| Identification | More | [Name]
Phenylacetaldehyde | [CAS]
122-78-1 | [Synonyms]
2-PHENYLACETALDEHYDE
ALPHA-TOLUALDEHYDE
ALPHA-TOLUIC ALDEHYDE
FEMA 2874
PHENYLACETALDEHYDE
PHENYL ACETIC ALDEHYDE
α-Toluic aldehyde
2-Phenylethanal
Acetaldehyde, phenyl-
Benzenacetaldehyde
Benzeneacetaldehyde
Hyacinthin
phenylacetadehyde
phenyl-acetaldehyd
Phenylacetaldehyde,50%
Phenylethanal
Phenylacetaldehyde solution
Phenylacetaldehydetech
PHENYLACETALDEHYDE, 90+%
PHENYLACETALDEHYDE 90+% FCC | [EINECS(EC#)]
204-574-5 | [Molecular Formula]
C8H8O | [MDL Number]
MFCD00006993 | [Molecular Weight]
120.15 | [MOL File]
122-78-1.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless to slightly yellow liquid | [Melting point ]
−10 °C(lit.) | [Boiling point ]
195 °C | [density ]
1.079 g/mL at 20 °C
| [vapor pressure ]
2.09hPa at 20℃ | [FEMA ]
2874 | [refractive index ]
n20/D 1.535(lit.)
| [Fp ]
188 °F
| [storage temp. ]
2-8°C
| [solubility ]
2.21g/l slightly soluble | [form ]
Liquid | [color ]
Clear colorless to pale yellow | [Specific Gravity]
1.075 (20/4℃) | [Odor]
at 10.00 % in dipropylene glycol. green sweet floral hyacinth clover honey cocoa | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases. | [Odor Type]
green | [Water Solubility ]
2.210 g/L (25 ºC) | [Sensitive ]
Air Sensitive | [JECFA Number]
1002 | [Merck ]
14,7265 | [BRN ]
385791 | [Dielectric constant]
4.8（20℃） | [LogP]
1.44 at 25℃ | [CAS DataBase Reference]
122-78-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzeneacetaldehyde(122-78-1) | [EPA Substance Registry System]
122-78-1(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,F | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
R11:Highly Flammable. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S37:Wear suitable gloves .
S24:Avoid contact with skin .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN 1170 3/PG 2 | [WGK Germany ]
2
| [RTECS ]
CY1420000
| [TSCA ]
Yes | [HS Code ]
29122990 | [Safety Profile]
Moderately toxic by
ingestion. Human skin irritant. Combustible
liquid. When heated to decomposition it
emits acrid smoke and irritating fumes. See
also ALDEHYDES. | [Toxicity]
LD50 orl-rat: 1550 mg/kg FCTXAV 17,377,79 |
| Hazard Information | Back Directory | [Description]
Phenylacetaldehyde(122-78-1) is an organic compound which can be naturally found in buckwheat, flowers, and communication pheromones from various insect orders. It is commonly used for the preparation of fragrance as well as flavors, and applied in flavored cigarettes and beverages because of its honey-like sweet character. It is also applied in the synthesis of polymers, such as polyesters, as a rate controlling additive in polymerization reactions and used in the preparation of more complex chemicals like resmethrin, where it acts as a building block.
