alpha-Methylcinnamaldehyde

Base Information

• Chemical Name: alpha-Methylcinnamaldehyde
• CAS No.: 101-39-3
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Hs Code.: 29122900
• European Community (EC) Number: 701-219-0,202-938-8
• UN Number: 1993
• UNII: 1C647N9853
• DSSTox Substance ID: DTXSID401018359
• Nikkaji Number: J161.351K,J33.986E
• Wikidata: Q27252223
• Mol file: 101-39-3.mol

Synonyms:ALPHA-METHYLCINNAMALDEHYDE;15174-47-7;101-39-3;(E)-2-METHYL-3-PHENYLACRYLALDEHYDE;2-Methyl-3-phenylacrylaldehyde;alpha-Methylcinnamylaldehyde;2-methyl-3-phenylprop-2-enal;a-Methylcinnamaldehyde;(E)-2-methyl-3-phenylprop-2-enal;2-Methyl-3-phenyl-2-propenal;(E)-2-Methyl-3-phenylpropenal;2-Propenal, 2-methyl-3-phenyl-;(2E)-2-Methyl-3-phenyl-2-propenal;(E)-Alpha-Methylcinnamaldehyde;FEMA No. 2697;(E)-2-Methyl-3-phenylacrolein;alpha-Methyl-trans-cinnamaldehyde;Cinnamaldehyde, .alpha.-methyl-;2-Methyl-3-phenylacrolein;2-Methyl-3-phenyl-2-propen-1-al;NSC 22283;trans-2-Methyl-3-phenyl-2-propenal;(2E)-2-methyl-3-phenylprop-2-enal;4-oxo-2-mercapto-thiazole-3-acetica acid;trans-Alpha-Methylcinnamaldehyde;alpha-Methyl-trans-cinnamaldeyhde;2-METHYL-3-PHENYLPROPENAL;alpha-Methylcinnamaldehyde [FHFI];Cinnamaldehyde, alpha-methyl;UNII-1C647N9853;alpha-Methylcinnimal;MFCD00006976;NSC-22283;NSC-49286;1C647N9853;EC 202-938-8;.alpha.-Methylcinnamaldehyde;2-07-00-00291 (Beilstein Handbook Reference);Cinnamaldehyde, alpha-methyl-;CCRIS 6257;EINECS 202-938-8;NSC 49286;a-methyl cinnamaldehyde;BRN 0507514;.alpha.-Methylcinnimal;a - methylcinnamaldehyde;AI3-26230;2-methylcinnamic aldehyde;Z-alpha-Methylcinnamaldehyde;.alpha.-Methylcinnamic aldehyde;DTXSID4025587;2-Propenal, 2-metil-3-fenil-;ALPHA-METHYL CINNAMYLALDEHYDE;-Methylcinnamaldehyde;3-Phenylmethacrolein;3-phenyl-2-methylpropenal;alpha-methyl-E-cinnamaldehyde;?-Methyl-trans-cinnamaldehyde;SCHEMBL186778;|A-Methyl-trans-cinnamaldehyde;DTXCID705587;(E)-2-Methyl-3-phenyl-propenal;alpha -Methyl-trans-cinnamaldehyde;Cinnamic aldehyde, .alpha.-methyl;DTXSID401018359;BCP24559;Tox21_200051;BBL012658;STL163654;(E)-2-methyl-3-phenyl-prop-2-enal;2-Methyl-3-phenyl-trans-prop-2-enal;AKOS000119680;AKOS025149199;CS-W016354;alpha-Methyl-trans-cinnamaldehyde, 98%;ALPHA-METHYLCINNAMALDEHYDE [FCC];(E)-.ALPHA.-METHYLCINNAMALDEHYDE;NCGC00091690-02;NCGC00257605-01;AS-35370;CAS-101-39-3;TRANS-.ALPHA.-METHYLCINNAMALDEHYDE;.ALPHA.-METHYL-TRANS-CINNAMALDEYHDE;.ALPHA.-METHYLCINNAMALDEHYDE [FHFI];2-Propenal, 2-methyl-3-phenyl-, (2E)-;M0584;alpha-Methylcinnamaldehyde, >=97%, FCC, FG;EN300-20034;EN300-736639;W-108917;Q27252223;F2191-0168;Z3219847417

