2-Phenylpropionaldehyde supplier

Name
2-PHENYLPROPIONALDEHYDE
EINECS 202-255-5
CAS No. 93-53-8
Article Data158
CAS DataBase
Density 0.981 g/cm³
Solubility 10μg/L
Melting Point 60 °C
Formula C₉H₁₀O
Boiling Point 202.339 °C at 760 mmHg
Molecular Weight 134.178
Flash Point 76.111 °C
Transport Information
Appearance clear colorless liquid
Safety 26-36/37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Hydratropaldehyde(6CI,7CI,8CI);2-Phenylpropanal;2-Phenylpropanaldehyde;2-Phenylpropionaldehyde;Cumene aldehyde;Hyacinthal;Hydratropic aldehyde;NSC 5231;a-Formylethylbenzene;a-Methyl-a-toluicaldehyde;a-Methylbenzeneacetaldehyde;a-Methylphenylacetaldehyde;a-Phenylpropionaldehyde;
PSA 17.07000
LogP 1.98900

Synthetic route

: 17596-79-1
(2S)-2-phenyl-1-propanamine

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With immobilised amine transaminase from the moderate halophilic bacterium Halomonas elongata; sodium pyruvate In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 760.051 Torr; for 3h; pH=8;	90%

: (2S,3S)-3-phenylbutane-1,2-diol

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With sodium periodate; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 4h;	77%

: 37778-99-7
(S)-2-phenyl-1-propanol

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With Dess-Martin periodane In dichloromethane for 1.66667h; Inert atmosphere;	74%
With Dess-Martin periodane In dichloromethane at 20℃; for 0.5h; Inert atmosphere;	70%
With Dess-Martin periodane
With sodium hydrogencarbonate; Dess-Martin periodane In dichloromethane Dess-Martin oxidation; Inert atmosphere; optical yield given as %ee;
Dess-Martin Oxidation;

: 292638-84-7
styrene

: 201230-82-2
carbon monoxide

A: 104-53-0
3-phenyl-propionaldehyde

B: 100-41-4
ethylbenzene

C: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; under 60004.8 Torr; for 55h;	A 42% B 3% C 31%
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; for 55h;	A 42% B 3% C 31%
With C44H32Cl4P2PtSn(2+); hydrogen at 40℃; under 30003 Torr; for 336h; Reagent/catalyst; Solvent; Temperature; Time; Pressure; chemoselective reaction;	A n/a B n/a C n/a

...Expand

: 292638-84-7
styrene

A: 104-53-0
3-phenyl-propionaldehyde

B: 100-41-4
ethylbenzene

C: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; under 60004.8 Torr; for 55h;	A 42% B 3% C 31%

...Expand

: 292638-84-7
styrene

: 201230-82-2
carbon monoxide

A: 104-53-0
3-phenyl-propionaldehyde

B: 100-41-4
ethylbenzene

C: 93-53-8
(S)-2-phenyl-propionaldehyde

D: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With [(2S,3S)-2,4-bis(diphenylphosphino)pentane]Pt(SnCl3)Cl; hydrogen In toluene at 40℃; under 51714.8 Torr; for 138h;	A 68.7 % Chromat. B n/a C 25% D 6.3%
With hydrogen; PtCl2 In toluene at 40℃; under 60004.8 Torr; for 160h; Product distribution; var. PtCl2-diphosphine 2,4-bis(diphenylphosphino)pentane (BDPP)-tin(II)fluoride catalytic system; other temp. and time;
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℃; under 76000 Torr; for 2h; Title compound not separated from byproducts;

...Expand

: C13H18O

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h;	23%

: C12H16O

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With ozone In dichloromethane at -78℃; for 0.0833333h;	23%

