Conditions | Yield |
---|---|
With hydrogen; 5% activated charcoal-supported ruthenium catalyst In ethanol at 120℃; under 120012 Torr; for 70 - 90h; Product distribution / selectivity; | 90% |
In water | 77% |
With hydrogen; 5% activated charcoal-supported ruthenium catalyst In water at 100 - 120℃; under 7500.75 - 90009 Torr; for 6 - 24h; Product distribution / selectivity; | 63% |
Conditions | Yield |
---|---|
With ruthenium on silica; hydrogen In tetrahydrofuran at 200℃; under 75007.5 Torr; for 12h; Temperature; Pressure; Time; | 87% |
malic acid dimethyl ester
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With hydrogen; CuO/ZnO/Al2O3 In tetrahydrofuran at 180℃; under 7500.75 - 75007.5 Torr; for 4h; Product distribution / selectivity; | 80% |
With potassium tert-butylate In 1,4-dioxane at 70℃; for 48h; Temperature; Time; | 62% |
With potassium borohydride In ethanol | |
With hydrogenchloride; sodium borohydrid In tetrahydrofuran; methanol; isopropyl alcohol; acetone | |
With hydrogen; [(MeC(CH2PPh2)3)Ru(acetonitrile)3](CF3SO3)2 In methanol at 100℃; under 30003 Torr; for 14h; Product distribution / selectivity; Inert atmosphere; Autoclave; | >= 99.9 %Chromat. |
malic acid
A
propylene glycol
B
Butane-1,4-diol
C
D,L-1,2,4-butanetriol
D
ethylene glycol
Conditions | Yield |
---|---|
With hydrogen; Ru-carbon In water at 135℃; under 258574 Torr; for 10h; Further byproducts given; | A 11% B 8% C 74% D 3% |
Conditions | Yield |
---|---|
Stage #1: homoalylic alcohol With formic acid; water; dihydrogen peroxide at 55 - 60℃; for 7h; Stage #2: With methanol; Marlon-AS3 at 55 - 85℃; for 3h; | 72% |
With sulfuric acid; water; dihydrogen peroxide | |
Stage #1: homoalylic alcohol With sodium periodate; acetic acid; lithium bromide at 95℃; for 18h; Prevost-Woodward reaction; Stage #2: With potassium carbonate In methanol at 25℃; for 24h; | |
With potassium permanganate |
rac-3,4-dihydroxybutyl bromide
A
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With 3-Hydroxytetrahydrofuran; trisodium arsenite; hydrogen bromide for 96h; Ambient temperature; | A 5% B 17% |
Conditions | Yield |
---|---|
With copper chromite; ethanol at 100 - 150℃; under 257428 Torr; Hydrogenation; | |
With ethanol; nickel at 100 - 150℃; under 257428 Torr; Hydrogenation; |
Conditions | Yield |
---|---|
With water; nickel at 60 - 100℃; under 147102 Torr; Hydrogenation; | |
With copper oxide-chromium oxide; water; silica gel at 80 - 100℃; under 147102 Torr; Hydrogenation; |
formaldehyd
A
D,L-1,2,4-butanetriol
B
1,2,3,4-butanetetrol
C
ethylene glycol
D
2-C-hydroxymethyltetritol
E
glycerol
Conditions | Yield |
---|---|
With calcium oxide Product distribution; Heating; reduction of formed monosacharides;; |
3-Benzoyloxytetrahydrofuran
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With titanium tetrachloride 1) CH2Cl2, 72h, reflux 2) saponification; Multistep reaction; |
4-Methoxy-benzoic acid tetrahydro-furan-3-yl ester
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With titanium tetrachloride; potassium carbonate 1) CH2Cl2, 72h, reflux 2) MeOH, 10h, r.t.; Yield given. Multistep reaction; |
2-6'-acetoxy-6'-formyloxy-4'-oxo-2'-hexenamido-3-hydroxy-2-cyclopenten-1-one
A
D,L-1,2,4-butanetriol
B
2-glycolamido-3-hydroxy-2-cyclopenten-1-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate; ozone 1.) dichloromethane, cooled with dry ice-acetone, 40 min.; 2.) ethanol, water, 30 min, cooling; room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given; | |
