57090-45-6

Basic information

• Product Name: (R)-(-)-3-Chloro-1,2-propanediol
• Synonyms: (2R)-3-CHLOROPROPANE-1,2-DIOL;GLYCEROL (R)-(-)-ALPHA-MONOCHLOROHYDRIN;(R)-GLYCEROL ALPHA-MONOCHLOROHYDRIN;(R)-(-)-ALPHA-CHLOROHYDRIN;(R)-ALPHA-GLYCEROL CHLOROHYDRIN;(R)-(-)-ALPHA-MONOCHLOROHYDRIN;(R)-3-CHLOROPROPANE-1,2-DIOL;(R)-(-)-3-CHLORO-1,2-PROPANEDIOL
• CAS NO: 57090-45-6
• Molecular Formula: C3H7ClO2
• Molecular Weight: 110.54
• EINECS: 435-560-9
• Product Categories: Chiral Compounds;Diols;chiral;Chiral Building Blocks;Simple Alcohols (Chiral);Synthetic Organic Chemistry;Chiral Compound
• Mol File: 57090-45-6.mol
• Article Data: 82

Chemical Properties

• Melting Point: -40°C
• Boiling Point: 213 °C(lit.)
• Flash Point: >230 °F
• Appearance: clear light yellow liquid
• Density: 1.321 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.04 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.48(lit.)
• Storage Temp.: 2-8°C
• PKA: 13.28±0.20(Predicted)
• Water Solubility: soluble
• BRN: 2202928
• CAS DataBase Reference: (R)-(-)-3-Chloro-1,2-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-3-Chloro-1,2-propanediol(57090-45-6)
• EPA Substance Registry System: (R)-(-)-3-Chloro-1,2-propanediol(57090-45-6)

Safety Data

• Hazard Codes: T
• Statements: 25-41-68-62-36/37/38-23/25-21
• Safety Statements: 26-28-39-45-36/37/39
• RIDADR: UN 2689 6.1/PG 3
• WGK Germany: 3
• RTECS: TY4025000
• F: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 57090-45-6(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

Definition

ChEBI: The (R)-stereoisomer of 3-chloro-1,2-propanediol.

InChI:InChI=1/C3H7ClO2/c4-1-3(6)2-5/h3,5-6H,1-2H2/t3-/m0/s1

Synthetic route

(R)-(-)-epichlorohydrin (51594-55-9) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (57044-24-3) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With hydrogenchloride	86%

[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine (82954-65-2) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (95589-30-3) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + C13H21ClO3 (95548-92-8, 95589-33-6) + C13H21ClO3 (95548-92-8, 95589-33-6)

Conditions	Yield
With sodium tetrahydroborate In ethanol	A 55% B n/a C n/a

epichlorohydrin (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (106-89-8) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (616-23-9) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4) + (S)-1,3-dichloro-1-propanol + epichlorohydrin (106-89-8)

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 (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With water at 20℃; for 8h; optical yield given as %ee;	A 45% B n/a

epichlorohydrin (106-89-8) → (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (95589-30-3) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With hydrogenchloride; sodium tetrahydroborate 2) MeOH, reflux, 3h; Yield given. Multistep reaction;

1-O-β-D-glucosyl-(2R)-3-chloropropylene glycol → (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With β-galactosidase In various solvent(s) at 35℃;

barium D-3-chloropropane-1,2-diol-1-phosphate → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With ethanol Yield given. Yields of byproduct given;

3-monochloro-1,2-propanediol (96-24-2) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4) + D-3-chloropropane-1,2-diol-1-phosphate

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;

C13H21ClO3 → (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With hydrogenchloride In methanol for 3h; Heating; Yield given;

1,2-diacetoxy-3-chloro-propane (869-50-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (78692-88-3) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

Conditions	Yield
With sulfuric acid for 1h; Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

3-chloroprop-1-ene (107-05-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (96-24-2) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (106-89-8) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (106-89-8) → (S)-epichlorohydrin (67843-74-7) + (R)-(-)-epichlorohydrin (51594-55-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (24423-98-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6) + (S)-3-chloropropan-1,2-diol (60827-45-4)