: 292638-84-7
styrene

: 201230-82-2
carbon monoxide

A: 104-53-0
3-phenyl-propionaldehyde

B: 93-53-8
(S)-2-phenyl-propionaldehyde

C: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; under 38000 Torr; for 43h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;	A 12% B n/a C n/a
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 60℃; under 38000 Torr; for 43h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;	A 8% B n/a C n/a
With PtCl2-SnCl2 complex of (4R,5R)-2,2-dimethyl-4,5-bis(diphenylphosphinomethyl)-1,3-dioxolan and its bis(dibenzophosphole) analogue; hydrogen In benzene at 40℃; under 160341 Torr; for 36h; Product distribution; var. temp., var. pressure, var. time, var. PtCl2-SnCl2 complexes, var. ratios of H2:CO; optical purity, selectivity, branched:normal ratio;

...Expand

: 292638-84-7
styrene

: 201230-82-2
carbon monoxide

A: 104-53-0
3-phenyl-propionaldehyde

B: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With (R,R)-<<(bicyclo<2.2.2>octane-2,3-diyl)bis(methylene)>bis<5H-benzophosphinindole>>PtCl2 (5a); hydrogen; tin(ll) chloride In benzene at 50℃; under 53200 - 114000 Torr; for 23h; Product distribution; other aromatic olefins; other platinum dichloride complex;
With Rh(acac)2(CO)2; C62H50N4O7P2; hydrogen at 40℃; under 2068.65 - 6205.94 Torr; for 4h; optical yield given as %ee; enantioselective reaction;
With (acetylacetonato)dicarbonylrhodium (l); C54H39NO2P2; hydrogen In toluene at 60℃; under 15001.5 Torr; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
With dicarbonylacetylacetonato rhodium (I); C41H50O3P2; hydrogen at 30℃; under 7500.75 Torr; for 16h; Temperature; Pressure; Time; Concentration; Autoclave; Inert atmosphere; enantioselective reaction;	A n/a B n/a
With 2,2',2'',2'''-(1,2-phenylenebis((1S,3S)-tetrahydro-5,8-dioxo-1H-(1,2,4)diazaphospholo(1,2-a)pyridazine-2,1,3(3H)-triyl))tetrakis(N-(1S)-1-phenylethyl)-benzamide; (acetylacetonato)dicarbonylrhodium (l); hydrogen In tetrahydrofuran at 60℃; under 8517.48 Torr; for 24h; Flow reactor; enantioselective reaction;	A n/a B n/a

...Expand

: 292638-84-7
styrene

: 201230-82-2
carbon monoxide

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With acetylacetonatodicarbonylrhodium(l); 3,5-bis<(4,4'-di-t-butyl-6,6'-dimethoxy-2,2'-biphenyl-1,1'-diyl)phosphite>-1,2-O-isopropylidene-D-xylofuranose; hydrogen In toluene at 25℃; under 6750.5 Torr; for 15h; Product distribution; var. ligands, pressures, temp., times;
With hydrogen; PtCl2-2,4-bis(diphenylphosphino)pentane (BDPP)-2SnCl2; tin(ll) chloride In toluene at 40℃; under 60004.8 Torr; for 160h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With hydrogen; 5)(CO)2> at 40℃; under 6750.5 Torr; for 5h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 934-10-1
3-phenylbut-1-ene

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With dimethylsulfide; ozone 1.) MeOH, O2, -78 deg C, 2.) -10 deg C, 1 h, RT, 1 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

: 34713-70-7
2-Phenylpropanal

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With diethylzinc
Multi-step reaction with 2 steps 1: Na2SO4 / benzene / 20 °C 2: 1.) MeI, 2.) aq. HCl / 1.) 60 deg C, 2.) n-pentane View Scheme

: 6956-37-2
(3,3-diethoxypropyl)benzene

A: 104-53-0
3-phenyl-propionaldehyde

B: 93-53-8
(S)-2-phenyl-propionaldehyde

C: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In acetone for 5h; Heating;

...Expand

: 25488-25-9
(2S,3S)-methylphenylalanine

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With indan-1,2,3-trione hydrate In water; benzene at 80℃; for 0.166667h;