With sodium tetrahydroborate; ozone 1.) dichloromethane, cooled with dry ice-acetone, 40 min.; 2.) ethanol, water, 30 min. cooling; room temperature, 30 min; Yield given. Multistep reaction. Yields of byproduct given; |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; RhCl(PPh3)3 at 130℃; for 0.5h; | 90 % Chromat. |
Conditions | Yield |
---|---|
With titanium silicate; dihydrogen peroxide at 24.9℃; for 6h; Title compound not separated from byproducts; |
Adipic acid
A
butane-1,2,3-triol
B
D,L-1,2,4-butanetriol
C
meso-erythritol
D
ethylene glycol
Conditions | Yield |
---|---|
Das Natriumsalz bei der reduzierenden Verseifung mit Ba(SH)2 in Butandiol-(1.2); |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With hydrogenchloride; methanol | |
With methanol; sulfuric acid |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With sodium nitrate Electrolysis.an einer Platinanode und reduzierende Verseifung des Reaktionsgemisches mit Ba(SH)2; |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With sodium nitrate Electrolysis.an einer Platinanode und reduzierende Verseifung des Reaktionsgemisches mit Ba(SH)2; |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With sodium nitrate Electrolysis.an einer Platinanode und reduzierende Verseifung des Reaktionsgemisches mit Ba(SH)2; |
Conditions | Yield |
---|---|
at 60 - 100℃; under 147102 Torr; Hydrogenation; |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With barytes |
1,2-dibromo-4-methoxy-butane
water
A
3-Hydroxytetrahydrofuran
B
D,L-1,2,4-butanetriol
C
4-methoxy-1,2-butanediol
dimethyl (S)-malate
A
D,L-1,2,4-butanetriol
B
(3S)-3-hydroxydihydrofuran-2(3H)-one
C
2-buten-4-olide
D
methyl 3,4-dihydroxybutanoate
Conditions | Yield |
---|---|
With hydrogen In Dimethyl ether at 56 - 110℃; under 120012 Torr; for 0.5 - 2h; Product distribution / selectivity; | A n/a B n/a C n/a D n/a |
Conditions | Yield |
---|---|
With hydrogen; Ni(30 wt%)/SiO2 In isopropyl alcohol at 90 - 120℃; under 68404.6 Torr; Product distribution / selectivity; | |
With hydrogen; nickel In isopropyl alcohol at 120℃; under 68404.6 Torr; for 6h; Product distribution / selectivity; | |
With hydrogen; 5%-palladium/activated carbon In isopropyl alcohol at 120℃; under 68404.6 Torr; for 5h; Product distribution / selectivity; |
(R)-dimethyl malate
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water | |
With sodium hydroxide In tetrahydrofuran; water |
Conditions | Yield |
---|---|
In tetrahydrofuran |
D-sorbitol
A
propylene glycol
B
ethanol
C
1.3-butanediol
D
D,L-1,2,4-butanetriol
E
XYLITOL
F
ethylene glycol
G
isopropyl alcohol
H
glycerol
I
2.3-butanediol
J
1,2-dihydroxybutane
Conditions | Yield |
---|---|
With potassium hydroxide; hydrogen; nickel-rhenium-on-carbon In water at 220℃; under 31029.7 - 62059.4 Torr; for 4h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
100% |
D,L-1,2,4-butanetriol
benzoyl chloride
(+/-)-1,2,4-tris(benzoyloxy)butane
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 25℃; | 100% |
D,L-1,2,4-butanetriol
2,2-diphenylacetaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; for 17h; | 100% |
D,L-1,2,4-butanetriol
orthobenzoic acid trimethyl ester
3-Benzoyloxytetrahydrofuran
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 2h; | 99% |
Conditions | Yield |
---|---|
sulfuric acid at 140℃; under 49.505 Torr; Product distribution / selectivity; Reactive distillation; Intramolecular dehydration; | 98% |
samarium(III) trifluoromethanesulfonate at 140℃; under 49.505 Torr; Product distribution / selectivity; Reactive distillation; Intramolecular dehydration; | 97% |
