Conditions | Yield |
---|---|
With Strong acid resin at 100℃; for 1h; Temperature; Reagent/catalyst; | 99.2% |
With phosphoric acid; hydrogen iodide; sodium iodide at 105℃; Reagent/catalyst; Autoclave; | 88% |
With water; sulfuric acid at 190℃; for 10h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; under 38002.6 Torr; for 2h; Pressure; Autoclave; | 99% |
With zinc bis(2,4-pentanedionate) monohydrate In benzene at 70℃; for 3h; Inert atmosphere; |
Conditions | Yield |
---|---|
With A35 resin acid at 100℃; for 2h; Temperature; Reagent/catalyst; | A n/a B 98% |
Conditions | Yield |
---|---|
With hexaethylene glycol bis(3-hexaethylene glycol imidazolium) dimesylate; potassium carbonate In water at 100℃; for 1h; Green chemistry; chemoselective reaction; | 96% |
With water; potassium carbonate at 90℃; for 0.5h; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With hydrogen In water at 190℃; under 31029.7 Torr; Temperature; Pressure; Reagent/catalyst; | 95% |
With 1,3-dimethyl-2-imidazolidinone; hydrogen at 170℃; under 60006 Torr; for 20h; Reagent/catalyst; Large scale; | 87% |
With hydrogen at 119.84℃; under 60006 Torr; for 1h; Autoclave; | 33% |
Conditions | Yield |
---|---|
With sulfuric acid; nickel In water | 95% |
With hydrogen at 80℃; under 15001.5 Torr; for 2h; Catalytic behavior; Reagent/catalyst; Green chemistry; | 76.9% |
Hydrogenation; |
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; silica gel In dichloromethane; isopropyl alcohol at 20℃; for 5h; | 95% |
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; silica gel In dichloromethane; isopropyl alcohol at 20℃; for 3h; | 92% |
A
3-tert-butyldimethylsilyloxy-1-propanol
B
trimethyleneglycol
Conditions | Yield |
---|---|
With MCM-41 In methanol for 4h; Ambient temperature; | A 91% B 3% |
With mesoporous silica MCM-41 In methanol at 20℃; for 4h; | A 91% B 3% |
Conditions | Yield |
---|---|
With borohydride exchange resin In methanol Ambient temperature; | 90% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In benzene at 80℃; | 87% |
With lithium aluminium tetrahydride In tetrahydrofuran | 74% |
With C17H38ClNORuS2; potassium tert-butylate; hydrogen In toluene at 110℃; under 775.743 Torr; for 24h; Reagent/catalyst; Temperature; Pressure; Inert atmosphere; | 67% |
trimethyleneglycol
Conditions | Yield |
---|---|
With cerium(III) chloride; sodium iodide In acetonitrile for 10h; Ambient temperature; | 87% |
Conditions | Yield |
---|---|
Stage #1: 3-benzyloxypropan-1-ol With isocyanate de chlorosulfonyle; sodium carbonate In dichloromethane for 20h; Heating; Stage #2: With sodium hydroxide In methanol at 20℃; for 1h; | 87% |
trimethyleneglycol
Conditions | Yield |
---|---|
With sodium hydrogen sulfate; silica gel In methanol; dichloromethane at 20℃; for 2.5h; | 87% |
6-hydroxy-3-oxa-2-hexanone
trimethyleneglycol
Conditions | Yield |
---|---|
With amberlite IR120 ion exchange resin In water; toluene at 75℃; under 3750.38 Torr; for 7h; Inert atmosphere; Autoclave; | 80.42% |
With amberlite IR120 ion exchange resin In water; toluene at 75℃; under 3750.38 Torr; for 7h; Inert atmosphere; Autoclave; | 80.29% |
With sodium methylate In methanol at 65℃; under 3750.38 Torr; for 4h; Inert atmosphere; Autoclave; | 80.37% |
3-tert-butyldimethylsilyloxy-1-propyl benzyl ether
