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67843-74-7

Basic Information
CAS No.: 67843-74-7
Name: Oxirane,2-(chloromethyl)-, (2S)-
Molecular Structure:
Molecular Structure of 67843-74-7 (Oxirane,2-(chloromethyl)-, (2S)-)
Formula: C3H5ClO
Molecular Weight: 92.52
Synonyms: Oxirane,(chloromethyl)-, (2S)- (9CI);Oxirane, (chloromethyl)-, (S)-;(+)-2-(Chloromethyl)oxirane;(+)-Epichlorohydrin;(S)-(Chloromethyl)oxirane;(S)-1-Chloro-2,3-epoxypropane;(S)-2-Chloromethyloxirane;BRN 1420784;(S)-Epichlorohydrin;2(S)-Epichlorohydrin;
EINECS: 203-439-8
Density: 1.205 g/cm3
Melting Point: 57 °C(lit.)
Boiling Point: 116.1 °C at 760 mmHg
Flash Point: 33.9 °C
Solubility: Insoluble in water
Appearance: Colorless to light yellow liquid
Hazard Symbols: ToxicT
Risk Codes: 45-10-23/24/25-34-43
Safety: 53-45
Transport Information: UN 2023 6.1/PG 2
PSA: 12.53000
LogP: 0.62400
Synthetic route
96-23-1

1,3-Dichloro-2-propanol

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC mutant P175S/W249P) In aq. phosphate buffer pH=8; Concentration; Reagent/catalyst; Temperature; pH-value; Solvent; Enzymatic reaction; enantioselective reaction;93.7%
With halohydrin dehalogenase mutant HheCPS F86N In aq. phosphate buffer at 37℃; pH=8; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;79.12%
3132-64-7

1,2-Epoxy-3-bromopropane

A

67843-74-7

(S)-epichlorohydrin

B

14437-88-8

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

Conditions
ConditionsYield
With (R,R)-Jacobsen catalyst; water In tetrahydrofuran at 4℃; for 24h;A n/a
B 93%
621-84-1

O-benzyl carbamate

106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

641617-19-8

[(R)-3-chloro-2-hydroxypropyl]carbamic acid benzyl ester

Conditions
ConditionsYield
With air; 4-nitro-benzoic acid; (R,R)-((t-Bu)4-salen)Co(II) In various solvent(s) at 0℃; for 24h;A n/a
B 87%
67800-61-7

(S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate)

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With sodium ethane-1,2-diolate In ethylene glycol for 0.25h; Ambient temperature;85%
106-89-8

epichlorohydrin

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With water; [(1-RR)-(Dibenzoyl-LTA)] at 5 - 20℃; for 7h; Product distribution / selectivity; Industry scale; Resolution of racemate;82%
With water; [(1-RR)-(Dibenzoyl-LTA)] at 5 - 20℃; for 3h; Product distribution / selectivity; Resolution of racemate;80%
With oligomeric (salen)Co(OSO2CF3); water at 20℃; for 15h;44%
67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With sodium hydroxide74%
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

57090-45-6

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

Conditions
ConditionsYield
With C72H102Co2F12N4O12P2; water at 0 - 20℃; for 3h; optical yield given as %ee;A 45%
B 53%
With water; (S,S)-(salen)cobalt(III)(OAc) at 0℃; for 19h;A 46%
B 45%
With C114H155Co3N8O14Pol; water; acetic acid at 20℃; for 3h; Resolution of racemate; optical yield given as %ee; enantioselective reaction;A 46%
B n/a

(S)-1,3-dichloro-1-propanol

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With potassium hydroxide In methanol Ambient temperature;51%
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

57090-45-6

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

C

60827-45-4

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

Conditions
ConditionsYield
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
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

96-24-2

3-monochloro-1,2-propanediol

Conditions
ConditionsYield
Stage #1: epichlorohydrin With C57H54CoN3O8 In dichloromethane at 20℃; for 0.25h;
Stage #2: With water In dichloromethane at 20℃; for 12h; Cooling with ice; enantioselective reaction;
A 46%
B n/a
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