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 (24423-98-1) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (51594-55-9) → (S)-epichlorohydrin (67843-74-7) + (2R)-3-chloro-1,2-propanediol (57090-45-6)

Conditions	Yield
With (R,R)-Jacobsen catalyst; water	A n/a B n/a

(S)-epichlorohydrin (67843-74-7) → (2R)-3-chloro-1,2-propanediol (57090-45-6)

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 (57090-45-6) + phosphorylcholine chloride (107-73-3) → L-glycero-3-phosphorylcholine (28319-77-9)

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 (57090-45-6) + p-toluenesulfonyl chloride (98-59-9) → (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate (83398-53-2)

Conditions	Yield
With pyridine for 1h; Ambient temperature;	98.6%
With hydrogenchloride	75%
With pyridine
With pyridine at 0 - 20℃; for 1h;

heptatriaconta-6,9,28,31-tetraen-19-one + (2R)-3-chloro-1,2-propanediol (57090-45-6) → 4-(R)-4-chloromethyl-2,2-di-octadeca-9,12-dienyl-[1,3]dioxolane

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 72h; Reflux; Water removal;	97%

dmap (1122-58-3) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → (S)-(-)-1-(2,3-dihydroxypropyl)-4-(dimethylamino)pyridinium chloride (942209-57-6)

Conditions	Yield
In acetonitrile at 65℃; for 24h;	96%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + trimethylamine (75-50-3) → (S)-2,3-dihydroxypropyltrimethylammonium chloride

Conditions	Yield
In water at 90℃; for 16h;	95.7%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + 2-benzyloxy-3-methylphenol (150710-99-9) → (R)-2-benzyloxy-3-(2,3-dihydroxypropoxy)toluene (335280-94-9)

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%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + dimethylglyoxal (431-03-8) + trimethyl orthoformate (149-73-5) → (2R,3R)-5-(chloromethyl)-2,3-dimethoxy-2,3-dimethyl-1,4-dioxane

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 (34966-51-3) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → (1S,5S)-5-(2,4-dichlorophenyl)-3,6,8-trioxabicyclo[3.2.1]octan-4-one

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	95%

phthalimide (136918-14-4) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → 1H-isoindole-1,3(2H)-dione, 2-[(2S)-2,3-dihydroxypropyl] (119835-88-0)

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 (57090-45-6) → (R)-4-chloromethyl-[1,3,2]dioxathiolane 2-oxide (146864-18-8)

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 (57090-45-6) + 2-allyloxyphenol (1126-20-1) → (R)-2-allyloxy-1-(2,3-dihydroxypropoxy)benzene (66901-82-4)

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 (57090-45-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-(-)-1-(tert-butylmethylsilanyloxy)-3-chloropropan-2-ol (136984-26-4)

Conditions	Yield
With 1H-imidazole In DMF (N,N-dimethyl-formamide) at 0 - 20℃;	92.4%

2’2’2’-trifluoro-2,4-dichloroacetophenone (92736-81-7) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → ((4R)-2-(2,4-dichlorophenyl)-2-trifluoromethyl-1,3-dioxolan-4-yl)methanol

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	91%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + para-thiocresol (106-45-6) → (R)-3-p-Tolylsulfanyl-propane-1,2-diol (127634-04-2)

Conditions	Yield
With sodium hydroxide at 100℃; for 2h;	90%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + acetone (67-64-1) → (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (57044-24-3)

Conditions	Yield
With toluene-4-sulfonic acid at 50℃; for 4h;	90%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone (58905-16-1) → C13H12Cl3N3O2

Conditions	Yield
With methanesulfonic acid In toluene at 40℃; for 4h;	90%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + N,N-dimethylammonium chloride (506-59-2) → (S)-3-(N,N-dimethylamino)propane-1,2-diol (666234-82-8)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 18h;	89%

(2R)-3-chloro-1,2-propanediol (57090-45-6) → (R)-oxiranemethanol (57044-25-4)

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;

2-(4-methylamino-phenyl)-benzofuran-5-ol + (2R)-3-chloro-1,2-propanediol (57090-45-6) → (R)-3-((2-(4-(methylamino)phenyl)benzofuran-5-yl)oxy)propane-1,2-diol