Chemical Property of alpha-Methylcinnamaldehyde

Chemical Property:

• Appearance/Colour: yellow liquid
• Vapor Pressure: 0.0171mmHg at 25°C
• Refractive Index: n20/D 1.605(lit.)
• Boiling Point: 254.604 °C at 760 mmHg
• Flash Point: 90.278 °C
• PSA: 17.07000
• Density: 1.015 g/cm³
• LogP: 2.28880
• Storage Temp.: Store below +30°C.
• Sensitive.: Air Sensitive
• Solubility.: Chloroform, Methanol (Slightly)
• Water Solubility.: <0.1 g/100 mL at 21℃
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 146.073164938
• Heavy Atom Count: 11
• Complexity: 152
• Transport DOT Label: Combustible Liquid

Purity/Quality:

99% ^*data from raw suppliers

alpha-Methylcinnamaldehyde >95.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1=CC=CC=C1)C=O
• Isomeric SMILES: C/C(=C\C1=CC=CC=C1)/C=O
• Description: α-Methylcinnamaldehyde has a characteristic cinnamon-type odor with a soft, spicy flavor. May be synthesized by condensing benzaldehyde with propionic aldehyde in the presence of a 1% caustic soda solution; also by the controlled hydrogenation of α-methylcinnamic aldehyde.
• Uses: alpha-Methyl-trans-cinnamaldehyde is a compound with antifungal activity for proteomics research use.

Technology Process of alpha-Methylcinnamaldehyde

There total 29 articles about alpha-Methylcinnamaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

propan-1-ol (71-23-8) + benzaldehyde (100-52-7) → 2-methyl-3-phenyl-2-propenal (101-39-3)

Guidance literature:

With Wilkinson's catalyst; boron trifluoride diethyl etherate; In toluene; at 30 - 80 ℃; Inert atmosphere;

DOI:10.1016/j.tetlet.2009.05.006

Reference yield: 89.0%

C6H5CHCOSO2CF3CH3 + carbon monoxide (201230-82-2) → 2-methyl-3-phenyl-2-propenal (101-39-3)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; hydrogen; palladium diacetate; In toluene; at 60 ℃; for 16h; under 3750.38 Torr; Autoclave;

DOI:10.1021/acs.orglett.9b00765

Reference yield: 44.0%

3-phenyl-2-methylpropen-1-tert-butyldimethylsilyl ether → 2-methyl-3-phenyl-2-propenal (101-39-3)

Guidance literature:

With 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In acetonitrile; at 40 ℃; for 72h;

DOI:10.1055/s-0035-1561498

upstream raw materials:

3-hydroxy-2-methyl-3-phenyl-propionaldehyde

benzaldehyde

propionaldehyde

3-chloro-2-methylcinnamaldehyde

Downstream raw materials:

3-methyl-5-phenyl-penta-2,4-dienoic acid

cyclohexyl-(2-methyl-3-phenyl-allyliden)-amine

2,6-dimethyl-7-phenyl-hepta-2,4,6-trienal

2-ethyl-6-methyl-7ξ-phenyl-hepta-2ξ,4ξ,6-trienal

Refernces

• 1、 Svec et al.. "-". . p. 777,784. Retrieved 1976.
• 2、 Chen, Qi,Zhang, Ji-Wei,Chen, Lu-Lu,Yang, Jun,Yang, Xin-Ling,Ling, Yun,Yang, Qing. "Design and synthesis of chitin synthase inhibitors as potent fungicides". . p. 1232 - 1237. Retrieved 2017.
• 3、 Hackhofer. "-". . p. 95,311. Retrieved 1901.
• 4、 -. "Method for synthesizing alpha-methylcinnamaldehyde from phenylpropionaldehyde". Paragraph 0011; 0051-0059. . Retrieved 2021/03/31.
• 5、 Zhang, Shaoke,Neumann, Helfried,Beller, Matthias. "Pd-Catalyzed Carbonylation of Vinyl Triflates to Afford α,β-Unsaturated Aldehydes, Esters, and Amides under Mild Conditions". . p. 3528 - 3532. Retrieved 2019/05/24.