Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating; | 100% |
With lithium aluminium tetrahydride In tetrahydrofuran for 4h; Heating; | 68% |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h; Reduction; | 44% |
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 6.5h; Heating; | 33% |
With lithium aluminium tetrahydride In tetrahydrofuran |
4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With water; hydrogen; sodium hydroxide at 120℃; under 6000.6 Torr; for 6h; Reagent/catalyst; | 95% |
With hydrogen; sodium hydroxide In water at 120℃; under 6000.6 Torr; for 7h; |
Conditions | Yield |
---|---|
With borane-THF for 18h; Heating; | 75% |
With lithium aluminium tetrahydride; diethyl ether | |
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h; | |
Multi-step reaction with 2 steps 1: H2SO4 2: sodium; ethanol View Scheme |
dimethyl 3-methylglutarate
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride | 75% |
With lithium aluminium tetrahydride In tetrahydrofuran for 24h; Heating; |
Conditions | Yield |
---|---|
With hydrogen; copper at 240℃; under 225018 Torr; for 5h; | 65% |
3,4-dihydro-2-methoxy-4-methyl-2H-pyran
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With copper oxide-chromium oxide; water; hydrogen at 180℃; under 144160 Torr; | |
With hydrogen; nickel; acetic acid at 150℃; under 66195.7 Torr; |
6-methoxy-4-methyl-3,6-dihydro-2H-pyran
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With hydrogenchloride und Hydrieren des Reaktionsgemisches an Raney-Nickel in neutraler Loesung bei 125grad; |
Conditions | Yield |
---|---|
With copper oxide-chromium oxide Hydrogenation; | |
With lithium aluminium tetrahydride; diethyl ether | |
With ethanol; sodium |
Conditions | Yield |
---|---|
With ethanol; nickel at 100℃; under 36775.4 Torr; Hydrogenation; |
3-methylenepentane-1,5-diol
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With 1,4-dioxane; nickel at 100℃; under 257428 Torr; Hydrogenation; |
1,5-diacetoxy-3-methylpentane
sodium methylate
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With methanol |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride |
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With copper chromite; hydrogen at 250℃; unter Druck; |
Conditions | Yield |
---|---|
at 250℃; under 147102 - 220652 Torr; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: CuI / tetrahydrofuran / 20 °C 1.2: TMSCl / tetrahydrofuran / -78 - 20 °C 2.1: lithium aluminum hydride / tetrahydrofuran / 24 h / Heating View Scheme |
2-ethoxy-4-methyl-3,4-dihydro-2H-pyran
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous sulfuric acid 2: Raney nickel; ethanol / 100 °C / 36775.4 Torr / Hydrogenation View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 200 °C 2: Raney nickel; dioxane / 100 °C / 257428 Torr / Hydrogenation View Scheme | |
Multi-step reaction with 3 steps 1.1: A-36 ion exchange resin / 100 °C / 1200.12 Torr / Autoclave; Large scale 1.2: hollow molecular sieve nanotubes supported silicotungstic acid catalyst / 105 - 155 °C / 825.08 Torr / Large scale 2.1: dicarbonyl(acetylacotonato)rhodium(I); C72H100O6P2; hydrogen / 24 h / 125 °C / 75007.5 Torr / Flow reactor 3.1: hydrogen / 150 - 240 °C / 1200.12 Torr / Flow reactor View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2 / Co2(CO)8 / 140 °C / 132391 Torr 2: LiAlH4 View Scheme |
Di-n-octyl phthalate
4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol
A
4-methyl-tetrahydro-pyran-2-one
B
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With manganese dioxide; copper chromite |
4-Methyl-3,4,5,6-tetrahydro-2H-pyran-2-ol
A
4-methyl-tetrahydro-pyran-2-one
B
3-methylpentane-1,5-diol
C
MPAE
Conditions | Yield |
---|---|
With sodium hydroxide; hydrogen; nickel In water at 120℃; under 6600.66 Torr; for 5h; pH=8.4 - 10.9; Product distribution / selectivity; | |
With hydrogen In water at 120℃; for 2h; Product distribution / selectivity; | |
With hydrogen; cobalt In water at 120℃; for 5h; Product distribution / selectivity; |
molybdenum hexacarbonyl
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With hydrogen In 1,4-dioxane |
Conditions | Yield |
---|---|
With dicarbonylacetylacetonato rhodium (I); hydrogen; molybdenum hexacarbonyl In 1,4-dioxane at 200℃; under 90009 - 112511 Torr; for 2.33333h; Schlenk technique; Autoclave; | |
With 5 wt% ruthenium/carbon; hydrogen In water at 100℃; under 105011 Torr; for 6.3h; | |