A
3-tert-butyldimethylsilyloxy-1-propanol
B
trimethyleneglycol
Conditions | Yield |
---|---|
With Ti-HMS; hydrogen; 5% Pd on active carbon In methanol under 760 Torr; for 4h; Ambient temperature; | A 80% B 7% |
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 24h; Title compound not separated from byproducts.; |
Conditions | Yield |
---|---|
With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)2Br; hydrogen; sodium t-butanolate In tetrahydrofuran at 120℃; under 22502.3 Torr; for 26h; Schlenk technique; Glovebox; Autoclave; | A 75% B 80% |
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In tetrahydrofuran at 140℃; for 2h; Autoclave; | A 99 %Chromat. B 99 %Chromat. |
With hydrogen In tetrahydrofuran at 159.84℃; under 45004.5 Torr; for 10h; |
Conditions | Yield |
---|---|
With ruthenium-carbon composite; hydrogen In water at 119.84℃; under 7500.75 - 60006 Torr; for 2h; Catalytic behavior; Autoclave; Sealed tube; | A 18% B 79% |
2-(3-Benzyloxy-propoxy)-tetrahydro-pyran
trimethyleneglycol
Conditions | Yield |
---|---|
With hydrogen; toluene-4-sulfonic acid; palladium dihydroxide In methanol under 760 Torr; for 4h; Ambient temperature; | 74% |
trimethyleneglycol
Conditions | Yield |
---|---|
In methanol for 0.5h; UV-irradiation; | 74% |
1,3-bis(benzyloxy)propane
trimethyleneglycol
Conditions | Yield |
---|---|
Stage #1: 1,3-bis(benzyloxy)propane With isocyanate de chlorosulfonyle; sodium carbonate In dichloromethane for 20h; Heating; Stage #2: With sodium hydroxide In methanol at 20℃; for 1h; | 70% |
Conditions | Yield |
---|---|
With hydrogen In ethanol at 150℃; under 37503.8 Torr; for 8h; Temperature; Pressure; Flow reactor; | 68% |
With ammonia borane; C28H28Cl2CoNP2; erbium(III) triflate In tetrahydrofuran at 45℃; for 8h; | 82 %Chromat. |
trimethyleneglycol
Conditions | Yield |
---|---|
With hydrogen at 110℃; under 22502.3 Torr; for 3h; | 65.9% |
2-p-toluenesulfonyloxy-1,3-propanediol
trimethyleneglycol
Conditions | Yield |
---|---|
With hydrogen; palladium In tetrahydrofuran at 130℃; under 15001.5 Torr; for 3h; Pressure; Reagent/catalyst; Solvent; Temperature; | 64.6% |
3-tert-butyldimethylsilyloxy-1-propyl benzyl ether
A
3-benzyloxypropan-1-ol
B
3-tert-butyldimethylsilyloxy-1-propanol
C
trimethyleneglycol
Conditions | Yield |
---|---|
In methanol under 760 Torr; for 20h; Ambient temperature; | A 6% B 64% C 9% |
Conditions | Yield |
---|---|
With C17H38ClNORuS2; potassium tert-butylate; hydrogen In toluene at 110℃; under 775.743 Torr; for 24h; Inert atmosphere; | 62% |
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh3)(CO); hydrogen In tetrahydrofuran at 120℃; under 38002.6 Torr; for 18h; Autoclave; Industrial scale; | |
With sodium tetrahydroborate; [fac-8-(2-diphenylphosphinoethyl)amidotrihydroquinoline]RuH(PPh)3(CO); hydrogen In tetrahydrofuran at 120℃; under 37503.8 Torr; for 18h; Inert atmosphere; Autoclave; |
Conditions | Yield |
---|---|
With hydrogen; molybdenum(IV) oxide In water at 150℃; under 78334.3 Torr; for 3h; Product distribution / selectivity; | 60% |
With hydrogen; molybdenum In ISOPAR K; water at 150℃; under 78334.3 Torr; for 3h; Product distribution / selectivity; | 57% |
With hydrogen In water at 100℃; under 78334.3 Torr; for 16h; Product distribution / selectivity; | 47% |
