4254-15-3

Basic information

• Product Name: (S)-(+)-1,2-Propanediol
• Synonyms: (S)-(+)-1,2-Dihydroxypropane (S)-(+)-Propylene Glycol;(S)-(+)-1,2-PROPANEDIOL FOR SYNTHESIS;(S)-(+)-1,2-Propanediol 96%;(S)-(+)-propylene glycero;(S)-(+)-Propane-1,2-diol;(S)-Propane-1,2-diol;L-(+)-PROPYLENE GLYCOL;(S)-(+)-PROPANEDIOL
• CAS NO: 4254-15-3
• Molecular Formula: C₃H₈O₂
• Molecular Weight: 76.09
• Product Categories: Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Compound;organic alcohol
• Mol File: 4254-15-3.mol
• Article Data: 109

Chemical Properties

• Melting Point: -59 °C
• Boiling Point: 186-188 °C765 mm Hg(lit.)
• Flash Point: 225 °F
• Appearance: Clear colorless/Liquid
• Density: 1.036 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.432(lit.)
• Storage Temp.: 2-8°C
• Solubility: Miscible with acetone, chloroform, ethanol (95%), glycerin, and water; soluble at 1 in 6 parts of ether; not miscible with light mineral oil or fixed oils, but will dissolve some essential oils.
• PKA: 14.49±0.20(Predicted)
• Explosive Limit: 2.6-12.6%(V)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Volatile
• Merck: 14,7855
• BRN: 1718871
• CAS DataBase Reference: (S)-(+)-1,2-Propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-1,2-Propanediol(4254-15-3)
• EPA Substance Registry System: (S)-(+)-1,2-Propanediol(4254-15-3)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 24/25-36/37/39-26
• WGK Germany: 1
• Hazardous Substances Data: 4254-15-3(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

(S)-(+)-1,2-Propanediol acts as an organic solvent and diluent used in pharmaceutical preparations. It is also used as a chiral synthetic intermediate and substrate for enzyme studies.

InChI:InChI=1/C6H12O3/c1-5-3-8-4-6(2-7)9-5/h5-7H,2-4H2,1H3/t5?,6-/m0/s1

Synthetic route

hydroxy-2-propanone (116-09-6) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); hydrogen bromide; hydrogen; (S)-[(5,6),(5’,6’)-bis(ethylenedioxy)biphenyl-2,2’ diyl]bis(diphenylphosphine) In ethanol; water at 60℃; under 825.083 Torr; for 1h; pH=1.34; Catalytic behavior; Pressure; Temperature; pH-value; Reagent/catalyst; Autoclave;	100%
With hydrogen; RuBr2[(S)-(C6H2OCH2CH2OP(C6H5)2)2] In methanol at 80℃; under 22501.8 Torr; for 40h;	89%
With potassium hydroxide; ammonium formate; 2-hydroxyethanethiol In water for 216h; GDH, FDH, NAD, pH = 7.5 - 8.3;	50%

(4S,1'R,2'S)-N(3)-[1'-(m-chlorobenzoyl)-2'-hydroxy-propan-1'-yl]-4-phenyl-5,5-dimethyloxazolidin-2-one (1067232-34-1) → (S)-1,2-Propanediol (4254-15-3) + (4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one (168297-84-5)

Conditions	Yield
With sodium tetrahydroborate In methanol for 0.166667h;	A 37% B 99%

(S)-Ethyl lactate (687-47-8) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 0.5h; Heating;	97%
Stage #1: (S)-Ethyl lactate With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 4h; Stage #2: With water In tetrahydrofuran; diethyl ether at 0℃;	86%
With lithium aluminium tetrahydride In diethyl ether	80%

(2S)-1-(benzyloxy)propan-2-ol (13807-91-5, 89401-28-5, 103129-25-5, 85483-97-2) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol for 30h;	96%

(S)-Methyl lactate (27871-49-4) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 0 - 20℃; for 2.25h;	90%
With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 1h;
With hydrogen; Nishimura catalyst <(45.9% Rh/19.9% Pt) oxide> In methanol at 25℃; under 75007.5 Torr;	77 % Spectr.

