60827-45-4

Basic information

• Product Name: (S)-(+)-3-Chloro-1,2-propanediol
• Synonyms: 1,2-PROPANEDIOL, 3-CHLORO-, (2S)-;GLYCEROL (S)-(+)-ALPHA-MONOCHLOROHYDRIN;(S)-α-Glycerol chlorohydrin ;Chloropropanediol,97%;(S)-3-CHLORO-1,2-PROPANDIOL;S-Chloropropanediol;(s)-3-chloro-2-propanedio;(S)-(+)-3-CHLORO-1,2-PROPANEDIOL , EE 98%
• CAS NO: 60827-45-4
• Molecular Formula: C₃H₇ClO₂
• Molecular Weight: 110.54
• EINECS: 202-492-4
• Product Categories: Chiral Compounds;Diols;chiral;API intermediates;Chiral Compound
• Mol File: 60827-45-4.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 213 °C(lit.)
• Flash Point: >230 °F
• Appearance: very deep yellow/
• Density: 1.322 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0374mmHg at 25°C
• Refractive Index: n20/D 1.480(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 13.28±0.20(Predicted)
• Water Solubility: Completely miscible in water
• BRN: 2202929
• CAS DataBase Reference: (S)-(+)-3-Chloro-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-3-Chloro-1,2-propanediol(60827-45-4)
• EPA Substance Registry System: (S)-(+)-3-Chloro-1,2-propanediol(60827-45-4)

Safety Data

• Hazard Codes: T
• Statements: 21-25-41-68-62-36/37/38-23/25
• Safety Statements: 26-28-39-45-36/37/39
• RIDADR: UN 2689 6.1/PG 3
• WGK Germany: 3
• RTECS: TY4202300
• F: 3-10
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 60827-45-4(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to orange-yellow liquid

InChI:InChI=1/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2/t3-/m1/s1

Synthetic route

(S,S)-Co(salen) + 1-methoxy-2-propanol (107-98-2) + epichlorohydrin (106-89-8) + 4-nitro-benzoic acid (62-23-7) → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
In water	99%

3-chloroprop-1-ene (107-05-1) → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
In Na4e(CN)610H2; water; ethyl acetate; toluene	66.8%

barium D-3-chloropropane-1,2-diol-1-phosphate → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With Dowex-50; sodium carbonate; alkaline phosphatase In water for 0.5h; Ambient temperature;	57%

2,3-Dichloro-1-propanol (616-23-9) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4) + (S)-1,3-dichloro-1-propanol + epichlorohydrin (106-89-8)

Conditions	Yield
With epoxide hydrolase from Agrobacterium radiobacter AD1; halohydrin dehalogenase from Agrobacterium radiobacter AD1; Tris-SO4 buffer In water at 30℃; for 20h; pH=7.5; kinetic resolution; Further byproducts given;	A n/a B n/a C 49.5% D n/a

epichlorohydrin (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With water; dimeric chiral (salen)Co complex linked with Al at 20℃; for 5h; Product distribution; Further Variations:; Catalysts;	A 46% B n/a C n/a
With water; Cr(III)-endo,endo-2,5-diaminonorbornane-salen In tetrahydrofuran at 20℃; for 42h;	A 46% B n/a C n/a
With chiral oligo-(salen)Co(OTs) complexes; lutidinium p-toluene sulfonate; water In dichloromethane; acetonitrile at 20℃; for 11h;	A 45% B n/a C n/a

epichlorohydrin (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With (S,S)-salen-Co(III)-OAc complex; H2O (dist.) at 0℃; for 14h;	A 46% B 45%
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water In tetrahydrofuran at 0 - 4℃; for 16h;	A 43% B n/a
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water at 5℃; for 5h;
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water enantioselective reaction;

epichlorohydrin (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water In tetrahydrofuran at 0 - 20℃;	A 43% B n/a C n/a
With (S,S)-(salen)Co(III)-OTs; water at 0 - 4℃; for 16h;	A 42.3% B n/a C n/a
With poly-salen-Co(III); water In tetrahydrofuran at 10℃; for 12h;
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water In tetrahydrofuran at 0 - 20℃; Title compound not separated from byproducts;

epichlorohydrin (106-89-8) → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With Jacobsen's catalyst; water; acetic acid In tetrahydrofuran at 0 - 4℃; for 12h;	43%