With ruthenium-carbon composite; hydrogen In water at 100℃; under 105011 Torr; for 16h; Catalytic behavior; Temperature; Pressure; |
α-methyl-δ-valerolactone
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With 5 wt% ruthenium/carbon; hydrogen In water at 100℃; under 105011 Torr; for 6.3h; |
Conditions | Yield |
---|---|
With ruthenium-carbon composite; hydrogen In water at 100℃; under 105011 Torr; for 3.5h; Catalytic behavior; Time; |
D,L-mevalonic acid
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sulfuric acid / 15 h / Reflux 2: hydrogen; ruthenium-carbon composite / water / 3.5 h / 100 °C / 105011 Torr View Scheme |
3-methyl-5-oxopentyl acetate
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With hydrogen at 150 - 240℃; under 1200.12 Torr; Flow reactor; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 135℃; for 41h; | 99.6% |
With Amberlyst 15 | 91% |
With toluene-4-sulfonic acid at 135 - 155℃; Dean-Stark; Large scale; | 3662 g |
With toluene-4-sulfonic acid at 135 - 155℃; for 41h; Large scale; | |
With toluene-4-sulfonic acid at 135 - 155℃; |
3-methylpentane-1,5-diol
(S)-4-methyltetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With horse liver alcohol dehydrogenase; oxygen; catalase; 7-(trifluoromethyl)-1,10-ethyleneisoalloxazinium chloride In aq. phosphate buffer at 20℃; for 13h; pH=8; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 97% |
With 2,6-dimethylpyridine; sodium perchlorate In acetonitrile for 10h; Electrolysis; | 96.4% |
With sodium perchlorate; (-)-sparteine In acetonitrile macroelectrolysis with 2,2,6,6-tetramethylpiperidine-1-yloxyl)-modified graphite felt electrodes; | 93.8% |
3-methylpentane-1,5-diol
p-toluenesulfonyl chloride
3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate)
Conditions | Yield |
---|---|
With dmap; triethylamine In acetonitrile at 20℃; for 3h; | 97% |
With triethylamine In dichloromethane at 20℃; for 18h; | 82.5% |
With pyridine at 20℃; for 2h; | |
With pyridine at 20℃; for 1h; |
Conditions | Yield |
---|---|
With oxygen In toluene at 110℃; for 1h; | 96% |
With hydrotalcite-supported copper nanoparticles In 1,3,5-trimethyl-benzene at 150℃; for 8h; Inert atmosphere; | 96% |
With [RuCl2(PPh3)2(2-PyCH21,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide In water for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry; | 96% |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 16h; Microwave irradiation; Inert atmosphere; Sealed tube; | 96% |
With 1,4-dioxane; copper oxide-chromium oxide; hydrogen at 250℃; under 147102 - 294203 Torr; |
3-methylpentane-1,5-diol
3-methyl-1,5-diiodopentane
Conditions | Yield |
---|---|
With phosphorus; iodine at 45℃; for 42h; Cooling with ice bath; | 87% |
With phosphorus; iodine | |
Multi-step reaction with 2 steps 1: 73 percent / PBr3 / 20 h / -10 - 20 °C 2: 89 percent / NaI / acetone / 3 h / Heating View Scheme |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 16h; Microwave irradiation; Inert atmosphere; Sealed tube; | 86% |
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 1h; | 85% |
With hydrogen bromide In octane; water at 147 - 148℃; for 12h; Dean-Stark; | 83% |
With phosphorus tribromide at -10 - 20℃; for 20h; Substitution; | 73% |
Conditions | Yield |
---|---|
With sodium hydroxide; tetra(n-butyl)ammonium hydroxide at 40℃; for 7h; | 85% |
3-methylpentane-1,5-diol
tert-butyldimethylsilyl chloride
5-(tert-butyldimethylsilyl)oxy-3-methyl-1-pentanol
Conditions | Yield |
---|---|
Stage #1: 3-methylpentane-1,5-diol With n-butyllithium In tetrahydrofuran; hexane at 20℃; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃; for 0.75h; Inert atmosphere; Stage #3: With water; ammonium chloride | 84% |
With sodium hydride In tetrahydrofuran Substitution; Silylation; | 83% |
Stage #1: 3-methylpentane-1,5-diol With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 0.5h; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; hexane at 20℃; | 52% |
Stage #1: 3-methylpentane-1,5-diol With sodium hydride In tetrahydrofuran Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran at 0℃; Inert atmosphere; | 51% |
3-methylpentane-1,5-diol
p-toluenesulfonyl chloride
5-hydroxy-3-methylpentyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 3.16667h; Inert atmosphere; | 84% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium hydroxide; catacxium A In toluene at 115℃; for 24h; Time; Sealed tube; chemoselective reaction; | 84% |
Conditions | Yield |
---|---|
