1,3-Dichloro-2-propanol
(S)-epichlorohydrin
Conditions | Yield |
---|---|
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% |
1,2-Epoxy-3-bromopropane
A
(S)-epichlorohydrin
B
(2R)-3-bromo-1,2-propanediol
Conditions | Yield |
---|---|
With (R,R)-Jacobsen catalyst; water In tetrahydrofuran at 4℃; for 24h; | A n/a B 93% |
O-benzyl carbamate
epichlorohydrin
A
(S)-epichlorohydrin
B
[(R)-3-chloro-2-hydroxypropyl]carbamic acid benzyl ester
Conditions | Yield |
---|---|
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% |
(S)-3-chloro-2-hydroxypropyl-1-(toluene-4-sulfonate)
(S)-epichlorohydrin
Conditions | Yield |
---|---|
With sodium ethane-1,2-diolate In ethylene glycol for 0.25h; Ambient temperature; | 85% |
epichlorohydrin
(S)-epichlorohydrin
Conditions | Yield |
---|---|
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% |
(R)-2,3-Dichloro-1-propanol
(S)-epichlorohydrin
Conditions | Yield |
---|---|
With sodium hydroxide | 74% |
epichlorohydrin
A
(S)-epichlorohydrin
B
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
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)-epichlorohydrin
Conditions | Yield |
---|---|
With potassium hydroxide In methanol Ambient temperature; | 51% |
epichlorohydrin
A
(S)-epichlorohydrin
B
(2R)-3-chloro-1,2-propanediol
C
(S)-3-chloropropan-1,2-diol
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 |
Conditions | Yield |
---|---|
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 |
epichlorohydrin
A
(S)-epichlorohydrin
B
(R)-(-)-epichlorohydrin
C
1,3-Dichloro-2-propanol
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% |
Methyl 4-hydroxyphenylacetate
epichlorohydrin
A
(S)-epichlorohydrin
B
methyl (R)-2-(4-(3-chloro-2-hydroxypropoxy)phenyl)acetate
Conditions | Yield |
---|---|
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 |
epichlorohydrin
phenol
A
(S)-epichlorohydrin
B
(R)-1-chloro-3-phenoxy-2-propanol
Conditions | Yield |
---|---|
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 |
epichlorohydrin
A
(S)-epichlorohydrin
B
(R)-(-)-epichlorohydrin
C
(2R)-3-chloro-1,2-propanediol
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% |
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; |
1,3-Dichloro-2-propanol
A
(S)-epichlorohydrin
B
(R)-(-)-epichlorohydrin
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)
A
(S)-epichlorohydrin
B
(R)-(-)-epichlorohydrin
Conditions | Yield |
---|---|
With sodium 2-hydroxyethoxide In ethylene glycol for 0.0833333h; Title compound not separated from byproducts; |
epichlorohydrin
A
(S)-epichlorohydrin
B
(R)-(-)-epichlorohydrin
C
(2R)-3-chloro-1,2-propanediol
D
(S)-3-chloropropan-1,2-diol
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; |
(R)-(-)-epichlorohydrin
(S)-epichlorohydrin
Conditions | Yield |
---|---|
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; |
tert-butyl carbamate
epichlorohydrin
A
(S)-epichlorohydrin
B
(R)-3-chloro-2-hydroxypropylcarbamic acid tert-butyl ester
Conditions | Yield |
---|---|
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 |
(R)-(-)-epichlorohydrin
A
(S)-epichlorohydrin
B
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With (R,R)-Jacobsen catalyst; water | A n/a B n/a |
aniline
epichlorohydrin
A
(S)-epichlorohydrin
B
(R)-(-)-epichlorohydrin
C
(S)-(+)-1-chloro-3-(phenylamino)-propan-2-ol
D
(R)-(+)-N-(3-chloro-2-hydroxypropyl)aniline
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 |
potassium cyanate
(S)-epichlorohydrin
(5S)-5-(chloromethyl)-1,3-oxazolidin-2-one
Conditions | Yield |
---|---|
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; |
(S)-epichlorohydrin
2-benzylamino-N-(4-benzyloxyphenyl)acetamide
2-{benzyl[(2S)-3-chloro-2-hydroxypropyl]amino}-N-(4-benzyloxyphenyl)acetamide
Conditions | Yield |
---|---|
With magnesium sulfate In methanol; dichloromethane at 35℃; for 72h; | 100% |
With magnesium sulfate In methanol; dichloromethane at 35℃; for 72h; |
(S)-epichlorohydrin
2-chloro-ethanol
(S)-1-(2-chloroethoxy)-3-chloropropan-2-ol
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
