1855-09-0

Basic information

• Product Name: 1-phenylpropane-1,2-diol
• Synonyms: 1-phenylpropane-1,2-diol;1,2-Dihydroxy-1-phenylpropane;Phenylpropanediol
• CAS NO: 1855-09-0
• Molecular Formula: C₉H₁₂O₂
• Molecular Weight: 152.19038
• EINECS: 217-452-1
• Mol File: 1855-09-0.mol
• Article Data: 52

Chemical Properties

• Melting Point: 56-57 °C
• Boiling Point: 294.6°C at 760 mmHg
• Flash Point: 144°C
• Appearance: /
• Density: 1.128g/cm³
• Vapor Pressure: 0.000728mmHg at 25°C
• Refractive Index: 1.557
• PKA: 14.09±0.20(Predicted)
• CAS DataBase Reference: 1-phenylpropane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenylpropane-1,2-diol(1855-09-0)
• EPA Substance Registry System: 1-phenylpropane-1,2-diol(1855-09-0)

Safety Data

• Hazardous Substances Data: 1855-09-0(Hazardous Substances Data)

Usage

Uses

1-Phenyl-1,2-propanediol is a reagent in pharmaceutical chemistry, used in the synthesis of nor(pseudo)ephedrine related compounds.

InChI:InChI=1/C9H12O2/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9-11H,1H3

Synthetic route

1-propenylbenzene (873-66-5) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With osmium(VIII) oxide; cinchona alkaloid on mesoporous SBA-15 silica support at 0℃; for 24h;	100%
With 4-methylmorpholine N-oxide; Mg(1-x)Al(x)(OH)2(Cl)2*zH2O-OsO4 In water; acetone; acetonitrile at 20℃;	96%
With 4-methylmorpholine N-oxide In water; acetone at 20℃; for 2h; Inert atmosphere;	96%

1-Phenylpropane-1,2-dione (579-07-7) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0℃; for 1h; Inert atmosphere;	95%
With hydrogen; cinchonidine; acetic acid In water at 20℃; under 5171.62 Torr; Autoclave;
With rabbit 3-hydroxyhexobarbital dehydrogenase (AKR1C29); NADPH In aq. phosphate buffer; ethyl acetate at 37℃; for 0.5h; pH=7.4; Catalytic behavior; Kinetics; Enzymatic reaction;
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃;

1-phenylpropene (637-50-3) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With oxygen; 4-methylmorpholine N-oxide In water; acetone at 25℃; for 2h;	94%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 3h;	81%
With seleno-L-cystine; water; dihydrogen peroxide at 20℃; for 168h; Optical yield = 32 %de; stereoselective reaction;	45%
With Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III); OsO4 immobilized on Amberlite XAD-4 In water; tert-butyl alcohol at 20℃; for 1.5h;
With dihydrogen peroxide; nitric acid; potassium iodide In water; acetonitrile at 24.84℃; under 760.051 Torr; for 4h; pH=Ca. 4;

1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-1-phenyl-2-propanone (163799-44-8) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1h; Heating;	90%

1-Phenylpropane-1,2-dione (579-07-7) → 3-phenyl-2-propanol (698-87-3) + 1-Phenyl-1-propanol (93-54-9) + 1-phenyl-1,2-propandiol (1855-09-0) + 1-phenyl-propan-1-one (93-55-0)

Conditions	Yield
With samarium diiodide; water In tetrahydrofuran at 20℃; for 0.166667h; Further byproducts given;	A 6% B 79% C 3% D 7%

(E)-1-Bromo-2-butene (4784-77-4, 39616-19-8, 29576-14-5) + benzaldehyde (100-52-7) → 1-phenyl-1,2-propandiol (1855-09-0) + 2-methyl-1-phenyl-3-butene-1-ol (25201-44-9)

Conditions	Yield
bis(cyclopentadienyl)titanium (III) chloride In tetrahydrofuran at 20℃; for 1.5h;	A 17% B 77%

cis-1-phenyl-1-propylene (766-90-5) → 1-phenyl-1,2-propandiol (1855-09-0) + C9H10(18)O + C9H12O(18)O + 1-phenylpropylene oxide (4436-22-0)

Conditions	Yield
With [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)]; dihydrogen peroxide; 18O-labeled water In acetonitrile at 0℃; for 3h; Catalytic behavior;	A 32% B 15% C 68% D n/a

acetone (67-64-1) + 1-phenylpropylene oxide (23355-97-7) → 1-phenyl-1,2-propandiol (1855-09-0) + 2,2,5-trimethyl-4-phenyl-1,3-dioxolane (164577-21-3)

Conditions	Yield
With Amberlyst 15 at 20℃; for 12h;	A 34% B 66%

allylbenzene (300-57-2) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
Stage #1: allylbenzene With sodium hydrogencarbonate; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 6h; Irradiation; Stage #2: With triphenylphosphine In acetonitrile at 20℃; for 3h;	66%