51594-55-9

(R)-(-)-epichlorohydrin

C

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%
14199-15-6

Methyl 4-hydroxyphenylacetate

106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

724776-52-7

methyl (R)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetate

Conditions
ConditionsYield
With (R,R)-Jacobsen(III)- catalyst immobilized by sulfonic acid functionalized SBA-16 mesoporous silica In tetrahydrofuran at 20℃; for 12h; optical yield given as %ee; enantioselective reaction;A 44%
B n/a
106-89-8

epichlorohydrin

108-95-2

phenol

A

67843-74-7

(S)-epichlorohydrin

B

140630-45-1

(R)-1-chloro-3-phenoxy-2-propanol

Conditions
ConditionsYield
With (R,R)-Jacobsen(III)- catalyst immobilized by sulfonic acid functionalized SBA-16 mesoporous silica In tetrahydrofuran at 20℃; for 12h; optical yield given as %ee; enantioselective reaction;A 43%
B n/a
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

51594-55-9

(R)-(-)-epichlorohydrin

C

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%
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

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;
96-23-1

1,3-Dichloro-2-propanol

A

67843-74-7

(S)-epichlorohydrin

B

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;
67800-61-7

(S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate)

A

67843-74-7

(S)-epichlorohydrin

B

51594-55-9

(R)-(-)-epichlorohydrin

Conditions
ConditionsYield
With sodium 2-hydroxyethoxide In ethylene glycol for 0.0833333h; Title compound not separated from byproducts;
106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

51594-55-9

(R)-(-)-epichlorohydrin

C

57090-45-6

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

D

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;
51594-55-9

(R)-(-)-epichlorohydrin

67843-74-7

(S)-epichlorohydrin

Conditions
ConditionsYield
With sodium citrate buffer; Agrobacterium radiobacter AD1 haloalcohol dehalogenase; sodium chloride at 22℃; pH=5.5; Product distribution; Further Variations:; pH-values;
With Agrobacterium radiobacter halohydrin dehalogenase; sodium chloride for 1h; pH=7.5; Tris-SO4 buffer; Enzymatic reaction;
4248-19-5

tert-butyl carbamate

106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

1072792-33-6

(R)-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester

Conditions
ConditionsYield
With (1R,2R)-(-)-N,N'-bis(3,5-di-tert-butylsalicydene)-1,2-cyclohexanediaminocobalt(II); 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; 4-nitro-benzoic acid at 20℃; for 8h; optical yield given as %ee; enantioselective reaction;
Stage #1: tert-butyl carbazate With chiral Co(III) polymeric salen complex In dichloromethane for 0.166667h;
Stage #2: epichlorohydrin In dichloromethane for 20h; enantioselective reaction;
A n/a
B n/a
51594-55-9

(R)-(-)-epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

57090-45-6

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

Conditions
ConditionsYield
With (R,R)-Jacobsen catalyst; waterA n/a
B n/a
62-53-3

aniline

106-89-8

epichlorohydrin

A

67843-74-7

(S)-epichlorohydrin

B

51594-55-9

(R)-(-)-epichlorohydrin

C

195455-97-1

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

D

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
590-28-3

potassium cyanate

67843-74-7

(S)-epichlorohydrin

169048-83-3

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

Conditions
ConditionsYield
In water for 15h; Heating;100%
With water for 15h; Reflux;60%
With magnesium sulfate In water at 100℃; for 5h;41%
In water Reflux;
In water for 19h; Reflux;
67843-74-7

(S)-epichlorohydrin

777934-39-1

2-benzylamino-N-(4-benzyloxyphenyl)acetamide

777934-41-5

2-{benzyl[(2S)-3-chloro-2-hydroxypropyl]amino}-N-(4-benzyloxyphenyl)acetamide

Conditions
ConditionsYield
With magnesium sulfate In methanol; dichloromethane at 35℃; for 72h;100%
With magnesium sulfate In methanol; dichloromethane at 35℃; for 72h;
67843-74-7

(S)-epichlorohydrin

107-07-3

2-chloro-ethanol

861852-07-5

(S)-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 1.5h;96%
With boron trifluoride diethyl etherate In toluene at 36 - 38℃; Large scale reaction;
67843-74-7

(S)-epichlorohydrin

1119-51-3

bromopentene

850715-25-2

(2S)-1-chlorooct-7-en-2-ol

Conditions
ConditionsYield
Stage #1: bromopentene With magnesium In tetrahydrofuran for 0.5h; Heating;
Stage #2: (S)-epichlorohydrin In tetrahydrofuran at -50 - 20℃; for 2h;
100%
67843-74-7

