methanol
2-bromo-2-nitropropane
sodium methylate
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 40℃; for 5h; Irradiation; | 96% |
at 40℃; for 5h; Product distribution; Irradiation; further primary alcohols; | 96% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In water; acetonitrile at 20℃; for 0.25h; Green chemistry; | 95% |
pyridoxal hydrochloride
A
1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol
B
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane for 6h; Heating; Title compound not separated from byproducts; | A n/a B 92% |
Conditions | Yield |
---|---|
With aluminum (III) chloride at 70℃; for 5.6h; Temperature; | 91% |
cyclopenta-1,3-diene
crotonaldehyde
A
(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde
C
(1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde
D
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With 3-(5-(2-(4-benzyl-2,2-dimethyl-5-oxoimidazolidin-1-yl)ethoxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium bromide; trifluoroacetic acid In methanol at 20℃; Catalytic behavior; Solvent; Reagent/catalyst; Diels-Alder Cycloaddition; | A n/a B n/a C n/a D 88% |
methanol
2,2-dinitropropane
sodium methylate
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 40℃; for 12h; Irradiation; | 84% |
at 40℃; for 12h; Product distribution; Irradiation; further primary alcohols; | 84% |
methanol
α-nitroisopropyl phenyl sulfone
sodium methylate
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 40℃; for 5h; Irradiation; | 82% |
at 40℃; for 5h; Product distribution; Irradiation; further primary alcohols; | 82% |
methanol
A
t-butyl bromide
trans-2-bromo-9-oxabicyclo<4.2.1>nonane
trans-2-bromo-9-oxabicyclo<3.3.1>nonane
D
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With N-Bromosuccinimide for 0.75h; Product distribution; Mechanism; further in CD3OD; | A 1.5% B n/a C n/a D 74% |
methanol
2-azido-2-nitropropane
sodium methylate
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 40℃; for 24h; Irradiation; | 74% |
at 40℃; for 24h; Product distribution; Irradiation; further primary alcohols; | 74% |
methyl 5-deoxy-5-C-(diethoxyphosphinyl)-2,3-O-isopropylidene-β-D-ribofuranoside
A
2,2-dimethoxy-propane
B
methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside
Conditions | Yield |
---|---|
With methanol; iodine for 4.5h; | A n/a B 73% |
12,12-dimethoxy-5,5-dimethyl-4,6-dioxatricyclo<7.2.1.02,8>dodec-10-ene
A
endo-7,7-dimethoxy-2,3-bis-hydroxymethylbicyclo[2.2.1]hept-5-ene
B
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In methanol Heating; | A 68% B n/a |
Conditions | Yield |
---|---|
With formylmorpholine-dimethylsulfate-adduct for 24h; Ambient temperature; | 52.9% |
With formylmorpholine-dimethylsulfate-adduct for 24h; Product distribution; Ambient temperature; var. other 1-dialkylamino-1-methoxycarbenium methyl sulfates; var. carbonyl compounds; rate of dimethyl ketal formation; | 52.9% |
AMBERLYST A 15; AMBERLITE IRA 96 at -36 - -34℃; Neat liquid(s); | 44.9% |
Conditions | Yield |
---|---|
50.31% |
Conditions | Yield |
---|---|
50.31% |
methanol
1-methyl-1-nitroethyl p-chlorophenyl sulphide
sodium methylate
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 40℃; for 2h; Irradiation; | 11% |
at 40℃; for 2h; Product distribution; Irradiation; further primary alcohols; | 11% |
methanol
di-isopropyl ether
A
2-methoxy-2-i-propyloxypropane
B
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With potassium hydroxide; tris (2,4-dibromophenyl)amine; lithium perchlorate at 40℃; electrochem. oxidation; | A 0.03% B 3.6% |
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation; | A 3% B 0.5% |
Conditions | Yield |
---|---|
With boron fluoride ether; mercury(II) oxide | |
With boron fluoride ether; mercury(II) diacetate |
Conditions | Yield |
---|---|
With boron fluoride ether; mercury(II) oxide at 40℃; |
Conditions | Yield |
---|---|
With phosphoric acid |
Conditions | Yield |
---|---|
With hydrogenchloride; methanol | |
With sulfuric acid |
Conditions | Yield |
---|---|
With methanol |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; mercury(II) oxide | |