: 75-24-1
trimethylaluminum

: 91327-70-7
(4R,5R)-2-((E)-Styryl)-[1,3]dioxolane-4,5-dicarboxylic acid bis-dimethylamide

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With ozone 1.) toluene, hexane, room temp.,12 h, 2.) MeOH, -78 deg C; Yield given. Multistep reaction;

: ((S)-2,2-Diethoxy-1-methyl-ethyl)-benzene

A: 104-53-0
3-phenyl-propionaldehyde

B: 93-53-8
(S)-2-phenyl-propionaldehyde

C: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In acetone for 5h; Heating;

...Expand

: [(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-1-yl]-[(R)-2-phenyl-prop-(E)-ylidene]-amine

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With hydrogenchloride; methyl iodide 1.) 60 deg C, 2.) n-pentane; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

: [(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-1-yl]-[(S)-2-phenyl-prop-(E)-ylidene]-amine

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With hydrogenchloride; methyl iodide 1.) 60 deg C, 2.) n-pentane; Yield given. Multistep reaction;

: 39166-22-8
1-(4-morpholino)-2-phenylpropene

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With L-Tartaric acid In ethanol; water at -60℃; for 0.5h; Product distribution; variation of chiral acids, solvent, temperature;

: 21129-06-6
2-phenylpropane-1,1-diyl diacetate

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With sodium hydroxide; Candida rugosa lipase In various solvent(s) for 1.16667h; Product distribution; pH=7; different substrates, enzymes, solvents and reaction times;

: 34713-70-7
2-Phenylpropanal

: 557-20-0
diethylzinc

A: 65878-64-0
(2S,3S)-erythro-2-phenylpentan-3-ol

B: 129647-84-3
(2R,3S)-threo-2-phenylpentan-3-ol

C: 127181-69-5
(2R,3R)-erythro-2-phenylpentan-3-ol

D: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With naphthalene; (R)-PDB In hexane Addition; Further byproducts given;

...Expand

: 214752-00-8
(E,2R,5S)-7-methyl-5-(2,4,6-trimethylbenzenesulfonyl)amino-2-phenyloct-3-ene

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 186801-24-1
N-((S)-1-Formyl-3-methyl-butyl)-2,4,6-trimethyl-benzenesulfonamide

Conditions

Conditions	Yield
Stage #1: (E,2R,5S)-7-methyl-5-(2,4,6-trimethylbenzenesulfonyl)amino-2-phenyloct-3-ene With ozone In hexane; chloroform at -78℃; ozonolysis; Stage #2: With zinc In hexane; chloroform at -78 - 0℃; for 0.166667h; Reduction; Title compound not separated from byproducts;

: 243860-93-7
(1S,2R,3S)-1,2-Dihydroxy-1,3-diphenylbutane

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
With sodium periodate In dichloromethane for 1h; Oxidation; oxidative cleavage; Title compound not separated from byproducts.;

: 292638-84-7
styrene

: 201230-82-2
carbon monoxide

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With furanoside diphosphite derived from D-(+)-glucose; hydrogen; acetylacetonatodicarbonylrhodium(l) In toluene at 20℃;
Stage #1: carbon monoxide With acetylacetonatodicarbonylrhodium(l); tris[(R)-2’-(benzyloxy)-1,1’-binaphthyl-2-yl]phosphite; hydrogen In toluene at 80℃; under 22502.3 Torr; for 3h; Stage #2: styrene In toluene regioselective reaction;
With hydrogen; acetylacetonatodicarbonylrhodium(l); (S,S,S)-BOBPHOS In toluene at 60℃; under 7500.75 Torr; for 16h; Product distribution / selectivity; Hydroformylation Reaction; Argonaut Endeavour parallel autoclave system;	n/a

: (E)-1,3-diphenyl-N-[(2-pyridyl)sulfonyl]prop-2-en-1-imine

: 544-97-8
dimethyl zinc(II)