(S)-1-triphenylmethoxypropan-2-ol (85550-19-2) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With silica gel supported sodium hydrogen sulfate In methanol; dichloromethane at 20℃;	81%

(2S)-2-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol (76946-21-9) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With hydrogenchloride In methanol for 12h;	80%

L,L-dilactide (4511-42-6) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With [RuH(CO)(BPy-tPNN*)]; hydrogen In tetrahydrofuran at 110℃; under 38002.6 Torr; for 12h; Inert atmosphere;	73%
With hydrogen In methanol at 100℃; under 112511 Torr; for 15h; Autoclave; stereoselective reaction;	80 %Chromat.

(S)-1-(9H-fluoren-9-yloxy)propan-2-ol (1369852-90-3) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol	73%

(R)-3-tosyloxy-1,2-propanediol (41274-09-3) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h;	72%

(S)-2-(benzyloxy)propan-1-ol (33106-64-8) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 1h;	70%
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 1h; Product distribution; reactions of derivatives;	70%

(S)-2-O-(4'-methoxybenzyl)propan-1,2-diol (122151-36-4) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 1h;	60%

(S)-2-(p-chlorobenzyloxy)-1-propanol (122151-37-5) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 1h;	56%

methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3) + (R)-propylene oxide (15448-47-2)

Conditions	Yield
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate; water at 0 - 20℃; for 12h;	A 50% B 48%
With [(R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminato(2-)]cobalt(III) acetate; water at 0 - 20℃; for 14h;	A 50% B 44%
With water; Cr(III)-endo,endo-2,5-diaminonorbornane-salen at 1℃; for 34h;	A 48% B 45%

methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3) + (S)-Propylene oxide (16088-62-3)

Conditions	Yield
With C72H102Co2F12N4O12P2; water at 0 - 20℃; for 2.5h; optical yield given as %ee;	A 50% B 43%
With (R,R)-N,N′-bis(3,5-di-tertbutylsalicylidene)-1,2-cyclohexanediaminocobalt(III) acetate In water at 0℃; for 14h; Inert atmosphere;	A 43% B 45%

methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With water In tetrahydrofuran at 0 - 20℃; for 18h; Catalytic behavior; Reagent/catalyst; enantioselective reaction;	49%
With (R,R)-(-)-N,N′-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminocobalt(II); water; acetic acid In toluene at 0 - 20℃;	41%
Co(Salen)/SBA-16-C8 In tetrahydrofuran; water at 9.84℃; for 28h;

L-Lactic acid (79-33-4) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran	48.6%
With lithium aluminium tetrahydride
With sulfuric acid; hydrogen; platinum(IV) oxide; rhenium(VII) oxide In water at 80℃; under 150015 Torr; for 5h; Product distribution / selectivity;	n/a
With sulfuric acid; hydrogen; platinum(IV) oxide In water at 80℃; under 150015 Torr; for 5h; Product distribution / selectivity;

methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3) + (2R)-propane-1,2-diol (4254-14-2) + (S)-Propylene oxide (16088-62-3)

Conditions	Yield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water at 20℃; for 14h;	A n/a B n/a C 46%
With water; (R,R)-[Co(salen)]2*GaCl3 at 20℃; for 3h;	A n/a B n/a C 43%
With Aspergillus niger epoxide hydrolases immobilized onto modified Eupergit C In aq. phosphate buffer; dimethyl sulfoxide at 25℃; for 4h; pH=6.5; Kinetics; Reagent/catalyst; pH-value; Enzymatic reaction; enantioselective reaction;	A n/a B n/a C 43%

methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3) + (2R)-propane-1,2-diol (4254-14-2) + (R)-propylene oxide (15448-47-2)