1-propenylbenzene (873-66-5) → 1-phenyl-1,2-propandiol (1855-09-0) + benzaldehyde (100-52-7) + 1-phenyl-propan-1-one (93-55-0) + benzoic acid (65-85-0) + 1-phenyl-acetone (103-79-7) + 1-phenylpropylene oxide (23355-97-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen In chlorobenzene at 120℃; under 759.8 Torr; Product distribution; Mechanism;	A 3.4% B 26.9% C 3.2% D 2.9% E 0.8% F 55.1%

cis-1-phenyl-1-propylene (766-90-5) → 1-phenyl-1,2-propandiol (1855-09-0) + C9H12O(18)O + 1-phenylpropylene oxide (4436-22-0)

Conditions	Yield
With [Fe(CF3SO3)2((S,S)-N,N’-bis(2-pyridylmethyl)-2,2’-bipyrrolidine)]; 18O-labeled water; 3-chloro-benzenecarboperoxoic acid In acetonitrile at 0℃; for 3h; Catalytic behavior;	A 53% B 47% C n/a

1-propenylbenzene (873-66-5) → 1-phenyl-1,2-propandiol (1855-09-0) + benzaldehyde (100-52-7) + 1-phenyl-propan-1-one (93-55-0) + benzoic acid (65-85-0) + 1-phenylpropylene oxide (23355-97-7) + cis-1-phenylpropene oxide (4541-87-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen In chlorobenzene at 100℃; under 759.8 Torr; Product distribution; Mechanism;	A 2.7% B 26.4% C 2.9% D 3.2% E 52.1% F 0.4%

ethanol (64-17-5) + benzaldehyde (100-52-7) → 1-phenyl-1,2-propandiol (1855-09-0) + 1,2-diphenyl-1,2-ethanediol (492-70-6, 655-48-1, 2325-10-2, 38270-73-4, 52340-78-0, 579-43-1)

Conditions	Yield
at 20℃; for 3h; pinacol coupling;	A 51% B 49%

acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester (19347-08-1) → 1-phenyl-1,2-propandiol (1855-09-0) + (R)-2-hydroxy-1-phenylpropan-1-one (5650-40-8, 65646-07-3, 91840-95-8, 65646-06-2) + (R)-1-oxo-1-phenylpropan-2-yl acetate (91111-01-2)

Conditions	Yield
With ammonium sulfate; D-glucose; Rhizopus oryzae NRRL 395; magnesium sulfate; zinc(II) sulfate In phosphate buffer; dimethyl sulfoxide at 30℃; for 60h; pH=6.0 - 6.5;	A n/a B 42% C n/a

cis-1-phenyl-1-propylene (766-90-5) → 1-phenyl-1,2-propandiol (1855-09-0) + benzaldehyde (100-52-7) + benzoic acid (65-85-0) + 1-phenyl-acetone (103-79-7) + 1-phenylpropylene oxide (23355-97-7) + cis-1-phenylpropene oxide (4541-87-1)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen; chlorobenzene at 80℃; under 759.8 Torr; Product distribution; Mechanism; other temperature;	A 2.1% B 38.7% C 6.3% D 3.5% E 33.1% F 1.8%

cis-1-phenyl-1-propylene (766-90-5) → 1-phenyl-1,2-propandiol (1855-09-0) + benzaldehyde (100-52-7) + 1-phenyl-propan-1-one (93-55-0) + benzoic acid (65-85-0) + 1-phenyl-acetone (103-79-7) + 1-phenylpropylene oxide (23355-97-7)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen In chlorobenzene at 120℃; under 759.8 Torr; Product distribution; Mechanism;	A 2.2% B 24.5% C 1.8% D 4% E 7.4% F 32.4%

methyl magnesium iodide (917-64-6) + 2-acetoxyacetophenone (2243-35-8) → 1-phenyl-1,2-propandiol (1855-09-0)

(1-bromoethyl)benzyl bromide (1196-45-8) + potassium acetate (127-08-2) + acetic acid (64-19-7) → 1-phenylpropene (637-50-3) + 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
Verseifen des Reaktionsgemisches mit alkoh. Kalilauge;

methyl magnesium iodide (917-64-6) + 1-phenyl-2-hydroxyethanone (582-24-1) → 1-phenyl-1,2-propandiol (1855-09-0) + 2,5-dimethyl-2,5-diphenyl-[1,4]dioxane (380640-28-8)

Conditions	Yield
With diethyl ether Zersetzung des Reaktionsprodukts mit Wasser und Essigsaeure;
Reagiert analog mit Aethylmagnesiumjodid;

phenylmagnesium bromide + 3-monochloro-1,2-propanediol (96-24-2) → 3-phenylpropane-1,2-diol (19881-97-1, 61475-32-9, 79299-22-2, 17131-14-5) + 1-phenyl-1,2-propandiol (1855-09-0)