(S)-epichlorohydrin

327-52-6

1-bromo-2,4,5-trifluorobenzene

1246960-15-5

(S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol

Conditions
ConditionsYield
Stage #1: 1-bromo-2,4,5-trifluorobenzene With isopropylmagnesium chloride In tetrahydrofuran at -20 - 3℃; for 1.16667h; Inert atmosphere;
Stage #2: With copper(l) iodide In tetrahydrofuran at -10℃; for 0.5h; Inert atmosphere;
Stage #3: (S)-epichlorohydrin In tetrahydrofuran at -10 - 0℃; for 2.5h; Inert atmosphere;
100%
Stage #1: 1-bromo-2,4,5-trifluorobenzene With magnesium; 1,2-dibromomethane In tetrahydrofuran at 20℃;
Stage #2: (S)-epichlorohydrin With copper(l) iodide In tetrahydrofuran at 0 - 20℃; for 2.5h; Product distribution / selectivity;
Stage #1: 1-bromo-2,4,5-trifluorobenzene With magnesium; ethylene dibromide In tetrahydrofuran at 20℃;
Stage #2: (S)-epichlorohydrin; copper(l) iodide In tetrahydrofuran at 0 - 20℃; for 2.5h; Product distribution / selectivity;
Stage #1: 1-bromo-2,4,5-trifluorobenzene With isopropylmagnesium chloride In tetrahydrofuran at 0 - 22℃; for 4h;
Stage #2: (S)-epichlorohydrin With copper(l) chloride In tetrahydrofuran at 25 - 40℃; for 5h;
Stage #3: With acetic acid In tetrahydrofuran; tert-butyl methyl ether
67843-74-7

(S)-epichlorohydrin

3218-49-3

3,4-dichloro-benzeneacetonitrile

910028-19-2

((1S,2R)-2-(aminomethyl)-2-(3,4-dichlorophenyl)cyclopropyl)methanol

Conditions
ConditionsYield
Stage #1: (S)-epichlorohydrin; 3,4-dichloro-benzeneacetonitrile With sodium hexamethyldisilazane In tetrahydrofuran at -15 - 4℃; Inert atmosphere;
Stage #2: With dimethylsulfide borane complex at -5 - 40℃; for 6.5h;
100%
67843-74-7

(S)-epichlorohydrin

13291-18-4

isopropenylmagnesium bromide

(S)-(2-methylallyl)oxirane

Conditions
ConditionsYield
Stage #1: isopropenylmagnesium bromide With copper(l) iodide; boron trifluoride diethyl etherate In tetrahydrofuran at -78 - -30℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-epichlorohydrin In tetrahydrofuran at -30℃; for 0.5h; Inert atmosphere;
Stage #3: With sodium hydroxide In dichloromethane at 35℃; for 30h; Inert atmosphere;
99%
Stage #1: isopropenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere;
Stage #2: (S)-epichlorohydrin In tetrahydrofuran at -30℃; for 0.5h; Inert atmosphere;
Stage #3: With sodium hydroxide In dichloromethane at 35℃; for 30h; Inert atmosphere;
10.29 g
67843-74-7

(S)-epichlorohydrin

103-49-1

dibenzylamine

565176-84-3

(S)-N,N-dibenzylamino-1-(oxiran-2-ylmethyl)methylamine

Conditions
ConditionsYield
Stage #1: (S)-epichlorohydrin; dibenzylamine In isopropyl alcohol at 0 - 20℃;
Stage #2: With potassium hydroxide In isopropyl alcohol at 0℃;
98.5%
With sodium hydroxide at 65 - 70℃; for 24h;95%
In isopropyl alcohol at 0℃; for 24h;91.5%
Stage #1: (S)-epichlorohydrin; dibenzylamine In methanol at 20℃; for 48h;
Stage #2: With potassium hydroxide In water; tert-butyl alcohol at 20℃; for 48h;
45.8%
67843-74-7

