51594-55-9

Basic information

• Product Name: (R)-(-)-Epichlorohydrin
• Synonyms: (R)-3-Chloro-1,2-epoxypropane;2-(Chlorometyl)oxirane;R(-)-2-(CHLOROMETHYL)OXIRANE;(R)-(-)-1-CHLORO-2,3-EPOXYPROPANE;(R)-1-CHLORO-2,3-EPOXYPROPANE;(R)-(-)-CHLOROMETHYLOXIRANE;(R)-CHLOROMETHYLOXIRANE;(R)-(-)-EPICHLOROHYDRIN
• CAS NO: 51594-55-9
• Molecular Formula: C₃H₅ClO
• Molecular Weight: 92.52
• EINECS: 424-280-2
• Product Categories: Industrial/Fine Chemicals;Methyl Halides;chiral;CHIRAL COMPOUNDS;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Oxiranes;Simple 3-Membered Ring Compounds;Synthetic Organic Chemistry;Chiral Compound;Methyl Halides;Ring Systems;Chiral Reagents;Heterocycles;Mutagenesis Research Chemicals
• Mol File: 51594-55-9.mol
• Article Data: 52

Chemical Properties

• Melting Point: -48°C
• Boiling Point: 114 °C(lit.)
• Flash Point: 33 °C
• Appearance: Clear colorless to very pale yellow/Liquid
• Density: 1.180 g/mL at 20 °C(lit.)
• Vapor Density: 3.29 (vs air)
• Vapor Pressure: 10 mm Hg ( 16.6 °C)
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: 2-8°C
• Explosive Limit: 21%
• Water Solubility: insoluble
• Merck: 14,3532
• BRN: 1420785
• CAS DataBase Reference: (R)-(-)-Epichlorohydrin(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-Epichlorohydrin(51594-55-9)
• EPA Substance Registry System: (R)-(-)-Epichlorohydrin(51594-55-9)

Safety Data

• Hazard Codes: T
• Statements: 45-10-23/24/25-34-43
• Safety Statements: 53-45
• RIDADR: UN 2023 6.1/PG 2
• WGK Germany: 3
• RTECS: RR0427000
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 51594-55-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to light yellow liqui

Uses

Different sources of media describe the Uses of 51594-55-9 differently. You can refer to the following data:
1. ((R)-Epichlorohydrin) R-enantiomer of Epichlorohydrin, an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA cross-links. It is used as a solvent for natural and synthetic resins, gums, cellulose esters and ethers, paints, varnishes, nail enamels and lacquers, cement for Celluloid. Also, it is used as stabilizer.
2. Building block for the synthesis of a key intermediate in the synthesis of stable PGI2 analogue UT-15.

InChI:InChI=1/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m0/s1

Synthetic route

(S)-1-Acetoxy-2-bromo-3-chloropropane → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With dmap; potassium carbonate In ethylene glycol at 30℃; for 0.333333h; Epoxidation;	95%

(R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate (83398-53-2) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With sodium ethane-1,2-diolate In ethylene glycol for 0.25h; Ambient temperature;	85%

3-chloro-2-hydroxypropyl methanesulfonate → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With sodium In ethylene glycol Ambient temperature;	85%

epichlorohydrin (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; water at 0 - 20℃;	82%
With water; [(1-SS)-(Dibenzoyl-DTA)] at 5 - 20℃; for 3h; Product distribution / selectivity; Resolution of racemate;	80%
Stage #1: epichlorohydrin With water; (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate at 5℃; for 4.5h; Stage #2: With ascorbic acid at 20℃; for 0.5h;	38.5%

(R)-glycidyl tosylate (113826-06-5) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With hydrogenchloride for 24h; Ambient temperature;	54%

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) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9) + 1,3-Dichloro-2-propanol (96-23-1)

Conditions	Yield
With hydrogenchloride; tert-butyl methyl ether; dimeric chiral (salen)Co complex linked with Al In diethyl ether at 0 - 5℃; for 2h; Product distribution; Further Variations:; Catalysts;	A n/a B n/a C 45%

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

Conditions	Yield
With water at 20℃; for 8h; optical yield given as %ee;	A 45% B n/a

(R)-2,3-dichloroprop-1-yl butyrate → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With potassium hydroxide In methanol for 1h; Ambient temperature;	43%