2,2-dichloro-1-phenylpropan-1-one (57169-51-4) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With sodium hydroxide; nickel

2-hydroxypropiophenone (5650-40-8) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With sodium tetrahydroborate

Dimethyl-(1-phenyl-allyloxy)-silane → 1-phenyl-1,3-propanediol (4850-49-1) + 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With dihydrogen peroxide; sodium hydrogencarbonate; dihydrogen hexachloroplatinate Yield given. Multistep reaction. Yields of byproduct given;

(1S,2S)-(-)-1-phenyl-1-propene oxide (4518-66-5) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With water Product distribution; enantioselectivity and regioselectivity by cytosolic and microsomal epoxide hydrolase;

(+)-(R,R)-β-methylstyrene oxide (14212-54-5) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
With water Product distribution; enantioselectivity and regioselectivity by cytosolic and microsomal epoxide hydrolase;

1-Phenylpropane-1,2-dione (579-07-7) → 1-phenyl-1,2-propandiol (1855-09-0) + (S)-2-hydroxypropiophenone (5650-40-8, 65646-06-2, 91840-95-8, 65646-07-3)

Conditions	Yield
Product distribution; bioreduction with baker's yeast; pH effect;

1-Phenylpropane-1,2-dione (579-07-7) → 1-Phenyl-1-propanol (93-54-9) + (RS)-2-phenyl-1-propanol (1123-85-9) + 1-phenyl-1,2-propandiol (1855-09-0) + benzyl alcohol (100-51-6)

Conditions	Yield
With lithium aluminium tetrahydride; oxygen at 110℃; under 759.8 Torr; Product distribution; 1.) oxidation, 2.) reductiv reactions of different α-diketones to different products;

1-phenylpropene (637-50-3) → 2-hydroxypropiophenone (5650-40-8) + 1-phenyl-1,2-propandiol (1855-09-0) + benzaldehyde (100-52-7)

Conditions	Yield
With laccase from Trametes versicolor; oxygen; benzotriazol-1-ol In water at 45℃; pH=4.5;

hydrogenchloride (7647-01-0) + 2-methyl-2-phenyloxirane (2085-88-3) → 1-phenyl-1,2-propandiol (1855-09-0)

Conditions	Yield
at 20℃;

methanol (67-56-1) + 1-phenyl-1,2-propandiol (1855-09-0) → benzoic acid methyl ester (93-58-3)

Conditions	Yield
With N-iodo-succinimide; 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride In dimethyl sulfoxide at 140℃; under 3750.38 Torr; for 12h; Molecular sieve;	98%

1-phenyl-1,2-propandiol (1855-09-0) → 1-phenyl-acetone (103-79-7)

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 2h; Inert atmosphere; regioselective reaction;	97%
With sulfuric acid at -19℃;
With sulfuric acid at 50 - 55℃;

1-phenyl-1,2-propandiol (1855-09-0) → 4-methyl-5-phenyl-1,3,2-dioxathiolan-2-one

Conditions	Yield
With thionyl chloride In tetrachloromethane for 1h; Heating;	92%

1-phenyl-1,2-propandiol (1855-09-0) → benzoic acid (65-85-0)

Conditions	Yield
With tert.-butylhydroperoxide; potassium tert-butylate In water at 80℃; for 8h;	92%
With 2-chloroanthracene-9,10-dione; oxygen In ethyl acetate for 30h; Irradiation;	81%

1-phenyl-1,2-propandiol (1855-09-0) + 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9) → C13H18O8P2

Conditions	Yield
Stage #1: 1-phenyl-1,2-propandiol In dichloromethane at 20℃; for 0.5h; Stage #2: 2-Chloro-2-oxo-1,3,2-dioxaphospholane In dichloromethane at 0 - 20℃; for 12h;	92%

1-phenyl-1,2-propandiol (1855-09-0) + 2-chloro-1,3,2-dioxaphospholan (822-39-9) → C13H18O6P2

Conditions	Yield
In dichloromethane at 0 - 20℃; for 12h;	92%

1-phenyl-1,2-propandiol (1855-09-0) → benzaldehyde (100-52-7) + benzoic acid (65-85-0)

Conditions	Yield
With sodium nitrate; water; oxygen In dimethyl sulfoxide at 130℃; for 24h;	A n/a B 90%

1-phenyl-1,2-propandiol (1855-09-0) → 2-hydroxypropiophenone (5650-40-8) + (RS)-1-hydroxy-1-phenylpropan-2-one (90-63-1)