A: 93-53-8
(S)-2-phenyl-propionaldehyde

B: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
Stage #1: (E)-1,3-diphenyl-N-[(2-pyridyl)sulfonyl]prop-2-en-1-imine; dimethyl zinc(II) With copper(I) thiophene-2-carboxylate; (R,S,S)-phosphoramidite monodentate Feringa ligand In toluene at -20℃; for 2h; Stage #2: With ozone In dichloromethane at -78℃; Stage #3: With dimethylsulfide for 0.333333h; Title compound not separated from byproducts;

...Expand

: 292638-84-7
styrene

A: 104-53-0
3-phenyl-propionaldehyde

B: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
With carbon monoxide; hydrogen; acetylacetonatodicarbonylrhodium(l); 3,4-bis[(R,R)-2,5-diphenyl-phospholan-1-yl]furan-2,5-dione In toluene at 80℃; under 7757.43 Torr; for 3h; Product distribution / selectivity;	A n/a B n/a
With carbon monoxide; hydrogen; acetylacetonatodicarbonylrhodium(l); (R,R)-2,3-bis(2,5-diphenyl-phospholan-1-yl)-quinoxaline In toluene at 80℃; under 7757.43 Torr; for 3h; Product distribution / selectivity;	A n/a B n/a

: 34713-70-7
2-Phenylpropanal

A: (R)-formic acid 1-phenylethyl ester

B: 948997-89-5
(S)-formic acid 1-phenylethyl ester

C: 93-53-8
(S)-2-phenyl-propionaldehyde

D: 93-53-8
(R)-2-phenylpropanal

Conditions

Conditions	Yield
With glucose-6-phosphate dehydrogenase; α-D-glucose 6-phosphate In various solvent(s) at 20℃; pH=7; Product distribution; Further Variations:; pH-values; Reagents; Temperatures; Baeyer-Villiger oxidation;
With phenylacetone monooxygenase from Thermobifida fusca; Tris-HCl buffer; D-glucose 6-phosphate at 27℃; pH=6; Product distribution; Further Variations:; pH-values; Baeyer-Villiger oxidation reaction;

...Expand

: 614-47-1
1,3-diphenyl-propen-3-one

n-Bu2CuLi: n-Bu2CuLi

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 80 percent / Et3N; TiCl4 / CH2Cl2 / 5 h / Heating 2.1: (R,S,S)-phosphoramidite monodentate Feringa ligand; copper thiophene-2-carboxylate / toluene / 2 h / -20 °C 2.2: O3 / CH2Cl2 / -78 °C 2.3: Me2S / 0.33 h View Scheme

: 5411-12-1, 7570-85-6, 7570-86-7, 61840-92-4, 61840-93-5, 67381-79-7, 70332-63-7
trans-(2S,3R)-epoxy-1,3-diphenylpropan-1-one

: 93-53-8
(S)-2-phenyl-propionaldehyde

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 8 percent / H2O / CH2Cl2; ethanol / 0.5 h 2: 95 percent / zinc borohydride / diethyl ether / 1 h 3: NaIO4 supported on silice gel / CH2Cl2 / 1 h View Scheme
Multi-step reaction with 3 steps 1: 95 percent / zinc borohydride / diethyl ether / 0.5 h 2: 93 percent / hexane / 1 h / 0 °C 3: NaIO4 supported on silice gel / CH2Cl2 / 1 h View Scheme

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 37778-99-7
(S)-2-phenyl-1-propanol

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;	96%
With sodium tetrahydroborate In methanol at -78 - 20℃; optical yield given as %ee;
With sodium tetrahydroborate In methanol at -78℃; for 1h; Inert atmosphere;
With sodium tetrahydroborate Inert atmosphere; optical yield given as %ee;