Conditions	Yield
With water; chiral ((substituted salen)Co)2-InCl3 at 20℃; for 2h;	A n/a B n/a C 45%
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water In tetrahydrofuran at 19.84℃; for 3h; Kinetics; Reagent/catalyst; Solvent; optical yield given as %ee; enantioselective reaction;	A n/a B n/a C 43%
With water; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; (R,R)-(salen)Co(III)(OAc) In tetrahydrofuran at 20℃; for 24h;
fluorous (R,R)-(salen)cobalt(III) In water at 25℃; for 24h; Title compound not separated from byproducts;

methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3) + (R)-propylene oxide (15448-47-2) + (S)-Propylene oxide (16088-62-3)

Conditions	Yield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; (salen)Co(III)-ZnCl2; water In dichloromethane at 19.84℃; for 3h; Kinetics; Reagent/catalyst; Solvent; optical yield given as %ee; enantioselective reaction;	A 43% B n/a C n/a
With 4CF3O3S(1-)*Co(3+)*Y(3+)*C36H52N2O2(2-); water In neat (no solvent) at 20℃; for 6h; Overall yield = 23 %; enantioselective reaction;	A n/a B n/a C n/a

(S)-1-[bis(4-methoxyphenyl)methoxy]propan-2-ol (1169946-48-8) → (S)-1,2-Propanediol (4254-15-3) + 4,4'-dianisylmethane (726-18-1)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol for 2h;	A 13% B n/a

(R)-3-iodo-1,2-propanediol (40425-15-8) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With sodium hydroxide; nickel Hydrogenation;

(S)-1-O-benzoyl-1,2-dihydroxypropane (141396-05-6) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With sodium hydroxide at 125℃;

formaldehyd (50-00-0) + methyloxirane (75-56-9, 16033-71-9) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
at 50℃; Erwaermen des Reaktionsgemisches mit Salzsaeure; dextrorotatory form;

propylene glycol (57-55-6) → (S)-1,2-Propanediol (4254-15-3)

2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester (951-98-4) → (S)-1,2-Propanediol (4254-15-3)

ethyl (S)-2-acetyloxypropanoate (20918-91-6) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating;

(S)-(-)-2-hydroxy-2,3,3-trimethylbutanoic acid (918-10-5) → (S)-1,2-Propanediol (4254-15-3)

1-Dimethylsilanyloxy-propan-2-one (141859-89-4) → (S)-1,2-Propanediol (4254-15-3) + (2R)-propane-1,2-diol (4254-14-2)

Conditions	Yield
With potassium carbonate; 1,2-bis((2R,5R)-2,5-diethylphosphoranylidene)benzene 1) CH2Cl2, 2 h, 20-25 deg C, 2) MeOH, 4 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With potassium carbonate; (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene 1) CH2Cl2, 2 h, 20-25 deg C, 2) MeOH, 4 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With potassium carbonate; (-)-1,2-bis[(2R,5R)-2,5-diisoprohylphospholano]benzene Product distribution; multistep reaction: asymmetric intramolecular hydrosilylation of hydroxyketones; other catalysts aand silylketones;

1-O-β-D-glucosyl-(2S)-propylene glycol (162427-78-3) → (S)-1,2-Propanediol (4254-15-3)

Conditions	Yield
With β-galactosidase In various solvent(s) at 35℃;

3,4-dihydro-2H-pyran (110-87-2) + (S)-1,2-Propanediol (4254-15-3) → (2S)-1-tetrahydropyranyloxy-2-hydroxypropane (81601-30-1)

Conditions	Yield
With hydrogenchloride for 24h; Product distribution; Ambient temperature; regioselective pyranylation of (S)-1,2-propanediol;	99%
With hydrogenchloride for 24h; Ambient temperature;	98%

