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Basic Information
| CAS No.: | 5469-26-1 |
|---|---|
| Name: | 1-Bromopinacolone |
| Article Data: | 71 |
| Molecular Structure: | |
|
|
|
| Formula: | C6H11 Br O |
| Molecular Weight: | 179.057 |
| Synonyms: | 1-Bromo-3,3-dimethyl-2-butanone;1-Bromo-3,3'-dimethyl-2-butanone; 1-Bromopinacolin; 1-Bromopinacolone;3,3-Dimethyl-2-oxobutyl bromide; Bromomethyl tert-butyl ketone;Bromopinacolone; NSC 25307; Pivaloylmethyl bromide; tert-Butyl bromomethylketone; a-Bromopinacolone |
| EINECS: | 226-794-0 |
| Density: | 1.331 |
| Melting Point: | -10 C |
| Boiling Point: | 188 - 192 C |
| Flash Point: | 75 ºC |
| Solubility: | Insoluble in water. |
| Appearance: | clear to ywllowish liquid |
| Hazard Symbols: |
|
| Risk Codes: | R36/37/38 |
| Safety: | 26-37/39 |
| Transport Information: | 200kgs |
| PSA: | 17.07000 |
| LogP: | 1.99650 |
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Synthetic route
Conditions
| Conditions | Yield |
|---|---|
| With cerium(III) nitrate hexahydrate; sulfuric acid; dihydrogen peroxide; lithium bromide In water; acetonitrile at 65 - 70℃; Catalytic behavior; Reagent/catalyst; Concentration; Time; Solvent; | 95% |
| With bromine In diethyl ether at 10 - 20℃; Inert atmosphere; | 93% |
| With bromine In diethyl ether at 10℃; for 0.5h; Cooling with ice; Inert atmosphere; | 93% |
Conditions
| Conditions | Yield |
|---|---|
| Stage #1: dimethyltitanocene; N,N-dimethylpivalamide In toluene at 65℃; Schlenk technique; Inert atmosphere; Stage #2: With bromine In toluene at -78℃; for 0.0333333h; Schlenk technique; Inert atmosphere; Stage #3: With water In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere; regioselective reaction; | 95% |
- 464-07-3, 20281-91-8
3,3-dimethyl-2-butanol
- 5469-26-1
1-Bromopinacolon
Conditions
| Conditions | Yield |
|---|---|
| With hydrogen bromide; dihydrogen peroxide In water; acetonitrile at 65 - 70℃; for 6h; Green chemistry; | 91% |
| With 3,3-dimethyl-butan-2-one; aluminum tri-tert-butoxide; pyridinium hydrobromide perbromide In toluene at 60℃; for 24h; | |
| With ammonium cerium (IV) nitrate; lithium bromide In water; acetonitrile at 65℃; for 3h; | 97 %Chromat. |
Conditions
| Conditions | Yield |
|---|---|
| With tetraethylammonium bromide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dichloromethane at 20℃; for 0.0833333h; regioselective reaction; | 91% |
Conditions
| Conditions | Yield |
|---|---|
| In tetrahydrofuran at 20℃; for 18h; | 70% |
- 75-97-8
3,3-dimethyl-butan-2-one
A
- 30263-65-1
1,1-dibromo-3,3-dimethylbutan-2-one
B
- 5469-26-1
1-Bromopinacolon
Conditions
| Conditions | Yield |
|---|---|
| With bromine In methanol for 12h; | A n/a B 49% |
| With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 24h; | A n/a B 79 % Spectr. |
- 30263-68-4
1,1-dibromo-3,3-dimethyl-butan-2-ol
- 5469-26-1
1-Bromopinacolon
Conditions
| Conditions | Yield |
|---|---|
| at 130 - 140℃; |
- 24467-08-1
4-bromo-2-tert-butyl-cyclopent-2-enone
- 5469-26-1
1-Bromopinacolon
- 17510-46-2
3,3-dimethyl-2-(trimethylsilyl)oxy-1-butene
- 5469-26-1
1-Bromopinacolon
Conditions
| Conditions | Yield |
|---|---|
| With boron trifluoride diethyl etherate; triphenylbismuth(V) difluoride; potassium bromide 1.) CH2Cl2, room temperature, 10 h, 2.) DMF, room temperature, 24 h; Yield given. Multistep reaction; | |
| With N-Bromosuccinimide In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; |
Conditions
| Conditions | Yield |
|---|---|
| With sodium hydrogencarbonate In isopropyl alcohol at 85℃; | 0.15 mmol |
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1-Bromopinacolone
Toxicity Data With Reference
| 1. | scu-gpg LDLo:500 mg/kg | BDKS** Studien uber die Pharmakologie des Pinakolins und einiger seiner Derivate mit besonderer Berucksichtigung der Kreislaufwirkung, Lennart Bang Dissertation .(Pharmakologischen Abteilung des Karolinischen Instituts,Stockholm, Sweden.: 1934) |
Safety Profile
Moderately toxic by subcutaneous route. A flammable liquid. When heated to decomposition it emits toxic vapors of Br−.
Standards and Recommendations
DOT Classification: 3; Label: Flammable Liquid