methoxyethene
trimethyl orthoformate
A
malonaldehydebis(dimethylacetal)
B
1,1,3,5,5-pentamethoxy-pentane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at -78℃; for 6h; | A 65% B 8% |
methanol
cyclohexa-1,4-diene
A
methyl 3,3-dimethoxypropionate
B
malonaldehydebis(dimethylacetal)
C
malonic acid dimethyl ester
Conditions | Yield |
---|---|
With hydrogenchloride; ozone -40 deg C, then ca. 30 min reflux; Yields of byproduct given; | A 60% B n/a C n/a |
With hydrogenchloride; ozone at -40℃; -40 deg C, then ca. 30 min reflux; Yield given; | A 60% B n/a C n/a |
With hydrogenchloride; ozone at -40℃; Product distribution; | A 60% B n/a C n/a |
Conditions | Yield |
---|---|
With iron(III) chloride; sodium hydrogencarbonate 1) 2 h, reflux; 2) 20 deg C, 2 h; | 36% |
With iron(III) chloride at 60℃; |
methanol
1,1,3-trimethoxy-3-acethoxypropane
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With boron fluoride ether |
methoxyethene
trifluoroborane diethyl ether
trimethyl orthoformate
A
1-ethoxy-1,3,3-trimethoxypropane
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With boron fluoride ether | |
at 84℃; under 37.5038 Torr; for 1h; Reactivity; Gas phase; | |
With boron trifluoride diethyl etherate Reactivity; Gas phase; | |
With boron fluoride ether |
Conditions | Yield |
---|---|
(i) N-methylpiperidine, (ii) HCl; Multistep reaction; |
Conditions | Yield |
---|---|
With hydrogenchloride |
methanol
(Z)-1,1,6,6-Tetramethoxy-3-hexen
A
methyl 3,3-dimethoxypropionate
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With hydrogenchloride; ozone 1.) -40 deg C, 2.) reflux, 1 h; Yield given. Multistep reaction; | |
With hydrogenchloride; reflux; ozone |
methanol
cyclopenta-1,3-diene
A
malonaldehydebis(dimethylacetal)
B
methyl 3-oxopropionate
C
3t-methoxy-propenal
D
3,3-dimethoxypropanal
Conditions | Yield |
---|---|
With 2,3-dimercapto-succinic acid; ozone 1) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given; | |
With 2,3-dimercapto-succinic acid; ozone 1) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With ozone In various solvent(s) for 0.5h; pH=8; Product distribution; Oxidation; |
all cis 5,8,11,14-eicosatetraenoic acid
A
malonaldehydebis(dimethylacetal)
B
acrolein
Conditions | Yield |
---|---|
With ozone In various solvent(s) for 0.5h; pH=8; Product distribution; Oxidation; |
vinyl acetate
iron(III) chloride
trimethyl orthoformate
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
at 60℃; reagiert analog mit Orthoameisensaeure-triaethylester in Gegenwart von FeCl3, AlCl3, SnCl2 oder SnCl4; | |
at 60℃; |
Conditions | Yield |
---|---|
With boron fluoride ether |
methanol
1,5-dimethylcyclohexa-1,4-diene
A
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; ozone In dichloromethane at -78℃; Title compound not separated from byproducts; | A 10 % Spectr. B 15 % Spectr. C 75 % Spectr. |
methanol
acrolein
A
malonaldehydebis(dimethylacetal)
B
1,1,3-trimethoxypropane
C
3-methoxy-1-propanal
Conditions | Yield |
---|---|
With carbon dioxide; oxygen; sodium phosphate; copper(l) chloride; palladium dichloride at 50℃; under 90007.2 Torr; for 24h; Michael addition; | A 17.5 % Chromat. B 54.6 % Chromat. C 26.2 % Chromat. |
methanol
acrolein
A
malonaldehydebis(dimethylacetal)
B
1,1,3-trimethoxypropane
C
3-methoxy-1-propanal
D
3,3-dimethoxypropanal
Conditions | Yield |
---|---|
