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.)

Flash point:

169 °F

storage temp. 

2-8°C

solubility 

Soluble in most fixed oils, propylene glycol. Insoluble in glycerin.

form 

Liquid

color 

Clear colorless

Odor

at 10.00 % in dipropylene glycol. fresh sharp green hyacinth leaf lilac

Odor Type

green

Water Solubility 

10μg/L

Sensitive 

Air Sensitive

JECFA Number

1467

BRN 

4291321

InChIKey

IQVAERDLDAZARL-UHFFFAOYSA-N

LogP

1.96

CAS DataBase Reference

93-53-8(CAS DataBase Reference)

EPA Substance Registry System

Benzeneacetaldehyde, .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

F 

9-23

TSCA 

Yes

HS Code 

29122990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-PHENYLPROPIONALDEHYDE Usage And Synthesis

Description

2-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 Properties

clear colorless liquid

Chemical Properties

2-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.

Chemical Properties

2-Phenylpropionaldehyde has an intense, green, floral odor reminiscent of hyacinth.

Occurrence

Reported found in microbially fermented tea and some varieties of mushrooms.

Uses

2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625).

Definition

ChEBI: 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 Methods

The 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 ℃.

Preparation

By 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 Description

2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor.

Flammability and Explosibility

Non flammable

Trade name

Floralozone (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 Methods

It 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(93-53-8)Related Product Information

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• 2-Methyl-3-(3,4-methylenedioxyphenyl)propanal
• 3-(4-METHOXY-PHENYL)-PROPIONALDEHYDE
• 2-PHENYLPROPIONALDEHYDE DIMETHYL ACETAL
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• 3-(2-FLUORO-PHENYL)-PROPIONALDEHYDE
• 2-(4-METHYLSULPHONYL-2-NITROPHENYL)MALONDIALDEHYDE, 95
• 3-(3-TRIFLUOROMETHYL-PHENYL)-PROPIONALDEHYDE
• A-METHYL-3-PHENOXYBENZENEACETALDEHYDE
• FEMA 3078
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• 3-(4-BROMO-PHENYL)-PROPIONALDEHYDE
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• BETA-PHENYLPROPIONALDEHYDE,3-PHENYLPROPIONALDEHYDE,PHENYLPROPYL ALDEHYDE ( 3-PHENYLPROPIONALDEHYDE ),Phenylpropionaldehyde
• 3-(4-FLUORO-PHENYL)-PROPIONALDEHYDE
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• 2-(4-isobutylphenyl)propionaldehyde oxime
• PHENYLPROPIOLALDEHYDE DIETHYL ACETAL