With methyl(triphenylphosphine)gold(I); methanesulfonic acid at 40℃; |
methanol
1,2-propanediene
A
2-Methoxypropene
B
2,2-dimethoxy-propane
C
acetone
Conditions | Yield |
---|---|
sodium hydroxide at 190℃; Rate constant; other temperatures; |
methanol
t-butyl heptafluoroperoxybutyrate
A
tert.-butylhydroperoxide
B
methyl heptafluorobutyrate
C
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 40℃; for 3h; Yield given. Yields of byproduct given; | |
In methanol at 10 - 40℃; for 3h; Rate constant; Kinetics; Thermodynamic data; ΔH(act.), ΔS(act.), various temperature; |
1,1-dimethoxycyclopropane
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol Product distribution; |
t-butyl heptafluoroperoxybutyrate
A
heptafluorobutyric Acid
B
2-Methoxypropene
C
tert-butyl heptafluorobutyrate
D
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
In nitrobenzene at 70℃; for 7h; Product distribution; | A 0.90 % Turnov. B 0.19 % Turnov. C 0.02 % Turnov. D 0.06 % Turnov. E 0.05 % Turnov. |
Conditions | Yield |
---|---|
With ammonium nitrite In methanol for 8h; Heating; | |
With sulfuric acid In methanol at 20℃; | |
With sodium montmorillonite In neat (no solvent) at 60℃; for 0.25h; Microwave irradiation; Green chemistry; | |
With toluene-4-sulfonic acid In methanol Reflux; Molecular sieve; |
methanol
prop-1-yne
A
2-Methoxypropene
B
2,2-dimethoxy-propane
C
acetone
Conditions | Yield |
---|---|
sodium hydroxide at 190℃; Rate constant; other temperatures; |
methanol
2-bromo-2-nitropropane
potassium methanolate
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
at 35℃; Product distribution; Mechanism; Irradiation; initial kinetic chain lengths; further alkoxides; with or without (t-Bu)2NO. or oxygen; |
3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one
2,2-dimethoxy-propane
methyl 2-methylazulene-1-carboxylate
Conditions | Yield |
---|---|
In toluene at 200℃; for 24h; | 100% |
In toluene at 200℃; | 100% |
at 160 - 190℃; | 92% |
2-Chloroadenosine
2,2-dimethoxy-propane
((3aR,4R,6R,6aR)-6-(6-amino-2-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; Cycloaddition; | 100% |
With perchloric acid In water at 20℃; for 8h; Reagent/catalyst; Inert atmosphere; | 88% |
With toluene-4-sulfonic acid In acetone at 45℃; | 85% |
1-thiophenyl-β-D-galactopyranoside
2,2-dimethoxy-propane
phenyl 1-thio-3,4-O-isopropylidene-6-O-(1-methoxyl-1-methylethyl)-β-D-galactopyranoside
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid at 20℃; for 24h; | 100% |
With scandium tris(trifluoromethanesulfonate) In acetone at 23℃; for 0.5h; Addition; | 86% |
With toluene-4-sulfonic acid In water at 20℃; for 4h; | 76% |
methyl 6-azido-6-deoxy-α-D-mannopyranoside
2,2-dimethoxy-propane
methyl 6-azido-6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside
Conditions | Yield |
---|---|
With CSA at 20℃; for 3h; | 100% |
With toluene-4-sulfonic acid for 1.5h; Ambient temperature; | 97% |
With toluene-4-sulfonic acid In acetone at 20℃; for 18h; Inert atmosphere; | 78% |
camphor-10-sulfonic acid at 20℃; for 1h; |
L-arabinose di(ethylthio)acetal
2,2-dimethoxy-propane
(4R,5S)-4-(bis(ethylthio)methyl)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone at 20℃; for 5h; | 100% |
With phosphorus pentoxide In acetone | 92% |
With phosphorus pentoxide In acetone at 40℃; for 0.25h; | 85% |
With toluene-4-sulfonic acid In acetone 1.) RT, 30 min, 2.) 40 deg C, 2 h; |
diethyl (2R,3R)-tartrate
2,2-dimethoxy-propane
A
diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 8h; Heating; Title compound not separated from byproducts.; | A 100% B n/a |
for 2.5h; Heating; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 100% |
diethyl bis(hydroxymethyl)malonate
2,2-dimethoxy-propane
2,2-Dimethyl-1,3-dioxacyclohexane-5,5-dicarboxylic acid,diethyl ester
Conditions | Yield |
---|---|
With APTS*H2O at 20℃; for 17h; | 100% |
With sulfuric acid In acetone at 20℃; for 19h; | 94% |
With toluene-4-sulfonic acid In acetone for 6h; Heating; | 90% |
N-benzyloxycarbonyl-L-serine methyl ester
2,2-dimethoxy-propane
N-benzyloxycarbonyl 4(S)-(1'-methoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 1h; Heating; | 100% |