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 (57090-45-6) + phosphorylcholine chloride, calcium salt (4826-71-5) → glycerolcholine phosphate (34688-34-1)

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 (57090-45-6) → (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane (57044-24-3)

Conditions	Yield
With toluene-4-sulfonic acid In acetone	85%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + tert-butylchlorodiphenylsilane (58479-61-1) → (R)-1-[(tert-butyldiphenylsilyl)oxy]-3-chloropropan-2-ol

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 (1029435-58-2) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → Ponesimod

Conditions	Yield
With potassium tert-butylate In ethanol at 20 - 88℃; for 24.5h;	84%

(2R)-3-chloro-1,2-propanediol (57090-45-6) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-5-(chloromethyl)-2,2,3,3,8,8,9,9-octamethyl-4,7-dioxa-3,8-disiladecane

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃;	84%
With 1H-imidazole In dichloromethane

benzophenone (119-61-9) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → (4R)-4-(chloromethyl)-2,2-diphenyl-1,3-dioxolane (139892-51-6)

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 (2380-94-1) + (2R)-3-chloro-1,2-propanediol (57090-45-6) → (R)-3-(4-indolyloxy)-propane-1,2-diol (74784-71-7)

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 (57090-45-6) + 7-(4-chlorophenylthio)-6,7-dihydro-1-(phenylsulfonyl)-1H-indol-4(5H)-one (157396-11-7) → (R)-(-)-1-chloro-3-<(1-phenylsulfonyl)-1H-indol-4-yloxy>-2-propanol + 4-(4-chlorophenylthio)-1-(phenylsulfonyl)-1H-indole

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%

Upstream product

• 100-83-4 meta-hydroxybenzaldehyde 
• 77-78-1 dimethyl sulfate 
• 7664-93-9 sulfuric acid 
• 7697-37-2 nitric acid 
• 591-31-1 3-methoxy-benzaldehyde 
• 96-24-2 3-monochloro-1,2-propanediol 
• 106-89-8 epichlorohydrin 
• 82954-65-2 [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine 
• 616-23-9 2,3-Dichloro-1-propanol 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 107-05-1 3-chloroprop-1-ene 
• 78692-88-3 (S)-3-chloro-1,2-diacetoxypropane 
• 869-50-1 1,2-diacetoxy-3-chloro-propane 
• 57044-24-3 (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 90742-94-2 S-1,2-dihydroxy-3-isopropylaminopropane 
• 83527-35-9 S-3,4-dihydroxy butyronitrile 
• 1518-61-2 3,4-dihydroxybutyric acid 
• 857419-46-6 (S)-2-(chloromethyl)-2,3-dihydrothieno[3,4-b][1,4]dioxine 
• 28319-77-9 L-glycero-3-phosphorylcholine 
• 57044-24-3 (R)-4-chloromethyl-2,2-dimethyl-1,3-dioxolane 
• 66901-82-4 (R)-2-allyloxy-1-(2,3-dihydroxypropoxy)benzene 
• 335280-94-9 (R)-2-benzyloxy-3-(2,3-dihydroxypropoxy)toluene 
• 203250-06-0 (R)-3-chloro-1-O-trityl-1,2-propanediol 
• 57044-25-4 (R)-oxiranemethanol 
• 82430-38-4 (S)-1-phenyl glycerol 
• 83398-53-2 (R)-3-chloro-2-hydroxypropyl 4-methylbenzenesulfonate 
• 127634-04-2 (R)-3-p-Tolylsulfanyl-propane-1,2-diol 
• 139892-53-8 (R)-2-Chloromethyl-1,4-dioxa-spiro[4.5]decane 

Relevant articles and documents

P-Tolyl glycerol ether: Is it possible to find more simple molecular organogelator with pronounced chirality driven properties?

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TRICYCLIC HETEROARYL COMPOUNDS USEFUL AS IRAK4 INHIBITORS

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Method for preparing aldehyde compounds through photocatalytic oxidation cracking β - hydroxyl compound C-C bond

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