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51594-55-9

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51594-55-9 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.

Check Digit Verification of cas no

The CAS Registry Mumber 51594-55-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,5,9 and 4 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 51594-55:
(7*5)+(6*1)+(5*5)+(4*9)+(3*4)+(2*5)+(1*5)=129
129 % 10 = 9
So 51594-55-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m0/s1

51594-55-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (E0581)  (R)-Epichlorohydrin  >98.0%(GC)

  • 51594-55-9

  • 5g

  • 280.00CNY

  • Detail
  • TCI America

  • (E0581)  (R)-Epichlorohydrin  >98.0%(GC)

  • 51594-55-9

  • 25g

  • 580.00CNY

  • Detail
  • Alfa Aesar

  • (L14198)  (R)-(-)-Epichlorohydrin, 98+%   

  • 51594-55-9

  • 1g

  • 352.0CNY

  • Detail
  • Alfa Aesar

  • (L14198)  (R)-(-)-Epichlorohydrin, 98+%   

  • 51594-55-9

  • 5g

  • 1000.0CNY

  • Detail
  • Alfa Aesar

  • (L14198)  (R)-(-)-Epichlorohydrin, 98+%   

  • 51594-55-9

  • 25g

  • 2234.0CNY

  • Detail
  • Aldrich

  • (540072)  (R)-(−)-Epichlorohydrin  99%

  • 51594-55-9

  • 540072-5G

  • 830.70CNY

  • Detail
  • Aldrich

  • (540072)  (R)-(−)-Epichlorohydrin  99%

  • 51594-55-9

  • 540072-25G

  • 2,438.28CNY

  • Detail

51594-55-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-epichlorohydrin

1.2 Other means of identification

Product number -
Other names (R)-Epichlorohydrin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:51594-55-9 SDS

51594-55-9Synthetic route

(S)-1-Acetoxy-2-bromo-3-chloropropane

(S)-1-Acetoxy-2-bromo-3-chloropropane

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
With sodium ethane-1,2-diolate In ethylene glycol for 0.25h; Ambient temperature;85%
3-chloro-2-hydroxypropyl methanesulfonate

3-chloro-2-hydroxypropyl methanesulfonate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
With sodium In ethylene glycol Ambient temperature;85%
epichlorohydrin
106-89-8

epichlorohydrin

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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)-glycidyl tosylate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
With hydrogenchloride for 24h; Ambient temperature;54%
epichlorohydrin
106-89-8

epichlorohydrin

A

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

B

(S)-3-chloropropan-1,2-diol
60827-45-4

(S)-3-chloropropan-1,2-diol

Conditions
ConditionsYield
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

epichlorohydrin

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

C

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

Conditions
ConditionsYield
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

epichlorohydrin

A

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

B

(2R)-3-chloro-1,2-propanediol
57090-45-6

(2R)-3-chloro-1,2-propanediol

Conditions
ConditionsYield
With water at 20℃; for 8h; optical yield given as %ee;A 45%
B n/a
(R)-2,3-dichloroprop-1-yl butyrate

(R)-2,3-dichloroprop-1-yl butyrate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Ambient temperature;43%
epichlorohydrin
106-89-8

epichlorohydrin

A

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

B

(2R)-3-chloro-1,2-propanediol
57090-45-6

(2R)-3-chloro-1,2-propanediol

C

(S)-3-chloropropan-1,2-diol
60827-45-4

(S)-3-chloropropan-1,2-diol

Conditions
ConditionsYield
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

epichlorohydrin

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

C

(2R)-3-chloro-1,2-propanediol
57090-45-6

(2R)-3-chloro-1,2-propanediol

Conditions
ConditionsYield
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

epichlorohydrin

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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

2,3-Dichloro-1-propanol

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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

1,3-Dichloro-2-propanol

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate)

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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

(S)-1-bromo-3-chloro-2-propyl acetate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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

(1S,2R,4R,4'R)-4'-Chloromethyl-4,7,7-trimethylbicyclo<2.2.1>heptane-2-spiro-2'-(1',3'-dioxolan)-3-one