(S)-1,2-Propanediol (4254-15-3) + carbonic acid dimethyl ester (616-38-6) → (S)-(+)-4-methyl[1,3]dioxolan-2-one (51260-39-0)

Conditions	Yield
With sodium methylate In methanol at 60 - 115℃; for 25h;	97%

(S)-1,2-Propanediol (4254-15-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (2S)-1-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-propanol (113534-13-7)

Conditions	Yield
With 1H-imidazole In dichloromethane at 0 - 20℃; for 4h;	96%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In dichloromethane for 5h; Ambient temperature;	90%
With dmap; triethylamine In dichloromethane at 22℃; for 18h;	90%

(S)-1,2-Propanediol (4254-15-3) + trityl chloride (76-83-5) → (S)-1-triphenylmethoxypropan-2-ol (85550-19-2)

Conditions	Yield
With pyridine for 7h; Ambient temperature;	93%
With triethylamine In dichloromethane at 0 - 20℃;	76%
With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide for 8h; Ambient temperature;	60%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;
With dmap; triethylamine In dichloromethane at 23℃; for 14h;

(S)-1,2-Propanediol (4254-15-3) + mono-4-methoxytrityl chloride (14470-28-1) → (R)-1-O-<(p-methoxyphenyl)diphenylmethyl>-1,2-propanediol (129247-67-2, 138247-71-9)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;	93%
With dmap; triethylamine In dichloromethane; ethyl acetate 1.) 0 deg C, 30 min, 2.) RT, 15 h;

(S)-1,2-Propanediol (4254-15-3) + C14H12I(1+)*C2F3O2(1-) → (S)-1-(((R)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)oxy)propan-2-ol

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); triethylamine; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In 1,2-dichloro-ethane at 40℃; for 24h; Inert atmosphere; Schlenk technique; diastereoselective reaction;	93%

(S)-1,2-Propanediol (4254-15-3) → (S)-(+)-4-methyl-2,2-dioxo-1,3,2-dioxathiolane (174953-30-1)

Conditions	Yield
Stage #1: (S)-1,2-Propanediol With thionyl chloride In dichloromethane at 20℃; Reflux; Inert atmosphere; Stage #2: With sodium periodate; ruthenium (III) chloride trihydrate In dichloromethane; water; acetonitrile at 0 - 20℃;	90%
With ruthenium trichloride; sodium periodate; thionyl chloride Yield given. Multistep reaction;
With ruthenium trichloride; sodium periodate; thionyl chloride 1.) CCl4, 60 deg C; 1.) CH3CN, H2O, 25 deg C; Yield given. Multistep reaction;

(S)-1,2-Propanediol (4254-15-3) + tris{2-[1-(dimethylamino)ethyl]phenyl}boroxine → 2-(2-[(1R,S)-1-(dimethylamino)ethyl]phenyl)-(4S)-4-methyl-1,3,2-dioxaborolane

Conditions	Yield
In toluene byproducts: H2O; heating equimolar amts. of the boroxine and (S)-1,2-propanediol in toluene;; concn.; distn.; elem. anal.;;	89%

(S)-1,2-Propanediol (4254-15-3) + C16H16I(1+)*C2F3O2(1-) → (S)-1-(((R)-2'-iodo-4,4',6,6'-tetramethyl-[1,1'-biphenyl]-2-yl)oxy)propan-2-ol

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); triethylamine; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In 1,2-dichloro-ethane at 40℃; for 24h; Inert atmosphere; Schlenk technique; diastereoselective reaction;	89%

(S)-1,2-Propanediol (4254-15-3) + acetic acid (64-19-7) → acetoxy bromide of S-(+)-propane-1,2-diol (10299-39-5)

Conditions	Yield
With hydrogen bromide	88%

(S)-1,2-Propanediol (4254-15-3) + acetic acid (64-19-7) → (S)-2-Acetoxypropanol (153904-73-5)