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)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate; (salen)Co(III)-AlCl3; 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 41%
With C8F17COOH; water; (R,R)-Co(III)(salen) In toluene at 20℃; for 15h;	A n/a B n/a C 40%
With chiral oligo-(salen)Co(OTs) complexes; lutidinium p-toluene sulfonate; water In dichloromethane; acetonitrile at 0 - 20℃; for 1.5h;	A n/a B n/a C 40%

epichlorohydrin (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With Agromyces mediolanus ZJB120203 epoxide hydrolase Resolution of racemate; enantioselective reaction;	A 21.5% B n/a
enantiomeric resolution by complexation gas chromatography on nickel(II)bis<(1R)-3-(heptafluorobutyryl)camphorate>;
With water; C6H15N*C44H61CoN2O10 at 5 - 20℃; for 3 - 9h; Product distribution / selectivity; Resolution of racemate;

2,3-Dichloro-1-propanol (616-23-9) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With potassium carbonate In dichloromethane at 25℃; for 144h; Product distribution; Mechanism; study of asymmetric cyclization using optically active Co(II)(Sal)2(R-CHXDA) type catalyst;

1,3-Dichloro-2-propanol (96-23-1) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With potassium carbonate; Co(II)(3,5-Cl,Cl-sal)2(S-CHXDA) (e.e. 1.) 130-150 deg C, 3 hr in vacuo; 2.) CH2Cl2, 25 deg C, 6 days; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With potassium carbonate In dichloromethane at 25℃; Product distribution; Mechanism; study of asymmetric cyclization using different optically active cobalt (salen) or nickel (salen) type complexes;
With potassium phosphate; [(R,R)-(salen)Co(II)]2*Al(NO3)3 In tetrahydrofuran at 20℃; for 3h;

(S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate) (67800-61-7) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With sodium 2-hydroxyethoxide In ethylene glycol for 0.0833333h; Title compound not separated from byproducts;

(S)-1-bromo-3-chloro-2-propyl acetate (95548-93-9) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With disodium 1,2-ethanedithiolate In ethylene glycol for 0.25h; Yield given;

(1S,2R,4R,4'R)-4'-Chloromethyl-4,7,7-trimethylbicyclo<2.2.1>heptane-2-spiro-2'-(1',3'-dioxolan)-3-one (95589-30-3) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With hydrogen bromide; sodium 2-hydroxyethoxide 1.) AcOH, 60 deg C, 5 h,; Yield given. Multistep reaction;

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;

epichlorohydrin (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9) + 1,3-Dichloro-2-propanol (96-23-1) + (2S)-1-azido-3-chloropropan-2-ol (681225-50-3) + (2R)-1-azido-3-chloropropan-2-ol (180587-77-3)

Conditions	Yield
With sodium azide; sodium acetate buffer; Agrobacterium radiobacter AD1 haloalcohol dehalogenase at 22℃; pH=4.5; Product distribution; Further Variations:; pH-values;

3-chloroprop-1-ene (107-05-1) → (R)-(-)-epichlorohydrin (51594-55-9)

Conditions	Yield
With tert.-butylhydroperoxide; Caldariomyces fumago chloroperoxidase at 20℃; for 1h; pH=5.5; aq. phosphate buffer; Ionic liquid; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	88.8 %Chromat.

carbon dioxide (124-38-9) + epichlorohydrin (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9) + (S)-4-(chloromethyl)-1,3-dioxolan-2-one (99968-48-6) + (R)-4-(chloromethyl)-1,3-dioxolan-2-one (99968-49-7)

Conditions	Yield
With tetrabutyl ammonium fluoride at 25℃; under 6000.6 Torr; for 8h; Autoclave; enantioselective reaction;	A n/a B n/a C n/a

aniline (62-53-3) + epichlorohydrin (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9) + (S)-(+)-1-chloro-3-(phenylamino)-propan-2-ol (195455-97-1) + (R)-(+)-N-(3-chloro-2-hydroxypropyl)aniline (195455-98-2)

Conditions	Yield
Stage #1: epichlorohydrin With C65H56CoN3O8 In dichloromethane at 27 - 28℃; for 0.166667h; Stage #2: aniline In dichloromethane at 27 - 28℃; enantioselective reaction;	A n/a B n/a C n/a D n/a

(R)-(-)-epichlorohydrin (51594-55-9) + n-heptylmagnesium bromide (13125-66-1) → (R)-1-chloro-2-decanol (261160-96-7)

