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ChemicalBook--->CAS DataBase List--->16789-84-7

16789-84-7

16789-84-7 Structure

16789-84-7 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack 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
Hazard InformationBack Directory
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 72, p. 5867, 2007 DOI: 10.1021/jo070477u
[Synthesis]

5-Nitrosalicylaldehyde

97-51-8

3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE

16789-84-7

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
Spectrum DetailBack Directory
[Spectrum Detail]

3-BROMO-2-HYDROXY-5-NITROBENZALDEHYDE(16789-84-7)1HNMR
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

3-bromo-2-hydroxy-5-nitrobenzaldehyde(16789-84-7)
[Alfa Aesar]

3-Bromo-2-hydroxy-5-nitrobenzaldehyde, 98%(16789-84-7)
[Sigma Aldrich]

16789-84-7(sigmaaldrich)
[TCI AMERICA]

3-Bromo-5-nitrosalicylaldehyde,>95.0%(GC)(T)(16789-84-7)
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