Stage #1: 3-methylpentane-1,5-diol With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1,1'-(2-nitroethene-1,1-diyl)dibenzene In tetrahydrofuran at 15℃; for 15h; | 82% |
Conditions | Yield |
---|---|
Stage #1: 3-methylpentane-1,5-diol With sodium hydride In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: propargyl bromide In tetrahydrofuran Inert atmosphere; | 80% |
3-methylpentane-1,5-diol
Conditions | Yield |
---|---|
With diphenylphosphoranyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 65℃; for 16h; | 76% |
Conditions | Yield |
---|---|
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide In toluene at 115℃; for 24h; Inert atmosphere; Sealed tube; diastereoselective reaction; | 76% |
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide In toluene at 115℃; for 24h; Sealed tube; Inert atmosphere; diastereoselective reaction; | 76% |
3-methylpentane-1,5-diol
all-trans-retinoic-acid
3-methyl-1,5-diretinylpentanediester
Conditions | Yield |
---|---|
Stage #1: 3-methylpentane-1,5-diol; all-trans-retinoic-acid With dmap; dicyclohexyl-carbodiimide In toluene at 20℃; for 15h; Darkness; Inert atmosphere; Stage #2: With hydrogenchloride In water; toluene | 74.5% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 5h; | 70% |
3-methylpentane-1,5-diol
2-[2'-hydroxy-3'-tert-butyl-5'-(2''-methoxycarbonylethyl)phenyl]-2H-benzotriazole
Conditions | Yield |
---|---|
With di(n-butyl)tin oxide at 170℃; for 20h; Dean-Stark; Inert atmosphere; | 65% |
3-methylpentane-1,5-diol
A
2-methylbutanedioic acid
B
3-methyl glutaric acid
Conditions | Yield |
---|---|
With dinitrogen tetraoxide In nitric acid at 60℃; Heating; | A 62% B 23% |
With dinitrogen tetraoxide In nitric acid at 50℃; Heating; | A 45% B 33% |
3-methylpentane-1,5-diol
(4R)-4-methyltetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With acetate buffer pH 5 In water at 30℃; for 48h; Gluconobacter roseus IAM 1841; | 57% |
Multi-step reaction with 3 steps 2: Jones oxidation 3: 1.) CH2N2, 2.) aq. HCl, MeOH View Scheme |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 12h; | 55% |
3-methylpentane-1,5-diol
phenylcarbonochloridothioate
O-(5-hydroxy-3-methylpentyl) O-phenyl thionocarbonate
Conditions | Yield |
---|---|
With pyridine; dmap In acetonitrile at 0℃; for 5h; | 54% |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; potassium hydroxide; catacxium A In toluene at 115℃; for 24h; Sealed tube; Overall yield = 77 percent; Overall yield = 135 mg; | A 51% B 26% |
3-methylpentane-1,5-diol
acryloyl chloride
3-methyl 1,5-pentanediol diacrylate
Conditions | Yield |
---|---|
With triethylamine; 2-hydroxyresorcinol In benzene at 50℃; for 0.5h; | 50% |
Molecular Structure of 3-Methyl-1,5-pentanediol (4457-71-0):
EINECS: 224-709-1
IUPAC Name: 3-Methylpentane-1,5-diol
Molecular Formula: C6H14O2
Molecular Weight: 118.174160 g/mol
XLogP3: 0.3
H-Bond Donor: 2
H-Bond Acceptor: 2
Canonical SMILES: CC(CCO)CCO
InChI: InChI=1S/C6H14O2/c1-6(2-4-7)3-5-8/h6-8H,2-5H2,1H3
InChIKey: SXFJDZNJHVPHPH-UHFFFAOYSA-N
Index of Refraction: 1.447
Molar Refractivity: 32.87 cm3
Molar Volume: 122.9 cm3
Surface Tension: 36.2 dyne/cm
Density: 0.961 g/cm3
Flash Point: 106.3 °C
Enthalpy of Vaporization: 54.08 kJ/mol
Boiling Point: 228.6 °C at 760 mmHg
Vapour Pressure: 0.0141 mmHg at 25 °C
Water Solubility: 2.617e+004 mg/L at 25 °C
Refractive Index: n20/D 1.454
BRN: 1697331
1. | ivn-mus LD50:320 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#01094 . |
Reported in EPA TSCA Inventory.
Safety Information of 3-Methyl-1,5-pentanediol (4457-71-0):
Safety Statements: 23-24/25
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24/25: Avoid contact with skin and eyes
RIDADR: 1987
WGK Germany: 1
RTECS: SA0800000
Poison by intravenous route. Flammable when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, dry chemical, CO2. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALCOHOL, DENATURED; ALCOHOLS, C6-12; ALCOHOLS, C9-11; ALCOHOLS, C12-13, ETHOXYLATED; ALCOHOLS, C12-15, ETHOXYLATED; ALCOHOLS, C12-16, ETHOXYLATED; ALCOHOLS, C14-15, ETHOXYLATED; ALCOHOLS, C16-18, ETHOXYLATED; ALCOHOLS, C8-10, ETHOXYLATED PROPOXYLATED; ALCOHOLS, C12-15, ETHOXYLATED PROPOXYLATED; ALCOHOLS, N.O.S..
3-Methyl-1,5-pentanediol (4457-71-0) is known as 1,5-Dihydroxy-3-methylpentane ; 4-01-00-02571 (Beilstein Handbook Reference) ; AI3-28481 ; NSC 6496 ; 1,5-Pentanediol, 3-methyl- ; 3-Methylpentane-1,5-diol .
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