3-Hydroxybenzyl alcohol
A
triethylene glucol monomethyl ether
B
3-Phenoxybenzyl alcohol
Conditions | Yield |
---|---|
A n/a B 87% |
dimethyl sulfate
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
With sodium hydroxide at 120℃; for 4h; | 59% |
With sodium hydroxide at 120℃; |
triethylene glycol benzyl methyl ether
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
With hydrogen; palladium | 97% |
2-[2-(2-methoxyethoxy)etoxy]acetic acid
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
Stage #1: 2-[2-(2-methoxyethoxy)etoxy]acetic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 22℃; for 0.333333h; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 1h; Stage #3: With potassium hydrogensulfate In tetrahydrofuran; ethyl acetate at 22℃; for 24h; | 17% |
A
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
With RG7 In toluene at 25℃; Equilibrium constant; |
dimethyl sulfate
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
A
triethylene glucol monomethyl ether
B
Triethylene glycol dimethyl ether
Conditions | Yield |
---|---|
Stage #1: 2,2'-[1,2-ethanediylbis(oxy)]bisethanol With sodium hydroxide at 55 - 60℃; for 0.166667h; Stage #2: dimethyl sulfate at 55 - 60℃; for 6h; | A 33% B n/a |
Conditions | Yield |
---|---|
With solid alkali In 1,4-dioxane; water | 15% |
Conditions | Yield |
---|---|
With phosphoric acid at 60 - 70℃; | |
With sodium methylate at 60 - 140℃; |
triethylene glycol monobenzyl ether
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NaOH 2: 97 percent / H2 / Pd View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aq. NaOH 2: aq. NaOH 3: 97 percent / H2 / Pd View Scheme |
methyl iodide
2,2'-[1,2-ethanediylbis(oxy)]bisethanol
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 2h; |
Conditions | Yield |
---|---|
With hydrogenchloride In 1,4-dioxane; water at 30℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.), var. temp.; |
2,5-dihydroxy-4-nitrobenzoic acid methyl ester
A
triethylene glucol monomethyl ether
B
methyl 2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-4-nitrobenzoate
Conditions | Yield |
---|---|
With potassium carbonate In acetone Inert atmosphere; Reflux; |
Conditions | Yield |
---|---|
With sodium methylate |
bicyclo[2.2.1]hept-5-ene-2-carboxylic acid 2-(2-[2-methoxyethoxy]ethoxy)ethyl ester
A
triethylene glucol monomethyl ether
B
bicyclo[2.2.1]hept-2-ene-5-carbonyl chloride
Conditions | Yield |
---|---|
With Citric acid buffer; phosphoric acid at 80℃; pH=3.1; Kinetics; Further Variations:; pH-values; Temperatures; |
triethylene glucol monomethyl ether
3,6,9-trioxadecyl iodide
Conditions | Yield |
---|---|
Stage #1: triethylene glucol monomethyl ether With 1H-imidazole; triphenylphosphine In tetrahydrofuran at 20℃; for 0.05h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 77% |
With 1H-imidazole; iodine; triphenylphosphine In toluene for 4h; Heating; | 53% |
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 2: NaI / acetone / 5 h / Heating View Scheme |
triethylene glucol monomethyl ether
1-chloro-3,6,9-trioxadecane
Conditions | Yield |
---|---|
With pyridine; thionyl chloride In chloroform for 3h; Heating; | 94% |
With pyridine; thionyl chloride In toluene at 60 - 80℃; for 3h; Cooling with ice; | 92% |
With pyridine; thionyl chloride In tetrahydrofuran | 90% |
triethylene glucol monomethyl ether
4-Nitrophthalonitrile
4-phthalonitrile
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 82% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 81% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 24h; | 75% |
triethylene glucol monomethyl ether
methanesulfonyl chloride
8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1.5h; | 100% |
With triethylamine In dichloromethane | 100% |
With triethylamine In dichloromethane at 0 - 20℃; for 2h; | 97% |
triethylene glucol monomethyl ether
carbonochloridic acid, chloromethyl ester
chloromethyl (2-(2-(2-methoxyethoxy)ethoxy)ethyl) carbonate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 0 - 20℃; for 22h; Inert atmosphere; | 99% |
With pyridine In dichloromethane at 0 - 20℃; | 99% |
With pyridine In dichloromethane | |
With pyridine In dichloromethane at 20℃; | |
With pyridine In dichloromethane at -78℃; for 3h; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 110℃; for 4h; Dean-Stark; Inert atmosphere; | 90% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 25℃; for 2h; | 86% |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 6h; | 86% |
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; for 5h; | 99% |
With triethylamine In tetrahydrofuran at 0 - 20℃; for 5h; | 99% |
In dichloromethane at 0 - 20℃; for 16.5h; | 67% |
triethylene glucol monomethyl ether
propargyl bromide