With carbon dioxide; polystyrene-supported benzoquinone; oxygen; palladium dichloride at 50℃; under 67505.4 Torr; for 12h; | A 46.7 % Chromat. B 12.9 % Chromat. C 3.9 % Chromat. D 20.4 % Chromat. |
vinyl acetate
trimethyl orthoformate
A
malonaldehydebis(dimethylacetal)
B
1,1,3-trimethoxy-3-acethoxypropane
Conditions | Yield |
---|---|
at 80℃; for 1h; Gas phase; | |
With boron trifluoride diethyl etherate at 80℃; under 22.5023 Torr; for 1h; Reactivity; Gas phase; |
vinyl acetate
trimethyl orthoformate
A
malonaldehydebis(dimethylacetal)
B
1,1,3-trimethoxy-3-acethoxypropane
C
1,3-diacetoxy-1,3-dimethoxy-propane
Conditions | Yield |
---|---|
With p-benzoquinone; PtCl2(PhCN)2 at 30℃; for 24h; | |
With p-benzoquinone at 30℃; for 2h; | |
With p-benzoquinone at 30℃; for 2.3h; | |
With p-benzoquinone for 2h; |
isobutyl vinyl ether
trimethyl orthoformate
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
Stage #1: isobutyl vinyl ether; trimethyl orthoformate; iron(III) chloride at -5 - 20℃; Stage #2: With sodium carbonate |
vinyl isopropyl ether
trimethyl orthoformate
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
iron(III) chloride at -15℃; for 7h; Product distribution / selectivity; | |
iron(III) chloride at 2℃; for 7h; Product distribution / selectivity; | |
iron(III) chloride at 35℃; for 7h; Product distribution / selectivity; |
vinyl isopropyl ether
trimethyl orthoformate
A
1,3,3-trimethoxy-1-(isopropoxy)propane
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
Stage #1: vinyl isopropyl ether; trimethyl orthoformate; iron(III) chloride at -5 - 20℃; Stage #2: With sodium carbonate |
-butyl vinyl ether
trimethyl orthoformate
A
1,3,3-trimethoxy-1-(n-butoxy)propane
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
Stage #1: -butyl vinyl ether; trimethyl orthoformate; iron(III) chloride at -5 - 20℃; Stage #2: With sodium carbonate |
vinyl propyl ether
trimethyl orthoformate
A
1,3,3-trimethoxy-1-(n-propoxy)propane
B
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
Stage #1: vinyl propyl ether; trimethyl orthoformate; iron(III) chloride at -5 - 20℃; Stage #2: With sodium carbonate |
5-Amino-1,3-dimethylpyrazole
malonaldehydebis(dimethylacetal)
1,3-dimethylpyrazolo<3,4-b>pyridine
Conditions | Yield |
---|---|
zinc(II) chloride In hydrogenchloride; ethanol for 1h; Heating; | 100% |
malonaldehydebis(dimethylacetal)
methyl 2-chloro-3-hydrazinylbenzoate hydrochloride
methyl 2-chloro-3-(1H-pyrazol-1-yl)benzoate
Conditions | Yield |
---|---|
In ethanol at 80℃; for 2h; | 100% |
In ethanol at 80℃; for 2h; | 100% |
Conditions | Yield |
---|---|
In ethanol at 100℃; for 20h; Autoclave; | 100% |
malonaldehydebis(dimethylacetal)
N-methylaniline
3-(N-Methylanilino)-2-propenal
Conditions | Yield |
---|---|
Stage #1: malonaldehydebis(dimethylacetal); N-methylaniline at 30℃; for 0.166667h; Stage #2: With hydrogenchloride In water at 24℃; for 2.5h; Temperature; | 99.6% |
malonaldehydebis(dimethylacetal)
trimethylsilyl cyanide
2,4,4-trimethoxybutanenitrile
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at 0℃; for 3h; | 99% |
With boron trifluoride diethyl etherate at 0℃; for 3h; Inert atmosphere; Neat (no solvent); | 92% |
With boron trifluoride diethyl etherate at 0℃; for 3h; |
malonaldehydebis(dimethylacetal)
nickel(II) acetate tetrahydrate
4,5-dimethyl-1,2-phenylenediamine
{7,16-dihydro-2,3,11,12-tetramethyldibenzo{b,i}{1,4,8,11}tetraazacyclotetradecinato-N5,N9,N14,N18}nickel(II)
