Conditions | Yield |
---|---|
With hydrogen; phosphotungstic acid 44-hydrate; [Fe(C5H4P(i-Pr)2)2Rh(C8H12)]BF4 In water; isopropyl alcohol at 20℃; under 5171.62 Torr; for 16h; | 100% |
With sodium tetrahydroborate at 0 - 20℃; | 99% |
1-chloro-3-hydroxypropane
sodium thiomethoxide
3-(methylthio)-1-propanol
Conditions | Yield |
---|---|
In 1,2-dimethoxyethane 1.) 3 h stirring; 2.) 30 min heating; | 80% |
With diethyl ether |
Conditions | Yield |
---|---|
With sodium carbonate; PtCl2(dppm) In acetone for 24h; Heating; | 69% |
Conditions | Yield |
---|---|
With mercury(II) diacetate; dibenzoyl peroxide im UV-Licht; | |
With mercury salt; oxygen Irradiation.im Licht; |
Conditions | Yield |
---|---|
With sodium hydroxide at 100℃; |
methyl 3-(methylthio)propionate
3-(methylthio)-1-propanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran |
Conditions | Yield |
---|---|
With sodium hydroxide |
allylmethyl sulfide
A
3-(methylthio)-1-propanol
B
1-(methylthio)propan-2-ol
Conditions | Yield |
---|---|
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide 1.) THF, 25 deg C, overnight, 2.) 1 h; Multistep reaction; |
Conditions | Yield |
---|---|
in Gegenwart von Licht; |
Conditions | Yield |
---|---|
at 100℃; |
3-hydroxypropyl thiocyanate
A
3-[(3-hydroxypropyl)disulfanyl]-1-propanol
B
3-(methylthio)-1-propanol
3-(methylthio)-1-propanol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; | 100% |
3-(methylthio)-1-propanol
2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 70℃; | 99% |
Conditions | Yield |
---|---|
With 1,5-dichloro-9,10-anthraquinone In dichloromethane for 1h; UV-irradiation; | 97% |
3-(methylthio)-1-propanol
3-methylthiopropyl chloride
Conditions | Yield |
---|---|
With thionyl chloride In chloroform for 4h; Wavelength; Reflux; | 96% |
With thionyl chloride; chloroform | |
With thionyl chloride In chloroform | |
With thionyl chloride In pyridine |
3-(methylthio)-1-propanol
p-toluenesulfonyl chloride
3-(methylthio)-1-propanol mono-p-toluenesulfonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at -20 - 20℃; | 96% |
With N,N,N',N'-tetramethylhexamethylenediamine; triethylamine In toluene at 20℃; Cooling with ice; | 96% |
With pyridine for 1h; | 95.1% |
Conditions | Yield |
---|---|
With (NH4)4[CuMo6O18(OH)6]·5H2O; oxygen; sodium sulfite In water; acetonitrile at 60℃; under 760.051 Torr; for 12h; | 96% |
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 20℃; for 24h; | 25% |
With 5H3N*5H(1+)*IMo6O24(5-); oxygen; sodium acetate In water; acetonitrile at 70℃; under 760.051 Torr; for 15h; Green chemistry; | 97 %Chromat. |
With 1-methyl-1H-imidazole; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C22H16BrCuF2N2O2 In acetonitrile at 20℃; for 24h; Reagent/catalyst; | 78 %Chromat. |
3-(methylthio)-1-propanol
6-bromohexanoic acid
6-bromo-hexanoic acid 3-methylsulfanyl-propyl ester
Conditions | Yield |
---|---|
With dmap; oligomeric alkyl cyclohexylcarbodiimide In dichloromethane at 20℃; for 2h; | 94% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; | 84% |
3-(methylthio)-1-propanol
4-ethyloctanoyl chloride
3-(methylthio)prop-1-yl 4-ethyloctanoate
Conditions | Yield |
---|---|
at 70℃; for 4h; | 94% |
3-(methylthio)-1-propanol
N-[(3E)-5-tert-butyl-2-(cyclobutylmethyl)-1-methyl-1,2-dihydro-3H-pyrazol-3-ylidene]-2-[3-(methylthio)propoxy]-5-(trifluoromethyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-(methylthio)-1-propanol With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: N-[(3E)-5-tert-butyl-2-(cyclobutylmethyl)-1-methyl-1,2-dihydro-3H-pyrazol-3-ylidene]-2-fluoro-5-(trifluoromethyl)benzamide In tetrahydrofuran for 2h; | 91% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Mitsunobu Displacement; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
Stage #1: sebacoyl chloride; C66H9NO4 With pyridine In toluene at 20℃; for 24h; Stage #2: 3-(methylthio)-1-propanol In toluene at 20℃; for 8h; Further stages.; | 87% |
3-(methylthio)-1-propanol
4-bromo-3,5-dimethylphenol
(3-(4-bromo-3,5-dimethylphenoxy)propyl)(methyl)sulfane
Conditions | Yield |
---|---|
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene at 20℃; for 18h; Mitsunobu reaction; | 87% |
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In toluene at 20℃; for 18h; Inert atmosphere; | 87% |
With di-tert-butyl-diazodicarboxylate; triphenylphosphine In dichloromethane for 3h; |
3-(methylthio)-1-propanol
ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-hydroxyphenyl)-1H-pyrrole-2-carboxylate
ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-(methylthio)propoxy)phenyl)-1H-pyrrole-2-carboxylate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 96h; | 85% |
