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2-PHENYLPROPIONALDEHYDE

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2-PHENYLPROPIONALDEHYDE Basic information
Description References
Product Name:2-PHENYLPROPIONALDEHYDE
Synonyms:FEMA 2886;DL-2-PHENYLPROPIONALDEHYDE;alpha-methyl-alpha-tolualdehyd;alpha-Methyl-alpha-toluic aldehyde;alpha-methyl-alpha-toluicaldehyde;alpha-methyl-benzeneacetaldehyd;alpha-Methylphenylacetaldehyde;alpha-Tolualdehyde, alpha-methyl-
CAS:93-53-8
MF:C9H10O
MW:134.18
EINECS:202-255-5
Product Categories:Aldehydes;Building Blocks;C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
Mol File:93-53-8.mol
2-PHENYLPROPIONALDEHYDE Structure
2-PHENYLPROPIONALDEHYDE Chemical Properties
Melting point 60°C
Boiling point 92-94 °C/12 mmHg (lit.)
density 1.002 g/mL at 25 °C (lit.)
vapor pressure 40Pa at 20℃
FEMA 2886 | 2-PHENYLPROPIONALDEHYDE
refractive index n20/D 1.517(lit.)
Fp 169 °F
storage temp. 2-8°C
solubility Soluble in most fixed oils, propylene glycol. Insoluble in glycerin.
form Liquid
color Clear colorless
Odorat 10.00 % in dipropylene glycol. fresh sharp green hyacinth leaf lilac
Odor Typegreen
Water Solubility 10μg/L
Sensitive Air Sensitive
JECFA Number1467
BRN 4291321
InChIKeyIQVAERDLDAZARL-UHFFFAOYSA-N
LogP1.96
CAS DataBase Reference93-53-8(CAS DataBase Reference)
EPA Substance Registry SystemBenzeneacetaldehyde, .alpha.-methyl- (93-53-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37/39
WGK Germany 3
RTECS CY1460000
9-23
TSCA Yes
HS Code 29122990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2-PHENYLPROPIONALDEHYDE Usage And Synthesis
Description2-phenylpropionaldehyde is also known as 2-phenylpropanal. It belongs to the family of phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 2- phenylpropionaldehyde is a naturally occurring compound in various foods including roasted nuts, cooked potatoes, cheese, wine, fruit, vegetables, coffee, tea, and cocoa. 2-phenylpropionaldehyde is used as a flavoring agent. Once absorbed, 2-phenylpropionaldehyde can be converted to phenyl-substituted carboxylic acids, which can be conjugated with glucuronic acid and excreted in the urine. 2-phenylpropionaldehyde can also undergo β- oxidation to benzoic acid or phenylacetic acid derivatives, which are conjugated with glycine or glutamine before being excreted in the urine.
References[1] WHO Food Additives Series: 54, Safety evaluation of certain food additives
[2] https://webgate.ec.europa.eu
Chemical Propertiesclear colorless liquid
Chemical Properties2-Phenylpropionaldehyde has an intense, green, floral odor reminiscent of hyacinth.
Chemical Properties2-PHENYLPROPIONALDEHYDE identified in dried mushroom, is a colorless liquid with a green hyacinth odor. Hydratropaldehyde can be hydrogenated to hydratropic alcohol, which is also used to a limited extent by reaction of p-ethylbenzyl chloride and isobutyric aldehyde in the presence of catalysts. The product is used in perfumes for, for example, household products.
OccurrenceReported found in microbially fermented tea and some varieties of mushrooms.
Uses2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625).
DefinitionChEBI: 2-phenylpropanal is a member of the class of phenylacetaldehydes that is phenylacetaldehyde in which a hydrogen alpha to the aldehyde carbonyl group has been replaced by a methyl group. The major species at pH 7.3.
Production MethodsThe most important synthetic route to 2-phenylpropionaldehyde is the rhodiumcatalyzed hydroformylation of styrene. The catalyst [HCo(CO)4] is unsuitable in this process because it favors the hydrogenation of styrene. The use of chiral rhodium complexes leads to the formation of optically active aldehydes when prochiral olefins, such as styrene, are used. Asymmetric hydroformylation, however, has so far found only small industrial application because of insufficient purity of the enantiomers. Other synthetic methods are the gas-phase oxidation of a-methylstyrene on Cu, Bi–Mo– P–SiO2, or Pd salt catalysts, the rearrangement of epoxidized a-methylstyrene, and the dehydrogenation of 2-phenyl-1-propanol on Ag catalysts at reaction temperatures of ca. 600 ℃.
PreparationBy alkaline condensation of acetophenone and ethyl chloroacetate; also by distillation of methylphenyl ethylene glycol in 91% yields (under atmospheric pressure).
Synthesis Reference(s)Journal of the American Chemical Society, 97, p. 5608, 1975 DOI: 10.1021/ja00852a062
Organic Syntheses, Coll. Vol. 3, p. 733, 1955
Tetrahedron Letters, 15, p. 3059, 1974
General Description2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor.
Flammability and ExplosibilityNon flammable
Trade nameFloralozone (IFF), Florazon (Symrise).
Safety Profile: Moderately toxic by ingestion. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Purification MethodsIt may contain up to 15% of acetophenone. Purify it via the bisulfite addition compound [Lodge & Heathcock J Am Chem Soc 109 3353 1987] and see Chapter 2 for preparation and decomposition of bisulfite adducts. [Beilstein 7 IV 695.]
2-PHENYLPROPIONALDEHYDE Preparation Products And Raw materials
Raw materialsEthyl chloroacetate-->Acetophenone-->1-Phenyl-1,2-ethanediol
Preparation Productsbeta-Methylphenethyl alcohol-->(S)-(+)-2-Phenylpropionic acid
Tag:2-PHENYLPROPIONALDEHYDE(93-53-8) Related Product Information
2-Phenylpropionaldehyde propyleneglycol acetal 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal 3-(4-METHOXY-PHENYL)-PROPIONALDEHYDE 2-PHENYLPROPIONALDEHYDE DIMETHYL ACETAL Lily aldehyde 3-(2-FLUORO-PHENYL)-PROPIONALDEHYDE 2-(4-METHYLSULPHONYL-2-NITROPHENYL)MALONDIALDEHYDE, 95 3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONALDEHYDE A-METHYL-3-PHENOXYBENZENEACETALDEHYDE FEMA 3078 2,2-dimethyl-3-phenylpropionaldehyde 3-(4-BROMO-PHENYL)-PROPIONALDEHYDE Florazone BETA-PHENYLPROPIONALDEHYDE,3-PHENYLPROPIONALDEHYDE,PHENYLPROPYL ALDEHYDE ( 3-PHENYLPROPIONALDEHYDE ),Phenylpropionaldehyde 3-(4-FLUORO-PHENYL)-PROPIONALDEHYDE cyclamen aldehyde 2-(4-isobutylphenyl)propionaldehyde oxime PHENYLPROPIOLALDEHYDE DIETHYL ACETAL