Conditions	Yield
With CuCN In tetrahydrofuran at 0℃; for 2h; Grignard reaction;	100%
With copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -20℃;
With CuCN

potassium cyanate (590-28-3) + (R)-(-)-epichlorohydrin (51594-55-9) → (5R)-5-(chloromethyl)-1,3-oxazolidin-2-one (169048-79-7)

Conditions	Yield
In water for 15h; Heating;	100%
With magnesium sulfate In water at 100℃; Inert atmosphere;	75%
With water for 15h; Reflux;	59%

(R)-(-)-epichlorohydrin (51594-55-9) + 2-chloro-ethanol (107-07-3) → (R)-1-(2-chloroethoxy)-3-chloropropan-2-ol (934346-53-9)

Conditions	Yield
With boron trifluoride diethyl etherate at 45℃; for 1.5h;	100%
With boron trifluoride diethyl etherate at 45℃; for 3h;	100%
With boron trifluoride diethyl etherate In tetrahydrofuran at 0 - 45℃; for 1.5h;	86.6%

(R)-(-)-epichlorohydrin (51594-55-9) + (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]-6-methylthiotetrahydropyran-3,4,5-triol → (2S,3R,4R,5S,6R)-2 [4-chloro-3-[[4-[[(2S)-oxiran-2-yl]methoxy]phenyl]methyl]phenyl]-6-methylthiotetrahydropyran-3,4,5-triol

Conditions	Yield
With potassium carbonate In ethanol at 73℃; for 5h;	100%

(R)-(-)-epichlorohydrin (51594-55-9) + (2S,3R,4R,5S,6R)-2-[4-chloro-3-[(3-fluoro-4-hydroxyphenyl)methyl]phenyl]-6-(methylthio)tetrahydropyran-3,4,5-triol → (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[3-fluoro-4-[[(2S)-oxiran-2-yl]methoxy]phenyl]methyl]phenyl]-6-methylthiotetrahydropyran-3,4,5-triol

Conditions	Yield
With potassium carbonate In ethanol at 75℃; for 5h;	100%

(R)-(-)-epichlorohydrin (51594-55-9) + (2S,3R,4R,5S,6S)-2-[4-chloro-3-[(4-hydroxyphenyl)methyl]phenyl]-6-methylthiotetrahydropyran-3,4,5-triol → (2S,3R,4R,5S,6S)-2-[4-chloro-3-[[4-[[(2S)-oxiran-2-yl]methoxy]phenyl]methyl]phenyl]-6-methylthiotetrahydropyran-3,4,5-triol

Conditions	Yield
With potassium carbonate In ethanol at 75℃; Inert atmosphere;	100%

(R)-(-)-epichlorohydrin (51594-55-9) + 4-bromoethoxybenzene (588-96-5) → (R)-1-chloro-3-(4-ethoxyphenyl)propane-2-ol

Conditions	Yield
Stage #1: 4-bromoethoxybenzene With magnesium In tetrahydrofuran at 60℃; for 2h; Grignard Reaction; Inert atmosphere; Stage #2: (R)-(-)-epichlorohydrin With copper(l) iodide In tetrahydrofuran at 20℃; for 1h; Grignard Reaction; Inert atmosphere;	100%

(R)-(-)-epichlorohydrin (51594-55-9) + N-(4-((3-hydroxyphenyl)diazenyl)phenyl)acetamide → (S)-N-(4-((3-(oxiran-2-ylmethoxy)phenyl)diazenyl)phenyl)acetamide

Conditions	Yield
Stage #1: N-(4-((3-hydroxyphenyl)diazenyl)phenyl)acetamide With potassium carbonate In butanone for 0.166667h; Stage #2: (R)-(-)-epichlorohydrin In butanone for 48h; Reflux;	100%

(R)-(-)-epichlorohydrin (51594-55-9) + ethyl trimethylsilyl methylphosphonite (208451-05-2) → ((R)-3-Chloro-2-trimethylsilanyloxy-propyl)-methyl-phosphinic acid ethyl ester

Conditions	Yield
With zinc(II) chloride at 70℃; for 4h;	99%

3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate (224323-51-7) + (R)-(-)-epichlorohydrin (51594-55-9) → (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

Conditions	Yield
With magnesium halide at 80℃; for 4h;	99%
With MgI2 etherate In neat (no solvent) at 20 - 65℃; stereoselective reaction;	97%
With MgI2*etherate In tetrahydrofuran at 20 - 65℃; Inert atmosphere;	96%

(R)-(-)-epichlorohydrin (51594-55-9) + 1-bromo-1-(trimethylsilyl)ethene (13683-41-5) → (R)-1-chloro-4-(trimethylsilyl)pent-4-en-2-ol