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
With hydrogen bromide; sodium 2-hydroxyethoxide 1.) AcOH, 60 deg C, 5 h,; Yield given. Multistep reaction;
epichlorohydrin
106-89-8

epichlorohydrin

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

C

(2R)-3-chloro-1,2-propanediol
57090-45-6

(2R)-3-chloro-1,2-propanediol

D

(S)-3-chloropropan-1,2-diol
60827-45-4

(S)-3-chloropropan-1,2-diol

Conditions
ConditionsYield
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

epichlorohydrin

A

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

B

1,3-Dichloro-2-propanol
96-23-1

1,3-Dichloro-2-propanol

C

(2S)-1-azido-3-chloropropan-2-ol
681225-50-3

(2S)-1-azido-3-chloropropan-2-ol

D

(2R)-1-azido-3-chloropropan-2-ol
180587-77-3

(2R)-1-azido-3-chloropropan-2-ol

Conditions
ConditionsYield
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

3-chloroprop-1-ene

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
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

carbon dioxide

epichlorohydrin
106-89-8

epichlorohydrin

A

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

B

(S)-4-(chloromethyl)-1,3-dioxolan-2-one
99968-48-6

(S)-4-(chloromethyl)-1,3-dioxolan-2-one

C

(R)-4-(chloromethyl)-1,3-dioxolan-2-one
99968-49-7

(R)-4-(chloromethyl)-1,3-dioxolan-2-one

Conditions
ConditionsYield
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

aniline

epichlorohydrin
106-89-8

epichlorohydrin

A

(S)-epichlorohydrin
67843-74-7

(S)-epichlorohydrin

B

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

C

(S)-(+)-1-chloro-3-(phenylamino)-propan-2-ol
195455-97-1

(S)-(+)-1-chloro-3-(phenylamino)-propan-2-ol

D

(R)-(+)-N-(3-chloro-2-hydroxypropyl)aniline
195455-98-2

(R)-(+)-N-(3-chloro-2-hydroxypropyl)aniline

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

n-heptylmagnesium bromide
13125-66-1

n-heptylmagnesium bromide

(R)-1-chloro-2-decanol
261160-96-7

(R)-1-chloro-2-decanol

Conditions
ConditionsYield
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

potassium cyanate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(5R)-5-(chloromethyl)-1,3-oxazolidin-2-one
169048-79-7

(5R)-5-(chloromethyl)-1,3-oxazolidin-2-one

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

2-chloro-ethanol
107-07-3

2-chloro-ethanol

(R)-1-(2-chloroethoxy)-3-chloropropan-2-ol
934346-53-9

(R)-1-(2-chloroethoxy)-3-chloropropan-2-ol

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

(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-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

(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
ConditionsYield
With potassium carbonate In ethanol at 73℃; for 5h;100%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(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-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

(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
ConditionsYield
With potassium carbonate In ethanol at 75℃; for 5h;100%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(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-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

(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
ConditionsYield
With potassium carbonate In ethanol at 75℃; Inert atmosphere;100%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

4-bromoethoxybenzene
588-96-5

4-bromoethoxybenzene

(R)-1-chloro-3-(4-ethoxyphenyl)propane-2-ol

(R)-1-chloro-3-(4-ethoxyphenyl)propane-2-ol

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

N-(4-((3-hydroxyphenyl)diazenyl)phenyl)acetamide

N-(4-((3-hydroxyphenyl)diazenyl)phenyl)acetamide

(S)-N-(4-((3-(oxiran-2-ylmethoxy)phenyl)diazenyl)phenyl)acetamide

(S)-N-(4-((3-(oxiran-2-ylmethoxy)phenyl)diazenyl)phenyl)acetamide

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

ethyl trimethylsilyl methylphosphonite
208451-05-2

ethyl trimethylsilyl methylphosphonite

((R)-3-Chloro-2-trimethylsilanyloxy-propyl)-methyl-phosphinic acid ethyl ester

((R)-3-Chloro-2-trimethylsilanyloxy-propyl)-methyl-phosphinic acid ethyl ester

Conditions
ConditionsYield
With zinc(II) chloride at 70℃; for 4h;99%
3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate
224323-51-7