Conditions	Yield
With hydrogen bromide	87%

(S)-1,2-Propanediol (4254-15-3) + acetic acid (64-19-7) → (S)-(-)-2-acetoxy-1-bromopropane (39968-99-5) + 1-Acetoxy-2-brompropan

Conditions	Yield
With hydrogen bromide at 0 - 20℃; for 1h;	A 87% B n/a

(S)-1,2-Propanediol (4254-15-3) + methanesulfonyl chloride (124-63-0) → (S)-methylethylene bis(methanesulfonate) (270577-16-7)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h; Mesylation;	86%
With triethylamine In dichloromethane

(S)-1,2-Propanediol (4254-15-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (S)-1-(bis(4-methoxyphenyl)(phenyl)methoxy)propan-2-ol (161106-18-9)

Conditions	Yield
With diethylamine In dichloromethane	85%
With dmap In pyridine Ambient temperature;	79%

(S)-1,2-Propanediol (4254-15-3) + 8-nitro-2-(4-oxopiperidin-1-yl)-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one (1396842-55-9) → 2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one (1161233-85-7)

Conditions	Yield
Stage #1: (S)-1,2-Propanediol With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 8-nitro-2-(4-oxopiperidin-1-yl)-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one In dichloromethane for 0.333333h; Inert atmosphere;	85%

(S)-1,2-Propanediol (4254-15-3) → (S)-(-)-2-acetoxy-1-bromopropane (39968-99-5)

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; for 0.75h;	85%

(S)-1,2-Propanediol (4254-15-3) + C14H12I(1+)*C2F3O2(1-) → (S)-1-(((S)-2'-iodo-6,6'-dimethyl-[1,1'-biphenyl]-2-yl)oxy)propan-2-ol

Conditions	Yield
With copper(II) bis(trifluoromethanesulfonate); triethylamine; 2,6-bis[(4R)-5,5-dihydro-4-phenyl-2-oxazolyl]pyridine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In 1,2-dichloro-ethane at 40℃; for 24h; Inert atmosphere; Schlenk technique; enantioselective reaction;	85%

(S)-1,2-Propanediol (4254-15-3) + 2-[(diethylamino)methyl]phenyl boronic acid (95753-24-5) → 2-(2-[(diethylamino)methyl]phenyl)-(4S)-4-methyl-1,3,2-dioxaborolane

Conditions	Yield
In toluene byproducts: H2O; heating equimolar amts. of the boronic acid and (S)-1,2-propanediol in toluene;; concn.; distn.; elem. anal.;;	84%

tert-butyl (1-phenylprop-2-yn-1-yl) carbonate + (S)-1,2-Propanediol (4254-15-3) → (S)-1-(((S)-1-phenylprop-2-yn-1-yl)oxy)propan-2-ol

Conditions	Yield
Stage #1: tert-butyl (1-phenylprop-2-yn-1-yl) carbonate With 2,6-bis[(4S)-4-methyl-4,5-dihydrooxazol-2-yl]pyridine; tetrakis(acetonitrile)copper(I)tetrafluoroborate In tetrahydrofuran at 20℃; for 0.166667h; Sealed tube; Stage #2: (S)-1,2-Propanediol With triethylamine; 10-hydroxy-4a,10a-dihydrobenzo[b][1,4]benzoxaborinine In tetrahydrofuran at -20℃; for 24h; Sealed tube; stereoselective reaction;	84%

2-[(N,N-diisopropylamino)methyl]phenylboronic acid (95753-26-7) + (S)-1,2-Propanediol (4254-15-3) → 2-(2-[(diisopropylamino)methyl]phenyl)-(4S)-4-methyl-1,3,2-dioxaborolane

Conditions	Yield
In toluene byproducts: H2O; heating equimolar amts. of the boronic acid and (S)-1,2-propanediol in toluene;; concn.; distn.; elem. anal.;;	83%

