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CAS 106-89-8
(+/-)-2-(Chloromethyl)oxirane2-(chloromethyl)oxirane2-(Chloromethyl)oxiraneEpichlorohydrin(+/-)-Epichlorohydrin
Codes: Carteolol Hydrochloride-011, METOPR-002, Bisoprolol-002, AZEL-002, Folic Acid-076, Timolol Maleate-002, RANO-008, Ketoconazole-018, SEVE-003, NAFT-002, Mosapride Citrate-024
Application context (from source-drug indications)
Ocular hypertensionCarteolol Hydrochloride/LatanoprostGlaucomaCarteolol Hydrochloride/LatanoprostOpen-angle glaucomaCarteolol Hydrochloride/LatanoprostAngina pectorisIvabradine Hydrochloride/Metoprolol TartrateHypertensionAmlodipine Besylate/Bisoprolol FumarateEssential hypertensionAmlodipine Besylate/Bisoprolol FumarateHypertensionOlmesartan Medoxomil/AzelnidipineEssential hypertensionEnalapril Maleate/Folic AcidOcular hypertensionBrimonidine Tartrate/Timolol MaleateGlaucomaBrimonidine Tartrate/Timolol MaleateOcular hypertensionBimatoprost/Timolol MaleateOpen-angle glaucomaBimatoprost/Timolol MaleateGlaucomaBimatoprost/Timolol MaleateAngina pectorisRanolazineMyocardial infarctionRanolazineAmyotrophic lateral sclerosisRanolazineStable anginaRanolazineCrohn's diseaseRanolazineInflammatory bowel diseaseRanolazineFungal infectionNaftifine hydrochloride/KetoconazoleOcular hypertensionTimolol MaleateGlaucomaTimolol MaleateOpen-angle glaucomaTimolol MaleateTrauma and injuryTimolol MaleateHypertensionTimolol MaleateMigraineTimolol MaleateHypertensionCarteolol HydrochlorideOcular hypertensionCarteolol HydrochlorideGlaucomaCarteolol HydrochlorideAngina pectorisCarteolol HydrochlorideArrhythmiaCarteolol HydrochlorideHypertensionMetoprolol SuccinateAngina pectorisMetoprolol SuccinateHeart failureMetoprolol SuccinateHyperthyroidismMetoprolol SuccinateArrhythmiaMetoprolol SuccinateCardiac neurosisMetoprolol SuccinateHypertensionBisoprolol FumarateAngina pectorisBisoprolol FumarateChronic obstructive pulmonary diseaseBisoprolol FumarateCardiac and vascular disordersBisoprolol FumarateAcute coronary syndromeBisoprolol FumarateFastingBisoprolol FumarateHypertensionAzelnidipineMegaloblastic anaemiaFolic AcidFolate deficiencyFolic AcidNeural tube defectFolic AcidAnaemiaFolic AcidHot flushesFolic AcidHyperhomocysteinaemiaFolic AcidCushing's syndromeKetoconazole头皮屑KetoconazolePityriasis versicolorKetoconazole皮肤念珠菌病KetoconazoleTineaKetoconazole脂溢性皮炎KetoconazoleHyperphosphataemiaSevelamer CarbonateChronic renal impairmentSevelamer CarbonateNephropathySevelamer CarbonateEnd-stage renal diseaseSevelamer CarbonateRenal impairmentSevelamer CarbonateHyperparathyroidismSevelamer Carbonate排尿困难NaftopidilBenign prostatic hyperplasiaNaftopidil增生NaftopidilGastritisMosapride CitrateEnteral feeding intoleranceMosapride CitrateIrritable bowel syndromeMosapride CitrateDyspepsiaMosapride CitrateConstipationMosapride Citrate
Source drugs (routes using this intermediate)
| Drug | Tier | Expiry |
|---|---|---|
| Carteolol Hydrochloride/Latanoprost | Tier C — Watch / trade | - |
| Ivabradine Hydrochloride/Metoprolol Tartrate | Tier C — Watch / trade | - |
| Amlodipine Besylate/Bisoprolol Fumarate | Tier C — Watch / trade | - |
| Olmesartan Medoxomil/Azelnidipine | Tier C — Watch / trade | - |
| Enalapril Maleate/Folic Acid | Tier C — Watch / trade | - |
| Brimonidine Tartrate/Timolol Maleate | Tier C — Watch / trade | - |
| Bimatoprost/Timolol Maleate | Tier C — Watch / trade | - |
| Ranolazine | Tier C — Watch / trade | - |
| Naftifine hydrochloride/Ketoconazole | Tier C — Watch / trade | - |
| Timolol Maleate | Tier C — Watch / trade | - |
| Carteolol Hydrochloride | Tier C — Watch / trade | - |
| Metoprolol Succinate | Tier C — Watch / trade | - |
| Bisoprolol Fumarate | Tier C — Watch / trade | - |
| Azelnidipine | Tier C — Watch / trade | - |
| Folic Acid | Tier C — Watch / trade | - |
| Ketoconazole | Tier C — Watch / trade | - |
| Sevelamer Carbonate | Tier B — Position early | - |
| Naftopidil | Tier C — Watch / trade | - |
| Mosapride Citrate | Tier C — Watch / trade | - |
Position in synthesis routes (up/downstream chain)
Ordered by route registration; left → right is the synthesis direction. The highlighted node is the current CAS; others link to their own profiles.