3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

1-bromo-1-(trimethylsilyl)ethene
13683-41-5

1-bromo-1-(trimethylsilyl)ethene

(R)-1-chloro-4-(trimethylsilyl)pent-4-en-2-ol

(R)-1-chloro-4-(trimethylsilyl)pent-4-en-2-ol

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

i-pentyl bromide
107-82-4

i-pentyl bromide

(R)-1-chloro-6-methylheptan-2-ol
929211-91-6

(R)-1-chloro-6-methylheptan-2-ol

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenol
1062669-89-9

4-(5-(2-(diethylamino)-6-methylpyridin-4-yl)-1,2,4-oxadiazol-3-yl)-2-ethyl-6-methylphenol

(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

(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

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

phenylmethyl 1-piperazinecarboxylate
31166-44-6

phenylmethyl 1-piperazinecarboxylate

(R)-benzyl 4-(3-chloro-2-hydroxypropyl)piperazine-1-carboxylate

(R)-benzyl 4-(3-chloro-2-hydroxypropyl)piperazine-1-carboxylate

Conditions
ConditionsYield
In ethanol at 20 - 50℃;98%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

7-fluoro-1-(piperazine-1-yl)isoquinoline trifluoroacetate

7-fluoro-1-(piperazine-1-yl)isoquinoline trifluoroacetate

7-fluoro-1-(4-{[(2S)-oxiran-2-yl]methyl}piperazin-1-yl)isoquinoline

7-fluoro-1-(4-{[(2S)-oxiran-2-yl]methyl}piperazin-1-yl)isoquinoline

Conditions
ConditionsYield
With sodium hydroxide In methanol at -10 - 4℃;98%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

Me2 AlCl

Me2 AlCl

trimethyl(propargyl)silane
13361-64-3

trimethyl(propargyl)silane

(R)-1-chloro-6-trimethylsilanyl-hex-4-yn-2-ol

(R)-1-chloro-6-trimethylsilanyl-hex-4-yn-2-ol

Conditions
ConditionsYield
With n-butyllithium In toluene97%
With n-butyllithium In toluene97%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide
5294-61-1

N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide

(R)-2-(4-(3-chloro-2-hydroxypropyl)piperazin-1-yl)-N-(2,6-dimethylphenyl)acetamide
1427177-24-9

(R)-2-(4-(3-chloro-2-hydroxypropyl)piperazin-1-yl)-N-(2,6-dimethylphenyl)acetamide

Conditions
ConditionsYield
In water at 15℃; for 1h;97%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

dibenzylamine
103-49-1

dibenzylamine

(R)-N,N-dibenzyl-1-(oxiran-2-yl)methanamine
316157-42-3

(R)-N,N-dibenzyl-1-(oxiran-2-yl)methanamine

Conditions
ConditionsYield
With sodium hydroxide In water; isopropyl alcohol at 10 - 25℃; Large scale;97%
In tetrahydrofuran Solvent; Reflux;91%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(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

(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

C18H28N2O3

C18H28N2O3

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

(2R)-1-chloro-5-(trimethylsilyl)pent-4-yn-2-ol
143724-90-7

(2R)-1-chloro-5-(trimethylsilyl)pent-4-yn-2-ol

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

N-(3,4-dichlorobenzyl)ethanoloamine
40172-06-3

N-(3,4-dichlorobenzyl)ethanoloamine

C12H16Cl3NO2
914927-61-0

C12H16Cl3NO2

Conditions
ConditionsYield
at 20℃; for 18h;96%
methanol
67-56-1

methanol

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

6-ethyl-o-toluidine
24549-06-2

6-ethyl-o-toluidine

(R)-1-((2-ethyl-6-methylphenyl)amino)-3-methoxypropan-2-ol
1578258-67-9

(R)-1-((2-ethyl-6-methylphenyl)amino)-3-methoxypropan-2-ol

Conditions
ConditionsYield
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

methyl (3-fluoro-4-morpholinophenyl)carbamate

(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

(5R)-5-(chloromethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolidinone

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

1-Phenyl-1H-tetrazole-5-thiol
86-93-1

1-Phenyl-1H-tetrazole-5-thiol

(2R)-1-chloro-3-[(1-phenyl-1,2,3,4-tetrazol-5-yl)mercapto]-2-propanol

(2R)-1-chloro-3-[(1-phenyl-1,2,3,4-tetrazol-5-yl)mercapto]-2-propanol

Conditions
ConditionsYield
With triethylamine In methanol at 20℃;96%
With triethylamine In methanol at 20℃;96%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