strong acid ion exchange resin (Amberlyst 15, H+ form) In 1,4-dioxane at 100℃; under 760.051 Torr; for 20h; Product distribution / selectivity; | 96% |
D,L-1,2,4-butanetriol
acetone
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 4h; | 98% |
With toluene-4-sulfonic acid at 20℃; for 20h; | 97% |
With toluene-4-sulfonic acid | 86% |
D,L-1,2,4-butanetriol
cyclohexanone
2-(1,4-dioxa-spiro[4.5]dec-2-yl)-ethanol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 0 - 20℃; | 97% |
D,L-1,2,4-butanetriol
2,2-dimethoxy-propane
(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanol
Conditions | Yield |
---|---|
In dichloromethane | 96.7% |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With water-d2; phospho(enol)pyruvic acid mono potassium salt; adenosine 5'-triphosphate disodium salt; barium(II) chloride; magnesium chloride; glycerol kinase from S. cerevisiae or from E. coli and pyruvate kinase In various solvent(s) for 1h; | 95% |
D,L-1,2,4-butanetriol
tert-butyldimethylsilyl chloride
1,4-di(tert-butyldimethylsilanyloxy)butan-2-ol
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; | 95% |
With 1H-imidazole In dichloromethane Inert atmosphere; chemoselective reaction; | |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; Cooling; |
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In toluene Reflux; Inert atmosphere; Dean-Stark; | 95% |
D,L-1,2,4-butanetriol
(6Z,9Z,28Z,31Z)-heptatriaconta-6,9,28,31-tetraen-19-one
2,2-dilinoleyl-4-(2-hydroxyethyl)-[1,3]-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 3h; Reflux; Molecular sieve; | 90% |
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark; | 47% |
With pyridinium p-toluenesulfonate In toluene Reflux; Inert atmosphere; | |
With pyridinium p-toluenesulfonate In toluene | |
With pyridinium p-toluenesulfonate In toluene Inert atmosphere; Reflux; Dean-Stark tube; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 3h; Reflux; Molecular sieve; | 90% |
With toluene-4-sulfonic acid In toluene for 3h; Reflux; Molecular sieve; | 90% |
D,L-1,2,4-butanetriol
(benzoyloxy)acetaldehyde diethyl acetal
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; for 0.1h; stereoselective reaction; | 90% |
D,L-1,2,4-butanetriol
1-amino-3-methylbenzene
1-m-tolyl-pyrrolidin-3-ol
Conditions | Yield |
---|---|
Stage #1: D,L-1,2,4-butanetriol With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 0.666667h; Molecular sieve; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: 1-amino-3-methylbenzene In toluene at 20℃; for 48.33h; Inert atmosphere; Schlenk technique; Sealed tube; Reflux; Green chemistry; | 90% |
D,L-1,2,4-butanetriol
hexaethylphosphoric triamide
2,7,8-trioxa-1-phosphabicyclo<3.2.1>octane
Conditions | Yield |
---|---|
at 100℃; | 89% |
3-chloro-1,1-diethoxy-propane
D,L-1,2,4-butanetriol
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction; | 89% |
D,L-1,2,4-butanetriol
ethenyltrimethylsilane
1,2,4-Tris-trimethylsiloxy-butan
Conditions | Yield |
---|---|
Wilkinson's catalyst In toluene at 130℃; for 6h; | 88% |
D,L-1,2,4-butanetriol
benzaldehyde
(+/-)-cis-4-(hydroxymethyl)-2-phenyl-1,3-dioxane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 4.5h; Heating; | 87% |
With toluene-4-sulfonic acid In toluene for 1h; Reflux; | 53% |
With molecular sieve; toluene-4-sulfonic acid In toluene Heating; |
(1,3-bis(diphenylphosphino)propane)Pt(CO3)
D,L-1,2,4-butanetriol
[(1,3-bis(diphenylphosphino)propane)]platinum(II)(1,2,4-butanetriolate)
Conditions | Yield |
---|---|
