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93-53-8 Usage

Description

2-phenylpropionaldehyde is also known as 2-phenylpropanal. It belongs to the family of phenylacetaldehydes. These are compounds containing a phenylacetaldehyde moiety, which consists of a phenyl group substituted at the second position by an acetalydehyde. 2- phenylpropionaldehyde is a naturally occurring compound in various foods including roasted nuts, cooked potatoes, cheese, wine, fruit, vegetables, coffee, tea, and cocoa. 2-phenylpropionaldehyde is used as a flavoring agent. Once absorbed, 2-phenylpropionaldehyde can be converted to phenyl-substituted carboxylic acids, which can be conjugated with glucuronic acid and excreted in the urine. 2-phenylpropionaldehyde can also undergo β- oxidation to benzoic acid or phenylacetic acid derivatives, which are conjugated with glycine or glutamine before being excreted in the urine.

References

[1] WHO Food Additives Series: 54, Safety evaluation of certain food additives [2] https://webgate.ec.europa.eu

Chemical Properties

Different sources of media describe the Chemical Properties of 93-53-8 differently. You can refer to the following data:
1. clear colorless liquid
2. 2-PHENYLPROPIONALDEHYDE identified in dried mushroom, is a colorless liquid with a green hyacinth odor. Hydratropaldehyde can be hydrogenated to hydratropic alcohol, which is also used to a limited extent by reaction of p-ethylbenzyl chloride and isobutyric aldehyde in the presence of catalysts. The product is used in perfumes for, for example, household products.
3. 2-Phenylpropionaldehyde has an intense, green, floral odor reminiscent of hyacinth.

Occurrence

Reported found in microbially fermented tea and some varieties of mushrooms.

Uses

2-Phenylpropionaldehyde is a precursor in the synthesis of N,N,β-Trimethyl-phenethylamine Hydrochloride (T796625).

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

General Description

2-Phenylpropionaldehyde is used in perfumes for its green hyacinth odor.

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.]

Check Digit Verification of cas no

The CAS Registry Mumber 93-53-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 3 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 93-53:
(4*9)+(3*3)+(2*5)+(1*3)=58
58 % 10 = 8
So 93-53-8 is a valid CAS Registry Number.
InChI:InChI=1/C9H10O/c1-8(7-10)9-5-3-2-4-6-9/h2-8H,1H3

93-53-8 Well-known Company Product Price

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  • Alfa Aesar

  • (B22436)  2-Phenylpropionaldehyde, 97%   

  • 93-53-8

  • 100g

  • 375.0CNY

  • Detail
  • Alfa Aesar

  • (B22436)  2-Phenylpropionaldehyde, 97%   

  • 93-53-8

  • 500g

  • 1091.0CNY

  • Detail

93-53-8SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Phenylpropionaldehyde

1.2 Other means of identification

Product number -
Other names Benzeneacetaldehyde, α-methyl-

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:93-53-8 SDS

93-53-8Synthetic route

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

(2S)-2-phenyl-1-propanamine

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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

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

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With sodium periodate; sodium hydrogencarbonate In dichloromethane at 0 - 20℃; for 4h;77%
(S)-2-phenyl-1-propanol
37778-99-7

(S)-2-phenyl-1-propanol

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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;
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

ethylbenzene
100-41-4

ethylbenzene

C

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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
styrene
292638-84-7

styrene

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

ethylbenzene
100-41-4

ethylbenzene

C

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With hydrogen; PtCl(SnCl3)<(S,S)-BDPP> In toluene at 40℃; under 60004.8 Torr; for 55h;A 42%
B 3%
C 31%
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

ethylbenzene
100-41-4

ethylbenzene

C

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

(S)-2-phenyl-propionaldehyde

D

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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;
C13H18O

C13H18O

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With ozone In dichloromethane at -78℃; for 0.0833333h;23%
C12H16O

C12H16O

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With ozone In dichloromethane at -78℃; for 0.0833333h;23%
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

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

(S)-2-phenyl-propionaldehyde

C

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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;
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

A

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

(S)-2-phenyl-propionaldehyde

B

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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;
3-phenylbut-1-ene
934-10-1

3-phenylbut-1-ene

A

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

(S)-2-phenyl-propionaldehyde

B

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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;
2-Phenylpropanal
34713-70-7

2-Phenylpropanal

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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
(3,3-diethoxypropyl)benzene
6956-37-2

(3,3-diethoxypropyl)benzene

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

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

(S)-2-phenyl-propionaldehyde

C

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In acetone for 5h; Heating;
(2S,3S)-methylphenylalanine
25488-25-9