: 25438-37-3
phenyl(trimethylsiloxy)acetonitrile

: 93-53-8
(S)-2-phenyl-propionaldehyde

A: 119788-70-4
3-Hydroxy-2,4-diphenyl-2-(trimethylsilyl)pentannitril

B: 119788-49-7
(2R*,3S*)-1,3-Diphenyl-2-(trimethylsilyloxy)-1-butanon

C: 119788-50-0
(2S*,3S*)-1,3-Diphenyl-2-(trimethylsilyloxy)-1-butanon

Conditions

Conditions	Yield
With lithium diisopropyl amide In diethyl ether at -78℃; for 2h; Product distribution; further solvent and time and temperature;	A 95% B n/a C n/a

...Expand

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 106-95-6
allyl bromide

: 2-phenyl-3-hydroxy-5-hexene

Conditions

Conditions	Yield
With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;	93%

: 623-73-4
diazoacetic acid ethyl ester

: 1072879-54-9
3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine

: 93-53-8
(S)-2-phenyl-propionaldehyde

: (2R,3R)-ethyl 1-(bis(4-methoxy-3,5-dimethylphenyl)methyl)-3-((S)-1-phenylethyl)aziridine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: 3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine With triphenylborane; (3S)-(+)-2,2'-diphenyl-(3,3'-biphenanthrene)-4,4'-diol In toluene at 80℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube; Stage #2: diazoacetic acid ethyl ester; (S)-2-phenyl-propionaldehyde In toluene at -10℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; stereoselective reaction;	92%

Yield

Stage #1: 3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine With triphenylborane; (3S)-(+)-2,2'-diphenyl-(3,3'-biphenanthrene)-4,4'-diol In toluene at 80℃; for 0.5h; Inert atmosphere; Schlenk technique; Sealed tube;
Stage #2: diazoacetic acid ethyl ester; (S)-2-phenyl-propionaldehyde In toluene at -10℃; for 24h; Molecular sieve; Inert atmosphere; Schlenk technique; stereoselective reaction;

92%

...Expand

: tris(trimethylsilyl)-propenyloxy-silane

: 93-53-8
(S)-2-phenyl-propionaldehyde

: (2S,3R,4S)-2,4-dimethyl-4-phenyl-3-tris(trimethylsilyl)siloxybutanal

Conditions

Conditions	Yield
With bis(trifluoromethanesulfonyl)amide In dichloromethane at -78℃; for 0.25h; Mukaiyama aldol reaction;	84%

: 1417175-94-0
C8H15BO2

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 1417175-86-0
C14H20O

Conditions

Conditions	Yield
With phenylborondichloride; potassium carbonate In dichloromethane at 20℃; for 48h; Inert atmosphere; enantioselective reaction;	83%
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction;	83%

: 93-53-8
(S)-2-phenyl-propionaldehyde

cyclodibromodi-μ-methylene<μ-(tetrahydrofuran)>trizinc: cyclodibromodi-μ-methylene<μ-(tetrahydrofuran)>trizinc

: 36617-88-6
(R)-3-phenyl-1-butene

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃;	82%

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 7782-24-3
(S)-2-Phenylpropionic acid

Conditions

Conditions	Yield
With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 0 - 20℃; for 2h;	79%
With potassium permanganate; magnesium sulfate In acetone Inert atmosphere;

: 1417175-76-8
C8H15BO2

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 1417175-87-1
C14H20O

Conditions

Conditions	Yield
With phenylborondichloride; potassium carbonate In dichloromethane at 20℃; for 48h; Inert atmosphere; enantioselective reaction;	78%
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction;	78%

: C8H15BO2

: 93-53-8
(S)-2-phenyl-propionaldehyde

: C14H20O

Conditions

Conditions	Yield
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction;	77%

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 343338-28-3
(S)-2-methylpropane-2-sulfinamide

: (SS,2S)-(2-Phenylpropylidene)tert-butyl-sulfinimine

Conditions

Conditions	Yield
With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;	76%

: 1223593-46-1
C33H68O2Si5

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 1223593-48-3
C39H70O3Si4

Conditions

Conditions	Yield
With bis(trifluoromethanesulfonyl)amide In dichloromethane; toluene at -78℃; for 0.5h; Inert atmosphere; enantioselective reaction;	75%

