ethyl vinyl ether
orthoformic acid triethyl ester
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
Stage #1: ethyl vinyl ether; orthoformic acid triethyl ester With boron trifluoride diethyl etherate at 20 - 38℃; Stage #2: With potassium carbonate at 20℃; for 2h; | 69.2% |
With iron(III) chloride | |
With boron fluoride ether |
vinyl isopropyl ether
orthoformic acid triethyl ester
A
malondialdehyde bis(diethyl acetal)
B
1,3,3-triethoxy-1-(isopropoxy)propane
Conditions | Yield |
---|---|
iron(III) chloride at -30℃; for 6h; Product distribution / selectivity; | A 6.5% B 42% |
iron(III) chloride at 0℃; for 6h; Product distribution / selectivity; | A 13.6% B 27% |
trimethylsiloxyethene
orthoformic acid triethyl ester
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With zinc(II) chloride In ethyl acetate for 3h; Ambient temperature; | 76.5% |
ethyl vinyl ether
orthoformic acid triethyl ester
A
malondialdehyde bis(diethyl acetal)
B
1,1,3,5,5-pentaethoxy-pentane
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 10℃; | A 64% B 17% |
Conditions | Yield |
---|---|
at 45℃; |
vinyl acetate
orthoformic acid triethyl ester
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With iron(III) chloride; sodium hydrogencarbonate 1) 2 h, reflux; 2) 20 deg C, 2 h; | 56% |
at 80℃; beim Erwaermen in Gegenwart von Katalysatoren (z.B. FeCl3, AlCl3, SnCl2, SnCl4, ZnCl2, HgCl2); |
2-ethoxy-1,3-dioxane
ethyl vinyl ether
A
malondialdehyde bis(diethyl acetal)
B
di(1,3-dioxan-2-yl)methane
C
2-(2,2-diethoxyethyl)-1,3-dioxane
Conditions | Yield |
---|---|
zinc(II) chloride In diethyl ether temperature below 30 deg C; | A n/a B n/a C 35% |
vinyl acetate
orthoformic acid triethyl ester
A
malondialdehyde bis(diethyl acetal)
B
acetic acid-(1,3,3-triethoxy-propyl ester)
C
1,3-diacetoxy-1,3-diethoxypropane
Conditions | Yield |
---|---|
With p-benzoquinone at 30℃; for 24h; |
2-Ethoxy-5,5-dimethyl-1,3-dioxane
ethyl vinyl ether
A
malondialdehyde bis(diethyl acetal)
B
bis(5,5-dimethyl-1,3-dioxan-2-yl)-methane
C
2-(2,2-diethoxyethyl)-5,5-dimethyl-1,3-dioxane
Conditions | Yield |
---|---|
zinc(II) chloride In diethyl ether temperature below 30 deg C; |
(E)-3-Ureido-but-2-enoic acid ethyl ester
orthoformic acid triethyl ester
acetylene
A
malondialdehyde bis(diethyl acetal)
B
1,1-diethoxypropane
C
1,1,4,4-tetraethoxy-2-butyne
Conditions | Yield |
---|---|
under 8826.09 - 12503.6 Torr; | |
at 170℃; under 8826.09 - 12503.6 Torr; |
ethanol
cyclohexa-1,4-diene
A
malondialdehyde bis(diethyl acetal)
B
ethyl 3,3-diethoxypropanoate
C
diethyl malonate
Conditions | Yield |
---|---|
With hydrogenchloride; ozone -40 deg C, then ca. 30 min reflux; | A n/a B 70% C n/a |
With hydrogenchloride; ozone -40 deg C, then ca. 30 min reflux; | A 70% B 70% C n/a |
With hydrogenchloride; ozone at -40℃; Product distribution; | A n/a B 70% C n/a |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ethanolic KOH-solution 2: hydrogen chloride View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: boron trifluoride; mercury(II) diacetate 2: iron(III) chloride View Scheme |
1,1-dichloro-3,3-diethoxy-propane
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOEt View Scheme |
1-chloro-3,3-diethoxy-propene
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: ion-exchange resin + form> 2: Na View Scheme |
Conditions | Yield |
---|---|
With hydrogenchloride |
ethanol
acetic acid-(1,3,3-triethoxy-propyl ester)
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With iron(III) chloride |
Conditions | Yield |
---|---|
at 45℃; |
Conditions | Yield |
---|---|
With hydrogenchloride |
ethanol
3-chloro-1,3-diethoxy-propene
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With sodium |
Conditions | Yield |
---|---|
(i) N-methylpiperidine, (ii) HCl; Multistep reaction; |
ethanol
1-chloro-3,3-diethoxy-propene
malondialdehyde bis(diethyl acetal)
vinyl acetate
iron(III) chloride
orthoformic acid triethyl ester
malondialdehyde bis(diethyl acetal)
iron(III) chloride
ethyl vinyl ether
orthoformic acid triethyl ester
malondialdehyde bis(diethyl acetal)
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
In ethanol for 2h; Reflux; | 100% |
Stage #1: malondialdehyde bis(diethyl acetal); trans-ethyl 4-hydrazinylcyclohexane-1-carboxylate hydrochloride In ethanol Reflux; Stage #2: With sodium hydrogencarbonate In ethanol; water | 100% |