| [Chemical Properties]
Phenylacetaldehyde has a harsh, green odor reminiscent of hyacinth on dilution. It has an unpleasant, pungent, bitter flavor, turning sweet and fruit-like at low levels. Since it readily undergoes oxidation and polymerizes, it must be stabilized by addition of antioxidants and by dilution with, for example, diethyl phthalate before use in compositions. | [Occurrence]
Identified among the constituents of several essential oils: neroli, Citrus sinensis leaves, other citrus species
(flowers and leaves), narcissus, magnolia, lily, rose and tea. It is reported found in over 170 natural products including apricot,
sour cherry, cooked apple, peach, fresh blackberry, crispbread, other types of bread, green tea, unprocessed rice, lemon balm, red
sage, black currant, bilberry, cranberry, other berries, grapes, raisins, melon, papaya, guava fruit, pineapple, asparagus, celery
leaves, carrot, parsley, peas, bell pepper, sweet pepper, peach, cabbage, peppermint oil, Scotch spearmint oil, mustard, vinegar,
onion, cooked potato, tomato, cinnamon bark, cassia leaf, ginger, many cheeses, milk, yogurt, boiled egg, cooked and cured
meats, beer, cognac, grape wines, cocoa, coffee, tea, roasted filbert, roasted peanut, soybean, pecans, cauliflower, broccoli, honey,
avocado, passion fruit, beans, mushrooms, trassi, mango, tamarind, rice, licorice, buckwheat, lovage root, pumpkin, sweet potato,
cassava, corn oil, malt, wort, dried bonito, loquat, pawpaw, maté, sweet grass oil, orange peel oil, grapefruit juice, endive, clam
and Chinese quince. | [Uses]
Phenylacetaldehyde is used for the preparation of fragrances and polymers like polyesters, which find application as a rate controlling additive in polymerization reactions. It is an active component of fragrances and floral scent due to its honey-like sweet character and finds application in flavored cigarettes and beverages. It is an insect attractant and utilized in blacklight trap for pests. It is also used as a building block in the synthesis of more complex chemicals, such as resmethrin. Furthermore, it is used in association with acetic anhydride and allyltrimethylsilane in three-component coupling process catalyzed by LiBF4 providing homoallylic acetates. | [Definition]
ChEBI: Phenylacetaldehyde(122-78-1) is an aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.
| [Aroma threshold values]
Detection: 4 ppb. Aroma characteristics at 1.0%: sweet, floral honey, rosy and slightly powdery with a
fermented note, cocoa and tobacco with a yellow tropical fruity nuance. | [Taste threshold values]
Taste characteristics at 5 ppm: floral and honey-like with a sweet floral, fruity, tobacco, with a yellow tropical
fruity waxy nuance. | [Synthesis Reference(s)]
Journal of the American Chemical Society, 99, p. 4536, 1977 DOI: 10.1021/ja00455a071
Tetrahedron Letters, 29, p. 1471, 1988 DOI: 10.1016/S0040-4039(00)80328-7 | [General Description]
Phenylacetaldehyde is an important aroma volatile found in tomato and roses. It has also been identified in potato, roasted cocoa beans and honey. Phenylacetaldehyde is also a potent moth attractant. | [Biochem/physiol Actions]
Phenylacetaldehyde is an insect attractant and can be used in blacklight trap for pests. It is constituent of floral scent. It is an intermediate in a variety of biochemical pathways. | [Production Methods]
The most important method industrially is the isomerization of styrene oxide. Ion-exchange resins, catalysis by chromium trioxide–tungsten trioxide on graphite or silicon dioxide–aluminum trioxide, and thermolysis are recommended for the rearrangement. Phenylacetaldehyde can also be synthesized by the direct oxidation of styrene in the presence of palladium salts and copper(II) chloride in aqueous solutions of glycol ethers. Other possibilities include the catalytic dehydrogenation of 2-phenylethanol on silver or gold catalysts, the hydroformylation of benzyl halides in the presence of dicobalt octacarbonyl and sodium carbonate in acetonitrile, and the Darzens glycide ester synthesis from benzaldehyde and alkyl chloroacetates.
| [Synthesis]
By Darzen glycidic ester synthesis from benzaldehyde; readily oxidizable to phenyl acetic acid. | [References]
https://en.wikipedia.org/wiki/Phenylacetaldehyde
https://www.alfa.com/zh-cn/catalog/A14263/
http://www.sigmaaldrich.com/catalog/product/aldrich/107395?lang=en®ion=US
|
|
|