CasNo: 93-53-8
Molecular Formula: C9H10O
Appearance: clear colorless liquid
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/ja00852a062Organic Syntheses, Coll. Vol. 3, p. 733, 1955Tetrahedron Letters, 15, p. 3059, 1974 |
Flammability and Explosibility |
Nonflammable |
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.] |
General Description |
2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor. Jilin Tianyun New Materials Co., Ltd. is a professional production enterprise that production, processing, and export, mainly engaged in various organic chemicals. The company has a wealth of professional experience, reliable product quality, reasonable prices, and products are exported to countries around the world, which can meet your diverse needs. In our business cooperation with clients, we always adhere to the principle of equality and mutual benefit, and are deeply trusted and recognized by our clients. If you are interested in our company and our products, please feel free to visit our website or contact us directly for more information.We look forward to establishing a long-term stable and win-win business relationship with you. |
InChI:InChI=1/C9H10O/c1-8(7-10)9-5-3-2-4-6-9/h2-8H,1H3
2-phenylpropionaldehyde is not expected to be phototoxic/photoallergenic. The environmental endpoints were evaluated; 2-phenylpropionaldehyde was found not to be persistent, bioaccumulative, and toxic (PBT) as per the International Fragrance Association (IFRA) Environmental Standards, and its risk quotients, based on its current volume of use in Europe and North America (i.e., Predicted Environmental Concentration/Predicted No Effect Concentration [PEC/PNEC]), are <1.
The influence of a stereocenter already present in the molecule on the selectivity displayed by almond oxynitrilase has been addressed, considering the substituted aldehydes (±)-2-phenylpropionaldehyde 1 and (±)-3-phenylbutyraldehyde 2 as model substrates. Only when the stereocenter was adjacent to the aldehyde group (as in 1) a strong influence on the selectivity of this enzyme was observed, resulting in the formation of the four possible cyanohydrins although in different ratio.
Rh(I) and Ir(I) cationic complexes [M(co...
High-performance liquid chromatography (...
styrene
carbon monoxide
3-phenyl-propionaldehyde
ethylbenzene
(S)-2-phenyl-propionaldehyde
(R)-2-phenylpropanal
Conditions | Yield |
---|---|
With [(2S,3S)-2,4-bis(diphenylphosphino)pentane]Pt(SnCl3)Cl; hydrogen; In toluene; at 40 ℃; for 138h; under 51714.8 Torr;
|
68.7 % Chromat. 25% 6.3% |
With hydrogen; PtCl2
|
|
With hydrogen; bis(benzonitrile)dichloroplatinum(II); tin(ll) chloride; (2S,4S)-2,4-bis[((S)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yl)oxy]pentane; In toluene; at 100 ℃; for 2h; under 76000 Torr; Title compound not separated from byproducts;
|
|
With hydrogen; bis(benzonitrile)dichloroplatinum(II); tin(ll) chloride; (2S,4S)-2,4-bis[((S)-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-2-yl)oxy]pentane; In toluene; at 17 ℃; for 70h; under 76000 Torr; Title compound not separated from byproducts;
|
|
With chiral bis(octahydrodinaphthodioxaphosphepin)-based ligand; hydrogen; tin(ll) chloride; bis(benzonitrile)dichloroplatinum(II); In toluene; at 23 ℃; for 20h; Title compound not separated from byproducts;
|
|
With hydrogen; [Rh(NBD)(S)-BINAPO]BF4; In toluene; at 40 ℃; for 15h; under 60004.8 Torr; Further Variations:; Catalysts; Solvents; Temperatures; Product distribution;
|
|
With hydrogen; chiral bis(phosphite)PtCl2-SnCl2; In toluene; at 100 ℃; for 2h; under 76000 Torr; Product distribution; other temp., times, solvent and catalyst;
