1570-95-2

Basic information

• Product Name: 2-Phenyl-1,3-propanediol
• Synonyms: 2-PHENYL-1,3-PROPANEDIOL;2-PHENYLPROPANE-1,3-DIOL;RARECHEM AL BD 1370;PPD;2-Phenyl-1,3-Propanediole;2-Phenylpropane-1,3-diol (PPD);2-phenyl-1,3-propanediole (intermediate of felbomatet);2-PHEVYL-1,3-PROPANEDIOL
• CAS NO: 1570-95-2
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19
• EINECS: 411-810-2
• Product Categories: Chemical intermediate for Felbamate;Organic Building Blocks;Oxygen Compounds;Polyols
• Mol File: 1570-95-2.mol
• Article Data: 47

Chemical Properties

• Melting Point: 53-56 °C(lit.)
• Boiling Point: 310.6 °C at 760 mmHg
• Flash Point: 153.8 °C
• Appearance: white powder
• Density: 1.131 g/cm³
• Vapor Pressure: 0.000255mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.26±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-Phenyl-1,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-1,3-propanediol(1570-95-2)
• EPA Substance Registry System: 2-Phenyl-1,3-propanediol(1570-95-2)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• WGK Germany: 1
• Hazardous Substances Data: 1570-95-2(Hazardous Substances Data)

Usage

Description

2-Phenyl-1,3-propanediol is an organic compound with the molecular formula C9H12O2. It is a colorless to pale yellow liquid with a mild, sweet odor. 2-Phenyl-1,3-propanediol is characterized by the presence of a phenyl group attached to a propanediol backbone, which grants it unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2-Phenyl-1,3-propanediol is used as a substrate for eukaryotic lipase enzymes, which are crucial in the pharmaceutical industry for the development of drugs targeting lipid metabolism and related disorders. Its ability to act as a substrate allows researchers to study enzyme activity and develop more effective medications.
Used in Chemical Synthesis:
2-Phenyl-1,3-propanediol is used as a key intermediate in the synthesis of various chemical compounds. For instance, it may be used to synthesize enantiomers of 2-phenyl-3-hydroxypropylcarbamate through a chemoenzymatic method. This application is significant in the production of chiral compounds, which are essential in the pharmaceutical, agrochemical, and fragrance industries due to their high specificity and selectivity.
Used in the Preparation of 2-Phenyl-1,3-propanedithiol:
2-Phenyl-1,3-propanediol is also employed in the preparation of 2-phenyl-1,3-propanedithiol, which is an important building block for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. The versatility of 2-phenyl-1,3-propanediol in synthesis makes it a valuable compound in the chemical industry.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1198, 1989 DOI: 10.1021/jo00266a038

InChI:InChI=1/C9H12O2/c10-6-9(7-11)8-4-2-1-3-5-8/h1-5,9-11H,6-7H2

Synthetic route

diethyl 2-phenylmalonate (83-13-6) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With diisobutylaluminium hydride In tetrahydrofuran for 2h; Mechanism; Product distribution; Ambient temperature; other reducing agents, var. time;	100%
With diisobutylaluminium hydride In tetrahydrofuran for 2h; Ambient temperature;	100%
Stage #1: diethyl 2-phenylmalonate With sodium hydroxide In tetrahydrofuran; water at 145℃; under 2280.15 Torr; for 0.933333h; Inert atmosphere; Stage #2: With tetrabutyl-ammonium chloride In tetrahydrofuran; water for 0.183333h; Inert atmosphere; Stage #3: With sodium hydroxide In tetrahydrofuran; water; toluene at 156℃; under 3800.26 Torr; for 3.13333h; Solvent; Temperature; Pressure; Inert atmosphere;	99.6%

ethyl 3-oxo-2-phenylpropanoate (17838-69-6) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With sodium tetrahydroborate In ethyl acetate; toluene at 50 - 55℃;	99.11%