In dichloromethane byproducts: CO2, H2O; under Ar; Pt-complex and 1.05 equiv of the triol dissolved in CH2Cl2, soln. stirred 2 h, soln. purged with Ar 4 times over a period of 3 h; evapn. (vac.), dried (vac., 1 h), dissolved in min. amt. CH2Cl2, layered with ether (crystn.), cryst. isolated, dried (vac.), elem. anal.; | 87% |
D,L-1,2,4-butanetriol
benzyl chloride
(+/-)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
With sodium hydride; sodium iodide In N,N-dimethyl-formamide for 12h; Ambient temperature; | 86% |
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In toluene Inert atmosphere; Reflux; | 86% |
D,L-1,2,4-butanetriol
m-Anisidine
1-(3-methoxy-phenyl)-pyrrolidin-3-ol
Conditions | Yield |
---|---|
Stage #1: D,L-1,2,4-butanetriol With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 20℃; for 0.666667h; Molecular sieve; Inert atmosphere; Schlenk technique; Green chemistry; Stage #2: m-Anisidine In toluene at 20℃; for 48.33h; Inert atmosphere; Schlenk technique; Sealed tube; Reflux; Green chemistry; | 86% |
Conditions | Yield |
---|---|
With C30H42N4O6Pd2(2+)*2CF3O3S(1-); p-benzoquinone In water; acetonitrile at 55℃; for 24h; Darkness; chemoselective reaction; | 85% |
With Candida boidinii KK912 In methanol; water at 30℃; for 48h; phosphate buffer (pH=7); other butanols; | 78.1% |
With phosphate buffer; Candida boidinii KK912 In methanol; water at 30℃; for 48h; | 78.1% |
With [(neocuproine)Pd(OAc)]2(OTf)2; oxygen In water; acetonitrile at 25℃; for 20h; Reagent/catalyst; Temperature; chemoselective reaction; | 71% |
With 2-Picolinic acid; manganese(II) perchlorate hexahydrate; butanedial; dihydrogen peroxide; sodium acetate In acetonitrile at 0 - 20℃; for 1h; Solvent; |
D,L-1,2,4-butanetriol
2,2-dimethoxy-propane
4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid | 85% |
With camphor-10-sulfonic acid In acetonitrile at 20℃; | 80% |
Stage #1: D,L-1,2,4-butanetriol; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate In acetone at 20℃; for 4h; Reflux; Stage #2: In methanol at 0℃; for 12h; | 74% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction; | 85% |
D,L-1,2,4-butanetriol
benzaldehyde dimethyl acetal
(+/-)-cis-4-(hydroxymethyl)-2-phenyl-1,3-dioxane
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; cobalt(II) chloride In acetonitrile at 20℃; Inert atmosphere; stereoselective reaction; | 84% |
Molecular Structure of Butane-1,2,4-triol (CAS NO.3068-00-6):
IUPAC Name: butane-1,2,4-triol
Empirical Formula: C4H10O3
Molecular Weight: 106.1204
H bond acceptors: 3
H bond donors: 3
Freely Rotating Bonds: 6
Polar Surface Area: 27.69 Å2
Index of Refraction: 1.486
Molar Refractivity: 25.14 cm3
Molar Volume: 87.4 cm3
Surface Tension: 55.6 dyne/cm
Density: 1.213 g/cm3
Flash Point: 153.9 °C
Enthalpy of Vaporization: 63.12 kJ/mol
Boiling Point: 303.9 °C at 760 mmHg
Vapour Pressure: 8.63E-05 mmHg at 25°C
Sensitive: Hygroscopic
BRN: 1733456
Melting point: -20°C
InChI
InChI=1/C4H10O3/c5-2-1-4(7)3-6/h4-7H,1-3H2
Smiles
C([C@@H](CO)O)CO
EINECS: 221-323-5
Product Categories: Organic Building Blocks; Oxygen Compounds; Polyols
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | 23gm/kg (23000mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 93, Pg. 152, 1953. |
Hazard Codes: Xi,Xn
Risk Statements: 36/37/38-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 1
RTECS: EK7176000
Butane-1,2,4-triol , with CAS number of 3068-00-6, can be called 1,2,4-Trihydroxybutane ; 1,3,4-Butanetriol ; 2-Deoxyerythritol ; (2R)-Butane-1,2,4-triol . It is a clear yellow to slightly brownish liquid.
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