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Phenylpropyl aldehyde, also known as 3-phenylpropanal or hydrocinnamaldehyde, is a colorless liquid with a strong, floral, slightly balsamic, and heavy hyacinth-like odor. It is found in various essential oils, such as Ceylon cinnamon and strawberry, and is used in organic synthesis and perfumery.

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  • 104-53-0 Structure
  • Basic information

    1. Product Name: Phenylpropyl aldehyde
    2. Synonyms: TIMTEC-BB SBB006730;PHENYLPROPYL ALDEHYDE;3-Phenylpropan-1-al;Benzenepropanal;Dihydrocinnamaldehyde;Phenylpropionaldehyde;Propionaidehyde, 3-phenyl-;3-PHENYL-1-PROPANAL
    3. CAS NO:104-53-0
    4. Molecular Formula: C9H10O
    5. Molecular Weight: 134.18
    6. EINECS: 203-211-8
    7. Product Categories: Aroma Chemicals;Aromatics Compounds;Aromatics
    8. Mol File: 104-53-0.mol
    9. Article Data: 1063
  • Chemical Properties

    1. Melting Point: -42 °C
    2. Boiling Point: 97-98 °C12 mm Hg(lit.)
    3. Flash Point: 203 °F
    4. Appearance: Clear colorless to light yellow/Liquid
    5. Density: 1.019 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.131mmHg at 25°C
    7. Refractive Index: n20/D 1.523(lit.)
    8. Storage Temp.: 2-8°C
    9. Solubility: 0.74mg/l
    10. Water Solubility: Miscible with chloroform, dichloromethane, ethyl acetate, alcohol and ether. Immiscible with water.
    11. Sensitive: Air Sensitive
    12. BRN: 1071910
    13. CAS DataBase Reference: Phenylpropyl aldehyde(CAS DataBase Reference)
    14. NIST Chemistry Reference: Phenylpropyl aldehyde(104-53-0)
    15. EPA Substance Registry System: Phenylpropyl aldehyde(104-53-0)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/38-36/37/38
    3. Safety Statements: 26-36-37/39
    4. WGK Germany: 2
    5. RTECS: MW4890000
    6. F: 10-23
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 104-53-0(Hazardous Substances Data)

104-53-0 Usage

Uses

1. Used in Perfumery:
Phenylpropyl aldehyde is used as a fragrance ingredient for its strong, floral, and hyacinth-like odor. It is particularly suitable for hyacinth and lilac compositions.
2. Used in Organic Synthesis:
Phenylpropyl aldehyde is used as a compound in organic synthesis, contributing to the production of various chemical products.
3. Used in Flavor Industry:
Phenylpropyl aldehyde is used as a flavoring agent for its green, melon, fruity, and citrus taste characteristics at 20 ppm.
4. Used in Research and Development:
The C1 and C3 position labelled with 13C of hydrocinnamaldehyde is subjected to mass spectrometry, which helps in elucidating the fragmentation pattern and further understanding its chemical properties.
5. Used in the Production of Dihydrocinnamaldehyde:
Phenylpropyl aldehyde can be selectively hydrogenated to obtain dihydrocinnamaldehyde with minimal byproducts, which is useful in various industrial applications.

Preparation

From phenyl propionitrile; also from cinnamic aldehyde diethylacetal.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 42, p. 1041, 1994 DOI: 10.1248/cpb.42.1041Tetrahedron Letters, 35, p. 1275, 1994 DOI: 10.1016/0040-4039(94)88042-5

Check Digit Verification of cas no

The CAS Registry Mumber 104-53-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 4 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 104-53:
(5*1)+(4*0)+(3*4)+(2*5)+(1*3)=30
30 % 10 = 0
So 104-53-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6,8H,4,7H2

104-53-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Phenylpropyl aldehyde

1.2 Other means of identification

Product number -
Other names Benzenepropanal

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:104-53-0 SDS

104-53-0Relevant articles and documents

Cluster Catalysed Selective Transfer Hydrogenation of α,β-Unsaturated Aldehydes

Bhaduri, Sumit,Sharma, Krishna

, p. 173 - 174 (1988)

H4Ru4(CO)8L4 (L=PBun3) catalyses selective transfer hydrogenation of α,β-unsaturated aldehydes to α,β-unsaturated alcohols; kinetic and deuterium labelling studies indicate involvement of cluster intermediates and no participation by the cluster hydrides.

