(R)-(-)-epichlorohydrin
(2R)-3-chloro-1,2-propanediol
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)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With hydrogenchloride | 86% |
[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium chloride; sodium nitrite In water at 10 - 20℃; for 24h; Substitution; | 82% |
(1S,2R,4R,4'R)-4'-Chloromethyl-4,7,7-trimethylbicyclo<2.2.1>heptane-2-spiro-2'-(1',3'-dioxolan)-3-one
A
(2R)-3-chloro-1,2-propanediol
B
C13H21ClO3
C
C13H21ClO3
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol | A 55% B n/a C n/a |
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 |
epichlorohydrin
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With water In tetrahydrofuran at 4℃; for 24h; | 50% |
In tetrahydrofuran; water | |
In tetrahydrofuran; water | |
With Co(salen) macrocycles 1(OTs) at 20℃; for 0.333333h; optical yield given as %ee; enantioselective reaction; |
2,3-Dichloro-1-propanol
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
D
epichlorohydrin
Conditions | Yield |
---|---|
With epoxide hydrolase from Agrobacterium radiobacter AD1; halohydrin dehalogenase from Agrobacterium radiobacter AD1; Tris-SO4 buffer In water at 30℃; for 20h; pH=7.5; kinetic resolution; Further byproducts given; | A n/a B n/a C 49.5% D n/a |
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 |
epichlorohydrin
A
(R)-(-)-epichlorohydrin
B
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With water at 20℃; for 8h; optical yield given as %ee; | A 45% B n/a |
epichlorohydrin
A
(R)-(-)-epichlorohydrin
B
(2R)-3-chloro-1,2-propanediol
C
(S)-3-chloropropan-1,2-diol
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
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% |
(1S,2R,4R,4'R)-4'-Chloromethyl-4,7,7-trimethylbicyclo<2.2.1>heptane-2-spiro-2'-(1',3'-dioxolan)-3-one
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With hydrogenchloride; sodium tetrahydroborate 2) MeOH, reflux, 3h; Yield given. Multistep reaction; |
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With β-galactosidase In various solvent(s) at 35℃; |
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With ethanol Yield given. Yields of byproduct given; |
3-monochloro-1,2-propanediol
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With sodium hydroxide; phospho(enol)pyruvic acid mono potassium salt; ATP; 2-hydroxyethanethiol; magnesium chloride In water at 27℃; for 120h; pH=7.5; Yield given. Yields of byproduct given; |
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 3h; Heating; Yield given; |
1,2-diacetoxy-3-chloro-propane
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With porcine pancreatic lipase; sodium methylate 1) H2O (pH:7), r.t., 2) MeOH, r.t., 4h; Multistep reaction; |
(S)-1,2-Diacetoxy-3-chloropropane
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With sulfuric acid for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
3-chloroprop-1-ene
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); 1,4-bis(dihydroquinidinyl)anthraquinone In water; tert-butyl alcohol at 0℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With dihydrogen peroxide In acetonitrile at 25℃; for 0.416667h; Title compound not separated from byproducts.; |
3-monochloro-1,2-propanediol
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With sodium hydroxide; sodium azide; acid phosphatase; pyruvate kinase; phosphoenolpyruvic acid; glycerol kinase from Streptomyces canus; potassium chloride; ATP; 2-hydroxyethanethiol; magnesium chloride 1.) H2O, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
epichlorohydrin
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With polistyrene-bound (R,R)-N-(3,5-di-t-butyl-6-hydroxy)benzylidene-N'-(3-t-butyl-2,5-dihydroxy)benzylidene-1,2-cyclohexanediamine; water In dichloromethane for 3h; Ambient temperature; Yield given; Yields of byproduct given. Title compound not separated from byproducts; | |
With water Jacobsen kinetic hydrolytic resolution; | |
Stage #1: epichlorohydrin With phthalic anhydride; C64H74Al2Cl2N4O4; bis(triphenylphosphine)iminium chloride In toluene at 25℃; for 3h; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 24h; Reagent/catalyst; Temperature; Inert atmosphere; enantioselective reaction; | A n/a B n/a |