(2S,3S)-methylphenylalanine

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With indan-1,2,3-trione hydrate In water; benzene at 80℃; for 0.166667h;
trimethylaluminum
75-24-1

trimethylaluminum

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

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

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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

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

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

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

(S)-2-phenyl-propionaldehyde

C

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In acetone for 5h; Heating;
[(S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-pyrrolidin-1-yl]-[(R)-2-phenyl-prop-(E)-ylidene]-amine

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

A

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

(S)-2-phenyl-propionaldehyde

B

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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

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

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With hydrogenchloride; methyl iodide 1.) 60 deg C, 2.) n-pentane; Yield given. Multistep reaction;
1-(4-morpholino)-2-phenylpropene
39166-22-8

1-(4-morpholino)-2-phenylpropene

A

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

(S)-2-phenyl-propionaldehyde

B

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
With L-Tartaric acid In ethanol; water at -60℃; for 0.5h; Product distribution; variation of chiral acids, solvent, temperature;
2-phenylpropane-1,1-diyl diacetate
21129-06-6

2-phenylpropane-1,1-diyl diacetate

A

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

(S)-2-phenyl-propionaldehyde

B

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
With sodium hydroxide; Candida rugosa lipase In various solvent(s) for 1.16667h; Product distribution; pH=7; different substrates, enzymes, solvents and reaction times;
2-Phenylpropanal
34713-70-7

2-Phenylpropanal

diethylzinc
557-20-0

diethylzinc

A

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

(2S,3S)-erythro-2-phenylpentan-3-ol

B

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

(2R,3S)-threo-2-phenylpentan-3-ol

C

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

(2R,3R)-erythro-2-phenylpentan-3-ol

D

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
With naphthalene; (R)-PDB In hexane Addition; Further byproducts given;
(E,2R,5S)-7-methyl-5-(2,4,6-trimethylbenzenesulfonyl)amino-2-phenyloct-3-ene
214752-00-8

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

A

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

(S)-2-phenyl-propionaldehyde

B

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

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

Conditions
ConditionsYield
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;
(1S,2R,3S)-1,2-Dihydroxy-1,3-diphenylbutane
243860-93-7

(1S,2R,3S)-1,2-Dihydroxy-1,3-diphenylbutane

A

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

(S)-2-phenyl-propionaldehyde

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With sodium periodate In dichloromethane for 1h; Oxidation; oxidative cleavage; Title compound not separated from byproducts.;
styrene
292638-84-7

styrene

carbon monoxide
201230-82-2

carbon monoxide

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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

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

dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

A

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

(S)-2-phenyl-propionaldehyde

B

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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;
styrene
292638-84-7

styrene

A

3-phenyl-propionaldehyde
104-53-0

3-phenyl-propionaldehyde

B

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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
2-Phenylpropanal
34713-70-7

2-Phenylpropanal

A

(R)-formic acid 1-phenylethyl ester

(R)-formic acid 1-phenylethyl ester

B

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

(S)-formic acid 1-phenylethyl ester

C

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

(S)-2-phenyl-propionaldehyde

D

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

(R)-2-phenylpropanal

Conditions
ConditionsYield
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;
1,3-diphenyl-propen-3-one
614-47-1

1,3-diphenyl-propen-3-one

n-Bu2CuLi

n-Bu2CuLi

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

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

Conditions
ConditionsYield
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
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

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

(S)-2-phenyl-1-propanol

Conditions
ConditionsYield
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;
phenyl(trimethylsiloxy)acetonitrile
25438-37-3

phenyl(trimethylsiloxy)acetonitrile

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

(S)-2-phenyl-propionaldehyde

A

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

3-Hydroxy-2,4-diphenyl-2-(trimethylsilyl)pentannitril

B

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

(2R*,3S*)-1,3-Diphenyl-2-(trimethylsilyloxy)-1-butanon

C

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

(2S*,3S*)-1,3-Diphenyl-2-(trimethylsilyloxy)-1-butanon

Conditions
ConditionsYield
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
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

allyl bromide
106-95-6

allyl bromide

2-phenyl-3-hydroxy-5-hexene

2-phenyl-3-hydroxy-5-hexene

Conditions
ConditionsYield
With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran at 20℃; for 0.333333h; Inert atmosphere;93%
diazoacetic acid ethyl ester
623-73-4

diazoacetic acid ethyl ester

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

3,3',5,5'-tetramethyl-4,4'-dimethoxy benzhydrylamine

(S)-2-phenyl-propionaldehyde
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