1-O-β-D-glucosyl-(2S)-3-chloropropylene glycol → (S)-3-chloropropan-1,2-diol (60827-45-4)

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

barium D-3-chloropropane-1,2-diol-1-phosphate → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With ethanol Yield given. Yields of byproduct given;

3-monochloro-1,2-propanediol (96-24-2) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4) + D-3-chloropropane-1,2-diol-1-phosphate

Conditions	Yield
With sodium hydroxide; phospho(enol)pyruvic acid mono potassium salt; ATP; 2-hydroxyethanethiol; magnesium chloride In water at 27℃; for 120h; pH=7.5; Yield given. Yields of byproduct given;

3-monochloro-1,2-propanediol (96-24-2) → (S)-3-chloropropan-1,2-diol (60827-45-4)

(S)-1,2-Diacetoxy-3-chloropropane (78692-88-3) → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With sodium methylate In methanol for 4h; Ambient temperature;

1,2-diacetoxy-3-chloro-propane (869-50-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With porcine pancreatic lipase; sodium methylate 1) H2O (pH:7), r.t., 2) MeOH, r.t., 4h; Multistep reaction;

(S)-1,2-Diacetoxy-3-chloropropane (78692-88-3) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With sulfuric acid for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3-chloroprop-1-ene (107-05-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); 1,4-bis(dihydroquinidinyl)anthraquinone In water; tert-butyl alcohol at 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With dihydrogen peroxide In acetonitrile at 25℃; for 0.416667h; Title compound not separated from byproducts.;

3-monochloro-1,2-propanediol (96-24-2) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With sodium hydroxide; sodium azide; acid phosphatase; pyruvate kinase; phosphoenolpyruvic acid; glycerol kinase from Streptomyces canus; potassium chloride; ATP; 2-hydroxyethanethiol; magnesium chloride 1.) H2O, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given;

epichlorohydrin (106-89-8) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With polistyrene-bound (R,R)-N-(3,5-di-t-butyl-6-hydroxy)benzylidene-N'-(3-t-butyl-2,5-dihydroxy)benzylidene-1,2-cyclohexanediamine; water In dichloromethane for 3h; Ambient temperature; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
With water Jacobsen kinetic hydrolytic resolution;
Stage #1: epichlorohydrin With phthalic anhydride; C64H74Al2Cl2N4O4; bis(triphenylphosphine)iminium chloride In toluene at 25℃; for 3h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere; enantioselective reaction;	A n/a B n/a

epichlorohydrin (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With water; poly(Co(III)(OTs)-salen-norbornene) In chlorobenzene at 20℃; for 0.5h; Product distribution; Further Variations:; Catalysts; reaction times;
Co(Salen)/SBA-16-C8 In tetrahydrofuran; water at 24.84℃; for 20h;
With C118H146Co2N4O14S2; water In acetonitrile at 20℃; optical yield given as %ee; enantioselective reaction;

N-(tert-butyloxycarbonyl)(2-trimethylsilylethyl)sulfonamide (145387-82-2) + epichlorohydrin (106-89-8) → (S)-3-chloropropan-1,2-diol (60827-45-4) + C13H28ClNO5SSi

Conditions	Yield
Stage #1: epichlorohydrin With water; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate In tetrahydrofuran at 0℃; for 3h; Stage #2: N-(tert-butyloxycarbonyl)(2-trimethylsilylethyl)sulfonamide In tetrahydrofuran at 0℃; for 3h;

N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide (198572-71-3) + epichlorohydrin (106-89-8) → (S)-3-chloropropan-1,2-diol (60827-45-4) + C14H19ClN2O7S

Conditions	Yield
Stage #1: epichlorohydrin With water; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate In tetrahydrofuran at 0 - 20℃; for 24h; Stage #2: N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide In tetrahydrofuran at 20℃; for 24h;

3-chloro-1-hydroxypropan-2-one (24423-98-1) → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With Serratia-derived glycerol dehydrogenase; NADH at 30℃; for 2h; pH=6.5; Aqueous phophate buffer; Enzymatic reaction;	n/a
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction;	n/a
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction;	n/a

3-chloro-1-hydroxypropan-2-one (24423-98-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction;	A n/a B n/a
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction;	A n/a B n/a
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction;	A n/a B n/a

(S)-epichlorohydrin (67843-74-7) → (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
Stage #1: With N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediaminocobalt(II); camphor-10-sulfonic acid; oxygen In tetrahydrofuran for 1h; Stage #2: (S)-epichlorohydrin With water In tetrahydrofuran at 20℃; for 20h;	95.4 %Chromat.

