Conditions | Yield |
---|---|
With water; sodium hydroxide In toluene Industrial scale; | 100% |
With sodium hydroxide | |
With hydrogenchloride |
1-methyl-1H-imidazole
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 3.5h; Heating; | A n/a B 94% |
1,2-dimethyl-1H-imidazole
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 3.5h; Heating; | A n/a B 94% |
α-picoline
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 2.2h; Heating; | A n/a B 80% |
picoline
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 3.8h; Heating; | A n/a B 76% |
5-(2-((tert-butyldimethylsilyl)oxy)ethyl)-4-methylthiazole
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With potassium hydrogen difluoride In methanol at 60℃; for 17h; | 75% |
pyridine-4-thiol
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 3h; Heating; | A n/a B 71% |
3,4-dichlorothiophenol
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 1h; Heating; | A n/a B 69% |
4-cyanophenol
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 4h; Heating; | A n/a B 68% |
3,4-Lutidin
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 24h; Heating; | A n/a B 64% |
4-Methoxybenzenethiol
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 1h; Heating; | A n/a B 64% |
1'-methylthiaminium diperchlorate
aniline
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 26h; Heating; | A n/a B 57% |
nicotinamide
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In methanol for 72h; Heating; | A n/a B 56% |
4-nitro-phenol
1'-methylthiaminium diperchlorate
A
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium hydroxide In methanol for 3.5h; Heating; | A n/a B 54% |
2,3-dichloro-2-methyl-tetrahydro-furan
thiocarboxamide
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With pyridine; formic acid |
2-ethoxy-3-chloro-2-methyl-tetrahydro-furan
thiocarboxamide
5-hydroxyethyl-4-methylthiazole
2-(4-methyl-2,5-dihydro-thiazol-5-yl)-ethanol
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sulfur | |
With potassium hexacyanoferrate(III) |
Conditions | Yield |
---|---|
With water; potassium carbonate |
VUF 8952
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite |
5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide | |
With water; nickel |
2-(2-bromo-4-methyl-thiazol-5-yl)-ethanol
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium hydroxide; palladium on activated charcoal Hydrogenation; | |
With acetic acid; zinc |
Conditions | Yield |
---|---|
Diazotization.anschliessende Reduktion mit wss. H3PO2; | |
(i) NaNO2, aq. H2SO4, (ii) NaH2PO2; Multistep reaction; |
2-amino-5-(2-hydroxyethyl)-4-methylthiazole
A
5-hydroxyethyl-4-methylthiazole
B
2-(2-chloro-4-methylthiazol-5-yl)ethanol
Conditions | Yield |
---|---|
With hydrogenchloride; copper(II) sulfate Diazotization.anschliessendes Erwaermen mit CuCl; |
(4-methyl-thiazol-5-yl)-acetic acid methyl ester
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
(4-methyl-thiazol-5-yl)-acetic acid ethyl ester
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With ethanol; sodium | |
With lithium aluminium tetrahydride; diethyl ether |
4-methyl-5-(β-acetoxyethyl)-2-thiazolinethione
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With hydrogenchloride; dihydrogen peroxide |
diethyl ether
3-chloro-3-acetylpropanol
thiocarboxamide
5-hydroxyethyl-4-methylthiazole
3-chloro-3-acetylpropanol
ethanol
thiocarboxamide
5-hydroxyethyl-4-methylthiazole
3-chloro-3-acetylpropanol
thiocarboxamide
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With α-picoline; ethyl acetate | |
With diethyl ether | |
With pyridine; ethyl acetate | |
With ethanol |
5-hydroxyethyl-4-methylthiazole
methyl iodide
3,4-dimethyl-5-(2-hydroxyethyl)thiazolium iodide
Conditions | Yield |
---|---|
at 60℃; for 3h; Autoclave; | 100% |
for 2h; Reflux; | 96.3% |
at 50℃; for 2h; | 96.2% |
Conditions | Yield |