5-(oxiran-2-ylmethoxy)-1,2,3,4-tetrahydroquinolin-2-one→5-(3-chloro-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one→decahydroquinoline-2,5-dione→5-Hydroxy-1,2,3,4-tetrahydroquinolin-2-one→(+/-)-2,3-Dihydroxychloropropane→(+/-)-2-(Chloromethyl)oxirane→1-Bromo-2,3-epoxypropane→1,1-Dimethylethylamine
Phenol→2-(Chloromethyl)oxirane→2-(phenoxymethyl)oxirane→N-Isopropylamine→Ethylene glycol monoisopropyl ether→(2-hydroxy-3-phenoxypropyl)(propan-2-yl)amine→Diethyl carbonate→5-(phenoxymethyl)-3-(propan-2-yl)-1,3-oxazolidin-2-one→5-[4-(chloromethyl)phenoxymethyl]-3-(propan-2-yl)-1,3-oxazolidin-2-one→3-(propan-2-yl)-5-(4-{[2-(propan-2-yloxy)ethoxy]methyl}phenoxymethyl)-1,3-oxazolidin-2-one
diphenylmethanamine→2-(chloromethyl)oxirane→1-benzhydrylazetidin-3-ol→2-cyanoacetic acid→1-benzhydrylazetidin-3-yl 2-cyanoacetate→1-benzhydrylazetidin-3-yl 3-amino-3-iminopropanoate acetate→isopropyl (E)-2-(3-nitrobenzylidene)-3-oxobutanoate
4-(Ethoxycarbonyl)aniline→(+/-)-2-(Chloromethyl)oxirane→Ethyl 4-[(3-chloro-2-hydroxypropyl)amino]benzoate→Ethyl 4-[(tert-butoxycarbonyl)(3-chloro-2-hydroxypropyl)amino]benzoate→Ethyl 4-[(tert-butoxycarbonyl)(3-chloro-2-oxopropyl)amino]benzoate→2,4,5-Triamino-6-hydroxypyrimidine sulfate→Ethyl 4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl](tert-butoxycarbonyl)amino]benzoate→4-[(2-Amino-4-oxo-3H-pteridin-6-yl)methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]benzoic acid→(S)-Glutamic acid diethyl ester→Diethyl N-(4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl](tert-butoxycarbonyl)amino]benzoyl)-L-glutamate
Brimonidine Tartrate/Timolol MaleateOptimised routesteps: 5total yield: 108.7g(Timolol Maleate (API))
4-(4-Morpholinyl)-1,2,5-thiadiazol-3-ol→(+/-)-2-(Chloromethyl)oxirane→2-Methylpropan-2-amine→1-(tert-Butylamino)-3-[[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propan-2-ol→(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol→3,4-Dichloro-1,2,5-thiadiazole→Diethylene oximide→4-(4-chloro-1,2,5-thiadiazol-3-yl)morpholine→[(5S)-3-tert-Butyl-1,3-oxazolidin-5-yl]methanol
2-(Chloromethyl)oxirane→(R)-(-)-2-(Chloromethyl)oxirane→3-Chloropropane-1,2(S)-diol→4-(4-Morpholinyl)-1,2,5-thiadiazol-3-ol→(2R)-1-Chloro-3-[[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propan-2-ol→4-[4-[(2S)-Oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl]morpholine→Sodium 4-(morpholin-4-yl)-1,2,5-thiadiazol-3-olate→(2S)-3-[[4-(Morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propane-1,2-diol→2-Methylpropan-2-amine→(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol
4-(4-Morpholinyl)-1,2,5-thiadiazol-3-ol→(+/-)-2-(Chloromethyl)oxirane→2-Methylpropan-2-amine→1-(tert-Butylamino)-3-[[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propan-2-ol→(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol→3,4-Dichloro-1,2,5-thiadiazole→Diethylene oximide→4-(4-chloro-1,2,5-thiadiazol-3-yl)morpholine→[(5S)-3-tert-Butyl-1,3-oxazolidin-5-yl]methanol