(S)-3-chloropropan-1,2-diol (60827-45-4) → (2RS,4S)-2-oxo-4-chloromethyl-1,3,2-dioxathiolane (146864-19-9)

Conditions	Yield
With thionyl chloride In tetrachloromethane for 2h; Reflux; Inert atmosphere;	100%
With thionyl chloride In dichloromethane for 2h;	94%
With thionyl chloride In tetrachloromethane for 2h; Inert atmosphere; Reflux;	89%

(S)-3-chloropropan-1,2-diol (60827-45-4) + 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-16-1) → C13H12Cl3N3O2

Conditions	Yield
With trifluorormethanesulfonic acid In toluene at 80℃; for 6h; Reagent/catalyst; Temperature;	99.7%

(S)-3-chloropropan-1,2-diol (60827-45-4) + C8H16B10O → C11H22B10O3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere;	97%

dmap (1122-58-3) + (S)-3-chloropropan-1,2-diol (60827-45-4) → (R)-(+)-1-(2,3-dihydroxypropyl)-4-(dimethylamino)pyridinium chloride (942209-56-5)

Conditions	Yield
In acetonitrile at 65℃; for 24h;	95%

(S)-3-chloropropan-1,2-diol (60827-45-4) + trimethylamine (75-50-3) → (R)-2,3-dihydroxypropyltrimethylammonium chloride

Conditions	Yield
In water at 90℃; for 16h;	90.5%

(S)-3-chloropropan-1,2-diol (60827-45-4) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → (2S,3S)-5-chloromethyl-2,3-dimethoxy-2,3-dimethyl-[1,4]dioxane (371160-90-6)

Conditions	Yield
With camphor-10-sulfonic acid In methanol for 1.5h; Heating;	90%
With camphor-10-sulfonic acid In methanol for 2h; Heating;

(S)-3-chloropropan-1,2-diol (60827-45-4) + 4-hydroxy-benzaldehyde (123-08-0) → C10H12O4

Conditions	Yield
With potassium carbonate; potassium iodide In acetonitrile for 12h; Reflux;	86%
With potassium carbonate; potassium iodide In acetonitrile for 12h; Reflux;	80%

heptatriaconta-6,9,28,31-tetraen-19-one + (S)-3-chloropropan-1,2-diol (60827-45-4) → 4-(S)-4-chloromethyl-2,2-di-octadeca-9,12-dienyl-[1,3]dioxolane

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 96h; Reflux; Water removal;	85%

(S)-3-chloropropan-1,2-diol (60827-45-4) + orthoformic acid triethyl ester (122-51-0) + dimethylglyoxal (431-03-8) → (2S,3S,5S)-5-chloromethyl-2,3-diethoxy-2,3-dimethyl-[1,4]dioxane

Conditions	Yield
With camphor-10-sulfonic acid In ethanol for 2h; Reflux;	85%

(S)-3-chloropropan-1,2-diol (60827-45-4) + trans-[3-fluoro-4-(1-oxo-tetrahydrothiopyran-4-yl)phenyl]carbamic acid isobutyl ester (288570-80-9) → [4(R)-trans]-3-[3-fluoro-4-(tetrahydro-1-oxido-2H-thiopyran-4-yl)phenyl]-5-(hydroxymethyl)-2-oxazolidinone (288570-88-7)

Conditions	Yield
With 2-methylbutan-2-ol (lithium salt) In N,N-dimethyl-formamide Alkylation; cyclization;	84%

4-Fluorophenol (371-41-5) + (S)-3-chloropropan-1,2-diol (60827-45-4) → (+)-(S)-3-(4-fluorophenoxy)-1,2-propanediol (104605-96-1)

Conditions	Yield
Stage #1: 4-Fluorophenol With sodium hydroxide In ethanol for 0.25h; Reflux; Heating; Stage #2: (S)-3-chloropropan-1,2-diol In ethanol for 16h; Reflux;	84%

