompounds =}}

}}

Crotonaldehyde is a chemical compound with the formula CH₃CH=CHCHO. The compound is usually sold as a mixture of the E- and Z-isomers, which differ with respect to the relative position of the methyl and formyl groups. The E-isomer is more common (data given in Table is for the E-isomer). This lachrymatory liquid is moderately soluble in water and miscible in organic solvents. As an unsaturated aldehyde, crotonaldehyde is a versatile intermediate in organic synthesis. It occurs in a variety of foodstuffs, e.g. soybean oils.{{Ullmanns |author=R. P. Schulz |author2=J. Blumenstein |author3=C. Kohlpaintner|title=Crotonaldehyde and Crotonic Acid|year=2005|doi=10.1002/14356007.a08_083}}