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| CAS No.: | 77-76-9 |
|---|---|
| Name: | 2,2-Dimethoxypropane |
| Molecular Structure: | |
|
|
|
| Formula: | C5H12O2 |
| Molecular Weight: | 104.149 |
| Synonyms: | Acetone,dimethyl acetal (6CI,8CI);2,2-Bis(methyloxy)propane;Acetone dimethyl ketal;NSC 62085; |
| EINECS: | 201-056-0 |
| Density: | 0.84 g/cm3 |
| Melting Point: | -47 °C |
| Boiling Point: | 83 °C at 760 mmHg |
| Flash Point: | -5oC |
| Solubility: | 18 g/100 mL (25 °C) |
| Appearance: | clear liquid |
| Hazard Symbols: |
 F, Xi
|
| Risk Codes: | 11-36-36/37/38 |
| Safety: | 26-9-37/39-33-16-33,37/39 |
| Transport Information: | UN 1993 3/PG 2 |
| PSA: | 18.46000 |
| LogP: | 1.01530 |
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| 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% |
- 58-56-0
pyridoxal hydrochloride
A
- 948-00-5
1,5-dihydro-3,3,8-trimethyl<1,3>dioxepino<5,6-y>pyridin-9-ol
B
- 77-76-9
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% |
- 542-92-7
cyclopenta-1,3-diene
- 123-73-9
crotonaldehyde
A
- 153380-53-1
(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde
C
- 249730-06-1
(1S,2S,3R,4R)-3-methylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde
D
- 77-76-9
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% |
| Conditions | Yield |
|---|---|
| at 40℃; for 12h; Irradiation; | 84% |
| at 40℃; for 12h; Product distribution; Irradiation; further primary alcohols; | 84% |
- 67-56-1
methanol
- 41774-06-5
α-nitroisopropyl phenyl sulfone
- 124-41-4
sodium methylate
- 77-76-9
2,2-dimethoxy-propane
| Conditions | Yield |
|---|---|
| at 40℃; for 5h; Irradiation; | 82% |
| at 40℃; for 5h; Product distribution; Irradiation; further primary alcohols; | 82% |
- 67-56-1
methanol
A
- 507-19-7
t-butyl bromide
- 32654-19-6, 89071-84-1, 92617-21-5
trans-2-bromo-9-oxabicyclo<4.2.1>nonane
- 32654-27-6, 89071-85-2, 92617-22-6
trans-2-bromo-9-oxabicyclo<3.3.1>nonane
D
- 77-76-9
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% |
- 67-56-1
methanol
- 85620-94-6, 107494-71-3
2-azido-2-nitropropane
- 124-41-4
sodium methylate
- 77-76-9
2,2-dimethoxy-propane
| Conditions | Yield |
|---|---|
| at 40℃; for 24h; Irradiation; | 74% |
| at 40℃; for 24h; Product distribution; Irradiation; further primary alcohols; | 74% |
- 90593-00-3
methyl 5-deoxy-5-C-(diethoxyphosphinyl)-2,3-O-isopropylidene-β-D-ribofuranoside
A
- 77-76-9
2,2-dimethoxy-propane
B
- 194412-32-3
methyl 5-deoxy-5-C-diethoxyphosphinyl-β-D-ribofuranoside
| Conditions | Yield |
|---|---|
| With methanol; iodine for 4.5h; | A n/a B 73% |
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Specification
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.