C19H28O4 → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With water; Selectfluor In acetonitrile at 20℃; for 5h;	94%

monomethyl phenylmalonate (33315-63-8) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With sodium tetrahydroborate; bromine In 1,2-dimethoxyethane at -10 - 20℃; for 0.5h;	92%

phenylmalonic acid (2613-89-0) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With borane In tetrahydrofuran at -30℃; for 144h;	91%
With borane In tetrahydrofuran at 0℃; Mechanism; other malonic acids; var. temperatures;	85%
With indium(III) bromide; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 15h; Inert atmosphere;	54%
With borane-THF In tetrahydrofuran at 0℃; Mechanism; other phenyl carboxylic acids; var. temp.;
In tetrahydrofuran

2-(4-methoxy-phenyl)-5-phenyl-[1,3]dioxane → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With water; Selectfluor In acetonitrile at 20℃; for 5h;	90%

2-phenyl-3-(tetrahydropyran-2-yloxy)propan-1-ol (466680-46-6) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With water; Selectfluor In acetonitrile at 20℃; for 5h;	89%

C18H21NO2 → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
In methanol for 0.5h; UV-irradiation;	89%

C18H38OSi4 → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
Stage #1: C18H38OSi4 With tetrabutyl ammonium fluoride In dihydrogen peroxide at 20℃; Stage #2: With potassium hydrogencarbonate In methanol at 65℃;	88%

α-fluorophenylmalonate dipotassium salt → 2-phenylpropane-1, 3-diol (1570-95-2) + 2-fluoro-2-phenyl-1,3-propanediol (211506-14-8)

Conditions	Yield
Stage #1: α-fluorophenylmalonate dipotassium salt With hydrogenchloride In tetrahydrofuran; 1,4-dioxane at 0 - 10℃; for 0.5h; Stage #2: With diborane In tetrahydrofuran; 1,4-dioxane at 2.5 - 20℃; for 18 - 24h; Product distribution / selectivity;	A n/a B 85%
Stage #1: α-fluorophenylmalonate dipotassium salt With diborane In tetrahydrofuran at 20℃; Stage #2: With hydrogenchloride In water Product distribution / selectivity;

C30H35NO4 → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
In methanol; acetonitrile UV-irradiation;	74%

methyl 2-formyl-2-phenylacetate (5894-79-1) + 4-methyl-2-pentanone (108-10-1) + Acetic formic anhydride (2258-42-6) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With hydrogenchloride; sodium borohydrid; tetrabutyl-ammonium chloride; sodium carbonate In tert-butyl methyl ether; water	70.05%

2-phenyl-1,3-propanedial (26591-66-2) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With lithium aluminium tetrahydride	46%

diethyl 2-phenylmalonate (83-13-6) → 2-phenylethanol (60-12-8) + 2-phenylpropane-1, 3-diol (1570-95-2) + Ethyl 2-phenylethanoate (101-97-3)

Conditions	Yield
With Na(PEG-400)2BH2 In tetrahydrofuran at 80℃; for 4h;	A 45% B 10% C 12%
With Na(PEG-400)2BH2 In tetrahydrofuran at 80℃; for 4h;	A 45% B 15% C 12%

phenylmalonic acid (2613-89-0) → 2-phenylethanol (60-12-8) + (RS)-2-phenyl-1-propanol (1123-85-9) + 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating; Yield given. Title compound not separated from byproducts;	A n/a B n/a C 33%
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating; Yields of byproduct given;	A n/a B n/a C 33%

diethyl 2-phenylmalonate (83-13-6) → 2-phenylethanol (60-12-8) + 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With sodium tetrahydroborate; sodium dihydrogenphosphate	A 10% B n/a
With ethanol; copper oxide-chromium oxide at 150℃; under 257428 Torr; Hydrogenation;

glycerol (56-81-5) + benzene (71-43-2) → 2-phenylpropane-1, 3-diol (1570-95-2) + 2,3-diphenyl-1-propanol (3536-29-6)

Conditions	Yield
With aluminium trichloride

2-phenyl-1,3-propanediol diacetate (98017-92-6) → 2-phenylpropane-1, 3-diol (1570-95-2) + 3-acetoxy-2-phenyl propanol (126986-28-5)

Conditions	Yield
1,3-disubstituted tetraalkyldistannoxane (X = Y = Cl) In methanol; chloroform for 48h; Ambient temperature; Yield given;

Butyric acid 3-butyryloxy-2-phenyl-propyl ester → 2-phenylpropane-1, 3-diol (1570-95-2) + (S)-2-phenyl-3-hydroxypropyl butyrate