3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)prop-1-yne
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 168h; Inert atmosphere; | 99% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0℃; Inert atmosphere; Stage #2: propargyl bromide With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; | 91% |
With sodium hydride; sodium iodide In tetrahydrofuran; toluene; mineral oil at 20℃; for 16h; Inert atmosphere; | 85% |
triethylene glucol monomethyl ether
epichlorohydrin
2-((2-(2-(2-methoxyethoxy)ethoxy)ethoxy)methyl)oxirane
Conditions | Yield |
---|---|
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 2h; Stage #2: epichlorohydrin In tetrahydrofuran; mineral oil at 20℃; for 20h; Reflux; | 91% |
With sodium hydride In tetrahydrofuran 1.) 2h, 2.) RT, 16h; 4h, reflux; | 86.6% |
With tetra(n-butyl)ammonium hydroxide; sodium hydroxide In water at 0 - 20℃; for 16h; Cooling with ice; | 79% |
triethylene glucol monomethyl ether
bromoacetic acid tert-butyl ester
tert-butyl (monomethoxy)triethylene glycol acetate
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 12h; | 98% |
Stage #1: triethylene glucol monomethyl ether With potassium tert-butylate In tert-butyl alcohol at 20℃; for 2h; Stage #2: bromoacetic acid tert-butyl ester In tert-butyl alcohol at 20℃; for 12h; | 75% |
With sodium hydride In tetrahydrofuran at 20 - 25℃; Cooling with ice; | 59.6% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: bromoacetic acid tert-butyl ester In tetrahydrofuran; hexane at 0 - 20℃; for 15h; Inert atmosphere; | 50% |
With sodium hydride In tetrahydrofuran |
triethylene glucol monomethyl ether
2-Bromoacetyl bromide
2-bromoacetic acid-2-[2-(2-methoxyethoxy)ethoxy]ethyl ester
Conditions | Yield |
---|---|
With triethylamine In diethyl ether at 0 - 20℃; for 0.683333h; Inert atmosphere; | 73% |
With triethylamine In dichloromethane at -78℃; Inert atmosphere; | 58% |
With triethylamine In dichloromethane at -78 - -20℃; Inert atmosphere; | |
With sodium hydrogencarbonate In acetonitrile at 0℃; for 0.166667h; Inert atmosphere; |
triethylene glucol monomethyl ether
3,6,9-trioxadecyl bromide
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0℃; for 5h; Inert atmosphere; | 84% |
With phosphorus tribromide In methanol; diethyl ether 1.) 0 deg C, 10 min, 2.) RT, 30 min; | 75% |
With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 50℃; for 12h; Inert atmosphere; | 70% |
di(succinimido) carbonate
triethylene glucol monomethyl ether
2,5-dioxopyrrolidin-1-yl (2-(2-(2-methoxyethoxy)ethoxy)ethyl)carbonate
Conditions | Yield |
---|---|
Stage #1: triethylene glucol monomethyl ether With triethylamine In dichloromethane at 0℃; for 0.25h; Stage #2: di(succinimido) carbonate In dichloromethane at 20℃; for 18h; | 75% |
With triethylamine In acetonitrile at 20℃; for 16.1667h; | 55% |
With triethylamine In acetonitrile at 20℃; | 20% |
With triethylamine In acetonitrile |
triethylene glucol monomethyl ether
D-glucal triacetate
A
2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
B
2-(2-(2-methoxyethoxy)ethoxy)ethanyl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
Conditions | Yield |
---|---|
With tellurium tetrachloride In dichloromethane at 0 - 20℃; for 0.25h; Ferrier Carbohydrate Rearrangement; Inert atmosphere; diastereoselective reaction; | A 86% B n/a |
With toluene-4-sulfonic acid In acetonitrile at 25℃; for 0.333333h; Sonication; | A 82% B n/a |
With tellurium tetrachloride In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Overall yield = 86%; Overall yield = 0.32g; | A n/a B n/a |
triethylene glucol monomethyl ether
3,5-dinitrobenoyl chloride
2‐[2‐(2‐methoxyethoxy)ethoxy]ethyl 3,5‐dinitrobenzoate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 1h; | 89.3% |
In N,N-dimethyl acetamide for 8h; cooling; | 69% |
With triethylamine In dichloromethane at 0 - 20℃; |
3-Bromothiophene
triethylene glucol monomethyl ether
3-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)thiophene
Conditions | Yield |
---|---|
Stage #1: triethylene glucol monomethyl ether With pyridine; copper(l) iodide; potassium tert-butylate In toluene at 20℃; for 0.5h; Stage #2: 3-Bromothiophene In toluene at 110℃; for 24h; | 68% |
Stage #1: triethylene glucol monomethyl ether With copper(l) iodide; potassium tert-butylate at 20℃; for 1h; Inert atmosphere; Stage #2: 3-Bromothiophene at 100℃; for 24h; Inert atmosphere; | 63% |
With sodium hydride; copper(I) bromide In N,N-dimethyl-formamide | 23% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere; Stage #2: 3-Bromothiophene With copper(I) bromide In N,N-dimethyl-formamide at 110℃; for 12h; Inert atmosphere; | 11.6 g |
Conditions | Yield |
---|---|