Conditions | Yield |
---|---|
With hydrogen In water at 179.84℃; under 22502.3 Torr; for 4h; Autoclave; | A 47% B 6% C 21% |
With hydrogen In water at 179.84℃; under 22502.3 Torr; for 10h; Autoclave; | A 34% B 14% C 40% |
With hydrogen In water at 119.84℃; under 60006 Torr; for 12h; Reagent/catalyst; | A n/a B n/a C 36% |
oxiranyl-methanol
A
propan-1-ol
B
propylene glycol
C
trimethyleneglycol
Conditions | Yield |
---|---|
With hydrogen In sulfolane at 119.84℃; under 37503.8 Torr; for 4h; | A n/a B n/a C 46.1% |
With hydrogen In sulfolane at 119.84℃; under 37503.8 Torr; for 4h; Reagent/catalyst; | A n/a B n/a C 11.7% |
With hydrogen In ethanol at 120℃; under 15001.5 Torr; for 5h; Reagent/catalyst; | |
With hydrogen In ethanol at 120℃; under 15001.5 Torr; for 5h; Reagent/catalyst; |
4-methoxy-benzaldehyde
trimethyleneglycol
2-(4-methoxy-phenyl)-[1,3]dioxane
Conditions | Yield |
---|---|
In benzene Cyclization; Heating; | 100% |
With toluene-4-sulfonic acid In toluene at 110℃; Condensation; | 100% |
toluene-4-sulfonic acid In toluene at 110℃; for 11h; | 100% |
chloroacetaldehyde dimethyl acetal
trimethyleneglycol
2-Chloromethyl-1,3-dioxane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Heating; | 100% |
Substitution; | 91% |
With sulfuric acid | |
sulfuric acid | |
With toluene-4-sulfonic acid at 115℃; for 5h; |
tert-butyldimethylsilyl chloride
trimethyleneglycol
3-tert-butyldimethylsilyloxy-1-propanol
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran | 100% |
With dmap; triethylamine In dichloromethane at 18℃; | 100% |
Stage #1: trimethyleneglycol With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 20℃; for 0.75h; | 99% |
Conditions | Yield |
---|---|
With Amberlyst 15 In benzene for 3h; Heating; | 100% |
With boron trifluoride diethyl etherate In toluene for 4.5h; Acetalization; Heating; | 96% |
With boron trifluoride diethyl etherate In toluene at 100℃; for 4.5h; | 96% |
tert-butylchlorodiphenylsilane
trimethyleneglycol
3-(tert-butyldiphenylsilyloxy)propan-1-ol
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran; hexane at -78 - 25℃; Substitution; Heating; | 100% |
Stage #1: trimethyleneglycol With sodium hydride In tetrahydrofuran at 20℃; for 1h; deprotonation; Stage #2: tert-butylchlorodiphenylsilane In tetrahydrofuran at 0℃; for 2h; silylation; | 100% |
With pyridine at 0 - 22℃; | 100% |
Conditions | Yield |
---|---|
With hydrogenchloride; tetrabutyl-ammonium chloride | 100% |
With chloro-trimethyl-silane In dichloromethane at 5 - 20℃; Reflux; Inert atmosphere; |
Conditions | Yield |
---|---|
With sulfuric acid In toluene Heating; | 100% |
2-bromo-3,5-dimethoxy-benzaldehyde
trimethyleneglycol
2-(2-Bromo-3,5-dimethoxyphenyl)-1,3-dioxane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 2h; Heating; | 100% |
With toluene-4-sulfonic acid In benzene for 2h; Heating; | 100% |
With tetra-N-butylammonium tribromide; orthoformic acid triethyl ester at 0 - 20℃; | 94% |
N-methyl-N-tert-butyldimethylsilyl-1,1,1-trifluoroacetamide
trimethyleneglycol
1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-propane
Conditions | Yield |
---|---|
With tert-butyldimethylsilyl chloride In acetonitrile for 0.0833333h; Product distribution; Ambient temperature; other tert-butyldimethylsilyl- donors; other alkohols; other solvent, temp. and time; | 100% |