Conditions	Yield
With sodium hydroxide; potassium chloride In tetrahydrofuran porcine pancreatic lipase;

dimethyl 2-phenylmalonate (37434-59-6) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 22h; Ambient temperature; Yield given;
With lithium aluminium tetrahydride In diethyl ether

ethanol (64-17-5) + diethyl 2-phenylmalonate (83-13-6) + copper oxide-chromium oxide catalyst → 2-phenylethanol (60-12-8) + 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
at 150℃; under 257428 Torr; Hydrogenation;

2-phenyl-1,3-propanediol diacetate (98017-92-6) → 2-phenylpropane-1, 3-diol (1570-95-2) + (R)-1-acetoxy-3-hydroxy-2-phenylpropane (110270-51-4)

Conditions	Yield
Bacillus cereus 809A In phosphate buffer at 30℃; pH=7.0; Title compound not separated from byproducts.;

2-methoxy-2-phenyl-1,3-propanediol → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
palladium-carbon In ethanol; toluene

2-nitro-2-phenyl-propane-1,3-diol (5428-02-4) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
palladium In methanol; hydrogen; toluene

diethyl malonate (105-53-3) → 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 12h; Heating / reflux;

2-(2-hydroxy-5-methoxyphenyl)-5-phenyl-1,3-dioxane (1079921-26-8) → 2-hydroxy-5-methoxybenzaldehyde (672-13-9) + 2-phenylpropane-1, 3-diol (1570-95-2)

Conditions	Yield
With water In methanol at 20℃; Quantum yield; Irradiation;	A n/a B 59 %Chromat.

2-phenylpropane-1, 3-diol (1570-95-2) + acetic anhydride (108-24-7) → 2-phenyl-1,3-propanediol diacetate (98017-92-6)

Conditions	Yield
With pyridine Acetylation;	100%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3h; Acetylation;	93%
With sulfuric acid
With triethylamine; dmap In dichloromethane for 1h; Ambient temperature; Yield given;
With pyridine at 20℃; Acetylation;

3,4-dihydro-2H-pyran (110-87-2) + 2-phenylpropane-1, 3-diol (1570-95-2) → C19H28O4

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In ethyl acetate at 20℃; for 1h;	98%

2-phenylpropane-1, 3-diol (1570-95-2) + vinyl benzoate (769-78-8) → (S)-3-hydroxy-2-phenylpropyl benzoate

Conditions	Yield
With (S,S)-2,6-bis{2-[hydroxy(biphenyl-4-yl)methyl]pyrrolidin-1-ylmethyl}-4-methylphenol; diethylzinc In toluene at -15℃; Inert atmosphere; optical yield given as %ee;	94%

2-phenylpropane-1, 3-diol (1570-95-2) + 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9) → C13H18O8P2

Conditions	Yield
Stage #1: 2-phenylpropane-1, 3-diol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-Chloro-2-oxo-1,3,2-dioxaphospholane In dichloromethane at 0 - 20℃; for 12h;	93%

2-phenylpropane-1, 3-diol (1570-95-2) + 2-chloro-1,3,2-dioxaphospholan (822-39-9) → C13H18O6P2

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	93%

2-phenylpropane-1, 3-diol (1570-95-2) + methanesulfonyl chloride (124-63-0) → 2-phenylpropane-1,3-diyl dimethanesulfonate (64923-68-8)

Conditions	Yield
With pyridine at 20℃; for 24h;	90%
With pyridine In dichloromethane at 0 - 20℃;
With triethylamine In dichloromethane at 0℃; Inert atmosphere;

2-phenylpropane-1, 3-diol (1570-95-2) + 3,5-dimethoxybenzaldehyde dimethyl acetal (59276-34-5) → C18H20O4

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 7h; Inert atmosphere;	90%

1,1,2-triphenyl-1,2-ethanediol (6296-95-3) + 2-phenylpropane-1, 3-diol (1570-95-2) → benzophenone (119-61-9) + 2,5-Diphenyl-1,3-dioxane (80001-45-2)

Conditions	Yield
With PTAB; N-benzyl-N,N,N-triethylammonium chloride; antimony(III) bromide In dimethyl sulfoxide at 20℃; for 42h;	A 89% B 85%