2-(Chloromethyl)oxirane→(R)-(-)-2-(Chloromethyl)oxirane→3-Chloropropane-1,2(S)-diol→4-(4-Morpholinyl)-1,2,5-thiadiazol-3-ol→(2R)-1-Chloro-3-[[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propan-2-ol→4-[4-[(2S)-Oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl]morpholine→Sodium 4-(morpholin-4-yl)-1,2,5-thiadiazol-3-olate→(2S)-3-[[4-(Morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propane-1,2-diol→2-Methylpropan-2-amine→(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol
2-chloroacetyl chloride→2,6-dimethylaniline→2-chloro-N-(2,6-dimethylphenyl)acetamide→2-((2-methoxyphenoxy)methyl)oxirane→2-methoxyphenol→2-(chloromethyl)oxirane→2,2'-azanediylbis(ethan-1-ol)→2-(bis(2-hydroxyethyl)amino)-N-(2,6-dimethylphenyl)acetamide→2-(bis(2-chloroethyl)amino)-N-(2,6-dimethylphenyl)acetamide→1-amino-3-(2-methoxyphenoxy)propan-2-ol
1,3-Dichlorobenzene→2-Bromoacetyl 2-bromoacetate→2-Bromoacetyl bromide→2-Bromo-1-(2,4-dichlorophenyl)ethanone→1,3-Diaza-2,4-cyclopentadiene→1-(2,4-Dichlorophenyl)-2-imidazolylethanone→1-[4-(4-Hydroxyphenyl)piperazin-1-yl]ethanone→(+/-)-2-(Chloromethyl)oxirane→1-[4-[4-(2,3-Dihydroxypropoxy)phenyl]piperazin-1-yl]ethan-1-one
4-(4-Morpholinyl)-1,2,5-thiadiazol-3-ol→(+/-)-2-(Chloromethyl)oxirane→2-Methylpropan-2-amine→1-(tert-Butylamino)-3-[[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propan-2-ol→(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol→3,4-Dichloro-1,2,5-thiadiazole→Diethylene oximide→4-(4-chloro-1,2,5-thiadiazol-3-yl)morpholine→[(5S)-3-tert-Butyl-1,3-oxazolidin-5-yl]methanol
2-(Chloromethyl)oxirane→(R)-(-)-2-(Chloromethyl)oxirane→3-Chloropropane-1,2(S)-diol→4-(4-Morpholinyl)-1,2,5-thiadiazol-3-ol→(2R)-1-Chloro-3-[[4-(morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propan-2-ol→4-[4-[(2S)-Oxiran-2-ylmethoxy]-1,2,5-thiadiazol-3-yl]morpholine→Sodium 4-(morpholin-4-yl)-1,2,5-thiadiazol-3-olate→(2S)-3-[[4-(Morpholin-4-yl)-1,2,5-thiadiazol-3-yl]oxy]propane-1,2-diol→2-Methylpropan-2-amine→(S)-1-(tert-butylamino)-3-((4-morpholino-1,2,5-thiadiazol-3-yl)oxy)propan-2-ol
5-(oxiran-2-ylmethoxy)-1,2,3,4-tetrahydroquinolin-2-one→5-(3-chloro-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolin-2-one→decahydroquinoline-2,5-dione→5-Hydroxy-1,2,3,4-tetrahydroquinolin-2-one→(+/-)-2,3-Dihydroxychloropropane→(+/-)-2-(Chloromethyl)oxirane→1-Bromo-2,3-epoxypropane→1,1-Dimethylethylamine
Phenol→2-(Chloromethyl)oxirane→2-(phenoxymethyl)oxirane→N-Isopropylamine→Ethylene glycol monoisopropyl ether→(2-hydroxy-3-phenoxypropyl)(propan-2-yl)amine→Diethyl carbonate→5-(phenoxymethyl)-3-(propan-2-yl)-1,3-oxazolidin-2-one→5-[4-(chloromethyl)phenoxymethyl]-3-(propan-2-yl)-1,3-oxazolidin-2-one→3-(propan-2-yl)-5-(4-{[2-(propan-2-yloxy)ethoxy]methyl}phenoxymethyl)-1,3-oxazolidin-2-one
diphenylmethanamine→2-(chloromethyl)oxirane→1-benzhydrylazetidin-3-ol→2-cyanoacetic acid→1-benzhydrylazetidin-3-yl 2-cyanoacetate→1-benzhydrylazetidin-3-yl 3-amino-3-iminopropanoate acetate→isopropyl (E)-2-(3-nitrobenzylidene)-3-oxobutanoate