Conditions	Yield
Stage #1: 1-bromo-1-(trimethylsilyl)ethene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃; for 1.25h; Reflux; Inert atmosphere; Stage #2: (R)-(-)-epichlorohydrin With copper(l) cyanide In tetrahydrofuran at -50 - -20℃; for 2h; Inert atmosphere; Schlenk technique;	99%

(R)-(-)-epichlorohydrin (51594-55-9) + i-pentyl bromide (107-82-4) → (R)-1-chloro-6-methylheptan-2-ol (929211-91-6)

Conditions	Yield
Stage #1: i-pentyl bromide With magnesium In diethyl ether Stage #2: (R)-(-)-epichlorohydrin With copper(l) iodide In diethyl ether at -78 - -20℃; for 12h;	98%

(R)-(-)-epichlorohydrin (51594-55-9) + 4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenol (1062669-89-9) → (S)-N,N-diethyl-4-(3-(3-ethyl-5-methyl-4-(oxiran-2-ylmethoxy)phenyl)-1,2,4-oxadiazol-5-yl)-6-methylpyridin-2-amine (1062670-10-3)

Conditions	Yield
Stage #1: (R)-(-)-epichlorohydrin; 4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenol With tetramethlyammonium chloride at 25℃; for 48h; Stage #2: With sodium hydroxide In methanol at 0 - 20℃; for 1h;	98%
With sodium hydroxide In water; isopropyl alcohol at 20℃; for 48h;	67%

(R)-(-)-epichlorohydrin (51594-55-9) + phenylmethyl 1-piperazinecarboxylate (31166-44-6) → (R)-benzyl 4-(3-chloro-2-hydroxypropyl)piperazine-1-carboxylate

Conditions	Yield
In ethanol at 20 - 50℃;	98%

(R)-(-)-epichlorohydrin (51594-55-9) + 7-fluoro-1-(piperazine-1-yl)isoquinoline trifluoroacetate → 7-fluoro-1-(4-{[(2S)-oxiran-2-yl]methyl}piperazin-1-yl)isoquinoline

Conditions	Yield
With sodium hydroxide In methanol at -10 - 4℃;	98%

(R)-(-)-epichlorohydrin (51594-55-9) + Me2 AlCl + trimethyl(propargyl)silane (13361-64-3) → (R)-1-chloro-6-trimethylsilanyl-hex-4-yn-2-ol

Conditions	Yield
With n-butyllithium In toluene	97%
With n-butyllithium In toluene	97%

(R)-(-)-epichlorohydrin (51594-55-9) + N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide (5294-61-1) → (R)-2-(4-(3-chloro-2-hydroxypropyl)piperazin-1-yl)-N-(2,6-dimethylphenyl)acetamide (1427177-24-9)

Conditions	Yield
In water at 15℃; for 1h;	97%

(R)-(-)-epichlorohydrin (51594-55-9) + dibenzylamine (103-49-1) → (R)-N,N-dibenzyl-1-(oxiran-2-yl)methanamine (316157-42-3)

Conditions	Yield
With sodium hydroxide In water; isopropyl alcohol at 10 - 25℃; Large scale;	97%
In tetrahydrofuran Solvent; Reflux;	91%

(R)-(-)-epichlorohydrin (51594-55-9) + (3aR,6R,7aR)-8,8-dimethyl-3-(pentan-3-ylideneamino)-1,3,4,5,6,7-hexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one (1051911-44-4) → C18H28N2O3

Conditions	Yield
Stage #1: (3aR,6R,7aR)-8,8-dimethyl-3-(pentan-3-ylideneamino)-1,3,4,5,6,7-hexahydro-2H-3a,6-methanobenzo[d]oxazol-2-one With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: (R)-(-)-epichlorohydrin In tetrahydrofuran; hexane at -78℃; for 0.0833333h;	97%

(R)-(-)-epichlorohydrin (51594-55-9) + trimethylsilylacetylene (1066-54-2) → (2R)-1-chloro-5-(trimethylsilyl)pent-4-yn-2-ol (143724-90-7)

Conditions	Yield
Stage #1: trimethylsilylacetylene With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; Stage #2: (R)-(-)-epichlorohydrin In tetrahydrofuran at -60℃; regioselective reaction;	96%
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at 30℃; for 22h;	90%
With n-butyllithium; boron trifluoride diethyl etherate Yield given. Multistep reaction;