: 3,3-bis(triethylsilyl) benzyl enol ether

: 93-53-8
(S)-2-phenyl-propionaldehyde

: C31H50O2Si2

Conditions

Conditions	Yield
Stage #1: 3,3-bis(triethylsilyl) benzyl enol ether With N,N,N,N,N,N-hexamethylphosphoric triamide; tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1.5h; Inert atmosphere; Stage #2: (S)-2-phenyl-propionaldehyde In tetrahydrofuran; pentane at -78℃; for 0.166667h; Inert atmosphere; diastereoselective reaction;	75%

: C8H15BO2

: 93-53-8
(S)-2-phenyl-propionaldehyde

: C14H20O

Conditions

Conditions	Yield
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction;	73%

: 1223592-76-4
acetone tris(triethylsilyl)silyl enol ether

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 1223593-43-8
C30H60O2Si4

Conditions

Conditions	Yield
With bis(trifluoromethanesulfonyl)amide In dichloromethane at 0 - 20℃; Inert atmosphere; enantioselective reaction;	72%

: 61550-02-5
(furan-2-yloxy)-trimethylsilane

: 1658-03-3
4-Methoxy-2-methylsulfenylaniline

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 1092853-68-3
C21H23NO3S

Conditions

Conditions	Yield
Stage #1: 4-Methoxy-2-methylsulfenylaniline; (S)-2-phenyl-propionaldehyde With magnesium sulfate at 22℃; for 0.166667h; Stage #2: (furan-2-yloxy)-trimethylsilane With N-[2-PPh2-benzylidene]-L-tert-leucine (4-methoxyphenyl)amide; silver(I) acetate; isopropyl alcohol In tetrahydrofuran at -78℃; for 20h; Mannich reaction;	68%

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: 1223593-43-8
C30H60O2Si4

: 93-53-8
(S)-2-phenyl-propionaldehyde

A: 1223593-48-3
C39H70O3Si4

B: C39H70O3Si4

Conditions

Conditions	Yield
Stage #1: C30H60O2Si4 With lithium hexamethyldisilazane In hexane; N,N-dimethyl-formamide at -40℃; Inert atmosphere; Stage #2: (S)-2-phenyl-propionaldehyde In hexane; N,N-dimethyl-formamide at -60℃; Inert atmosphere; optical yield given as %de; enantioselective reaction;	A 66% B n/a

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: 79218-15-8
tert-butyl (E)-crotonate

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 1071938-25-4
(2R,3R,4S)-tert-butyl 3-hydroxy-2-ethyl-4-phenylpentanoate

Conditions

Conditions	Yield
Stage #1: tert-butyl (E)-crotonate; (S)-2-phenyl-propionaldehyde; chiral Rh(Phebox) In toluene at 50℃; for 0.5h; Stage #2: With potassium fluoride; tetrabutyl ammonium fluoride; water In tetrahydrofuran; N,N-dimethyl-formamide at 50℃; for 16h; Further stages.;	61%

: 97-93-8
triethylaluminum

: 93-53-8
(S)-2-phenyl-propionaldehyde

: 88790-26-5
(R,R)/(S,S)-2-phenylpentan-3-ol

Conditions

Conditions	Yield
With methyllithium In diethyl ether; dichloromethane at -78℃;	56%

: C18H22Si

: 93-53-8
(S)-2-phenyl-propionaldehyde

A: C19H22O

B: C19H22O

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -60℃; for 24h; Sakurai-Hosomi Allylation; Schlenk technique; Glovebox; Inert atmosphere;	A 53% B n/a

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: 93-53-8
(S)-2-phenyl-propionaldehyde