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

Conditions
ConditionsYield
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%
tris(trimethylsilyl)-propenyloxy-silane

tris(trimethylsilyl)-propenyloxy-silane

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

(S)-2-phenyl-propionaldehyde

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

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

Conditions
ConditionsYield
With bis(trifluoromethanesulfonyl)amide In dichloromethane at -78℃; for 0.25h; Mukaiyama aldol reaction;84%
C8H15BO2
1417175-94-0

C8H15BO2

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

(S)-2-phenyl-propionaldehyde

C14H20O
1417175-86-0

C14H20O

Conditions
ConditionsYield
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%
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

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

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

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

(R)-3-phenyl-1-butene

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 20℃;82%
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

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

(S)-2-Phenylpropionic acid

Conditions
ConditionsYield
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;
C8H15BO2
1417175-76-8

C8H15BO2

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

(S)-2-phenyl-propionaldehyde

C14H20O
1417175-87-1

C14H20O

Conditions
ConditionsYield
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

C8H15BO2

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

(S)-2-phenyl-propionaldehyde

C14H20O

C14H20O

Conditions
ConditionsYield
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction;77%
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

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

(S)-2-methylpropane-2-sulfinamide

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

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

Conditions
ConditionsYield
With titanium(IV) isopropylate In tetrahydrofuran at 20℃; for 6h; Inert atmosphere;76%
C33H68O2Si5
1223593-46-1

C33H68O2Si5

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

(S)-2-phenyl-propionaldehyde

C39H70O3Si4
1223593-48-3

C39H70O3Si4

Conditions
ConditionsYield
With bis(trifluoromethanesulfonyl)amide In dichloromethane; toluene at -78℃; for 0.5h; Inert atmosphere; enantioselective reaction;75%
3,3-bis(triethylsilyl) benzyl enol ether

3,3-bis(triethylsilyl) benzyl enol ether

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

(S)-2-phenyl-propionaldehyde

C31H50O2Si2

C31H50O2Si2

Conditions
ConditionsYield
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

C8H15BO2

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

(S)-2-phenyl-propionaldehyde

C14H20O

C14H20O

Conditions
ConditionsYield
With phenylborondichloride; potassium carbonate In dichloromethane for 3h; diastereoselective reaction;73%
acetone tris(triethylsilyl)silyl enol ether
1223592-76-4

acetone tris(triethylsilyl)silyl enol ether

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

(S)-2-phenyl-propionaldehyde

C30H60O2Si4
1223593-43-8

C30H60O2Si4

Conditions
ConditionsYield
With bis(trifluoromethanesulfonyl)amide In dichloromethane at 0 - 20℃; Inert atmosphere; enantioselective reaction;72%
(furan-2-yloxy)-trimethylsilane
61550-02-5

(furan-2-yloxy)-trimethylsilane

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

4-Methoxy-2-methylsulfenylaniline

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

(S)-2-phenyl-propionaldehyde

C21H23NO3S
1092853-68-3

C21H23NO3S

Conditions
ConditionsYield
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%
C30H60O2Si4
1223593-43-8

C30H60O2Si4

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

(S)-2-phenyl-propionaldehyde

A

C39H70O3Si4
1223593-48-3

C39H70O3Si4

B

C39H70O3Si4

C39H70O3Si4

Conditions
ConditionsYield
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
tert-butyl (E)-crotonate
79218-15-8

tert-butyl (E)-crotonate

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

(S)-2-phenyl-propionaldehyde

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

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

Conditions
ConditionsYield
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%
triethylaluminum
97-93-8

triethylaluminum

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

(S)-2-phenyl-propionaldehyde

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

(R,R)/(S,S)-2-phenylpentan-3-ol

Conditions
ConditionsYield
With methyllithium In diethyl ether; dichloromethane at -78℃;56%
C18H22Si

C18H22Si

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

(S)-2-phenyl-propionaldehyde

A

C19H22O

C19H22O

B

C19H22O

C19H22O

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -60℃; for 24h; Sakurai-Hosomi Allylation; Schlenk technique; Glovebox; Inert atmosphere;A 53%
B n/a
(S)-2-phenyl-propionaldehyde
93-53-8