---|---|
With phosphorus tribromide In dichloromethane at 0℃; for 7h; Reflux; | 99% |
With phosphorus tribromide | |
With hydrogen bromide |
5-hydroxyethyl-4-methylthiazole
methanesulfonyl chloride
5-(2-methylsulfonyloxyethyl)-4-methylthiazole
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 25℃; for 4.25h; Solvent; Cooling with ice; | 99% |
With triethylamine In dichloromethane for 1.58333h; Inert atmosphere; | 68% |
With triethylamine In dichloromethane | 67% |
3,4-dihydro-2H-pyran
5-hydroxyethyl-4-methylthiazole
5-<2-<(tetrahydro-2H-pyran-2-yl)oxy>ethyl>-4-methylthiazole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane for 8.5h; Heating; | 99% |
Conditions | Yield |
---|---|
With thionyl chloride for 3h; Reflux; | 98% |
With thionyl chloride for 2h; Heating; | 96% |
With phosphorus pentachloride In dichloromethane for 3h; Heating; | 95% |
5-hydroxyethyl-4-methylthiazole
amyl iodide
bis(trifluoromethane)sulfonimide lithium
Conditions | Yield |
---|---|
Stage #1: 5-hydroxyethyl-4-methylthiazole; amyl iodide In acetonitrile at 60℃; for 24h; Inert atmosphere; Stage #2: bis(trifluoromethane)sulfonimide lithium In hexane; water at 20℃; for 3h; Inert atmosphere; | 98% |
5-hydroxyethyl-4-methylthiazole
1,11-diiodoundecane
Conditions | Yield |
---|---|
In acetonitrile for 72h; Inert atmosphere; Reflux; | 98% |
5-hydroxyethyl-4-methylthiazole
1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene
C19H24N2O2S
Conditions | Yield |
---|---|
dibutyltin dilaurate In toluene at 80℃; for 4.16667h; | 97% |
5-hydroxyethyl-4-methylthiazole
1,9-diiodononane
Conditions | Yield |
---|---|
In acetonitrile for 72h; Inert atmosphere; Reflux; | 97% |
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With nitric acid; acetic anhydride In dichloromethane at 5℃; for 2h; Temperature; Time; | 96.8% |
With nitric acid; urea at -10 - -5℃; for 0.5h; pH=7; Nitration; | 82% |
With sulfuric acid; nitric acid at 0 - 5℃; for 3h; | 53% |
5-hydroxyethyl-4-methylthiazole
allyl bromide
5-(2-allyloxyethyl)-4-methylthiazole
Conditions | Yield |
---|---|
Stage #1: 5-hydroxyethyl-4-methylthiazole With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Cooling with ice; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; | 96% |
Stage #1: 5-hydroxyethyl-4-methylthiazole With potassium tert-butylate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; | 96% |
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium methylate In methanol Heating; | 96% |
5-hydroxyethyl-4-methylthiazole
1,ω-diiodoheptane
Conditions | Yield |
---|---|
In acetonitrile for 72h; Inert atmosphere; Reflux; | 94% |
5-hydroxyethyl-4-methylthiazole
bromoacetic acid tert-butyl ester
3-(2-tert-butoxy-2-oxoethyl)-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide
Conditions | Yield |
---|---|
In acetonitrile for 12h; Reflux; | 93.2% |
In acetonitrile for 1.5h; Reflux; | 91.4% |
In acetonitrile at 85℃; | 91.4% |
In acetonitrile at 85℃; for 20h; | |
In acetonitrile for 1.5h; | 83.9 g |
5-hydroxyethyl-4-methylthiazole
ethyl bromoacetate
3-Ethoxycarbonylmethyl-5-(2-hydroxy-ethyl)-4-methyl-thiazol-3-ium; bromide
Conditions | Yield |
---|---|
In ethanol for 4h; Reflux; | 93% |
In ethanol for 2h; Heating; | 73% |
for 3h; Reflux; | 50 g |
5-hydroxyethyl-4-methylthiazole
4-ethyloctanoyl chloride
C16H27NO2S
Conditions | Yield |
---|---|
at 70℃; for 4h; | 93% |
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
In chloroform for 16h; Reflux; Schlenk technique; | 93% |
5-hydroxyethyl-4-methylthiazole
propargyl bromide
4-methyl-5-(2-(prop-2-ynyloxy)ethyl)thiazole
Conditions | Yield |
---|---|
Stage #1: 5-hydroxyethyl-4-methylthiazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: propargyl bromide In tetrahydrofuran at 0℃; | 92% |
5-hydroxyethyl-4-methylthiazole
1-iodohexadecane
bis(trifluoromethane)sulfonimide lithium