(R)-(-)-epichlorohydrin (51594-55-9) + N-(3,4-dichlorobenzyl)ethanoloamine (40172-06-3) → C12H16Cl3NO2 (914927-61-0)

Conditions	Yield
at 20℃; for 18h;	96%

methanol (67-56-1) + (R)-(-)-epichlorohydrin (51594-55-9) + 6-ethyl-o-toluidine (24549-06-2) → (R)-1-((2-ethyl-6-methylphenyl)amino)-3-methoxypropan-2-ol (1578258-67-9)

Conditions	Yield
Stage #1: methanol; (R)-(-)-epichlorohydrin; 6-ethyl-o-toluidine at 70℃; for 6h; Reflux; Stage #2: With potassium hydroxide at 10 - 30℃; for 8h;	96%

methyl (3-fluoro-4-morpholinophenyl)carbamate (212325-40-1) + (R)-(-)-epichlorohydrin (51594-55-9) → (5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

Conditions	Yield
Stage #1: methyl-(3-fluoro-4-morpholinophenyl)carbamate With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1.16667h; Stage #2: (R)-(-)-epichlorohydrin In tetrahydrofuran; hexane at -10 - 55℃; for 4.66667h;	96%

(R)-(-)-epichlorohydrin (51594-55-9) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → (2R)-1-chloro-3-[(1-phenyl-1,2,3,4-tetrazol-5-yl)mercapto]-2-propanol

Conditions	Yield
With triethylamine In methanol at 20℃;	96%
With triethylamine In methanol at 20℃;	96%

(R)-(-)-epichlorohydrin (51594-55-9) + 2-(benzylamino)-N-(3,4-difluorophenyl)acetamide → 2-{benzyl[(2R)-3-chloro-2-hydroxypropyl]amino}-N-(3,4-difluorophenyl)acetamide

Conditions	Yield
With magnesium sulfate In methanol; dichloromethane at 20 - 35℃;	96%

(R)-(-)-epichlorohydrin (51594-55-9) + 4-sulfanylphenol (637-89-8) → (R)-4-((3-chloro-2-hydroxypropyl)thio)phenol

Conditions	Yield
With potassium carbonate In ethanol at 20℃; for 8.25h; Cooling with ice;	96%

(R)-(-)-epichlorohydrin (51594-55-9) + isopropylmagnesium bromide (920-39-8) → C6H13ClO

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at -10 - 25℃; for 12h; Inert atmosphere;	96%

(R)-(-)-epichlorohydrin (51594-55-9) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With (R)-2-chloropropionic acid In water at 80 - 90℃; for 15h; Reagent/catalyst; Temperature;	95.57%
With (R,R)-Jacobsen catalyst; water In tetrahydrofuran at 4℃; for 24h;	41%
Stage #1: With N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediaminocobalt(II); camphor-10-sulfonic acid; oxygen In tetrahydrofuran for 1h; Stage #2: (R)-(-)-epichlorohydrin With water In tetrahydrofuran at 20℃; for 20h;	93.7 %Chromat.

(R)-(-)-epichlorohydrin (51594-55-9) + N-[4-(3-morpholinon-4-yl)phenyl]-5-chloro-2-thiophenecarboxamide → (R)-N-(2,3-epoxy-1-propyl)-N-[4-(3-morpholinon-4-yl)phenyl]-5-chloro-2-thiophenecarboxamide

Conditions	Yield
Stage #1: N-[4-(3-morpholinon-4-yl)phenyl]-5-chloro-2-thiophenecarboxamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: (R)-(-)-epichlorohydrin at 50 - 60℃; for 3h;	95.5%

(R)-(-)-epichlorohydrin (51594-55-9) + hydrogen cyanide (74-90-8) → (R)-γ-chloro-β-hydroxybutyronitrile (84367-31-7)

Conditions	Yield
With triethylamine In water at 25℃; for 8h; Temperature;	95.05%
With trimethylamine In toluene at 60℃; for 5h; Temperature; Autoclave;

Upstream product

• 113826-06-5 (R)-glycidyl tosylate 
• 95589-30-3 (1S,2R,4R,4'R)-4'-Chloromethyl-4,7,7-trimethylbicyclo<2.2.1>heptane-2-spiro-2'-(1',3'-dioxolan)-3-one 
• 106-89-8 epichlorohydrin 
• 95548-93-9 (S)-2-Acetoxy-1-bromo-3-chloropropane 
• 83398-53-2 (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate 
• 67800-61-7 (S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate) 
• 96-23-1 1,3-Dichloro-2-propanol 
• 616-23-9 2,3-Dichloro-1-propanol 
• 62-53-3 aniline 
• 124-38-9 carbon dioxide 
• 107-05-1 3-chloroprop-1-ene 