(S)-epichlorohydrin

1119-18-2

1-butynyllithium

1026660-51-4

(S)-1-chlorohept-4-yn-2-ol

Conditions
ConditionsYield
With boron trifluoride diethyl etherate98%
1121-24-0

ortho-mercaptophenol

67843-74-7

(S)-epichlorohydrin

1588421-61-7

(R)-3-[(2-hydroxyphenyl)thio]-1,2-epoxypropane

Conditions
ConditionsYield
With pyridine In water at 20℃; for 24h; enantiospecific reaction;98%
Stage #1: ortho-mercaptophenol With pyridine In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: (S)-epichlorohydrin In N,N-dimethyl-formamide at 140℃; for 0.166667h; Inert atmosphere; Microwave irradiation;
67843-74-7

(S)-epichlorohydrin

N-[4-(3-morpholinon-4-yl)phenyl]-2-thiophene chloride

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

Conditions
ConditionsYield
Stage #1: N-[4-(3-morpholinon-4-yl)phenyl]-2-thiophene chloride With lithium tert-butoxide In tetrahydrofuran at 20℃; for 0.333333h;
Stage #2: (S)-epichlorohydrin at 50 - 60℃; for 3h;
98%
67843-74-7

(S)-epichlorohydrin

103-49-1

dibenzylamine

1236384-02-3

(S)-3-chloro-2-hydroxypropyl dibenzylamine

Conditions
ConditionsYield
With calcium chloride at 33℃; under 608.041 - 912.061 Torr; for 8h; Product distribution / selectivity;97%
With calcium chloride In dichloromethane at 33℃; for 8h; Product distribution / selectivity;97%
In dichloromethane at 25℃; for 20h; Solvent; Temperature;95.16%
In ethanol for 6h; Reflux;28.3 g
at 25 - 30℃; for 18h;
67843-74-7

(S)-epichlorohydrin

1066-54-2

trimethylsilylacetylene

148516-13-6

(S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -60℃; for 0.5h;
Stage #2: (S)-epichlorohydrin With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -60℃; for 2h;
96%
With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -60℃; for 2h;96%
With n-butyllithium; boron trifluoride diethyl etherate 1.) THF, -78 deg C, 25 min, 2.) THF, -30 deg C, 18 h; Multistep reaction;
67-56-1

methanol

67843-74-7

(S)-epichlorohydrin

201230-82-2

carbon monoxide

86728-93-0

methyl (S)-4-chloro-3-hydroxybutanoate

Conditions
ConditionsYield
With 3-HYDROXYPYRIDINE; dicobalt octacarbonyl In tetrahydrofuran at 55℃; under 31028.9 Torr; for 9h;96%
4-aminopyridine; dicobalt octacarbonyl In tert-butyl alcohol at 40℃; under 7500.75 Torr; for 5h; Product distribution / selectivity;92%
4-aminopyridine; dicobalt octacarbonyl at 33℃; under 7500.75 Torr; for 25h; Product distribution / selectivity;85%
67843-74-7

(S)-epichlorohydrin

5294-61-1

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

1427177-25-0

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

Conditions
ConditionsYield
In water at 15℃; for 1h;96%

(R)-2-hydroxy-2'-(methoxymethoxy)-1,1'-binaphthalene

67843-74-7

(S)-epichlorohydrin

2-[(S)-glycidyloxy]-2'-(methoxymethyloxy)-1,1'-binaphthalene

Conditions
ConditionsYield
Stage #1: (R)-2-hydroxy-2'-(methoxymethoxy)-1,1'-binaphthalene With tetrabutylammomium bromide; potassium hydroxide In tetrahydrofuran at 20℃; for 0.166667h;
Stage #2: (S)-epichlorohydrin In tetrahydrofuran at 20℃; for 20h;
96%
67843-74-7

(S)-epichlorohydrin

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

(S)-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 lithium tert-butoxide In tetrahydrofuran at 20℃; for 0.333333h;
Stage #2: (S)-epichlorohydrin at 50 - 60℃; for 3h;
96%
67843-74-7

(S)-epichlorohydrin

(S)-(-)-1-bromo-3-chloro-2-propanol

Conditions
ConditionsYield
With dilithium tetrabromonickelate(II) In tetrahydrofuran 1) 0 degC, 2 h, 2) r.t., 1 h;95%
67843-74-7