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere; Stage #3: With sulfuric acid In tetrahydrofuran; water for 3h; Reflux; | 98% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide In tetrahydrofuran; mineral oil at 20℃; for 12h; Inert atmosphere; Stage #3: With sulfuric acid; water In tetrahydrofuran for 3h; Inert atmosphere; Reflux; | 89% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil for 0.5h; Inert atmosphere; Stage #2: 1,3,6,9,12-pentaoxa-2-thiacyclotetradecane 2,2-dioxide With sulfuric acid In tetrahydrofuran; water; mineral oil at 20℃; pH=3; Inert atmosphere; | 84% |
triethylene glucol monomethyl ether
ethyl bromoacetate
methoxytriethyleneglycol carboxylic acid ethyl ester
Conditions | Yield |
---|---|
Stage #1: triethylene glucol monomethyl ether With tetrabutylammomium bromide; sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: ethyl bromoacetate In tetrahydrofuran at 0 - 20℃; | 78.74% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Williamson Ether Synthesis; Stage #2: ethyl bromoacetate In tetrahydrofuran; mineral oil at 0 - 20℃; for 2h; Williamson Ether Synthesis; | 56% |
With sodium hydride In 1,2-dimethoxyethane for 1h; | 42% |
C17H12O3
triethylene glucol monomethyl ether
2-[2-(2-methoxyethoxy)ethoxy]ethyl 3-(4-methylphenyl)-1-oxo-1H-indene-2-carboxylate
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 20℃; | 67% |
2-chloromethyl-3-chloroprop-1-ene
triethylene glucol monomethyl ether
3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-({2-[2-(2-methoxyethoxy)ethoxy]ethoxy}methyl)propene
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20 - 65℃; for 12.25h; Inert atmosphere; | 81% |
With sodium hydride In tetrahydrofuran at 65℃; | 35% |
With sodium hydride In tetrahydrofuran at 65℃; for 24h; | |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 0.5h; Inert atmosphere; Stage #2: 2-chloromethyl-3-chloroprop-1-ene In tetrahydrofuran; mineral oil at 20 - 65℃; Inert atmosphere; | |
With sodium hydride In tetrahydrofuran at 65℃; for 12h; Inert atmosphere; |
triethylene glucol monomethyl ether
4,4'-(5,5-difluoro-1,9-diphenyl-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,5,2]triazaborinine-3,7-diyl)diphenol
2-(N-tert-butoxycarbonylamino)ethanol
C46H49BF2N4O7
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16.33h; | 39% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; | 39% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Mitsunobu reaction; | 33% |
triethylene glucol monomethyl ether
toluene-4-sulfonic acid
2-(2-(2-methoxyethoxy)ethoxy)ethyl p-toluenesulfonate
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; water at 0℃; for 3h; | 99% |
With triethylamine In tetrahydrofuran; dichloromethane at 20℃; for 24h; Inert atmosphere; | 81.6% |
triethylene glucol monomethyl ether
tert-Butyl acrylate
tert-butyl 2,5,8,11-tetraoxatetradecan-14-oate
Conditions | Yield |
---|---|
With sodium methylate at 20℃; | 75.3% |
Stage #1: triethylene glucol monomethyl ether With sodium In tetrahydrofuran at 20 - 50℃; Inert atmosphere; Stage #2: tert-Butyl acrylate In tetrahydrofuran at 20 - 40℃; | 65% |
With hydrogenchloride In tetrahydrofuran |
triethylene glucol monomethyl ether
phthalocyanine silicon(IV) dichloride
bis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)silicon phthalocyanine
Conditions | Yield |
---|---|
With sodium hydride In toluene at 120℃; for 24h; Inert atmosphere; | 54% |
With sodium hydride In toluene Inert atmosphere; Reflux; | 32.91% |
With sodium hydride In toluene at 125℃; for 16h; | 25% |
With potassium carbonate In toluene for 14h; Inert atmosphere; Reflux; | 15.6% |
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide at 0 - 60℃; for 12h; | 70% |
With sodium hydride In N,N-dimethyl-formamide at 80℃; for 12h; | 70% |
Stage #1: triethylene glucol monomethyl ether With sodium hydride In N,N-dimethyl-formamide at 0℃; Stage #2: 2-chloro-4-(6-(piperidin-1-yl)naphthalen-2-yl)nicotinonitrile In N,N-dimethyl-formamide at 0 - 60℃; for 12h; | 70% |
triethylene glucol monomethyl ether
Conditions | Yield |
---|---|
With 2,2,4,4,6,6-hexachloro-1,3,5-triaza-2,4,6-triphosphorine; sodium hydride In tetrahydrofuran at 20℃; for 5.5h; Inert atmosphere; Cooling with ice; | 75% |
triethylene glucol monomethyl ether
10,12-docosadiynedioic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 18h; | 84% |
1. | skn-rbt 10 mg/24H open MLD | AIHAAP American Industrial Hygiene Association Journal. 23 (1962),95. | ||
2. | eye-rbt 500 mg/24H MLD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,634. | ||
3. | orl-rat LD50:11,300 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 23 (1962),95. | ||
4. | skn-rbt LD50:7100 mg/kg | AIHAAP American Industrial Hygiene Association Journal. 23 (1962),95. |
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