Conditions	Yield
With 3,3-dimethyldioxirane In acetone Ambient temperature;	A 85% B n/a
With 3,3-dimethyldioxirane In acetone Ambient temperature;
With NADH‐dependent oxidase from Streptococcus mutans; NAD In aq. phosphate buffer at 40℃; for 24h; pH=6.5; Reagent/catalyst; pH-value; Temperature; Enzymatic reaction;

1-phenyl-1,2-propandiol (1855-09-0) → 2-hydroxypropiophenone (5650-40-8)

Conditions	Yield
With tert.-butylhydroperoxide; Rh2(Msip)4; sodium hydrogencarbonate In dichloromethane; water at 40℃; for 24h; Sealed tube; chemoselective reaction;	85%

1-phenyl-1,2-propandiol (1855-09-0) + methyl iodide (74-88-4) → 1,2-dimethoxy-1-phenylpropane (42746-57-6)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 16h;	77%

1-Phenylprop-1-yne (673-32-5) + 1-phenyl-1,2-propandiol (1855-09-0) → (E)-2-hydroxy-2-methyl-1,3-diphenylpent-3-en-1-one

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; dodecacarbonyl-triangulo-triruthenium; 1-Adamantanecarboxylic acid In m-xylene at 130℃; for 20h; Inert atmosphere; Sealed tube; regioselective reaction;	74%

1-phenyl-1,2-propandiol (1855-09-0) → benzaldehyde (100-52-7)

Conditions	Yield
With oxygen; cetyltrimethylammonim bromide In water at 20℃; under 760.051 Torr; for 5h; Irradiation; Green chemistry;	72%
In water; acetonitrile at 40℃;
With sodium periodate; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 1.5h;
With Na0274MnO2*6H2O; oxygen In butan-1-ol at 100℃; under 760.051 Torr; for 6h; Green chemistry;	94 %Chromat.

1-phenyl-1,2-propandiol (1855-09-0) → benzoic acid (65-85-0) + 1-Phenylpropane-1,2-dione (579-07-7)

Conditions	Yield
With oxone; 2-iodo-3,4,5,6-tetramethylbenzoic acid In water; acetonitrile at 20℃; for 3h;	A 30% B 62%

1-phenyl-1,2-propandiol (1855-09-0) + p-toluidine (106-49-0) → 3,5-dimethyl-2-phenyl-1H-indole (41018-81-9)

Conditions	Yield
With [Ru(CO)2(4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene)]2; [Ru(CO)2(4,5-bis(diphenylphosphino)-9,9-dimethyl-9H-xanthene)]2; toluene-4-sulfonic acid In tert-Amyl alcohol at 120℃; regioselective reaction;	61%

1-phenyl-1,2-propandiol (1855-09-0) + toluene (108-88-3) → Benzyl acetate (140-11-4) + benzoic acid benzyl ester (120-51-4)

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; acetonitrile at 80℃; for 24h; Sealed tube;	A 54% B 51%

1-phenyl-1,2-propandiol (1855-09-0) → (1R,2R)-1-phenylpropane-1,2-diol (40421-51-0) + (1S,2R)-1-phenylpropane-1,2-diol (40560-98-3) + (S)-2-hydroxypropiophenone (5650-40-8, 65646-06-2, 91840-95-8, 65646-07-3)

Conditions	Yield
With sodium alginate and calcium chloride immobilized Candida parapsilosis ATCC 7330 cell In 2,2,4-trimethylpentane; water; acetone at 25℃; for 72h; stereoselective reaction;	A n/a B 41.59% C 42.34%

Upstream product

• 917-64-6 methyl magnesium iodide 
• 2243-35-8 2-acetoxyacetophenone 
• 1196-45-8 (1-bromoethyl)benzyl bromide 
• 127-08-2 potassium acetate 
• 64-19-7 acetic acid 
• 96-24-2 3-monochloro-1,2-propanediol 
• 766-90-5 cis-1-phenyl-1-propylene 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 637-50-3 1-phenylpropene 
• 108-86-1 bromobenzene 
• 873-66-5 1-propenylbenzene 
• 2327-99-3 1-phenylpropadiene 
• 57169-51-4 2,2-dichloro-1-phenylpropan-1-one 
• 582-24-1 1-phenyl-2-hydroxyethanone 

Downstream Products

• 34713-70-7 2-Phenylpropanal 
• 1196-45-8 (1-bromoethyl)benzyl bromide 
• 380640-28-8 2,5-dimethyl-2,5-diphenyl-[1,4]dioxane 
• 103-79-7 1-phenyl-acetone 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 100-52-7 benzaldehyde 
• 5650-40-8 2-hydroxypropiophenone 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 159992-91-3 2,2,4-trimethyl-5-phenyldioxolan 
• 159992-92-4 2,2,4-trimethyl-5-phenyldioxolan 
• 123485-24-5 (1R,2S)-1,2-diacetoxy-1-phenylpropane 
• 123485-25-6 (1R,2R)-1,2-diacetoxy-1-phenylpropane 

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