(S)-1,2-Propanediol (4254-15-3) + 2,4,6-tris(2-(trifluoromethyl)-phenyl)-1,3,5,2,4,6-trioxatriborinane → (4S)-4-methyl-2-[2-(trifluoromethyl)phenyl]-1,3,2-dioxaborolane

Conditions	Yield
In toluene byproducts: H2O; heating equimolar amts. of the boroxine and (S)-1,2-propanediol in toluene;; concn.; distn.; elem. anal.;;	83%

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethylbenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (879545-38-7) + (S)-1,2-Propanediol (4254-15-3) → C3H8O2*C21H25ClO5

Conditions	Yield
In tert-butyl methyl ether at 20℃; for 24h;	83%

(S)-1,2-Propanediol (4254-15-3) + 2,4,6-tris[2-(methoxymethyl)phenyl]boroxine (95753-07-4) → 2-[2-(methoxymethyl)phenyl]-(4S)-4-methyl-1,3,2-dioxaborolane

Conditions	Yield
In toluene byproducts: H2O; heating equimolar amts. of the boroxine and (S)-1,2-propanediol in toluene;; concn.; distn.; elem. anal.;;	81%

cycl-isopropylidene malonate (2033-24-1) + bis-(4-bromo-benzylidene)-hydrazine (24523-45-3, 41097-38-5) + (S)-1,2-Propanediol (4254-15-3) → 7,14-bis(4-bromophenyl)-2,11,11-trimethyl-1,4,10,12-tetraoxadispiro[4.2.5.2]pentadecane-9,13-dione

Conditions	Yield
With acetic acid at 80℃; for 8h;	81%

Upstream product

• 141859-89-4 1-Dimethylsilanyloxy-propan-2-one 
• 79-33-4 L-Lactic acid 
• 141396-05-6 (S)-1-O-benzoyl-1,2-dihydroxypropane 
• 40425-15-8 (R)-3-iodo-1,2-propanediol 
• 687-47-8 (-)-ethyl lactate 
• 41274-09-3 (R)-3-tosyloxy-1,2-propanediol 
• 57-55-6 propylene glycol 
• 100-52-7 benzaldehyde 
• 16088-62-3 (S)-Propylene oxide 
• 4511-42-6 L,L-dilactide 
• 1369852-90-3 (S)-1-(9H-fluoren-9-yloxy)propan-2-ol 
• 75-56-9 methyloxirane 
• 85550-19-2 (S)-1-triphenylmethoxypropan-2-ol 
• 17392-83-5 (R)-Methyl lactate 

Downstream Products

• 50980-84-2 propane-1,2-diol dibutyrate 
• 71232-79-6 1-Brom-2-benzoyloxypropan 
• 81601-30-1 (2S)-1-tetrahydropyranyloxy-2-hydroxypropane 
• 33106-64-8 (S)-2-(benzyloxy)propan-1-ol 
• 87037-69-2 (R)-2-(benzyloxy)propan-1-ol 
• 13807-91-5 (2S)-1-(benzyloxy)propan-2-ol 
• 85550-19-2 (S)-1-triphenylmethoxypropan-2-ol 
• 123-38-6 propionaldehyde 
• 262423-83-6 (S)-2-hydroxy-propyl methanesulfonate 
• 16088-60-1 1-bromo-2(S)-hydroxypropane 
• 134236-23-0 (S)-1,2-diacetoxypropane 
• 51260-39-0 (S)-(+)-4-methyl[1,3]dioxolan-2-one 
• 51293-27-7 -1-Trityloxy-2-propyltosylat 

Relevant articles and documents

Stereochemistry of Nucleophilic Displacement on Two Phosphoric Monoesters and a Phosphoguanidine: The Role of Metaphosphate

