| Identification | Back Directory | [Name]
4-(BOC-AMINO)BUTYL BROMIDE | [CAS]
164365-88-2 | [Synonyms]
tert-Butyl (4-bromobutyl)
N-Boc 4-broMobutan-1-aMine
tert-Butyl 4-bromobutylcarbamate
ert-butylN-(4-bromobutyl)carbamate
4-(BOC-AMINO)BUTYL BROMIDE ISO 9001：2015 REACH
N-(tert-Butoxycarbonyl)-1-broMobutan-4-ylaMine
4-(Boc-aMino)butyl broMide technical, >=90% (AT)
N-(4-BroMobutyl)carbaMic Acid 1,1-DiMethylethyl Ester
Carbamic acid,N-(4-bromobutyl)-, 1,1-dimethylethyl ester | [EINECS(EC#)]
200-158-5 | [Molecular Formula]
C9H18BrNO2 | [MDL Number]
MFCD06201020 | [MOL File]
164365-88-2.mol | [Molecular Weight]
252.15 |
| Chemical Properties | Back Directory | [Boiling point ]
308.8±25.0 °C(Predicted) | [density ]
1.228 | [storage temp. ]
2-8°C | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly) | [form ]
Low-Melting Solid | [pka]
12.76±0.46(Predicted) | [color ]
White to Pale Yellow | [InChI]
InChI=1S/C9H18BrNO2/c1-9(2,3)13-8(12)11-7-5-4-6-10/h4-7H2,1-3H3,(H,11,12) | [InChIKey]
GKGFAEREWWZBKY-UHFFFAOYSA-N | [SMILES]
C(OC(C)(C)C)(=O)NCCCCBr |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Low Melting Solid | [Uses]
4-(Boc-amino)butyl bromide can be used:
- For the synthesis of N-Boc-aminoalkoxyphenyl derivatives, precursor to pharmacophore elements for the treatment of glaucoma.
- For the synthesis of various aloperine derivatives with potential application as anti-HIV agents.
- For the modification of 4,5,6,7-tetrabromobenzotriazole (TBB) derivatives to generate improved CK2 inhibitors.
| [reaction suitability]
reagent type: cross-linking reagent | [Synthesis]
General procedure for the synthesis of tert-butyl N-(4-bromobutyl) carbamate from 4-(N-tert-butoxycarbonylamino)-1-butanol: 4-(N-tert-butoxycarbonylamino)-1-butanol (1.06 g, 5.788 mmol) was dissolved in anhydrous THF (54 mL), followed by the addition of triphenylphosphine (2.86 g, 10.92 mmol, 1.9 equiv) . Carbon tetrabromide (3.62 g, 10.92 mmol, 1.9 eq.) was added slowly with stirring. The reaction mixture was stirred at room temperature for 3 h. After stirring, the reaction mixture was filtered through a diatomaceous earth pad to remove by-products and the filter cake was washed with ether. The filtrate was concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel fast column chromatography (eluent: hexane/ethyl acetate, 3:1) to afford tert-butyl N-(4-bromobutyl)carbamate (1.73 g, quantitative yield) as a white solid. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 1151 - 1155
[2] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 11, p. 1156 - 1161
[3] Patent: WO2017/53360, 2017, A1. Location in patent: Paragraph 0154
[4] Patent: WO2017/96045, 2017, A1. Location in patent: Paragraph 00884
[5] Patent: WO2012/9309, 2012, A1. Location in patent: Page/Page column 58 |
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