| Identification | More | [Name]
3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE | [CAS]
16789-84-7 | [Synonyms]
3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE
3-BROMO-2-HYDROXY-5-NITROBENZENECARBALDEHYDE
3-BROMO-5-NITROSALICYLALDEHYDE
AKOS BC-1820
ASISCHEM R25237 | [EINECS(EC#)]
625-126-9 | [Molecular Formula]
C7H4BrNO4 | [MDL Number]
MFCD00051833 | [Molecular Weight]
246.01 | [MOL File]
16789-84-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
146-149 °C | [Boiling point ]
299.6±40.0 °C(Predicted) | [density ]
1.928±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
powder to crystal | [pka]
3.38±0.44(Predicted) | [color ]
Light orange to Yellow to Green | [Sensitive ]
Air Sensitive | [BRN ]
1213613 | [InChI]
InChI=1S/C7H4BrNO4/c8-6-2-5(9(12)13)1-4(3-10)7(6)11/h1-3,11H | [InChIKey]
BESBCGANGAEHPM-UHFFFAOYSA-N | [SMILES]
C(=O)C1=CC([N+]([O-])=O)=CC(Br)=C1O | [CAS DataBase Reference]
16789-84-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [RIDADR ]
UN 2811 6.1/PG 3
| [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [PackingGroup ]
III | [HS Code ]
2913000090 | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral |
| Hazard Information | Back Directory | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 72, p. 5867, 2007 DOI: 10.1021/jo070477u | [Synthesis]
General procedure for the synthesis of 3-bromo-2-hydroxy-5-nitrobenzaldehyde from 5-nitrosalicylaldehyde: 2-hydroxy-5-nitrobenzaldehyde (2.0 g, 12 mmol) and dichloromethane (30 mL) were added to a 100 mL two-necked flask, followed by the addition of bromine (2.24 g, 14 mmol) dropwise. The reaction mixture was stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched with saturated aqueous sodium thiosulfate (100 mL) and the mixture was transferred to a separatory funnel for layering. The aqueous phase was extracted with ethyl acetate (100 mL × 2). The organic phases were combined, washed with saturated brine (80 mL × 2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/petroleum ether, v/v = 1/20) to afford 3-bromo-2-hydroxy-5-nitrobenzaldehyde as a yellow solid (2.89 g, 98% yield). Mass spectrum (ES-API, cation mode) m/z: 246.9 [M + 2]+. | [References]
[1] Organic Letters, 2011, vol. 13, # 1, p. 26 - 29
[2] Tetrahedron Letters, 2005, vol. 46, # 51, p. 8959 - 8963
[3] Patent: WO2017/36404, 2017, A1. Location in patent: Page/Page column 115
[4] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[5] Patent: CN108623615, 2018, A. Location in patent: Paragraph 0332; 0547; 0548; 0549 |
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