malondialdehyde bis(diethyl acetal)
(S)-4-Benzyl-2-oxazolidinone
Conditions | Yield |
---|---|
With sulfuric acid In chloroform diastereoselective reaction; | 99% |
malondialdehyde bis(diethyl acetal)
1,3-dichloro-1,3-diethoxypropane
Conditions | Yield |
---|---|
With phosphorus trichloride at 50℃; for 6h; | 98.5% |
With tetrachloromethane; phosphorus pentachloride | |
With pyridine; tetrachloromethane; thionyl chloride | |
With phosphorus pentachloride; trichlorophosphate |
(S)-4-(3,4-dimethoxybenzyl)oxazolidin-2-one
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With sulfuric acid In chloroform at 20℃; for 12h; Pictet-Spengler Synthesis; diastereoselective reaction; | 98% |
malondialdehyde bis(diethyl acetal)
2,6-diamino-3H-pyrimidin-4-one
C11H12N8O2
Conditions | Yield |
---|---|
With acetic acid for 3.5h; Heating; | 97% |
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With pyridine for 2h; Heating; | 96% |
malondialdehyde bis(diethyl acetal)
1.3-butanediol
bis(4-methyl-1,3-dioxan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation exchange resin In benzene at 120 - 130℃; heating until alcohol liberation was complete; | 95% |
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With pyridine for 2h; Heating; | 95% |
malondialdehyde bis(diethyl acetal)
1-bromo-2-ethoxyethene
2-bromo-1,1,3,5,5-pentaethoxy-pentane
Conditions | Yield |
---|---|
With zinc(II) chloride In ethyl acetate for 5.5h; Ambient temperature; | 94% |
With boron trifluoride diethyl etherate |
2-methyl-2,4-pentanediol
malondialdehyde bis(diethyl acetal)
bis(4,4,6-trimethyl-1,3-dioxan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin at 110 - 120℃; heating until alcohol liberation was complete; | 94% |
malondialdehyde bis(diethyl acetal)
2,2-Dimethyl-1,3-propanediol
bis(5,5-dimethyl-1,3-dioxan-2-yl)-methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin at 110 - 120℃; heating until alcohol liberation was complete; | 94% |
3-methyl-butane-1,3-diol
malondialdehyde bis(diethyl acetal)
bis(4,4-dimethyl-1,3-dioxan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin In benzene at 120 - 130℃; heating until alcohol liberation was complete; | 93% |
malondialdehyde bis(diethyl acetal)
propylene glycol
bis(4-methyl-1,3-dioxolan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin at 110 - 120℃; heating until alcohol liberation was complete; | 93% |
malondialdehyde bis(diethyl acetal)
2-Thiobarbituric acid
Conditions | Yield |
---|---|
With hydrogenchloride for 1.5h; Heating; | 93% |
malondialdehyde bis(diethyl acetal)
3-nitro-pyrazolo[1,5-a]pyrimidine
Conditions | Yield |
---|---|
With acetic acid | 92.5% |
malondialdehyde bis(diethyl acetal)
ethylene glycol
di(1,3-dioxolan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin at 110 - 120℃; heating until alcohol liberation was complete; | 92% |
malondialdehyde bis(diethyl acetal)
2.3-butanediol
bis(4,5-dimethyl-1,3-dioxolan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin at 110 - 120℃; heating until alcohol liberation was complete; | 91% |
malondialdehyde bis(diethyl acetal)
1,2-diamino-benzene
[(dibenzo[b,i]-1,4,8,11-tetraaza[14]annulene)platinum(II)]
Conditions | Yield |
---|---|
With CH3COOH; NaCH3COO In ethanol; water complex reacted with o-phenylenediamine at 60°C in aq. EtOH for 30 min, AcOH and tetraethoxypropane added, mixt. refluxed for 2 h, NaOAcadded, refluxed for 16 h; ppt. filtered while hot, washed with H2O, EtOH, ether, sublimated in vac. at 300°C, 0.01 Torr.; | 91% |
malondialdehyde bis(diethyl acetal)
4-(trifluoromethyl)phenylhydrazine hydrochloride
1-(4-trifluoromethyl-phenyl)-1H-pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 75℃; for 2h; | 91% |
malondialdehyde bis(diethyl acetal)
2,3-dimethyl-2,3-butane diol
1,3-bis(4',4',5',5'-tetramethyl-1,3-dioxolan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin In benzene at 120 - 130℃; heating until alcohol liberation was complete; | 90% |
Conditions | Yield |
---|---|
With perchloric acid In ethanol for 2h; Heating; | 90% |
malondialdehyde bis(diethyl acetal)
trimethyleneglycol
di(1,3-dioxan-2-yl)methane