: 513-81-5
2,3-dimethyl-buta-1,3-diene

: (R)-4,5-dimethyl-2-((S)-1-phenylethyl)-3,6-dihydro-2H-pyran

Conditions

Conditions	Yield
With N,N'-((11bS,11b'S)-azanediylbis(2,6-bis(3,5-bis(perfluoropropyl)phenyl)-4λ5-dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine-4-yl-4-ylidene))bis(1,1,1-trifluoromethanesulfonamide) In methyl cyclohexane at -78 - -20℃; for 48h; Reagent/catalyst; Diels-Alder Cycloaddition; Molecular sieve; diastereoselective reaction;	48%

: C18H22Si

: 93-53-8
(S)-2-phenyl-propionaldehyde

A: C19H22O

B: C19H22O

Conditions

Conditions	Yield
With titanium tetrachloride In dichloromethane at -60℃; for 24h; Sakurai-Hosomi Allylation; Schlenk technique; Glovebox; Inert atmosphere; diastereoselective reaction;	A 47% B n/a

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: 158813-39-9
2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane

: 93-53-8
(S)-2-phenyl-propionaldehyde

: (2S,3R,Z)-6-chloro-2-phenylhex-5-en-3-ol

Conditions

Conditions	Yield
With (2S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-2-(3-hydroxyadamantan-1-yl) 1-(isoindolin-2-yl)ethan-1-one; zinc dimethoxide In toluene at 22℃; for 14h; Glovebox; Inert atmosphere; Sealed tube; stereoselective reaction;	32%

2-Phenylpropionaldehyde Consensus Reports

CUMENE ALDEHYDE(93-53-8) is reported in EPA TSCA Inventory.

2-Phenylpropionaldehyde Specification

The 2-Phenylpropionaldehyde, with the CAS registry number 93-53-8, is also known as alpha-Methyltolualdehyde. Its EINECS registry number is 202-255-5. This chemical's molecular formula is C₉H₁₀O and molecular weight is 134.1751. Its IUPAC name is called 2-phenylpropanal. This chemical is clear colorless liquid. This chemical can be used as flavors. Besides, it is mainly used for the preparation of melons, almonds, cherries, peaches, plums and other flavor.

Physical properties of 2-Phenylpropionaldehyde: (1)ACD/LogP: 2.113; (2)ACD/LogD (pH 5.5): 2.11; (3)ACD/LogD (pH 7.4): 2.11; (4)ACD/BCF (pH 5.5): 23.77; (5)ACD/BCF (pH 7.4): 23.77; (6)ACD/KOC (pH 5.5): 336.17; (7)ACD/KOC (pH 7.4): 336.17; (8)#H bond acceptors:1; (9)#Freely Rotating Bonds: 2; (10)Index of Refraction: 1.506; (11)Molar Refractivity: 40.625 cm³; (12)Molar Volume: 136.824 cm³; (13)Polarizability: 16.105 10-24cm³; (14)Surface Tension: 34.3320007324219 dyne/cm; (15)Density: 0.981 g/cm³; (16)Flash Point: 76.111 °C; (17)Enthalpy of Vaporization: 43.856 kJ/mol; (18)Boiling Point: 202.339 °C at 760 mmHg; (19)Vapour Pressure: 0.293999999761581 mmHg at 25°C

Preparation of 2-Phenylpropionaldehyde: This chemical can be prepared by 2-methyl-2-phenyl-oxirane.

Uses of 2-Phenylpropionaldehyde: It can be used to produce 3-hydroxy-2-methyl-2-phenyl-propionaldehyde. This reaction will need reagent water and K₂CO₃.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC(C=O)C1=CC=CC=C1
(2)InChI: InChI=1S/C9H10O/c1-8(7-10)9-5-3-2-4-6-9/h2-8H,1H3
(3)InChIKey: IQVAERDLDAZARL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
rabbit	LD50	skin	> 5gm/kg (5000mg/kg)		National Technical Information Service. Vol. OTS0572460,
rat	LD50	oral	2800mg/kg (2800mg/kg)	BEHAVIORAL: COMA SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Product Name

2-PHENYLPROPIONALDEHYDE

Synthetic route

2-Phenylpropionaldehyde Consensus Reports

2-Phenylpropionaldehyde Specification

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