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
A
(S)-1,2-Propanediol
B
(4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol for 0.166667h; | A 37% B 99% |
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
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol for 30h; | 96% |
(S)-Methyl lactate
(S)-1,2-Propanediol
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
(S)-1,2-Propanediol
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
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 12h; | 80% |
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
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol | 73% |
(R)-3-tosyloxy-1,2-propanediol
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 4h; | 72% |
(S)-2-(benzyloxy)propan-1-ol
(S)-1,2-Propanediol
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
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 1h; | 60% |
(S)-2-(p-chlorobenzyloxy)-1-propanol
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 1h; | 56% |
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% |
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
(S)-1,2-Propanediol
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; |
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
A
(S)-1,2-Propanediol
B
(2R)-propane-1,2-diol
C
(S)-Propylene oxide
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
A
(S)-1,2-Propanediol
B
(2R)-propane-1,2-diol
C
(R)-propylene oxide
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
A
(S)-1,2-Propanediol
B
(R)-propylene oxide
C
(S)-Propylene oxide
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
A
(S)-1,2-Propanediol
B
4,4'-dianisylmethane
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol for 2h; | A 13% B n/a |
(R)-3-iodo-1,2-propanediol
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With sodium hydroxide; nickel Hydrogenation; |
(S)-1-O-benzoyl-1,2-dihydroxypropane
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With sodium hydroxide at 125℃; |
Conditions | Yield |
---|---|
at 50℃; Erwaermen des Reaktionsgemisches mit Salzsaeure; dextrorotatory form; |
ethyl (S)-2-acetyloxypropanoate
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether for 1h; Heating; |
1-Dimethylsilanyloxy-propan-2-one
A
(S)-1,2-Propanediol
B
(2R)-propane-1,2-diol
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
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With β-galactosidase In various solvent(s) at 35℃; |
3,4-dihydro-2H-pyran
(S)-1,2-Propanediol
(2S)-1-tetrahydropyranyloxy-2-hydroxypropane
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
carbonic acid dimethyl ester
(S)-(+)-4-methyl[1,3]dioxolan-2-one
Conditions | Yield |
---|---|
With sodium methylate In methanol at 60 - 115℃; for 25h; | 97% |
(S)-1,2-Propanediol
tert-butyldimethylsilyl chloride
(2S)-1-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-2-propanol
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% |
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
mono-4-methoxytrityl chloride
(R)-1-O-<(p-methoxyphenyl)diphenylmethyl>-1,2-propanediol
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
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
(S)-(+)-4-methyl-2,2-dioxo-1,3,2-dioxathiolane
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
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
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
acetic acid
acetoxy bromide of S-(+)-propane-1,2-diol
Conditions | Yield |
---|---|
With hydrogen bromide | 88% |
Conditions | Yield |
---|---|
With hydrogen bromide | 87% |
Conditions | Yield |
---|---|
With hydrogen bromide at 0 - 20℃; for 1h; | A 87% B n/a |
(S)-1,2-Propanediol
methanesulfonyl chloride
(S)-methylethylene bis(methanesulfonate)
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1h; Mesylation; | 86% |
With triethylamine In dichloromethane |
(S)-1,2-Propanediol
4,4'-dimethoxytrityl chloride
(S)-1-(bis(4-methoxyphenyl)(phenyl)methoxy)propan-2-ol
Conditions | Yield |
---|---|
With diethylamine In dichloromethane | 85% |
With dmap In pyridine Ambient temperature; | 79% |
(S)-1,2-Propanediol
8-nitro-2-(4-oxopiperidin-1-yl)-6-(trifluoromethyl)-4H-benzo[e][1,3]thiazin-4-one
2-[(2S)-2-methyl-1,4-dioxa-8-azaspiro[4.5]dec-8-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one
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
(S)-(-)-2-acetoxy-1-bromopropane
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid at 20℃; for 0.75h; | 85% |
(S)-1,2-Propanediol
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
2-[(diethylamino)methyl]phenyl boronic acid
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% |
(S)-1,2-Propanediol
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
(S)-1,2-Propanediol
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
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
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
In tert-butyl methyl ether at 20℃; for 24h; | 83% |
(S)-1,2-Propanediol
2,4,6-tris[2-(methoxymethyl)phenyl]boroxine
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
bis-(4-bromo-benzylidene)-hydrazine
(S)-1,2-Propanediol
Conditions | Yield |
---|---|
With acetic acid at 80℃; for 8h; | 81% |
IUPAC Name:propane-1,2-diol
Molecular Formula:C3H8O2
Molecular Weight:76.094420 g/mol
Appearance:clear colorless liquid
Melting Point:-59 °C
Boiling Point:186-188 °C at 765 mm Hg(lit.)
Flash Point:225 °F
Solubility:water
alpha:16 °(c=neat)
density:1.036 g/mL at 20 °C(lit.)
refractive index:n20/D 1.432(lit.)
Sensitive:Hygroscopic
Merck:14,7855
BRN:1718871
Synonyms of S-1,2-Propanediol(4254-15-3):
(S)-(+)-Propane-1,2-diol;(S)-Propane-1,2-diol;L-(+)-PROPYLENE GLYCOL;(S)-(+)-PROPANEDIOL;(S)-(+)-PROPYLENE GLYCEROL;(S)-(+)-PROPYLENE GLYCOL;(S)-(+)-1,2-DIHYDROXYPROPANE;(S)-(+)-1,2-PROPANEDIOL;(S)-(+)-1,2-Propanediol
Categories of S-1,2-Propanediol(4254-15-3):
Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Compound
First Aid Measures of S-1,2-Propanediol(4254-15-3):
Eyes:Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:Get medical aid. Wash mouth out with water.
Inhalation:Remove from exposure and move to fresh air immediately.
Storage of S-1,2-Propanediol(4254-15-3):
Store in a cool, dry place. Store in a tightly closed container.
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