| Identification | Back Directory | [Name]
1,1-Dibromoformaldoxime | [CAS]
74213-24-4 | [Synonyms]
1,1-DibromoformaL
broMonitrile oxide
DIBROMOFORMALDOXIME
1-Dibromoformaldoxime
1,1-DIBROMOFORMALDOXIME
hydroxycarbonimidic dibromide
1,1-dibromo-formaldehyde oxime
N-Hydroxycarbonimidic dibromide
Carbonimidic dibromide, hydroxy-
Carbonimidic dibromide, N-hydroxy-
N-(dibromomethylidene)hydroxylamine
Dibromoformaldoxime in molar solution
Carbonimidic dibromide,hydroxy- (9CI) | [Molecular Formula]
CHBr2NO | [MDL Number]
MFCD06796211 | [MOL File]
74213-24-4.mol | [Molecular Weight]
202.83 |
| Chemical Properties | Back Directory | [Melting point ]
65-68 °C | [Boiling point ]
230.0±23.0 °C(Predicted) | [density ]
2.70±0.1 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Store in freezer, under -20°C | [solubility ]
Chloroform (Very Slightly, Heated), Methanol | [form ]
Solid | [pka]
7.52±0.11(Predicted) | [color ]
White to Dark Orange | [InChI]
InChI=1S/CHBr2NO/c2-1(3)4-5/h5H | [InChIKey]
AWBKQZSYNWLCMW-UHFFFAOYSA-N | [SMILES]
C(/Br)(\Br)=N/O |
| Hazard Information | Back Directory | [Uses]
Dibromoformaldoxime is a reagent that undergoes cycloaddition with alkynes to prepare substituted 3-bromo-isoxazoles in high yield. | [Synthesis Reference(s)]
Tetrahedron Letters, 25, p. 387, 1984 DOI: 10.1016/S0040-4039(00)99890-3 | [Synthesis]
General procedure for the synthesis of 1,1-dibromoformaldehyde oxime from 2-oxoacetic acid: hydroxylamine hydrochloride (10 mmol) was added to a stirred aqueous (50 mL) solution of glyoxalic acid (10 mmol), and the reaction mixture was stirred for 24 hours at room temperature. Subsequently, sodium bicarbonate (20 mmol) was slowly added, followed by dichloromethane (60 mL). Bromine (1 mL) was added dropwise to the well-stirred two-phase mixture at 6 °C for 20 min. After the addition of bromine, stirring of the reaction mixture was continued for 3 hours. Upon completion of the reaction, the organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL). The organic extracts were combined, dried with magnesium sulfate, filtered and concentrated under reduced pressure. The residue was recrystallized with hexane (50 mL) to give 1.60 g (81% yield) of a white crystal product with a melting point of 65-66 °C (literature value 19: 63-65 °C). | [References]
[1] Tetrahedron Letters, 2015, vol. 56, # 13, p. 1635 - 1637
[2] EJNMMI Research, 2018, vol. 8,
[3] Angewandte Chemie - International Edition, 2017, vol. 56, # 13, p. 3703 - 3707
[4] Angew. Chem., 2017, vol. 129, # 13, p. 3757 - 3761,5
[5] Patent: WO2010/127978, 2010, A1. Location in patent: Page/Page column 51 |
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