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide reflux for 10 h; filtn., chromy.; elem. anal.;; | 99% |
Conditions | Yield |
---|---|
With acetic acid at 110℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 60℃; for 4h; | 98% |
With hydrogenchloride In ethanol for 1h; Heating; | 93% |
With hydrogenchloride In methanol for 1h; Reflux; | 90% |
With hydrogenchloride; water In ethanol for 4h; Reflux; | 85% |
With hydrogenchloride In ethanol; water Heating; |
N-(3-isopropoxy-propyl)-3-cyano-4-methyl-2-pyridone
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
In ethanol for 21h; Heating / reflux; | 98% |
1-butyl-4-methyl-2,6-dioxo-1,2,5,6-tetrahydropyridine-3-carbonitrile
malonaldehydebis(dimethylacetal)
C25H27N4O4(1-)*K(1+)
Conditions | Yield |
---|---|
With potassium acetate In butan-1-ol at 100 - 110℃; for 4.5h; Heating / reflux; | 98% |
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 90℃; for 16h; | 98% |
1-phenylpyrazol-5-amine
malonaldehydebis(dimethylacetal)
1-phenyl-1H-pyrazolo[3,4-b]pyridine
Conditions | Yield |
---|---|
zinc(II) chloride In hydrogenchloride; ethanol for 1h; Heating; | 97% |
malonaldehydebis(dimethylacetal)
2,2-Dimethyl-1,3-propanediol
bis(5,5-dimethyl-1,3-dioxan-2-yl)-methane
Conditions | Yield |
---|---|
With hydrogenchloride at 140℃; for 0.5h; | 97% |
With o-toluenesulfonic acid In toluene | 85% |
With toluene-4-sulfonic acid In toluene Heating; | 85% |
With toluene-4-sulfonic acid In toluene at 80 - 90℃; |
malonaldehydebis(dimethylacetal)
5-chloro-2-nitrophenylhydrazine
1-(5-chloro-2-nitro-phenyl)-1H-pyrazole
Conditions | Yield |
---|---|
With sulfuric acid In ethanol; acetic acid for 6h; Heating; | 97% |
malonaldehydebis(dimethylacetal)
1-(2,5-difluoro-phenyl)-1H-pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride; water In ethanol for 17h; Heating / reflux; | 97% |
malonaldehydebis(dimethylacetal)
[14C]urea
pyrimidin-2[(14)C]-ol hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 85℃; for 1.3h; | 97% |
malonaldehydebis(dimethylacetal)
[15N2]pyrazole
Conditions | Yield |
---|---|
With hydrazinium sulfate In ethanol; water at 75℃; for 2h; | 96.3% |
With [15N2]-hydrazinium sulfate In ethanol; water at 20 - 75℃; for 24.25h; | 67% |
malonaldehydebis(dimethylacetal)
trimethyleneglycol
di(1,3-dioxan-2-yl)methane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 110℃; for 24h; | 96% |
With o-toluenesulfonic acid In toluene | 92% |
With toluene-4-sulfonic acid In toluene Heating; | 92% |
malonaldehydebis(dimethylacetal)
3-hydrazinobenzoic acid
Conditions | Yield |
---|---|
In ethanol; water for 2h; Heating / reflux; | 96% |
In ethanol; water for 48h; Reflux; | 73% |
With acetic acid In water at 150℃; for 0.0833333h; Microwave irradiation; |
malonaldehydebis(dimethylacetal)
2-(trifluoromethyl)phenylhydrazine
1-(2-(trifluoromethyl)phenyl)-1H-pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water at 80 - 90℃; for 3h; | 96% |
With hydrogenchloride In ethanol; water Heating; | |
With hydrogenchloride In ethanol; water at 90℃; for 3h; |
malonaldehydebis(dimethylacetal)
5-pyridin-4-yl-2H-pyrazol-3-yl-amine
2-(pyridin-4-yl)pyrazolo[1.5-a]pyrimidine
Conditions | Yield |
---|---|
With acetic acid at 110℃; for 16h; | 96% |
N-ethyl-3-cyano-4-methyl-2-pyridone
N-(3-isopropoxy-propyl)-3-cyano-4-methyl-2-pyridone
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With potassium acetate In 4-methyl-2-pentanone at 104 - 106℃; for 3h; | 95.5% |