2-phenylpropane-1, 3-diol (1570-95-2) + benzaldehyde dimethyl acetal (1125-88-8) → trans-2,5-diphenyl-1,3-dioxane

Conditions	Yield
With zinc(II) chloride In chloroform at 20℃; Inert atmosphere;	88%

2-phenylpropane-1, 3-diol (1570-95-2) + phenylboronic acid (98-80-6) → C15H15BO2

Conditions	Yield
In toluene for 6h; Reflux; Dean-Stark;	88%

2-phenylpropane-1, 3-diol (1570-95-2) + 4-chlorobenzaldehyde dimethyl acetal (3395-81-1) → trans-2-(4-chlorophenyl)-5-phenyl-1,3-dioxane

Conditions	Yield
With zinc(II) chloride In chloroform at 20℃; Inert atmosphere;	87%

2-phenylpropane-1, 3-diol (1570-95-2) + 4-trifluoromethylbenzyl chloride (939-99-1) → (S)-2-phenyl-3-(p-trifluoromethylbenzyloxy)propan-1-ol

Conditions	Yield
With (R)-2,4-dimethyl-7-(2-(trityloxy)naphthalen-1-yl)-5H-benzo[c]naphtho[2,3-e][1,2]oxaborinin-5-ol; potassium carbonate; potassium iodide In acetonitrile at 20℃; for 24h; Sealed tube; enantioselective reaction;	87%

2-phenylpropane-1, 3-diol (1570-95-2) → 1-(1,3-dichloropropan-2-yl)benzene (67168-95-0)

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride at 100 - 110℃;	85%

2-phenylpropane-1, 3-diol (1570-95-2) + p-Anisaldehyde dimethyl acetal (2186-92-7) → trans-2-(4-methoxyphenyl)-5-phenyl-1,3-dioxane

Conditions	Yield
With zinc(II) chloride In chloroform at 20℃; Inert atmosphere;	85%

Trimethyl orthoacetate (1445-45-0) + 2-phenylpropane-1, 3-diol (1570-95-2) → 3-acetoxy-2-phenyl propanol (126986-28-5)

Conditions	Yield
With toluene-4-sulfonic acid	85%

2-phenylpropane-1, 3-diol (1570-95-2) + 3,5-Dimethoxyaniline (10272-07-8) → C17H15NO2

Conditions	Yield
With tetrafluoroboric acid diethyl ether; {[(PCy3)(CO)RuH]4(μ-O)(μ-OH)2}; cyclopentene In 1,4-dioxane at 150℃; for 14h; Sealed tube; Schlenk technique; Inert atmosphere; regioselective reaction;	84%

di-tert-butyl dicarbonate (24424-99-5) + 2-phenylpropane-1, 3-diol (1570-95-2) → carbonic acid tert-butyl ester 3-hydroxy-2-phenyl-propyl ester

Conditions	Yield
With cerium(III) chloride In tetrahydrofuran	83%

2-phenylpropane-1, 3-diol (1570-95-2) → (1,3-dibromopropan-2-yl)benzene (85291-68-5)

Conditions	Yield
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 4.5h; Inert atmosphere;	81%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 2h; Schlenk technique;	79%
With N-Bromosuccinimide; triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h;	66%
With pyridine; phosphorus tribromide

Upstream product

• 83-13-6 diethyl 2-phenylmalonate 
• 56-81-5 glycerol 
• 71-43-2 benzene 
• 2613-89-0 phenylmalonic acid 
• 64-17-5 ethanol 
• 33315-63-8 monomethyl phenylmalonate 
• 108-86-1 bromobenzene 
• 17838-69-6 ethyl 3-oxo-2-phenylpropanoate 
• 111-42-2 2,2'-iminobis[ethanol] 
• 504-63-2 trimethyleneglycol 
• 98-80-6 phenylboronic acid 
• 1079921-26-8 2-(2-hydroxy-5-methoxyphenyl)-5-phenyl-1,3-dioxane 
• 105-53-3 diethyl malonate 
• 5428-02-4 2-nitro-2-phenyl-propane-1,3-diol 