(S)-3-chloropropan-1,2-diol (60827-45-4) + 2-methoxy-phenol (90-05-1) → (S)-guaifenesin (61248-76-8)

Conditions	Yield
	77%
With sodium hydroxide In N,N-dimethyl-formamide at 210℃; for 0.25h; Microwave irradiation;	64%
Stage #1: 2-methoxy-phenol With sodium hydroxide In ethanol; water Heating; Stage #2: (S)-3-chloropropan-1,2-diol In ethanol; water Heating;	63%

(S)-3-chloropropan-1,2-diol (60827-45-4) + ortho-cresol (95-48-7) → (S)-(-)-3-(2-methylphenoxy)propane-1,2-diol (59-47-2, 52153-43-2, 118205-96-2, 52153-44-3)

Conditions	Yield
Stage #1: ortho-cresol With sodium hydroxide In ethanol; water for 0.5h; Reflux; Stage #2: (S)-3-chloropropan-1,2-diol In ethanol; water for 3h; Reflux;	77%

2-(4-methylamino-phenyl)-benzofuran-5-ol + (S)-3-chloropropan-1,2-diol (60827-45-4) → (S)-3-((2-(4-(methylamino)phenyl)benzofuran-5-yl)oxy)propane-1,2-diol

Conditions	Yield
Stage #1: 2-(4-methylamino-phenyl)-benzofuran-5-ol With sodium hydroxide In ethanol; water at 80℃; for 1h; Stage #2: (S)-3-chloropropan-1,2-diol In ethanol; water at 80℃; for 3h;	76.2%

3,4-dihydro-2H-pyran (110-87-2) + (S)-3-chloropropan-1,2-diol (60827-45-4) → (S)-1-Chloro-3-(tetrahydro-pyran-2-yloxy)-propan-2-ol

Conditions	Yield
bismuth(III) nitrate In dichloromethane at 20℃; for 0.3h;	76%

Upstream product

• 616-23-9 2,3-Dichloro-1-propanol 
• 106-89-8 epichlorohydrin 
• 107-98-2 1-methoxy-2-propanol 
• 62-23-7 4-nitro-benzoic acid 
• 67843-74-7 (S)-epichlorohydrin 
• 24423-98-1 3-chloro-1-hydroxypropan-2-one 
• 107-05-1 3-chloroprop-1-ene 
• 198572-71-3 N-(tert-butoxycarbonyl)-2-nitrobenzenesulfonamide 
• 145387-82-2 N-(tert-butyloxycarbonyl)(2-trimethylsilylethyl)sulfonamide 
• 96-24-2 3-monochloro-1,2-propanediol 
• 78692-88-3 (S)-3-chloro-1,2-diacetoxypropane 
• 869-50-1 1,2-diacetoxy-3-chloro-propane 

Downstream Products

• 444335-16-4 (R)-3-(4-bromo-3-fluorophenyl)-5-(hydroxylmethyl)oxazolidin-2-one 
• 666234-81-7 (R)-3-(N,N-dimethylamino)propane-1,2-diol 
• 97798-48-6 (S)-(2,3-dihydroxypropyl) phenyl sulfide 
• 119702-04-4 (S)-3-(2-hydroxyphenoxy)propane-1,2-diol 
• 1012305-73-5 (2S)-3-(4-(4-fluorophenyl)-5-(2-(isopropylamino)pyridin-4-yl)-1H-imidazol-2-ylthio)propane-1,2-diol 
• 1012305-71-3 (2S)-3-(4-(4-fluorophenyl)-5-(2-(3-methylbutan-2-ylamino)pyridin-4-yl)-1H-imidazol-2-ylthio)propane-1,2-diol 
• 56715-37-8 (2S)-1-(2-cyanophenoxy)-2,3-propanediol 
• 70987-78-9 (S)-Glycidyl tosylate 
• 82079-44-5 D-β-Chlorolactic acid 
• 487041-52-1 4(R)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-thiopran-4-yl)phenyl]-5-(hydroxymethyl)-2-oxazolidinone 
• 148460-02-0 (S)-3-(4-cyanophenoxy)-propane-1,2-diol 

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