2-(benzylamino)-N-(3,4-difluorophenyl)acetamide

2-(benzylamino)-N-(3,4-difluorophenyl)acetamide

2-{benzyl[(2R)-3-chloro-2-hydroxypropyl]amino}-N-(3,4-difluorophenyl)acetamide

2-{benzyl[(2R)-3-chloro-2-hydroxypropyl]amino}-N-(3,4-difluorophenyl)acetamide

Conditions
ConditionsYield
With magnesium sulfate In methanol; dichloromethane at 20 - 35℃;96%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

4-sulfanylphenol
637-89-8

4-sulfanylphenol

(R)-4-((3-chloro-2-hydroxypropyl)thio)phenol

(R)-4-((3-chloro-2-hydroxypropyl)thio)phenol

Conditions
ConditionsYield
With potassium carbonate In ethanol at 20℃; for 8.25h; Cooling with ice;96%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

isopropylmagnesium bromide
920-39-8

isopropylmagnesium bromide

C6H13ClO

C6H13ClO

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran at -10 - 25℃; for 12h; Inert atmosphere;96%
(R)-(-)-epichlorohydrin
51594-55-9

(R)-(-)-epichlorohydrin

(2R)-3-chloro-1,2-propanediol
57090-45-6

(2R)-3-chloro-1,2-propanediol

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

N-[4-(3-morpholinon-4-yl)phenyl]-5-chloro-2-thiophenecarboxamide

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

(R)-N-(2,3-epoxy-1-propyl)-N-[4-(3-morpholinon-4-yl)phenyl]-5-chloro-2-thiophenecarboxamide

Conditions
ConditionsYield
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

(R)-(-)-epichlorohydrin

hydrogen cyanide
74-90-8

hydrogen cyanide

(R)-γ-chloro-β-hydroxybutyronitrile
84367-31-7

(R)-γ-chloro-β-hydroxybutyronitrile

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

51594-55-9Relevant articles and documents

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

Solís-Mu?ana, Pablo,Salam, Joanne,Ren, Chloe Z.-J.,Carr, Bronte,Whitten, Andrew E.,Warr, Gregory G.,Chen, Jack L.-Y.

supporting information, p. 3207 - 3213 (2021/06/01)

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.).

Exploring the Biocatalytic Scope of a Novel Enantioselective Halohydrin Dehalogenase from an Alphaproteobacterium

Xue, Feng,Ya, Xiangju,Xiu, Yuansong,Tong, Qi,Wang, Yuqi,Zhu, Xinhai,Huang, He

, p. 629 - 637 (2019/01/25)

A gene encoding halohydrin dehalogenase from an alphaproteobacterium (AbHHDH) was identified, cloned and over-expressed in Escherichia coli. AbHHDH was able to catalyze the stereoselective dehalogenation of prochiral and racemic halohydrins. It showed the highest enantioselectivity in the dehalogenation of 20?mM (R,S)-2-bromo-1-phenylethanol, which yielded (S)-2-bromo-1-phenylethanol with 99% ee and 34.5% yield. Moreover, AbHHDH catalyzed the azidolysis of epoxides with low to moderate (S)-enantioselectivity. The highest enantioselectivity (E = 18.6) was observed when (R,S)-benzyl glycidyl ether was used as the substrate. A sequential kinetic resolution catalyzed by HHDH was employed for the synthesis of chiral 1-chloro-3-phenoxy-2-propanol. We prepared enantiopure (S)-isomer with a high enantiopurity of ee > 99% and a yield of 30.7% (E-value: 21.3) by kinetic resolution of 20?mM substrate. The (S)-isomer with 99% ee readily obtained from 40 to 150?mM (R,S)-1-chloro-3-phenoxy-2-propanol. Taken together, the results of this study demonstrate the applicability of this HHDH for the production of optically active compounds. [Figure not available: see fulltext.].

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

Rajasekar, Prabhakaran,Pandey, Swechchha,Paithankar, Harshad,Chugh, Jeetender,Steiner, Alexander,Boomishankar, Ramamoorthy

supporting information, p. 1873 - 1876 (2018/02/23)

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.

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