With tert-butyldimethylsilyl chloride In acetonitrile for 0.0833333h; Ambient temperature; other silylating agents; | 100% |
1,2 bis (tricosa 10,12 diynoyl)-sn-3-glycerophosphocholine, DC8,9PC
trimethyleneglycol
DC8,9 phosphatidylhydroxypropanol
Conditions | Yield |
---|---|
With acetate buffer In isopropyl alcohol at 37℃; for 10h; phospholipase D; | 100% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene Heating; | 100% |
6-allyl-2,6-dimethyl-1-cyclohexene-1-carbaldehyde
trimethyleneglycol
6-allyl-2,6-dimethyl-1-cyclohexene-1-carbaldehyde trimethyleneacetal
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In benzene for 4h; Heating; | 100% |
m-bromobenzoic aldehyde
trimethyleneglycol
2-(3-bromophenyl)-[1,3]dioxane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 15.5h; Reflux; Dean-Stark; | 100% |
With toluene-4-sulfonic acid In toluene for 2.5h; Heating; | 99% |
With toluene-4-sulfonic acid In toluene at 20℃; for 2.5h; | 96% |
3-(N-Ethylamino)phenylboronic acid
trimethyleneglycol
N-Ethyl-3-(1,3,2-dioxaborinan-2-yl)aniline
Conditions | Yield |
---|---|
In toluene for 14h; Etherification; Cyclization; Heating; | 100% |
In toluene refluxed, 14 h; evapd. to dryness; column chromy. (silica gel-ethyl acetate); | >99 |
3-hydroxy-5-methylphenyl 2-(methylsulfonyl)benzenesulfonate
trimethyleneglycol
3-[5-methyl-3-[2-(methylsulfonyl)phenylsulfonyloxy]phenoxy]propanol
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu reaction; | 100% |
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine Condensation; | |
With bithionol; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran Mitsunobu reaction; |
7,10-dimethoxy-5,6,11,12-tetrahydro-2-naphthacenecarbaldehyde
trimethyleneglycol
7,10-dimethoxy-5,6,11,12-tetrahydro-2-naphthacenecarbaldehyde 1,3-propylene acetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 3h; Condensation; Heating; | 100% |
trimethyleneglycol
C11H19BO2
2-[(1E,4Z,6Z)-1,4,6-undecatrien-1-yl]-1,2,3-dioxaborinane
Conditions | Yield |
---|---|
In pentane at 20℃; for 10h; | 100% |
4-formylphenylboronic acid,
trimethyleneglycol
Conditions | Yield |
---|---|
In toluene at 135℃; for 5h; Inert atmosphere; Dean-Stark; | 100% |
In toluene for 12h; Reflux; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 3h; Inert atmosphere; Reflux; | 100% |
(R)-3-methyl-4,4-bis(phenylsulfonyl)butanal
trimethyleneglycol
(R)-2-(2-methyl-3,3-bis(phenylsulfonyl)propyl)-1,3-dioxane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 100% |
3-fluoro-4-formylbenzonitrile
trimethyleneglycol
4-(1,3-Dioxan-2-yl)-3-fluorobenzonitrile
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 6h; Reflux; | 100% |
tetramethylphosphorodiamidous acid
trimethyleneglycol
1,3,2-dioxaphosphinan-2-oxide
Conditions | Yield |
---|---|
In tetrahydrofuran at 70℃; for 2h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
In toluene for 2h; Reflux; | 100% |
carbonic acid dimethyl ester
trimethyleneglycol
propane-1,3-diyl dimethyl dicarbonate
Conditions | Yield |
---|---|
at 120℃; for 7h; Molecular sieve; | 100% |
In neat (no solvent) at 120℃; for 1h; Molecular sieve; Green chemistry; | 99% |
With dicobalt octacarbonyl at 180℃; for 1h; | 98% |
With magnesium oxide at 80℃; under 760.051 Torr; for 4h; | 91.3% |
