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156272

Sigma-Aldrich

3,5-Dinitrobenzoyl chloride

≥96.5%

Synonym(s):

DNBC, NSC 2697

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About This Item

Linear Formula:
(O2N)2C6H3COCl
CAS Number:
99-33-2
Molecular Weight:
230.56
Beilstein/REAXYS Number:
990249
EC Number:
202-750-6
MDL number:
MFCD00007248
UNSPSC Code:
12352100
PubChem Substance ID:
57647511
NACRES:
NA.21

vapor density

7.6 (vs air)

Quality Level

100

assay

≥96.5%

form

solid

bp

196 °C/11 mmHg (lit.)

mp

68-69 °C (lit.)

functional group

acyl chloride
nitro

SMILES string

[O-][N+](=O)c1cc(cc(c1)[N+]([O-])=O)C(Cl)=O

InChI

1S/C7H3ClN2O5/c8-7(11)4-1-5(9(12)13)3-6(2-4)10(14)15/h1-3H

InChI key

NNOHXABAQAGKRZ-UHFFFAOYSA-N

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General description

Crystals of 3,5-dinitrobenzoyl chloride (DNBC) belong to the orthorhombic crystal system and space group Pna21. It is widely used reagent for the detection of alcohols.

Application

3,5-Dinitrobenzoyl chloride may be used for the quantitative estimation of hydroxyl groups in pyridine. It may be used in the synthesis of following:
  • 3,5-diamino-N-cyclopropylbenzamide
  • 3,5-dinitro-N-cyclopropylbenzamide
  • 4-(3,5-dinitrophenyl)-6-(dipropan-2-ylamino)-2H-1,3,5-thiadiazine-2-thione4


3,5-Dinitrobenzoyl chloride may also be used as derivatizing agent for the following:

  • biogenic amines present in fermented foods, which can be determined using liquid chromatography method(LC)
  • polyamines, present in biological fluids, which can be determined using high performance liquid chromatography(HPLC)

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL6543
BCCK7971
BCCH1851
BCCJ5187
BCCF5716

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Synthesis and characterization of aromatic poly (amides) based on 3, 5-diamino-N-cyclopropylbenzamide.
Tundidor-Camba A, et al.
Royal Society of Chemistry Advances, 5(29), 23057-23066 (2015)
Rapid Determination of Organic Hydroxyl Groups with 3, 5,-Dinitrobenzoyl Chloride.
Robinson Jr WT, et al.
Analytical Chemistry, 33(8), 1030-1034 (1961)
3, 5-Dinitrobenzoyl chloride.
Wang HY, et al.
Acta Crystallographica Section E, Structure Reports Online, 65(10), o2460-o2460 (2009)
A Markowska et al.
Roczniki Akademii Medycznej w Bialymstoku (1995), 42(1), 129-140 (1997-01-01)
A carbocyclic analogue of distamycin was obtained, in which the N-methylpyrrole rings were substituted by disubstituted benzene rings. Additionally, N-chloro- or N-bromoacetyl groups, displaying alkylating properties, were introduced. The synthesis, starting from 3,5-dinitrobenzoyl chloride, consisted of five stages.
Jiu-gao Yu et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 38(3), 191-195 (2003-07-02)
To prepare a novel creatinine adsorbent with anti-renal failure activity. A novel starch ester was prepared under heterogeneous condition by the reaction of starch (ST) and 3, 5-dinitrobenzoyl chloride (DNBZ-Cl). The products were characterized by means of elemental analysis, FTIR
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