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; |
3-chloro-1-hydroxypropan-2-one
A
(2R)-3-chloro-1,2-propanediol
B
(S)-3-chloropropan-1,2-diol
Conditions | Yield |
---|---|
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction; | A n/a B n/a |
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction; | A n/a B n/a |
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction; | A n/a B n/a |
3-chloro-1-hydroxypropan-2-one
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With Candida-derived reductase; NADH at 30℃; for 2h; pH=6.5; Aqueous phophate buffer; Enzymatic reaction; | n/a |
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction; | n/a |
With potassium dihydrogenphosphate; D-glucose In water at 30℃; for 24h; pH=5.5; Aqueous phophate buffer; Microbiological reaction; | 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 |
(S)-epichlorohydrin
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With sulfuric acid In water at 108℃; for 6h; | |
With sulfuric acid In water at 108℃; for 6h; |
(2R)-3-chloro-1,2-propanediol
phosphorylcholine chloride
L-glycero-3-phosphorylcholine
Conditions | Yield |
---|---|
Stage #1: phosphorylcholine chloride With potassium hydroxide In methanol for 1h; Stage #2: (2R)-3-chloro-1,2-propanediol In methanol at 65℃; for 16h; Temperature; | 99% |
Stage #1: phosphorylcholine chloride With potassium hydroxide In ethanol for 0.5h; Stage #2: (2R)-3-chloro-1,2-propanediol In ethanol at 75 - 85℃; for 6h; | 79.6% |
(2R)-3-chloro-1,2-propanediol
p-toluenesulfonyl chloride
(R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With pyridine for 1h; Ambient temperature; | 98.6% |
With hydrogenchloride | 75% |
With pyridine | |
With pyridine at 0 - 20℃; for 1h; |
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 72h; Reflux; Water removal; | 97% |
dmap
(2R)-3-chloro-1,2-propanediol
(S)-(-)-1-(2,3-dihydroxypropyl)-4-(dimethylamino)pyridinium chloride
Conditions | Yield |
---|---|
In acetonitrile at 65℃; for 24h; | 96% |
(2R)-3-chloro-1,2-propanediol
trimethylamine
Conditions | Yield |
---|---|
In water at 90℃; for 16h; | 95.7% |
(2R)-3-chloro-1,2-propanediol
2-benzyloxy-3-methylphenol
(R)-2-benzyloxy-3-(2,3-dihydroxypropoxy)toluene
Conditions | Yield |
---|---|
Stage #1: 2-benzyloxy-3-methylphenol; cesium fluoride In N,N-dimethyl-formamide for 1h; Stage #2: (2R)-3-chloro-1,2-propanediol In N,N-dimethyl-formamide at 60℃; for 5h; Further stages.; | 95% |
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In methanol at 90℃; | 95% |
With camphor-10-sulfonic acid In methanol for 2h; Heating; |
2,4-dichloro-α-oxo-benzeneacetic ethyl ester
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With caesium carbonate In N,N-dimethyl-formamide at 20℃; | 95% |
phthalimide
(2R)-3-chloro-1,2-propanediol
1H-isoindole-1,3(2H)-dione, 2-[(2S)-2,3-dihydroxypropyl]
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 5h; Reagent/catalyst; Temperature; Time; Gabriel Amine Synthesis; | 94.9% |
(2R)-3-chloro-1,2-propanediol
(R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide
Conditions | Yield |
---|---|
With thionyl chloride In dichloromethane | 94% |
With thionyl chloride In tetrachloromethane for 2h; Reflux; Inert atmosphere; | 94% |
(2R)-3-chloro-1,2-propanediol
2-allyloxyphenol
(R)-2-allyloxy-1-(2,3-dihydroxypropoxy)benzene
Conditions | Yield |
---|---|
Stage #1: 2-allyloxyphenol; cesium fluoride In N,N-dimethyl-formamide for 1h; Stage #2: (2R)-3-chloro-1,2-propanediol In N,N-dimethyl-formamide at 60℃; for 5h; Further stages.; | 93% |
(2R)-3-chloro-1,2-propanediol
tert-butyldimethylsilyl chloride
(R)-(-)-1-(tert-butylmethylsilanyloxy)-3-chloropropan-2-ol
Conditions | Yield |
---|---|
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 0 - 20℃; | 92.4% |
2’2’2’-trifluoro-2,4-dichloroacetophenone
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; | 91% |
(2R)-3-chloro-1,2-propanediol
para-thiocresol
(R)-3-p-Tolylsulfanyl-propane-1,2-diol
Conditions | Yield |
---|---|
With sodium hydroxide at 100℃; for 2h; | 90% |
(2R)-3-chloro-1,2-propanediol
acetone
(R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 50℃; for 4h; | 90% |
(2R)-3-chloro-1,2-propanediol
1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone
Conditions | Yield |