(S)-2-phenyl-propionaldehyde

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

2,3-dimethyl-buta-1,3-diene

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

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

Conditions
ConditionsYield
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

C18H22Si

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

(S)-2-phenyl-propionaldehyde

A

C19H22O

C19H22O

B

C19H22O

C19H22O

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -60℃; for 24h; Sakurai-Hosomi Allylation; Schlenk technique; Glovebox; Inert atmosphere; diastereoselective reaction;A 47%
B n/a
2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane
158813-39-9

2-(Z-3-chloroprop-2-enyl)-4,4,5,5-tetramethyl-1,2,3-dioxaborolane

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

(S)-2-phenyl-propionaldehyde

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

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

Conditions
ConditionsYield
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%

93-53-8Relevant articles and documents

Chiral diphosphite-modified rhodium(0) nanoparticles: Catalyst reservoir for styrene hydroformylation

Axet, M. Rosa,Castillon, Sergio,Claver, Carmen,Philippot, Karine,Lecante, Pierre,Chaudret, Bruno

, p. 3460 - 3466 (2008)

The organometallic synthesis of rhodium nanoparticles stabilized with diphosphite ligands is described. These nanoparticles were investigated as catalysts in the styrene hydroformylation reaction, and their activity and selectivity were compared with those of similar molecular complexes. NMR spectroscopic studies performed during the course of the catalytic reaction showed that the synthesized nanoparticles are not stable and produce molecular species. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Rhodium catalysed asymmetric hydroformylation with diphosphite ligands based on sugar backbones

Buisman,Martin,Vos,Klootwijk,Kramer,Van Leeuwen

, p. 719 - 738 (1995)

Chiral disphosphite ligands (PP) prepared from {(2,2'-biphenyl-1,1'-diyl), (4,4',6, 6'-tetra-t-butyl-2,2'-biphenyl-1,1'-diyl), 4,4'-di-t-butyl-6,6'-dimethoxy-2,2'-biphenyl-1,1'-diyl) and di(2-t-butyl, 6-methylphenyl)} phosphorochloridites and sugar backbones {1,2-O-isopropylidene-D-xylofuranose, methyl-2,3-O-isopropylidene-α-D-mannopyranoside and (methyl-3,6-anhydro)-α-D-mannopyranoside, α-D-glucopyranoside and β-D-galactopyranoside} have been used in the rhodium catalysed asymmetric hydroformylation of styrene. Enantioselectivities up to 64% have been obtained with stable hydridorhodium diphosphite dicarbonyl catalysts (HRhPP(CO)2). High regioselectivities (up to 97%) to the branched aldehyde were found at relatively mild reaction conditions (T = 25-40°C, 9-45 bar of syngas pressure). The solution structures of HRhPP(CO)2 catalysts have been studied by 31P and 1H NMR spectroscopy. Bidentate coordination of the diphosphite ligand to the rhodium centre takes place in a bis-equatorial way. A relation between the trigonal bipyramidal structure and the enantioselectivity of the HRhPP(CO)2 complex is found. Rigid ligands with unsuitable geometries for bidentate coordination probably coordinate as monodentates and give rise to unstable catalysts and low selectivities during catalysis.

Tunable furanoside diphosphite ligands. A powerful approach in asymmetric catalysis

Dieguez, Montserrat,Ruiz, Aurora,Claver, Carmen

, p. 2957 - 2963 (2003)

A series of highly tunable furanoside diphosphite ligands, derived from readily available D-(+)-xylose and D-(+)glucose, are discussed. Their modular nature allows a facile systematic variation in the configuration of the stereo-centres at the ligand bridge and in the biaryl substituents. This enabled to select a ligand for each particular reaction that provided enantioselectivities that are comparable to those of the best catalysts previously reported in different asymmetric reactions. The Royal Society of Chemistry 2003.

Deracemization through photochemical E/Z isomerization of enamines

Huang, Mouxin,Luo, Sanzhong,Pan, Tianrun,Zhang, Long

, p. 869 - 874 (2022/03/07)

Catalytic deracemization of a-branched aldehydes is a direct strategy to construct enantiopure a-tertiary carbonyls, which are essential to pharmaceutical applications. Here, we report a photochemical E/Z isomerization strategy for the deracemization of a-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. A variety of racemic a-branched aldehydes could be directly transformed into either enantiomer with high selectivity. Rapid photodynamic E/Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the enantioenrichment. This study presents a distinctive photochemical E/Z isomerization strategy for externally tuning enamine catalysis.

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

Luo, Yier,Ouyang, Guanghui,Tang, Yuping,He, Yan-Mei,Fan, Qing-Hua

, p. 8176 - 8184 (2020/07/15)

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

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