4-(Ethoxycarbonyl)aniline→(+/-)-2-(Chloromethyl)oxirane→Ethyl 4-[(3-chloro-2-hydroxypropyl)amino]benzoate→Ethyl 4-[(tert-butoxycarbonyl)(3-chloro-2-hydroxypropyl)amino]benzoate→Ethyl 4-[(tert-butoxycarbonyl)(3-chloro-2-oxopropyl)amino]benzoate→2,4,5-Triamino-6-hydroxypyrimidine sulfate→Ethyl 4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl](tert-butoxycarbonyl)amino]benzoate→4-[(2-Amino-4-oxo-3H-pteridin-6-yl)methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]benzoic acid→(S)-Glutamic acid diethyl ester→Diethyl N-(4-[[(2-amino-4-oxo-1,4-dihydropteridin-6-yl)methyl](tert-butoxycarbonyl)amino]benzoyl)-L-glutamate
1,3-Dichlorobenzene→2-Bromoacetyl 2-bromoacetate→2-Bromoacetyl bromide→2-Bromo-1-(2,4-dichlorophenyl)ethanone→1,3-Diaza-2,4-cyclopentadiene→1-(2,4-Dichlorophenyl)-2-imidazolylethanone→1-[4-(4-Hydroxyphenyl)piperazin-1-yl]ethanone→(+/-)-2-(Chloromethyl)oxirane→1-[4-[4-(2,3-Dihydroxypropoxy)phenyl]piperazin-1-yl]ethan-1-one
2-methylbutan-1-amine hydrochloride(1:x)→2-methylbutan-1-amine hydrochloride(1:x)→2-(chloromethyl)oxirane→5-((3-((4-(aminomethyl)-2-methylhexyl)amino)-2-hydroxypropyl)amino)-2-ethyl-4-methylpentan-1-aminium chloride
2-(chloromethyl)oxirane→5-((3-((4-(aminomethyl)-2-methylhexyl)amino)-2-hydroxypropyl)amino)-2-ethyl-4-methylpentan-1-aminium chloride→prop-2-en-1-amine→(E)-2,2'-(diazene-1,2-diyl)bis(2-methylpropanamide) dihydrochloride→5-((3-((4-(aminomethyl)-2-methylhexyl)amino)-2-hydroxypropyl)amino)-2-ethyl-4-methylpentan-1-aminium
2-methylbutan-1-amine hydrochloride(1:x)→2-(chloromethyl)oxirane→5-((3-((4-(aminomethyl)-2-methylhexyl)amino)-2-hydroxypropyl)amino)-2-ethyl-4-methylpentan-1-aminium chloride
naphthalen-1-ol→2-(chloromethyl)oxirane→2-((naphthalen-1-yloxy)methyl)oxirane→1-(2-methoxyphenyl)piperazine hydrochloride
[4-(4-Fluorobenzyl)-2-morpholinyl]methylamine→Sulfuric acid 1-[4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→Phosphoric acid 1-[4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→1-[4-[(4-Fluorophenyl)methyl]morpholin-2-yl]methanamine hydrogen chloride→2-Methylpropane-1,2,3-tricarboxylic acid 1-[4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→4-Fluorobenzaldehyde→2-Hydroxyethylamine→2-[(E)-[(4-Fluorophenyl)methylidene]amino]ethan-1-ol→2-[[(4-Fluorophenyl)methyl]amino]ethan-1-ol→2-[(Oxiran-2-yl)methyl]-1H-isoindole-1,3(2H)-dione→1,3-Dihydro-1,3-dioxoisoindole→1,3-Dihydro-1,3-dioxoisoindole potassium salt→(+/-)-Epichlorohydrin
(4-Fluorophenyl)methanone→1-Amino-2-hydroxyethane→2-(4-Fluorobenzylamino)ethanol→(+/-)-2-(Chloromethyl)oxirane→1-chloro-3-{[(4-fluorophenyl)methyl](2-hydroxyethyl)amino}propan-2-ol→2-(chloromethyl)-4-[(4-fluorophenyl)methyl]morpholine→{4-[(4-fluorophenyl)methyl]morpholin-2-yl}methanol→{4-[(4-fluorophenyl)methyl]morpholin-2-yl}methyl 4-methylbenzene-1-sulfonate→[(2S)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl phenylmethanesulfonate→[(2R)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methyl phenylmethanesulfonate→[(2R)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→[(2S)-4-[(4-fluorophenyl)methyl]morpholin-2-yl]methanamine→4-Amino-5-chloro-2-ethoxybenzoic acid
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