ChemicalBook > CAS DataBase List > Phenylacetaldehyde

Phenylacetaldehyde

Product Name
Phenylacetaldehyde
CAS No.
122-78-1
Chemical Name
Phenylacetaldehyde
Synonyms
Benzeneacetaldehyde;2-PHENYLACETALDEHYDE;Hyacinthin;Phenylethanal;2-Phenylethanal;phenylacetadehyde;FEMA 2874;α-Tolualdehyde;Benzenacetaldehyde;ALPHA-TOLUALDEHYDE
CBNumber
CB7852954
Molecular Formula
C8H8O
Formula Weight
120.15
MOL File
122-78-1.mol
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Phenylacetaldehyde Property

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 | PHENYLACETALDEHYDE
refractive index 
n20/D 1.535(lit.)
Flash point:
188 °F
storage temp. 
2-8°C
solubility 
2.21g/l slightly soluble
form 
Liquid
Specific Gravity
1.075 (20/4℃)
color 
Clear colorless to pale yellow
Odor
at 10.00 % in dipropylene glycol. green sweet floral hyacinth clover honey cocoa
Odor Type
green
Water Solubility 
2.210 g/L (25 ºC)
Sensitive 
Air Sensitive
Merck 
14,7265
JECFA Number
1002
BRN 
385791
Dielectric constant
4.7999999999999998
Dielectric constant
4.8(20℃)
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.
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
Phenylacetaldehyde (122-78-1)
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Safety

Hazard Codes 
Xn,F
Risk Statements 
22-36/37/38-43-11
Safety Statements 
26-36-37-24-16-7
RIDADR 
UN 1170 3/PG 2
WGK Germany 
2
RTECS 
CY1420000
TSCA 
Yes
HS Code 
29122990
Toxicity
LD50 orl-rat: 1550 mg/kg FCTXAV 17,377,79
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H317May cause an allergic skin reaction

H412Harmful to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
W287407
Product name
Phenylacetaldehyde
Purity
≥95%, FCC, FG
Packaging
1kg
Price
$186
Updated
2024/03/01
Sigma-Aldrich
Product number
W287407
Product name
Phenylacetaldehyde
Purity
≥95%, FCC, FG
Packaging
5kg
Price
$713
Updated
2024/03/01
Sigma-Aldrich
Product number
W287407
Product name
Phenylacetaldehyde
Purity
≥95%, FCC, FG
Packaging
10Kg
Price
$1180
Updated
2024/03/01
Sigma-Aldrich
Product number
107395
Product name
Phenylacetaldehyde
Purity
≥90%
Packaging
25ml
Price
$23.7
Updated
2024/03/01
Sigma-Aldrich
Product number
107395
Product name
Phenylacetaldehyde
Purity
≥90%
Packaging
100ml
Price
$85.6
Updated
2024/03/01
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Phenylacetaldehyde Chemical Properties,Usage,Production

Description

Phenylacetaldehyde 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 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.

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.

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

Phenylacetaldehyde can be synthesized 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&region=US

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View Lastest Price from Phenylacetaldehyde manufacturers

Ouhuang Engineering Materials (Hubei) Co., Ltd
Product
Phenylacetaldehyde 122-78-1
Price
US $20.00/kg
Min. Order
1kg
Purity
99.9%
Supply Ability
200000kg
Release date
2024-04-28
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Phenylacetaldehyde 122-78-1
Price
US $200.00-95.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-04-25
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Phenylacetaldehyde solution 122-78-1
Price
US $100.00/kg
Min. Order
1kg
Purity
99
Supply Ability
5000
Release date
2024-04-25

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