(S)-epichlorohydrin

56522-24-8

tert-butyldimethylsilyl cyanide

884902-55-0

(3S)-3-[(tert-butyldimethylsilyl)oxy]-4-chlorobutanenitrile

Conditions
ConditionsYield
With potassium cyanide; 18-crown-6 ether95%
67843-74-7

(S)-epichlorohydrin

791856-68-3

6-(4-bromophenyl)-1,2,3,4-tetrahydro-1,5-naphthyridine

944152-87-8

(+)-(S)-6-(4-bromophenyl)-1-(3-chloro-2-hydroxypropyl)-1,2,3,4-tetrahydro-1,5-naphthyridine

Conditions
ConditionsYield
With ytterbium(III) triflate In dichloromethane at 60℃; for 5h;95%
67843-74-7

(S)-epichlorohydrin

107-92-6

butyric acid

890051-54-4

butyric acid-3-chloro-(S)-2-hydroxy-propyl ester

Conditions
ConditionsYield
With chromium chloride at 60℃; for 24h;95%
Stage #1: butyric acid With N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediaminocobalt(II); oxygen at 50℃; for 1h;
Stage #2: (S)-epichlorohydrin With diisopropylamine at 20℃; for 24h;
82.0 %Chromat.
693-03-8

n-butyl magnesium bromide

67843-74-7

(S)-epichlorohydrin

1224174-07-5

(S)-1-chlorohept-6-en-2-ol

Conditions
ConditionsYield
With copper(l) iodide In tetrahydrofuran at -78℃;95%
67843-74-7

(S)-epichlorohydrin

57260-71-6

1-t-Butoxycarbonylpiperazine

335165-58-7

tert-butyl 4-[[(2S)-oxiran-2-yl]methyl]piperazine-1-carboxylate

Conditions
ConditionsYield
In ethanol for 12h;95%
67843-74-7

(S)-epichlorohydrin

100-51-6

benzyl alcohol

Conditions
ConditionsYield
Stage #1: (S)-epichlorohydrin With tetrabutylammomium bromide; sodium hydroxide In water at 20℃;
Stage #2: benzyl alcohol In water at 20℃; regioselective reaction;
95%
67843-74-7

(S)-epichlorohydrin

92-66-0

4-bromo-1,1'-biphenyl

1573000-28-8

(S)-1-([1,1’-biphenyl]-4-yl)-3-chloropropan-2-ol

Conditions
ConditionsYield
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran at 40 - 50℃; for 2h;
Stage #2: (S)-epichlorohydrin With copper(l) iodide In tetrahydrofuran at -15 - 5℃; for 2h;
95%
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran at 45 - 50℃; for 0.166667h;
Stage #2: With copper(l) iodide In tetrahydrofuran at -10 - 5℃; for 0.5h;
Stage #3: (S)-epichlorohydrin In tetrahydrofuran for 4h;
92%
Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78 - -10℃; for 2.5h; Inert atmosphere;
Stage #2: (S)-epichlorohydrin In tetrahydrofuran; hexane at 20℃; for 5h;
85%
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran at 45 - 50℃; Inert atmosphere; Industrial scale;
Stage #2: With copper(l) iodide In tetrahydrofuran at -20 - -15℃; for 0.5h; Industrial scale;
Stage #3: (S)-epichlorohydrin Reagent/catalyst; Temperature; Industrial scale; Further stages;
48.7 kg
Stage #1: 4-bromo-1,1'-biphenyl With iodine; magnesium In tetrahydrofuran at 35 - 45℃; Inert atmosphere;
Stage #2: (S)-epichlorohydrin With copper(l) iodide In tetrahydrofuran at -20 - -15℃; Inert atmosphere;
45.4 g
67843-74-7

(S)-epichlorohydrin

3695-77-0

triphenylmethanethiol

(S)-1-chloro-3-(tritylthio)propan-2-ol

Conditions
ConditionsYield
With potassium fluoride In methanol at 20℃; for 72h;95%
67843-74-7

(S)-epichlorohydrin

109-69-3

n-Butyl chloride

81007-64-9

(S)-1-chloroheptane-2-ol

Conditions
ConditionsYield
Stage #1: n-Butyl chloride With iodine; magnesium In tetrahydrofuran at 80℃; for 1h; Inert atmosphere;
Stage #2: (S)-epichlorohydrin With copper(l) cyanide In tetrahydrofuran at -78 - -20℃; for 3h; Inert atmosphere;
95%
92-54-6