Novel C-C bond cleavage under mild, neutral conditions: Conversion of electron-deficient aryl alkyl ketones to aryl carboxylic esters

Zhang, Nan,Vozzolo, Joseph

, p. 1703 - 1704 (2002)

A novel, unique way to cleave the carbon-carbon bond in aryl alkyl ketones under mild, neutral conditions is described. Treatment of aryl alkyl ketones in a refluxing mixture of N,N-dimethylformamide dimethyl acetal and methanol for 16 h provided aryl car

Oxidative deprotection of tetrahydropyranyl and trimethylsilyl ethers in water using 1,4-dichloro-1,4-diazoniabicyclo[2,2,2]octane bis-chloride under neutral conditions

Tajbakhsh, Mahmood,Habibzadeh, Setareh

, p. 259 - 262 (2007)

The oxidative deprotection of trimethylsilyl and tetrahydropyranyl ethers in water using 1,4-dichloro-1,4-diazonia-bicyclo[2,2,2]octane bis-chloride as a new efficient reagent under neutral conditions is described. The DABCO was regenerated, rechlorinated and reused several times.

Synthesis and fungicidal activity study of novel daphneolone analogs with 2,6-dimethylmorpholine

Xu, Gao-Fei,Yang, Xin-Ling,Lei, Peng,Liu, Xi-Li,Zhang, Xue-Bo,Ling, Yun

, p. 555 - 558 (2016)

A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI) or elemental analysis, 13C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 μmol/L against Valsa Mali, superior to lead compound I. In addition, preliminary structure-activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.

Microwave-assisted fast fabrication of a nanosized Pt3Co alloy on reduced graphene oxides

Shi, Juanjuan,Nie, Renfeng,Zhang, Mengyuan,Zhao, Mengsi,Hou, Zhaoyin

, p. 2029 - 2037 (2014)

Ultrafine and homogenously dispersed Pt3Co alloy nanoparticles were fabricated on reduced graphene oxide (RGO) in a few minutes under microwave irradiation. Characterization results confirmed that microwave irradiation was important for higher metal utilization, the easy control of alloy composition, improved dispersion of the Pt3Co particles and minimizing the re-graphitization of the parent RGO by comparison with conventional solvent-thermal and impregnation methods. This Pt3Co/RGO-MW catalyst was extremely active and selective during the hydrogenation of cinnamaldehyde to cinnamyl alcohol. The calculated specific activity of each Pt atom in the Pt3Co/RGO-MW at 70 °C was 23.8 min-1.

Simple and efficient water soluble thioligands for rhodium and iridium catalyzed biphasic hydrogenation

Di Dio, Sabrina,Marchetti, Mauro,Paganelli, Stefano,Piccolo, Oreste

, p. 205 - 210 (2011)

The activity of catalytic systems derived from the interaction between Rh(CO)2acac and [Ir(COD)Cl]2, respectively, with the water soluble thioligands (L)-Cysteine (1) and (S)-Captopril (2), was tested in the aqueous biphasic hydrogenation of some representative α,β-unsaturated compounds as 2-cyclohexen-1-one (I), trans-cinnamaldehyde (V) and [3-(1,3-benzodioxol-5-yl)-2-methylpropenal] (X), precursor of the fragrance Helional (XI). The precatalyst Rh/Cap was able to hydrogenate cyclohexenone even at low pressure at 60 °C in a neutral medium while Rh/Cy required either higher pressure and temperature or an alkaline medium. The iridium based catalysts, Ir/Cy and Ir/Cap, showed an analogous trend though their activities were lower than those of the related rhodium catalysts. All the catalysts were easily recycled without significant loss of activity. The rhodium catalysts were also used in the hydrogenation of the above aldehydes V and X and their activity was strongly enhanced when ethylene glycol was used as organic solvent or co-solvent.