With toluene-4-sulfonic acid | 99% |
With toluene-4-sulfonic acid In benzene for 1h; Heating; | 97% |
(2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol
2,2-dimethoxy-propane
(2S,3S,4S)-5-Benzyloxy-1,3-isopropylidenedioxy-2,4-dimethylpentane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 5.5h; | 100% |
(7S,13E,16S,17R,18R)-2-Benzoyl-7-tert-butyldimethylsilyloxy-17,18-dihydroxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13-diene-1,21-dione
2,2-dimethoxy-propane
(7S,13E,16S,17R,18R)-2-Benzoyl-7-tert-butyldimethylsilyloxy-17,18-isopropylidenedioxy-16,18-dimethyl-10-phenyl[11]cytochalasa-6(12),13-diene-1,21-dione
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In chloroform | 100% |
With toluene-4-sulfonic acid In chloroform at 20℃; for 5h; Cyclization; Etherification; | 99% |
(S)-4-(2',5'-dimethoxy-3',4',6'-trimethylphenyl)-2-methyl-1,2-butanediol
2,2-dimethoxy-propane
(S)-4-<2-(2,5-dimethoxy-3,4,6-trimethylphenyl)ethyl>-2,2,4-trimethyl-1,3-dioxorane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid for 0.25h; Ambient temperature; | 100% |
toluene-4-sulfonic acid optical purity more than 95percent; |
2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester
2,2-dimethoxy-propane
methyl [(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]carboxylate
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In acetone | 100% |
With boron trifluoride diethyl etherate In acetone at 20℃; for 3.5h; | 92% |
With boron trifluoride diethyl etherate In acetone at 20℃; for 2h; | 91% |
threo (2S,3R)-3-(4-methoxyphenyl)-1,1-bis(p-tolylthio)propane-2,3-diol
2,2-dimethoxy-propane
(4S,5R)-trans-4--5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Ambient temperature; | 100% |
(2S,3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hex-5-ene-2,4-diol
2,2-dimethoxy-propane
tert-Butyl-diphenyl-((4S,5S,6R)-2,2,5-trimethyl-6-vinyl-[1,3]dioxan-4-ylmethoxy)-silane
Conditions | Yield |
---|---|
100% |
cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene
2,2-dimethoxy-propane
(3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 100% |
toluene-4-sulfonic acid at 18℃; for 1h; | 99% |
With toluene-4-sulfonic acid In acetone at 20℃; for 0.5h; | 98% |
(S)-3-Benzylsulfanyl-propane-1,2-diol
2,2-dimethoxy-propane
(-)-(S)-(2,3-isopropylidenedioxy)propyl benzyl sulfide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Ambient temperature; | 100% |
2,2-dimethoxy-propane
D-Ribono-1,4-lactone
2,3-O-isopropylidene-D-ribonic-γ-lactone
Conditions | Yield |
---|---|
With hydrogen cation In acetone | 100% |
With boron trifluoride diethyl etherate In acetone at 20℃; for 1.5h; Condensation; | 90% |
With boron trifluoride diethyl etherate In acetone at 20℃; Inert atmosphere; | 86% |
5,6-exo-dihydroxy-2-(N-methylcarbamoyl)-2-azabicyclo<2.2.1>heptan-3-one
2,2-dimethoxy-propane
5,6-exo-dimethylmethylenedioxy-2-(N-methylcarbamoyl)-2-azabicyclo<2.2.1>heptan-3-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetone for 0.666667h; Ambient temperature; | 100% |
With toluene-4-sulfonic acid In acetone |
Methanesulfonic acid (2S,3R,4S,5R)-2-benzyloxymethyl-5-((4S,5R)-5-ethyl-2,2,4-trimethyl-[1,3]dioxolan-4-yl)-3,5-dihydroxy-4-methyl-pentyl ester
2,2-dimethoxy-propane
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 25℃; for 16h; | 100% |
(2S,3R)-2,3-Dihydroxy-4-methyl-5-phenylpent-4-ene
2,2-dimethoxy-propane
(4R,5R)-2,2,4-Trimethyl-5-((E)-1-methyl-2-phenyl-vinyl)-[1,3]dioxolane
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene | 100% |
4-(R,S)-(t-butoxycarbonylamino)-3-oxo-1,2-diazolidine
2,2-dimethoxy-propane
C11H19N3O3
Conditions | Yield |
---|---|
camphor-10-sulfonic acid In methanol for 1h; Heating; | 100% |
(3S,5S)-6-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)-3,5-dihydroxyhexane
2,2-dimethoxy-propane
(3S,5S)-6-<(benzyloxy)methyl>-4-<1-(tert-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxacyclohexane
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid for 1h; | 100% |
With camphor-10-sulfonic acid | 99% |
(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((1S,2S)-1,2-dihydroxy-2-thiazol-2-yl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