4-phenyl-1-piperazine

67843-74-7

(S)-epichlorohydrin

C13H18N2O

Conditions
ConditionsYield
With sodium hydroxide In water at 75℃; for 0.25h;95%
67843-74-7

(S)-epichlorohydrin

89343-06-6

tris-iso-propylsilyl acetylene

638222-25-0

(2S)-1-chloro-5-(triisopropylsilanyl)pent-4-yn-2-ol

Conditions
ConditionsYield
Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium; boron trifluoride-tetrahydrofuran complex In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: (S)-epichlorohydrin In tetrahydrofuran; hexane at -78℃; for 2h; Hiroa reaction;
94%
74-96-4

ethyl bromide

67843-74-7

(S)-epichlorohydrin

141339-40-4

S-1-chloromethyl-1-butanol

Conditions
ConditionsYield
Stage #1: ethyl bromide With iodine; magnesium In diethyl ether for 1.5h; Reflux;
Stage #2: (S)-epichlorohydrin With copper(l) cyanide In tetrahydrofuran; diethyl ether at -78 - -20℃; for 3h;
Stage #3: With ammonium chloride In tetrahydrofuran; diethyl ether; water
94%
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Specification

The (S)-(+)-Epichlorohydrin with CAS registry number of 67843-74-7 is also known as Oxirane, (chloromethyl)-, (S)-. The IUPAC name is (2S)-2-(Chloromethyl)oxirane. It belongs to product categories of Industrial/Fine Chemicals; Chiral; Chiral Compounds; Chiral Building Blocks; Glycidyl Compounds, etc. (Chiral); Oxiranes; Simple 3-Membered Ring Compounds; Synthetic Organic Chemistry. Its EINECS registry number is 203-439-8. In addition, the formula is C3H5ClO and the molecular weight is 92.52. This chemical is a colorless to light yellow liquid and should be stored in sealed containers away from acid, alkali, metal alloy and oxidizing agents.

Physical properties about (S)-(+)-Epichlorohydrin are: (1)ACD/LogP: 0.45; (2)ACD/LogD (pH 5.5): 0.45; (3)ACD/LogD (pH 7.4): 0.45; (4)ACD/BCF (pH 5.5): 1.29; (5)ACD/BCF (pH 7.4): 1.29; (6)ACD/KOC (pH 5.5): 41.84; (7)ACD/KOC (pH 7.4): 41.84; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 1; (10)Index of Refraction: 1.443; (11)Molar Refractivity: 20.37 cm3; (12)Molar Volume: 76.7 cm3; (13)Surface Tension: 35.6 dyne/cm; (14)Density: 1.205 g/cm3; (15)Flash Point: 33.9 °C; (16)Enthalpy of Vaporization: 33.98 kJ/mol; (17)Boiling Point: 116.1 °C at 760 mmHg; (18)Vapour Pressure: 22 mmHg at 25 °C.

Preparation of (S)-(+)-Epichlorohydrin: it is prepared by reaction of (S)-2,3-dichloropropanol. The reaction needs reagent KOH and solvent methanol at ambient temperature. The yield is about 51%.

(S)-(+)-Epichlorohydrin is prepared by reaction of (S)-2,3-dichloropropanol.

Uses of (S)-(+)-Epichlorohydrin: it is used to produce (S)-1-chloro-2-heptanol by reaction with butylmagnesium bromide. The reaction occurs with reagent CuBr2*SMe and solvents diethyl ether, tetrahydrofuran at -30 °C for 5 hours. The yield is about 60%.

(S)-(+)-Epichlorohydrin is used to produce (S)-1-chloro-2-heptanol by reaction with butylmagnesium bromide.

When you are using this chemical, please be cautious about it. As a chemical, it is toxic by inhalation, in contact with skin and if swallowed. It may cause burns, sensitisation by skin contact and even cancer. Besides, it is flammable. During using it, obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1C(O1)CCl
2. Isomeric SMILES: C1[C@H](O1)CCl
3. InChI: InChI=1S/C3H5ClO/c4-1-3-2-5-3/h3H,1-2H2/t3-/m1/s1
4. InChIKey: BRLQWZUYTZBJKN-GSVOUGTGSA-N