|
|
With (2S,4S)-2-(dibenzophospholyl)-4-(diphenylphosphino)pentane; hydrogen; tin(ll) chloride; bis(benzonitrile)dichloroplatinum(II); In toluene; at 24 ℃; for 45h; under 148200 Torr; Further Variations:; Catalysts; Temperatures; Pressures; Kinetics; Product distribution;
|
|
With hydrogen; tris(pentafluorophenyl)borate; In toluene; at 100 ℃; for 24h; under 60006 Torr; Title compound not separated from byproducts.;
|
|
With C24H23Cl3P2Pt; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 24h; under 30003 Torr; optical yield given as %ee; chemoselective reaction; Autoclave; Inert atmosphere;
|
|
With (R(P),R(P))-cis-bis(1-propyl-3-methyl-3-phospholano)-dichloro-platinum(II); hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 96h; under 60006 Torr; optical yield given as %ee; regioselective reaction; Inert atmosphere;
|
|
With cis-[bis(1-ethyl-3-methyl-3-phospholeno)-dichloro-platinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 60 ℃; for 72h; under 60006 Torr; Reagent/catalyst; Temperature; Time; enantioselective reaction; Inert atmosphere; Autoclave;
|
29 % ee |
With PtCl2{(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane}; hydrogen; tin(ll) chloride; In toluene; at 60 ℃; for 18h; under 60006 Torr; Temperature; enantioselective reaction; Inert atmosphere; Autoclave;
|
40 % ee |
With PtCl2{(-)-(2S,4S)-2,4-bis(diphenylphosphino)pentane}; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 3h; under 60006 Torr; Temperature; enantioselective reaction; Inert atmosphere; Autoclave;
|
7 % ee |
With cis-[bis((S)-1-isopropyl-3-methyl-3-phospholeno)dichloroplatinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 24h; under 60006 Torr; Temperature; enantioselective reaction; Inert atmosphere; Autoclave;
|
10 % ee |
With cis-[bis((R)-4-chloro-1-phenyl-5-methyl-1,2,3,6-tetrahydrophosphinino)-dichloroplatinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 10h; under 60006 Torr; Temperature; Time; chemoselective reaction; Catalytic behavior; Inert atmosphere;
|
8 % ee |
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 40 ℃; for 120h; under 30003 Torr; Temperature; enantioselective reaction; Autoclave; Schlenk technique;
|
32 % ee |
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 60 ℃; for 120h; under 60006 Torr; enantioselective reaction; Autoclave; Schlenk technique;
|
16 % ee |
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 23h; under 30003 Torr; Temperature; enantioselective reaction; Autoclave; Schlenk technique;
|
24 % ee |
With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 100 ℃; for 23h; under 60006 Torr; Temperature; enantioselective reaction; Autoclave; Schlenk technique;
|
24 % ee |
With (S)-5,5 ′-bis[di(3,5-xylyl)phosphino]-4,4 ′-bi-1,3-benzodioxole; di-μ-chlorobis(norbornadiene)dirhodium(I); hydrogen; at 60 ℃; for 24h; under 60006 Torr; Autoclave; Schlenk technique;
|
styrene
carbon monoxide
3-phenyl-propionaldehyde
ethylbenzene
(S)-2-phenyl-propionaldehyde
Conditions | Yield |
---|---|
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP>; In toluene; at 40 ℃; for 55h; under 60004.8 Torr;
|
31% 3% 42% |
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP>; In toluene; at 40 ℃; for 55h;
|
42% 3% 31% |
With C44H32Cl4P2PtSn(2+); hydrogen; at 40 ℃; for 336h; under 30003 Torr; Reagent/catalyst; Solvent; Temperature; Time; Pressure; chemoselective reaction;
|
49 % ee |
2-Phenylpropanal
styrene
carbon monoxide
3-phenylbut-1-ene
(2S,3R)-threo-2-phenylpentan-3-ol
(2S,3S)-erythro-2-phenylpentan-3-ol
methyl (3R,4S)-3-hydroxy-4-phenylpentanoate
Methyl-erythro-3-Hydroxy-4-phenylvalerat