Conditions | Yield |
---|---|
Stage #1: 5-hydroxyethyl-4-methylthiazole; 1-iodohexadecane In acetonitrile at 70℃; for 48h; Inert atmosphere; Stage #2: bis(trifluoromethane)sulfonimide lithium In hexane; water at 20℃; for 3h; Inert atmosphere; | 92% |
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With methyl iodide In acetonitrile for 1.5h; Reflux; | 91% |
5-hydroxyethyl-4-methylthiazole
1-Iodododecane
bis(trifluoromethane)sulfonimide lithium
Conditions | Yield |
---|---|
Stage #1: 5-hydroxyethyl-4-methylthiazole; 1-Iodododecane In acetonitrile at 70℃; for 49h; Inert atmosphere; Stage #2: bis(trifluoromethane)sulfonimide lithium In hexane; water at 20℃; for 3h; Inert atmosphere; | 90% |
5-hydroxyethyl-4-methylthiazole
allyl iodid
bis(trifluoromethane)sulfonimide lithium
Conditions | Yield |
---|---|
Stage #1: 5-hydroxyethyl-4-methylthiazole; allyl iodid In acetonitrile at 70℃; for 14h; Inert atmosphere; Stage #2: bis(trifluoromethane)sulfonimide lithium In hexane; water at 20℃; for 2h; Inert atmosphere; | 89% |
5-hydroxyethyl-4-methylthiazole
suberoyl chloride
Octanedioic acid bis-[2-(4-methyl-thiazol-5-yl)-ethyl] ester
Conditions | Yield |
---|---|
With pyridine In diethyl ether for 1.5h; Ambient temperature; | 88% |
5-hydroxyethyl-4-methylthiazole
1,10-diiododecane
Conditions | Yield |
---|---|
In acetonitrile for 72h; Heating; | 88% |
In acetonitrile for 72h; Inert atmosphere; Reflux; | 80% |
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium methylate In methanol Heating; | 88% |
5-hydroxyethyl-4-methylthiazole
Conditions | Yield |
---|---|
With sodium methylate In methanol Heating; | 88% |
Conditions | Yield |
---|---|
With Aliquat 336; potassium hydroxide In benzene at 80℃; for 16h; Time; | 88% |
Molecular Formula: C6H9NOS
Molecular Weight: 143.21
EINECS: 205-272-6
Index of Refraction: 1.564
Molar Refractivity: 38.63 cm3
Molar Volume: 118.7 cm3
Surface Tension: 49.8 dyne/cm
Density: 1.206 g/cm3
Flash Point: 109.7 °C
Enthalpy of Vaporization: 53.95 kJ/mol
Boiling Point: 272.4 °C at 760 mmHg
Vapour Pressure: 0.00297 mmHg at 25 °C
Sensitive: Stench
Appearance: Colorless to light yellow liqui
Structure of 4-Methyl-5-thiazoleethanol (CAS NO.137-00-8):
IUPAC Name: 2-(4-Methyl-1,3-thiazol-5-yl)ethanol
Canonical SMILES: CC1=C(SC=N1)CCO
InChI: InChI=1S/C6H9NOS/c1-5-6(2-3-8)9-4-7-5/h4,8H,2-3H2,1H3
InChIKey: BKAWJIRCKVUVED-UHFFFAOYSA-N
Product Category of 4-Methyl-5-thiazoleethanol (CAS NO.137-00-8): Thiazole;Alkohols;thiazole Flavor
4-Methyl-5-thiazoleethanol (CAS NO.137-00-8) is used for nuts, dairy products, meat products, etc, and also is used as pharmaceutical intermediates.
4-Methyl-5-thiazoleethanol (CAS NO.137-00-8) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65.
Hazard Codes: Xi
The Risk Statements:
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
7/9: Keep container tightly closed and in a well-ventilated place
24/25: Avoid contact with skin and eyes
WGK Germany: 3
F:13
Hazard Note: Irritant/Stench
4-Methyl-5-thiazoleethanol , its cas register number is 137-00-8. It also can be called Sulfurol ; 4-Methyl-5-(2'-hydroxyethyl)-thiazole ; 5-(2-Hydroxyethyl)-4-methylthiazole ; 4-Methyl-5-beta-hydroxyethyl thiazole ; and 4-Methyl-5-hydroxyethylthiazole . It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Or in the eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. While, it's inhaled: Remove from exposure and move to fresh air immediately. Then you have the ingesting of the product: Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
In addition, 4-Methyl-5-thiazoleethanol (CAS NO.137-00-8) could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials. And also prevent it to broken down into hazardous decomposition products: Nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
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