---|---|
With methanesulfonic acid In toluene at 40℃; for 4h; | 90% |
(2R)-3-chloro-1,2-propanediol
N,N-dimethylammonium chloride
(S)-3-(N,N-dimethylamino)propane-1,2-diol
Conditions | Yield |
---|---|
With sodium hydroxide In water at 20℃; for 18h; | 89% |
(2R)-3-chloro-1,2-propanediol
(R)-oxiranemethanol
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane for 18h; Ambient temperature; | 88% |
With potassium carbonate In dichloromethane other reagent: Cs2CO3; | |
With potassium phosphate In dichloromethane for 3h; Product distribution / selectivity; Heating / reflux; | |
With potassium carbonate In dichloromethane at 20℃; for 24h; | |
With potassium carbonate In dichloromethane at 20℃; for 20h; |
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
Stage #1: 2-(4-methylamino-phenyl)-benzofuran-5-ol With sodium hydroxide In ethanol; water at 80℃; for 1h; Stage #2: (2R)-3-chloro-1,2-propanediol In ethanol; water at 80℃; for 3h; | 87.7% |
(2R)-3-chloro-1,2-propanediol
phosphorylcholine chloride, calcium salt
glycerolcholine phosphate
Conditions | Yield |
---|---|
Stage #1: phosphorylcholine chloride, calcium salt With potassium oxalate In water at 20℃; for 2h; Stage #2: (2R)-3-chloro-1,2-propanediol With potassium hydroxide In ethanol for 6h; | 86% |
(2R)-3-chloro-1,2-propanediol
(R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone | 85% |
(2R)-3-chloro-1,2-propanediol
tert-butylchlorodiphenylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 20℃; for 4h; | 85% |
(2Z,5Z)-5-[(3-chloro-4-hydroxyphenyl)methylene]-3-(o-tolyl)-2-propyliminothiazolidin-4-one
(2R)-3-chloro-1,2-propanediol
Conditions | Yield |
---|---|
With potassium tert-butylate In ethanol at 20 - 88℃; for 24.5h; | 84% |
(2R)-3-chloro-1,2-propanediol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 20℃; | 84% |
With 1H-imidazole In dichloromethane |
benzophenone
(2R)-3-chloro-1,2-propanediol
(4R)-4-(chloromethyl)-2,2-diphenyl-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Reflux; | 82% |
With toluene-4-sulfonic acid In toluene Heating; | |
With toluene-4-sulfonic acid In toluene for 18h; Reflux; Dean-Stark; |
1H-indol-4-ol
(2R)-3-chloro-1,2-propanediol
(R)-3-(4-indolyloxy)-propane-1,2-diol
Conditions | Yield |
---|---|
Stage #1: 1H-indol-4-ol With potassium carbonate In acetonitrile for 2h; Reflux; Stage #2: (2R)-3-chloro-1,2-propanediol In acetonitrile for 16h; Reflux; | 82% |
(2R)-3-chloro-1,2-propanediol
7-(4-chlorophenylthio)-6,7-dihydro-1-(phenylsulfonyl)-1H-indol-4(5H)-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; copper dichloride In benzene for 1h; Heating; | A 81% B 6% |
With toluene-4-sulfonic acid In benzene for 1.5h; Heating; | A 77% B 4% |
The (R)-3-Chloro-1,2-propanediol, with the CAS registry number 57090-45-6, is also known as 1,2-Propanediol, 3-chloro-, (R)-. It belongs to the product categories of Chiral Compounds; Diols; Chiral; Chiral Building Blocks; Simple Alcohols (Chiral); Synthetic Organic Chemistry; Chiral Compound. Its EINECS registry number is 435-560-9. This chemical's molecular formula is C3H7ClO2 and molecular weight is 110.54. Its IUPAC name is called (2R)-3-chloropropane-1,2-diol. This chemical is clear light yellow liquid. The product should be sealed and stored at 2-8 °C.
Physical properties of (R)-3-Chloro-1,2-propanediol: (1)ACD/LogP: -0.76; (2)ACD/LogD (pH 5.5): -0.76; (3)ACD/LogD (pH 7.4): -0.76; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 9.21; (7)ACD/KOC (pH 7.4): 9.21; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.473; (12)Molar Refractivity: 23.82 cm3; (13)Molar Volume: 84.8 cm3; (14)Surface Tension: 45.8 dyne/cm; (15)Density: 1.303 g/cm3; (16)Flash Point: 113.3 °C; (17)Enthalpy of Vaporization: 52.26 kJ/mol; (18)Boiling Point: 213 °C at 760 mmHg; (19)Vapour Pressure: 0.0374 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical that at low levels can cause damage to health. It is harmful in contact with skin. Besides, it is toxic if swallowed. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C(C(CCl)O)O
(2)Isomeric SMILES: C([C@H](CCl)O)O
(3)InChI: InChI=1S/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2/t3-/m0/s1
(4)InChIKey: SSZWWUDQMAHNAQ-VKHMYHEASA-N
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