A hybrid polyketone-SiO2 support for palladium catalysts and their applications in cinnamaldehyde hydrogenation and in 1-phenylethanol oxidation

Antonetti, Claudia,Toniolo, Luigi,Cavinato, Gianni,Forte, Claudia,Ghignoli, Chiara,Ishak, Randa,Cavani, Fabrizio,Raspolli Galletti, Anna Maria

, p. 40 - 50 (2015)

An organic-inorganic hybrid material, PK-SiO2 (PK = polyketone), was employed as support for Pd catalysts. Their synthesis was carried out by MW irradiation of an ethanol solution of Pd(OAc)2 in the presence of the support. The obtai

Nanosized transition metals in controlled environments of phyllosilicate-mesoporous silica composites as highly thermostable and active catalysts

Ciotonea, Carmen,Dragoi, Brindusa,Ungureanu, Adrian,Chirieac, Alexandru,Petit, Sabine,Royer, Sebastien,Dumitriu, Emil

, p. 7665 - 7667 (2013)

Stabilization of transition metals in nano-phyllosilicate phases generated by digestion of mesoporous silica is reported as an efficient route for the formation of highly dispersed metallic nanoparticles with outstanding catalytic activity. The Royal Society of Chemistry.

Asymmetric hydroformylation of styrene catalyzed by carbohydrate diphosphite-Rh(I) complexes

Dieguez, Montserrat,Pamies, Oscar,Ruiz, Aurora,Claver, Carmen

, p. 827 - 833 (2002)

A series of new chelating diphosphite ligands with a furanoside backbone and axially chiral biphenyl or binaphthyl moieties have been synthesized. Their Rh(I) complexes have been tested as catalyst precursors for the asymmetric hydroformylation of styrene. Systematic variation in chirality at both chiral sugar backbone stereocenters (C-3 and C-5) and either the axial chiral biphenyl or binaphthyl substituents revealed a remarkable effect on the selectivity of the hydroformylation catalysts. In this way, by judicious choice of these elements, both regio- and enantioselectivities can be optimized. Thus, both high enantioselectivity (up to 93% S) and regioselectivity in 2-phenylpropanal (up to 98.8%) were found under mild reaction conditions (15-40°C, 10 bar of syngas) for the ligand with a glucofuranoside backbone and bis(trimethylsilyl)-2,2′-biphenyl moiety. The solution structures of HRh(L-L)(CO)2 complexes have been studied by high pressure NMR and IR. Varying the configuration of the binaphthyl moieties revealed a remarkable effect on the diphosphite coordination modes on the intermediate HRh(L-L)(CO)2 species and, therefore, on enantioselectivity. Enantioselectivity was highest for ligands with a strong bis-equatorial coordination preference.

Dendritic nanoreactor encapsulating Rh complex catalyst for hydroformylation

Mizugaki, Tomoo,Miyauchi, Yasuaki,Murata, Makoto,Ebitani, Kohki,Kaneda, Kiyotomi

, p. 286 - 287 (2005)

A Rh phosphine complex was encapsulated within the surface alkylated poly(propylene imine) dendrimers through ionic interactions. The resulting dendrimer complexes functioned as nanoreactors for hydroformylation of olefins. The congested surface of dendrimers with long alkyl chains favored hydroformylation of higher olefins. One-pot three reactions composed of hydroformylation, the Knoevenagel reaction, and hydrogenation proceeded within the dendritic nanoreactor. Copyright

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