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415774

Sigma-Aldrich

5′-Chloro-2′-hydroxy-3′-nitroacetophenone

99%

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About This Item

Linear Formula:
ClC6H2(OH)(NO2)COCH3
CAS Number:
Molecular Weight:
215.59
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

mp

132-135 °C (lit.)

SMILES string

CC(=O)c1cc(Cl)cc(c1O)[N+]([O-])=O

InChI

1S/C8H6ClNO4/c1-4(11)6-2-5(9)3-7(8(6)12)10(13)14/h2-3,12H,1H3

InChI key

IUNBIQBAYUBIFD-UHFFFAOYSA-N

General description

5′-Chloro-2′-hydroxy-3′-nitroacetophenone (5-chloro-3-nitro-2-hydroxyacetophenone) is a nitro derivative of ortho-hydroxy aryl ketone. Its crystal structure has been studied by X-ray diffraction. It forms complex with 2-aminobenzoic acid (anthranilic acid), in which the nitro group is turned by approximately 40°C.

Application

5′-Chloro-2′-hydroxy-3′-nitroacetophenone may be used for the synthesis of 6-chloro-8-nitro-4-oxo-4H-chromene-3-carbaldehyde.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yoshinobu Ishikawa
Acta crystallographica. Section E, Structure reports online, 70(Pt 5), o547-o547 (2014-05-27)
In the title compound, C10H4ClNO5, the non-H atoms of the 6-chloro-chromone unit are coplanar (r.m.s. deviation = 0.017 Å) with the largest deviation from the mean plane [0.031 (2) Å] being found for the C=O C atom. The nitro group (NO2) is inclined
Phase transition and intramolecular hydrogen bonding in nitro derivatives of ortho-hydroxy acetophenones
Filarowski, A., et al.
Journal of Molecular Structure, 785(1), 7-13 (2006)

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