2,2-dimethoxy-propane
(4S,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-5-((4R,5S)-2,2-dimethyl-5-thiazol-2-yl-[1,3]dioxolan-4-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With o-toluenesulfonic acid; magnesium sulfate; acetone for 4h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In dichloromethane at 23℃; | 100% |
DL-(1α,2α,3β,4β,5α,7α)-2,5-Dibrom-8-oxabicyclo<5.1.0>octan-3,4-diol
2,2-dimethoxy-propane
DL-(1α,2α,3β,4β,5α,7α)-2,5-Dibrom-3,4-O-isopropyliden-8-oxabicyclo<5.1.0>octan-3,4-diol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Heating; | 100% |
(2R,3R)-4-(tert-butyl-diphenyl-silanyloxy)-1,1-bisethylsulfanyl-butane-2,3-diol
2,2-dimethoxy-propane
4-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-erythrose diethyl dithioacetal
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid In acetone for 4h; Ambient temperature; | 100% |
With toluene-4-sulfonic acid In acetone Yield given; |
(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one
2,2-dimethoxy-propane
(22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 100% |
With camphor-10-sulfonic acid In dichloromethane; acetonitrile for 1h; Ambient temperature; | 98% |
With toluene-4-sulfonic acid In dichloromethane for 1h; Ambient temperature; Yield given; |
(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropane-1,2-diol
2,2-dimethoxy-propane
tert-Butyl-dimethyl-((R)-2,2,4-trimethyl-[1,3]dioxolan-4-ylmethoxy)-silane
Conditions | Yield |
---|---|
camphor-10-sulfonic acid for 3h; Ambient temperature; | 100% |
(S)-1-benzyloxy-2-methylpropane-2,3-diol
2,2-dimethoxy-propane
4-benzyloxymethyl-2,2,4-trimethyl-1,3-dioxolane
Conditions | Yield |
---|---|
camphor-10-sulfonic acid for 3h; Ambient temperature; | 100% |
1. Introduction of 2,2-Dimethoxypropane
2,2-Dimethoxypropane, is an organic compound and an alkylating reagent. Dimethoxypropane is an intermediate for the synthesis of 2-methoxypropene.
2. Properties of 2,2-Dimethoxypropane
Melting Point: -47 °C
Boiling point: 83 °C at 760 mmHg
Storage Temperature: Flammables area
Density: 0.84 g/cm3
Refractive index: n20/D 1.378(lit.)
Water Solubility: 18 g/100 mL (25 °C)
Stability: Stable. Highly flammable - note low flash point. Vapour may form an explosive mixture with air. May form explosive peroxides when exposed to air. Incompatible with strong oxidizing agents.
Index of Refraction: 1.379
Molar Refractivity: 28.66 cm3
Molar Volume: 123.8 cm3
Surface Tension: 21.1 dyne/cm
Enthalpy of Vaporization: 31.01 kJ/mol
Vapour Pressure: 85.6 mmHg at 25°C
XLogP3-AA: 0.6
H-Bond Donor: 0
H-Bond Acceptor: 2
3. Structure Descriptors of 2,2-Dimethoxypropane
Canonical SMILES: CC(C)(OC)OC
InChI: InChI=1S/C5H12O2/c1-5(2,6-3)7-4/h1-4H3
InChIKey: HEWZVZIVELJPQZ-UHFFFAOYSA-N
4. Safety Information of 2,2-Dimethoxypropane
A very dangerous fire hazard when exposed to heat, flame or oxidizers. When heated to 210°C it burns with a cool flame and then explodes. Explosive reaction with metal perchlorates (e.g., manganese(II) perchlorate; nickel(II) perchlorate) above 65°C. When heated to decomposition it emits acrid smoke and fumes.
Hazard Codes F,Xi
Risk Statements 11-36-36/37/38
R11:Highly flammable.
R36:Irritating to eyes.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-9-37/39-33-16-33,37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S9:Keep container in a well-ventilated place.
S37/39:Wear suitable gloves and eye/face protection.
S33:Take precautionary measures against static discharges.
S16:Keep away from sources of ignition.
S37/39:Wear suitable gloves and eye/face protection.
RIDADR UN 1993 3/PG 2
WGK Germany 2
F 10-21
HazardClass 3
PackingGroup II
HS Code 29110000
5. Use of 2,2-Dimethoxypropane
2,2-Dimethoxypropane is used as a pharmaceutical intermediate, mainly used for hydroxyl protection and dehydration.
6. Preparation of 2,2-Dimethoxypropane
The reaction mechanism for this reaction is sketched below. It is an acid catalysed process. Acids like camphorsulfonic acid or tosic acid can be used.
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