Downstream Products

• 40893-99-0 3-bromo-2-phenyl-propan-1-ol 
• 85291-68-5 (1,3-dibromopropan-2-yl)benzene 
• 110270-51-4 (R)-1-acetoxy-3-hydroxy-2-phenylpropane 
• 110230-69-8 (S)-1-acetoxy-3-hydroxy-2-phenylpropane 
• 98017-92-6 2-phenyl-1,3-propanediol diacetate 
• 33581-45-2 3-methoxy-2-phenylpropanol 
• 6274-58-4 3-chloro-2-phenyl-1-propanol 
• 126986-28-5 3-acetoxy-2-phenyl propanol 
• 466680-46-6 2-phenyl-3-(tetrahydropyran-2-yloxy)propan-1-ol 
• 119-61-9 benzophenone 
• 80001-45-2 2,5-Diphenyl-1,3-dioxane 
• 25451-53-0 2-phenyl-1,3-propanediol monocarbamate 
• 109482-33-9 2-phenyl-3-methoxy-propanol carbamate 
• 109482-31-7 4-phenyl-1,3-dioxolan-2-one-4-yl-methanol carbamate 

Relevant articles and documents

Exceptionally Slow Reduction of Phenylmalonic Acid by Borane-THF via Cyclic (Phenylmalonoxy)barane

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Effect of Temperature on Borane Reduction of Representative Malonic Acids

The controlled reaction of phenylmalonic acid (1a) with borane-THF at appropriate temperature makes available (phenylmalonyldioxy)borane , which has been characterized.Reduction of 2a or of the corresponding acid 1a proceeds at 0 deg C at the same rate.The reaction, however, is incomplete, showing only 33percent product formed in 4 h.Diethylmalonic acid (1b), which possesses no α-hydrogen, and the (diethylmalonyldioxy)borane (2b) are reduced at the same rate to the corresponding cyclic dialkoxyborane 5b.These results suggest that the reduction proceeds through intermediate formation of 2.The rates of the borane reduction for a series of malonic acids (1a-h) have been systematically studied and compared at 0 deg C and at -20 deg C.The reductions of aromatic substituted malonic acids (1f-h) are quite sluggish with substantial (46-72percent) α-metalation occurring at 0 deg C.Aliphatic alkylmalonic acids (1d-e) are reduced in 24 h with 34-40percent of α-metalation.At -20 deg C, most malonic acids are completely reduced in times ranging from 24 h for aliphatic (1c-e) to 3 days for aromatic (1f-h) compounds, with only 2-24percent α-metalation.The reduction of 1b at either 0 deg C or -20 deg C is completed in 8 h.At an appropriate lower temperature the reduction successfully competes with the α-metalation.

Novel highly potent and selective sigma1 receptor antagonists effectively block the binge eating episode in female rats

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Arylsilylation of Electron-Deficient Alkenes via Cooperative Photoredox and Nickel Catalysis

Carbosilylation of alkenes can be an efficient approach to the synthesis of organosilicon compounds. However, few general methods of carbosilylation are known. Here, we introduce a strategy for arylsilylation of electron-deficient terminal alkenes by combining photoredox-catalyzed silyl radical generation, innate reactivity of silyl radical with alkene, and Ni-catalyzed aryl-Alkyl cross-coupling. This cooperative photoredox and nickel catalysis operates under mild conditions. It employs readily available alkenes, aryl bromides, and silane as reagents, and it produces useful synthetic building blocks in a modular manner.

Method for highly efficiently synthesizing 2-phenyl-1,3-propylene glycol

The invention discloses a method for highly efficiently synthesizing 2-phenyl-1,3-propylene glycol. The method includes the following steps that firstly a silicate active agent is prepared; secondly,ethyl benzoacetate, methyl formate and diisopropyl carbodiimide are used as raw materials for condensation reaction; alpha-formyl ethyl phenylacetate is prepared; then sodium borohydride is used as ahydrogenation reductant, the prepared silicate active agent promotes a reduction reaction, and alpha-formyl ethyl phenylacetate is reduced to prepare 2-phenyl-1,3-propylene glycol. The 2-phenyl-1,3-propylene glycol prepared by the method is high in purity, high in yield, short in reaction time and low in cost.