2,3-dimethyl-2,3-butane diol
malonaldehydebis(dimethylacetal)
1,3-bis(4',4',5',5'-tetramethyl-1,3-dioxolan-2-yl)methane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 1h; Heating; | 95% |
With toluene-4-sulfonic acid In benzene at 90℃; for 2h; | 95% |
With toluene-4-sulfonic acid In benzene at 90℃; for 2h; Condensation; | 95% |
With 4 A molecular sieve; toluene-4-sulfonic acid In benzene Heating; |
malonaldehydebis(dimethylacetal)
indan-1,2,3-trione hydrate
(E)-3-Hydroxy-2-(2-hydroxy-1,3-dioxo-indan-2-yl)-propenal
Conditions | Yield |
---|---|
In water at 50 - 55℃; for 2h; | 95% |
malonaldehydebis(dimethylacetal)
(2S,4S)-pentane-2,4-diol
malonedialdehyde bis[(S,S)-1,3-dimethylpropylene] acetal
Conditions | Yield |
---|---|
With o-toluenesulfonic acid In toluene | 95% |
With toluene-4-sulfonic acid In toluene Heating; | 95% |
malonaldehydebis(dimethylacetal)
ethylene glycol
di(1,3-dioxolan-2-yl)methane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene Heating; | 95% |
With o-toluenesulfonic acid In toluene |
malonaldehydebis(dimethylacetal)
4-(tert-butyl)-1,2-diaminobenzene
nickel(II) acetate tetrahydrate
{7,16-dihydro-2,12-di-tert-butyldibenzo{b,i}{1,4,8,11}tetraazacyclotetradecinato-N5,N9,N14,N18}nickel(II)
Conditions | Yield |
---|---|
In water; N,N-dimethyl-formamide reflux for 12 h; filtn., washing (water), chromy., elem. anal.; | 95% |
malonaldehydebis(dimethylacetal)
4-methoxyphenylhydrazine hydrochloride
1-(4-methoxyphenyl)-1H-pyrazole
Conditions | Yield |
---|---|
In ethanol for 1h; Reflux; | 95% |
In ethanol; water Reflux; | 82.6% |
4-methoxycarbonyl-2-nitrophenylhydrazine
malonaldehydebis(dimethylacetal)
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol; water for 2.5h; Reflux; | 95% |
Conditions | Yield |
---|---|
With hydrogenchloride at 50 - 60℃; for 0.5h; | 93% |
IUPAC Name: 1,1,3,3-Tetramethoxypropane
Synonyms of 1,1,3,3-Tetramethoxypropane (CAS NO.203-037-2): Malonaldehyde bis(dimethyl acetal) ; Malonaldehyde tetramethyl acetal ; Tetramethoxypropane ; Malonaldehyde, bis(dimethyl acetal) (8CI) ; Propane, 1,1,3,3-tetramethoxy-
CAS NO: 203-037-2
Molecular Formula: C7H16O4
Molecular Weight: 164.20
Molecular Structure:
EINECS: 203-037-2
H bond acceptors: 4
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 36.92 Å2
Index of Refraction: 1.401
Molar Refractivity: 41.37 cm3
Molar Volume: 170.2 cm3
Surface Tension: 25.8 dyne/cm
Density: 0.964 g/cm3
Flash Point: 54.4 °C
Enthalpy of Vaporization: 40.21 kJ/mol
Boiling Point: 183 °C at 760 mmHg
Vapour Pressure: 1.08 mmHg at 25°C
Water solubility: Immiscible
Sensitive: Moisture Sensitive
Appearance: 1,1,3,3-Tetramethoxypropane (CAS NO.203-037-2) is clear colourless to yellow-brown liquid.
SMILES: O(C)C(OC)CC(OC)OC
InChI: InChI=1/C7H16O4/c1-8-6(9-2)5-7(10-3)11-4/h6-7H,5H2,1-4H3
InChIKey: XHTYQFMRBQUCPX-UHFFFAOYAP
Std. InChI: InChI=1S/C7H16O4/c1-8-6(9-2)5-7(10-3)11-4/h6-7H,5H2,1-4H3
Std. InChIKey: XHTYQFMRBQUCPX-UHFFFAOYSA-N
Safety Information of 1,1,3,3-Tetramethoxypropane (CAS NO.203-037-2) :
Hazard Codes: F
Risk Statements: 10-36/37/38
R10: Flammable.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 16-26-36/37/39
S16:Keep away from sources of ignition.
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.
RIDADR: UN 1993 3/PG 3
WGK Germany: 1
F: 21
Hazard Note: Irritant
HazardClass: 3
PackingGroup: III
HS Code: 29110000
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