3-(methylthio)-1-propanol
lasalocid (X 537 A)
Conditions | Yield |
---|---|
With ethanol; dicyclohexyl-carbodiimide In diethyl ether for 5h; Heating; | 84% |
Conditions | Yield |
---|---|
In tetrahydrofuran at -5℃; for 2h; Alkaline conditions; | 83% |
3-(methylthio)-1-propanol
p-toluenesulfonyl chloride
3-(methylsulfonyl)propyl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
Stage #1: 3-(methylthio)-1-propanol; p-toluenesulfonyl chloride With dmap; triethylamine In dichloromethane at 20℃; for 3h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane; water at 20℃; for 2h; | 82% |
3-(methylthio)-1-propanol
4-nitro-3-methoxyphenol
Conditions | Yield |
---|---|
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 25℃; for 12h; | 81.2% |
Conditions | Yield |
---|---|
In hexane addn. of 1 equiv. of Al-compound to soln. of alcohol at -78°C, warming to room temp., stirring overnight; elem. anal.; | 80% |
3-(methylthio)-1-propanol
acryloyl chloride
acrylic acid 3-methylthiopropyl ester
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 18h; | 80% |
3-(methylthio)-1-propanol
methanesulfonyl chloride
3-(methylthio)propyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.5h; | 79% |
With triethylamine In pyridine for 72h; Ambient temperature; Yield given; | |
With triethylamine In dichloromethane at 0 - 20℃; for 3.5h; |
1-(tert-butyl) 2-ethyl 5-hydroxy-1H-indole-1,2-dicarboxylate
3-(methylthio)-1-propanol
1-(1,1-dimethylethyl) 2-ethyl 5-{[3-(methylthio)propyl]oxy}-1H-indole-1,2-dicarboxylate
Conditions | Yield |
---|---|
With triphenylphosphine In dichloromethane at 45℃; for 1h; | 76% |
3-(methylthio)-1-propanol
3-(pyridin-4-yl)acrylic acid
Conditions | Yield |
---|---|
Stage #1: 3-(methylthio)-1-propanol; 3-(pyridin-4-yl)acrylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; Inert atmosphere; | 72% |
Conditions | Yield |
---|---|
With dmap In toluene at 0 - 25℃; for 16h; | 69% |
3-(methylthio)-1-propanol
N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-fluoro-5-(trifluoromethyl)benzamide
N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-[3-(methylthio)propoxy]-5-(trifluoromethyl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-(methylthio)-1-propanol With potassium tert-butylate In tetrahydrofuran at 20℃; for 0.333333h; Stage #2: N-{(3E)-5-tert-butyl-1-methyl-2-[(2R)-tetrahydrofuran-2-ylmethyl]-1,2-dihydro-3H-pyrazol-3-ylidene}-2-fluoro-5-(trifluoromethyl)benzamide In tetrahydrofuran at 20℃; for 2h; | 67% |
m-chloroperoxybenzoic acid
3-(methylthio)-1-propanol
sodium sulfite
3-(methylsulfonyl)propan-1-ol
Conditions | Yield |
---|---|
In dichloromethane; water | 66% |
N-hydroxyphthalimide
3-(methylthio)-1-propanol
2-[3-(methylsulfanyl)propoxy]-1H-isoindole-1,3(2H)-dione
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 25℃; for 5h; | 65% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 18.5h; Inert atmosphere; | 42.2% |
With di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 20℃; for 18.5h; Inert atmosphere; | 42.2% |
3-(methylthio)-1-propanol
cinnamoyl chloride
3-(methylthio)-1-propyl 3-phenyl-2-propenoate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 20℃; | 60% |
With triethylamine In tetrahydrofuran at 20℃; | 60% |
Molecular Structure of 3-Methylthiopropanol (CAS NO.505-10-2):
IUPAC Name: 3-Methylsulfanylpropan-1-ol
Canonical SMILES: CSCCCO
InChI: InChI=1S/C4H10OS/c1-6-4-2-3-5/h5H,2-4H2,1H3
InChIKey: CZUGFKJYCPYHHV-UHFFFAOYSA-N
Molecular Weight: 106.1866 [g/mol]
Molecular Formula: C4H10OS
XLogP3-AA: 0.5
H-Bond Donor: 1
H-Bond Acceptor: 1
EINECS: 208-004-6
Index of Refraction: 1.479
Molar Refractivity: 30.11 cm3
Molar Volume: 106 cm3
Surface Tension: 35.4 dyne/cm
Density: 1.001 g/cm3
Flash Point: 90.6 °C
Enthalpy of Vaporization: 49.53 kJ/mol
Boiling Point: 189.3 °C at 760 mmHg
Vapour Pressure: 0.156 mmHg at 25 °C
Appearance: Colorless Liquid
Product Categories: Aliphatics; API intermediates; Various Intermediates; sulfide Flavor; Intermediates; Sulfur & Selenium Compounds; Aliphatic; Sulfides flavors
3-Methylthiopropanol (CAS NO.505-10-2) is used as a flavor.
Safety Information of 3-Methylthiopropanol (CAS NO.505-10-2):
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-24/25-36/37/39
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
3-Methylthiopropanol (CAS NO.505-10-2), its Synonyms are 1-Propanol, 3-(methylthio)- ; 3-(Methylthio)-1-propanol ; 3-(Methylthio)propanol ; 3-(Methylthio)propyl alcohol ; 3-Hydroxypropyl methyl sulfide ; 3-Methylmercapto-1-propanol ; Methionol ; Methyl 3-hydroxypropylsulfide ; gamma-Hydroxypropyl methyl sulfide ; gamma-Methylmercaptopropyl alcohol .
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