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin In benzene at 120 - 130℃; heating until alcohol liberation was complete; | 89% |
malondialdehyde bis(diethyl acetal)
aniline hydrochloride
phenyl[3-phenylaminoprop-2-en-1-ylidene]ammonium chloride
Conditions | Yield |
---|---|
In methanol Heating; Reflux; | 89% |
malondialdehyde bis(diethyl acetal)
2-(trifluoromethyl)phenylhydrazine hydrochloride
1-(2-(trifluoromethyl)phenyl)-1H-pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 75℃; for 2h; | 88% |
malondialdehyde bis(diethyl acetal)
3-Chloro-6-hydrazinopyridazine
3-chloro-6-(1H-pyrazol-1-yl)pyridazine
Conditions | Yield |
---|---|
With acetic acid In ethanol for 3h; Reflux; | 86% |
Conditions | Yield |
---|---|
With perchloric acid In ethanol at 80℃; Inert atmosphere; | 86% |
2-amino-3-hydroxypyridine
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With perchloric acid In ethanol at 80℃; for 12h; Inert atmosphere; | 85% |
malondialdehyde bis(diethyl acetal)
phenylhydrazine hydrochloride
1-phenylpyrazole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 75℃; for 2h; | 84% |
With ethanol |
malondialdehyde bis(diethyl acetal)
5-amino-3-methyl-N-phenylpyrazole-4-carboxamide
2-methyl-N-phenylpyrazolo<1,5-a>pyrimidine-3-carboxamide
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol at 60 - 80℃; for 2h; | 84% |
malondialdehyde bis(diethyl acetal)
Conditions | Yield |
---|---|
With hydrogenchloride In water for 24h; | 84% |
With hydrogenchloride In ethanol; water for 24h; |
Product Name: Malonaldehyde bis(diethyl acetal) (CAS NO.122-31-6)
Molecular Formula: C11H24O4
Molecular Weight: 220.31g/mol
Melting Point: -90 °C
Boiling point: 220 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 42.2 °C
Density: 0.932 g/cm3
Refractive index: n20/D 1.411(lit.)
Water Solubility: insoluble
Index of Refraction: 1.42
Molar Refractivity: 59.9 cm3
Molar Volume: 236.3 cm3
Surface Tension: 27.9 dyne/cm
Enthalpy of Vaporization: 43.78 kJ/mol
Vapour Pressure: 0.171 mmHg at 25°C
XLogP3-AA: 1.8
H-Bond Donor: 0
H-Bond Acceptor: 4
Structure Descriptors of Malonaldehyde bis(diethyl acetal) (CAS NO.122-31-6):
IUPAC Name: Malonaldehyde bis(diethyl acetal)
Canonical SMILES: CCOC(CC(OCC)OCC)OCC
InChI: InChI=1S/C11H24O4/c1-5-12-10(13-6-2)9-11(14-7-3)15-8-4/h10-11H,5-9H2,1-4H3
InChIKey: KVJHGPAAOUGYJX-UHFFFAOYSA-N
Classification Code: tion data; Skin / Eye Irritant
Malonaldehyde bis(diethyl acetal) (CAS NO.122-31-6) is used as a medicine and dye intermediates, can be used as preservatives in intermediate agricultural products.
1. | skn-rbt 500 mg/24H MLD | 85JCAE Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,262. | ||
2. | eye-rbt 500 mg | AMIHBC AMA Archives of Industrial Hygiene and Occupational Medicine. 4 (1951),119. | ||
3. | mmo-sat 4 µmol/plate | CNREA8 Cancer Research. 40 (1980),276. | ||
4. | orl-rat LD50:1610 mg/kg | TXAPA9 Toxicology and Applied Pharmacology. 7 (1965),826. | ||
5. | ipr-mus LD50:200 mg/kg | NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) No. AD277-689 . |
Poison by intraperitoneal route. Moderately toxic by ingestion. Mutation data reported. An eye irritant. Flammable when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.
Safety information of Malonaldehyde bis(diethyl acetal) (CAS NO.122-31-6):
Hazard Codes: Xn
Risk Statements: 22
R22: Harmful if swallowed
Safety Statements: 36/37/39-26
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR: 1993
WGK Germany: 3
RTECS: ON8750000
HazardClass: 3.2
PackingGroup: III
HS Code: 29110000
Malonaldehyde bis(diethyl acetal) , its CAS NO. is 122-31-6, the synonyms are Malonaldehyde diethyl acetal ; Malonaldehyde tetraethyl acetal ; Malonaldehyde tetraethyl diacetal ; Malondialdehyde tetraethylacetal ; Malonaldehyde bis(diethyl acetal) ; Propane, 1,1,3,3-tetraethoxy- ; Tetraethoxy propane ; Tetraethoxypropane ; Tetraethyl malondialdehyde acetal . Malonaldehyde bis(diethyl acetal) (CAS NO.122-31-6) is stable under normal temperatures and pressures but incompatible with strong oxidizing agents, strong acids.Hazardous decomposition products are carbon monoxide, carbon dioxide.Keep away from heat, sparks, and flame. Keep away from sources of ignition. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Flammables-area.
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