Downstream Products

• 112009-61-7 (R)-1-chloro-2-hydroxy-3-phenylpropane 
• 115378-16-0 (R)-1-chloro-3-(phenylthio)propan-2-ol 
• 71031-03-3 (R)-phenyl glycidyl ether 
• 181140-34-1 (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione 
• 161596-47-0 (S)-N-glycidylphthalimide 
• 709041-46-3 5-[((2R)oxiran-2-yl)methoxy]-2-(2,4-dichlorophenyl)benzoxazole 
• 139668-40-9 ethyl (3-chloro-2(R)-hydroxypropyl)benzylphosphinate 
• 1076243-03-2 1-(4-chlorobenzyl)-4-[(2S)-oxiran-2-ylmethyl]-1,4-diazepan-5-one 
• 139668-46-5 ethyl (3-chloro-2(R)-hydroxypropyl)(cyclohexylmethyl)phosphinate 
• 30569-34-7 N,N-bis(oxiran-2-ylmethyl)benzenesulfonamide 
• 70987-80-3 4-[(2S)-Oxiranylmethoxy]benzonitrile 
• 96-24-2 3-monochloro-1,2-propanediol 
• 901233-98-5 (R)-1-chloro-3-(4-chloro-3-methyl-phenyl)-propan-2-ol 
• 868405-66-7 N-[3-chloro-2-(R)-hydroxypropyl]-3-fluoro-4-(morpholin-4-yl)aniline 

Relevant articles and documents

An Amphiphilic (salen)Co Complex – Utilizing Hydrophobic Interactions to Enhance the Efficiency of a Cooperative Catalyst

An amphiphilic (salen)Co(III) complex is presented that accelerates the hydrolytic kinetic resolution (HKR) of epoxides almost 10 times faster than catalysts from commercially available sources. This was achieved by introducing hydrophobic chains that increase the rate of reaction in one of two ways – by enhancing cooperativity under homogeneous conditions, and increasing the interfacial area under biphasic reaction conditions. While numerous strategies have been employed to increase the efficiency of cooperative catalysts, the utilization of hydrophobic interactions is scarce. With the recent upsurge in green chemistry methods that conduct reactions ‘on water’ and at the oil-water interface, the introduction of hydrophobic interactions has potential to become a general strategy for enhancing the catalytic efficiency of cooperative catalytic systems. (Figure presented.).

Molecular modification of a halohydrin dehalogenase for kinetic regulation to synthesize optically pure (S)-epichlorohydrin

Asymmetric synthesis of chiral epichlorohydrin (ECH) from 1,3-dichloro-2-propanol (1,3-DCP) using halohydrin dehalogenases (HHDHs) is of great value due to the 100% theoretical yield and high enantioselectivity. The vital problem in the asymmetric synthesis is to prepare optically pure ECH. In this study, key amino acid residues located at halide ion channels of HheC (P175S/W249P) (HheCPS) were modified to regulate the kinetic parameters. HheCPS I81W, F86N and V94R were constructed with the corresponding halide ion channels destroyed. The catalytically efficiencies (kcat/Km) of the three mutants exhibited 0.38-, 0.23- and 0.23-fold decrease toward (S)-ECH and the reverse reaction was significantly inhibited. As the results, (S)-ECH was synthesized with >99% enantiomeric excess (e.e.) and 63.42%, 67.08% and 57.01% yields, respectively, under 20 mM 1,3-DCP as substrate. To our knowledge, this is the first investigation of the molecule kinetic modification of HHDHs and also the first report for the biosynthesis of optically pure (S)-ECH from 1,3-DCP using HHDHs.

Imido-P(v) trianion supported enantiopure neutral tetrahedral Pd(II) cages

Charge-neutral chiral hosts are attractive due to their ability to recognize a wide range of guest functionalities and support enantioselective processes. However, reports on such charge-neutral cages are very scarce in the literature. Here, we report an enantiomeric pair of tetrahedral Pd(ii) cages built from chiral tris(imido)phosphate trianions and oxalate linkers, which exhibit enantioselective separation capabilities for epichlorohydrin, β-butyrolactone, and 3-methyl- and 3-ethyl cyclopentanone.