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139033

Sigma-Aldrich

2-Chloro-5-nitrobenzaldehyde

97%

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About This Item

Linear Formula:
ClC6H3(NO2)CHO
CAS Number:
6361-21-3
Molecular Weight:
185.56
Beilstein/REAXYS Number:
743764
EC Number:
228-830-0
MDL number:
MFCD00007293
UNSPSC Code:
12352100
PubChem Substance ID:
24848375
NACRES:
NA.22

Quality Level

100

assay

97%

mp

75-77 °C (lit.)

functional group

aldehyde
chloro
nitro

SMILES string

[H]C(=O)c1cc(ccc1Cl)[N+]([O-])=O

InChI

1S/C7H4ClNO3/c8-7-2-1-6(9(11)12)3-5(7)4-10/h1-4H

InChI key

VFVHWCKUHAEDMY-UHFFFAOYSA-N

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General description

2-Chloro-5-nitrobenzaldehyde undergoes condensation reaction with 2-methyl-1-propenylbenzimidazole to yield (E,Z)-2-(2-chloro-5-nitrostyryl)-1-(1-propenyl)benzimidazole. It reacts with 5-aminopyrazoles to yield symmetrical bispyrazolo[3,4-]pyridines.

Application

2-Chloro-5-nitrobenzaldehyde was used in the synthesis of 5-nitro-2-(1H-pyrrol-1-yl)benzaldehyde.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
04506BH
S35519
S35518
08822TD
09420MV

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Reactions of 5-amino-1, 2-azoles with aromatic and heterocyclic o-chloroaldehydes:[1+ 1] versus [2+ 1] cyclocondensation.
Abramov MA, et al.
Tetrahedron, 57(44), 9123-9129 (2001)
D E Bacelo et al.
Acta crystallographica. Section C, Crystal structure communications, 53 ( Pt 7), 907-909 (1997-07-15)
The title compound, C18H14ClN3O2, was synthesized by the condensation of 2-chloro-5-nitrobenzaldehyde with 2-methyl-1-propenylbenzimidazole, and the molecule comprises a 2-chloro-5-nitrobenzene and a 1-(Z)-propenylbenzimidazole. The two aromatic moieties are conjugated through the vinyl group. The dihedral angle between the two rings is
Morita-Baylis-Hillman route to 4H-pyrrolo [1, 2-a][1] benzazepine derivatives.
Park SP, et al.
Tetrahedron, 65(24), 4703-4708 (2009)

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