Stage #1: bromopentene With magnesium In tetrahydrofuran for 0.5h; Heating; Stage #2: (S)-epichlorohydrin In tetrahydrofuran at -50 - 20℃; for 2h; | 100% |
(S)-epichlorohydrin
1-bromo-2,4,5-trifluorobenzene
(S)-1-chloro-3-(2,4,5-trifluorophenyl)propan-2-ol
Conditions | Yield |
---|---|
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 |
(S)-epichlorohydrin
3,4-dichloro-benzeneacetonitrile
((1S,2R)-2-(aminomethyl)-2-(3,4-dichlorophenyl)cyclopropyl)methanol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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 |
(S)-epichlorohydrin
dibenzylamine
(S)-N,N-dibenzylamino-1-(oxiran-2-ylmethyl)methylamine
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate | 98% |
ortho-mercaptophenol
(S)-epichlorohydrin
(R)-3-[(2-hydroxyphenyl)thio]-1,2-epoxypropane
Conditions | Yield |
---|---|
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; |
(S)-epichlorohydrin
Conditions | Yield |
---|---|
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% |
(S)-epichlorohydrin
dibenzylamine
(S)-3-chloro-2-hydroxypropyl dibenzylamine
Conditions | Yield |
---|---|
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; |
(S)-epichlorohydrin
trimethylsilylacetylene
(S)-1-chloro-2-hydroxy-5-trimethylsilyl-4-pentyne
Conditions | Yield |
---|---|
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; |
methanol
(S)-epichlorohydrin
carbon monoxide
methyl (S)-4-chloro-3-hydroxybutanoate
Conditions | Yield |
---|---|
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% |
(S)-epichlorohydrin
N-(2,6-dimethylphenyl)-2-(piperazin-1-yl)acetamide
(S)-2-(4-(3-chloro-2-hydroxypropyl)piperazin-1-yl)-N-(2,6-dimethylphenyl)acetamide
Conditions | Yield |
---|---|
In water at 15℃; for 1h; | 96% |
(S)-epichlorohydrin
Conditions | Yield |
---|---|
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% |
(S)-epichlorohydrin
Conditions | Yield |
---|---|
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% |
(S)-epichlorohydrin
Conditions | Yield |
---|---|
With dilithium tetrabromonickelate(II) In tetrahydrofuran 1) 0 degC, 2 h, 2) r.t., 1 h; | 95% |
(S)-epichlorohydrin
tert-butyldimethylsilyl cyanide
(3S)-3-[(tert-butyldimethylsilyl)oxy]-4-chlorobutanenitrile
Conditions | Yield |
---|---|
With potassium cyanide; 18-crown-6 ether | 95% |
(S)-epichlorohydrin
6-(4-bromophenyl)-1,2,3,4-tetrahydro-1,5-naphthyridine
(+)-(S)-6-(4-bromophenyl)-1-(3-chloro-2-hydroxypropyl)-1,2,3,4-tetrahydro-1,5-naphthyridine
Conditions | Yield |
---|---|
With ytterbium(III) triflate In dichloromethane at 60℃; for 5h; | 95% |
(S)-epichlorohydrin
butyric acid
butyric acid-3-chloro-(S)-2-hydroxy-propyl ester
Conditions | Yield |
---|---|
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. |
n-butyl magnesium bromide
(S)-epichlorohydrin
(S)-1-chlorohept-6-en-2-ol
Conditions | Yield |
---|---|
With copper(l) iodide In tetrahydrofuran at -78℃; | 95% |
(S)-epichlorohydrin
1-t-Butoxycarbonylpiperazine
tert-butyl 4-[[(2S)-oxiran-2-yl]methyl]piperazine-1-carboxylate
Conditions | Yield |
---|---|
In ethanol for 12h; | 95% |
(S)-epichlorohydrin
benzyl alcohol
(S)-benzyl glycidyl ether
Conditions | Yield |
---|---|
Stage #1: (S)-epichlorohydrin With tetrabutylammomium bromide; sodium hydroxide In water at 20℃; Stage #2: benzyl alcohol In water at 20℃; regioselective reaction; | 95% |
(S)-epichlorohydrin
4-bromo-1,1'-biphenyl
(S)-1-([1,1’-biphenyl]-4-yl)-3-chloropropan-2-ol
Conditions | Yield |
---|---|
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 |
(S)-epichlorohydrin
triphenylmethanethiol
Conditions | Yield |
---|---|
With potassium fluoride In methanol at 20℃; for 72h; | 95% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In water at 75℃; for 0.25h; | 95% |
(S)-epichlorohydrin
tris-iso-propylsilyl acetylene
(2S)-1-chloro-5-(triisopropylsilanyl)pent-4-yn-2-ol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
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%.
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%.
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
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