For the role of monomeric metaphosphate and the nature of the transition states in the alcoholysis of phosphoric monoesters to be examined, phenyl phosphate and 2,4-dinitrophenyl phosphate have been synthesized and the stereochemical course of the methanolysis of phenyl phosphate monoanion and of dinitrophenyl phosphate dianion has been evaluated. Phosphocreatine has also been synthesized and the stereochemical course of the methanolysis of this molecule determined.In each case, complete inversion of configuration at phosphorus is observed.It is clear that metaphosphate, if it exists as a true intermediate in these reactions in protic solvent, does not leave the solvent cage in which it is generated.Indeed, product formation occurs more rapidly than rotation of the putative metaphosphate intermediate.These displacements must therefore occur by preassociative mechanisms in which there may be some assistance from the incoming nucleophile.The present results do not allow a distinction to be made between a "preassociative concerted" path (that is, an SN2-like displacement via a very loose transition state) and a "preassociative stepwise" path via a metaphosphate intermediate of very short lifetime.

THE CONFIGURATIONS OF (-)-2,3,3-TRIMETHYL-2-HYDROXYBUTANOIC ACID, Me3CC(Me)(OH)CO2H, (-)-3,3,4-TRIMETHYL-3-HYDROXY-1-PENTYNE AND (-)-3-t-BUTYL-3-METHYL-1-CHLOROALLENE

The configurations of the title compounds are reassigned, based on stereoselective syntheses of the hydroxyacid and corresponding glycol and application of Cram's, Prelog's and Sharpless' rules.

Mild electrocatalytic hydrogenation of lactic acid to lactaldehyde and propylene glycol

Reduction of fermentation-derived lactic acid (LA) offers a renewables-based pathway to propylene glycol (PG), a large-scale commodity chemical, currently manufactured by the oxidation of petroleum-derived propene. Complementing our previously described catalytic hydrogenation of LA to PG, we now report electrocatalytic hydrogenation (ECH) of LA in an aqueous electrolyte using constant current electrolysis. A reticulated vitreous carbon (RVC) electrode serves to agglomerate, support, and supply current to a 5% Ru/C powder catalyst, the same catalyst used in the classical hydrogenations. The ECH conditions are mild (ambient pressure, 70 °C vs 1500 psi H2, 150 °C) relative to the chemical hydrogenation. More surprisingly, the major electrohydrogenation product is lactaldehyde (LAL), with small quantities of PG also formed. Variable current studies in the range of 10-100 mA show an increase in product yields and a shift in selectivity toward PG with increasing current. Experiments carried out with different acids as electrolytes reveal a distinct effect of the anion on the yields of the two products. In situ ATR-FTIR studies of the ECH of LA point to a chelating bidentate carboxylate adsorption mode for lactate on the Ru surface and offer insight into the effects of electrolyte anions on surface adsorption and reactivity.

Enantiodivergent syntheses of (+)- and (?)-1-(2,6-dimethylphenoxy)propan-2-ol: A way to access (+)- and (?)-mexiletine from D-(+)-mannitol

Chiron approach was used to acquire optically pure (R)- and (S)-1-(2,6-dimethylphenoxy)propan-2-ol, immediate precursors of (S)- and (R)-mexiletines, respectively. Two different routes were followed from a D-mannitol-derived optically pure common precursor to get the enantiomeric alcohols separately. Comparison of their specific rotation values with the corresponding literature values as well as exact mirror-image relationship between their CD curves proved their high enantiopurity. These alcohols were then transformed to the corresponding amine-drugs in an efficient one-step process instead of two steps described in the literature.

Kinetic Resolution of 1,2-Diols via NHC-Catalyzed Site-Selective Esterification

A kinetic resolution of 1,2-diols bearing both a secondary and a primary alcohol motif through an N-heterocyclic carbene-catalyzed oxidative acylation reaction has been developed. A site- and enantioselective esterification reaction is involved for this process. Both the monoacylated diols obtained and the remaining enantioenriched 1,2-diols are versatile building blocks for the preparation of functional molecules with proven biological activities.