5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carboxaldehyde
trimethyleneglycol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 4h; Dean-Stark; Reflux; | 100% |
2-bromo-3,5-dimethylbenzaldehyde
trimethyleneglycol
Conditions | Yield |
---|---|
Stage #1: 2-bromo-3,5-dimethylbenzaldehyde; trimethyleneglycol With toluene-4-sulfonic acid In chloroform for 18h; Reflux; Stage #2: With potassium carbonate In chloroform at 25℃; | 100% |
trimethyleneglycol
Conditions | Yield |
---|---|
With methanol; N-Bromosuccinimide; trimethyl orthoformate In dichloromethane at 0 - 20℃; for 20h; | 100% |
2-O-benzyl-5-bromo-2-hydroxy-3-methoxybenzaldehyde
trimethyleneglycol
2-(benzyloxy)-5-bromo-3-methoxybenzaldehyde trimethylene acetal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 1h; Heating; | 99.7% |
Molecule structure of 1,3-Propanediol (CAS NO.504-63-2):
IUPAC Name: Propane-1,3-diol
Molecular Weight: 76.09442 g/mol
Molecular Formula: C3H8O2
Density: 1.041 g/cm3
Melting Point: -32 °C
Boiling Point: 214.4 °C at 760 mmHg
Flash Point: 79.4 °C
Index of Refraction: 1.433
Molar Refractivity: 19.01 cm3
Molar Volume: 73 cm3
Surface Tension: 41 dyne/cm
Enthalpy of Vaporization: 52.42 kJ/mol
Vapour Pressure: 0.0343 mmHg at 25 °C
Water Solubility: 100 g/L
XLogP3: -1
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Exact Mass: 76.05243
MonoIsotopic Mass: 76.05243
Topological Polar Surface Area: 40.5
Heavy Atom Count: 5
Canonical SMILES: C(CO)CO
InChI: InChI=1S/C3H8O2/c4-2-1-3-5/h4-5H,1-3H2
InChIKey: YPFDHNVEDLHUCE-UHFFFAOYSA-N
EINECS: 207-997-3
Product Categories: alpha,omega-Alkanediols; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes; Cell culture
1,3-Propanediol (CAS NO.504-63-2) is a solvent and used as an wood paint and antifreeze. It mainly used as a building block in the production of polymers. It also can be formulated into a variety of industrial products including composites, coatings, laminates, moldings, aliphatic polyesters.
1,3-Propanediol may be chemically made by the hydration of acrolein, or by the hydroformylation of ethylene oxide to afford 3-hydroxypropionaldehyde. The aldehyde is hydrogenated to give 1,3-propanediol.
1. | dnd-rat-orl 2100 mg/kg/10W-C | CBINA8 Chemico-Biological Interactions. 50 (1984),87. | ||
2. | orl-rat LDLo:10 g/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 72 (1941),227. | ||
3. | ims-rat LDLo:6 g/kg | JPETAB Journal of Pharmacology and Experimental Therapeutics. 72 (1941),227. | ||
4. | orl-mus LD50:4773 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 49 (1979),385. |
Reported in EPA TSCA Inventory.
Safety Statements: 23-24/25
S23:Do not breathe vapour.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 1
RTECS: TY2010000
HS Code: 29053980
Mildly toxic by ingestion. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also 1,2-PROPANEDIOL.
1,3-Propanediol (CAS NO.504-63-2) is also named as 1,3-Dihydroxypropane ; 1,3-Propylene glycol ; 1,3-Propylenediol ; 2-(Hydroxymethyl)ethanol ; 2-Deoxyglycerol ; 4-01-00-02493 (Beilstein Handbook Reference) ; AI3-01851 ; BRN 0969155 ; NSC 65426 ; PG ; Trimethylene glycol ; beta-Propylene glycol ; omega-Propanediol . 1,3-Propanediol (CAS NO.504-63-2) is clear oily liquid.
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