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D194255

Sigma-Aldrich

1,3-Dinitrobenzene

97% anhydrous basis

Synonym(s):

1,3-Dinitrobenzene, DNB, Meta-dinitrobenzene, m-Dinitrobenzene

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100 MG
$155.00

About This Item

Linear Formula:
C6H4(NO2)2
CAS Number:
99-65-0
Molecular Weight:
168.11
Beilstein:
1105654
EC Number:
202-776-8
MDL number:
MFCD00007222
UNSPSC Code:
12352100
PubChem Substance ID:
24893577
NACRES:
NA.22

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Quality Level

100

Assay

97% anhydrous basis

form

solid

impurities

≤10.0% H2O

bp

297 °C (lit.)

mp

84-86 °C (lit.)

density

1.368 g/mL at 25 °C (lit.)

SMILES string

[O-][N+](=O)c1cccc(c1)[N+]([O-])=O

InChI

1S/C6H4N2O4/c9-7(10)5-2-1-3-6(4-5)8(11)12/h1-4H

InChI key

WDCYWAQPCXBPJA-UHFFFAOYSA-N

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(S)[(Sp)-2-(Diphenylphosphino)ferrocenyl]-4-isopropyloxazoline 97%

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(S)[(Sp)-2-(Diphenylphosphino)ferrocenyl]-4-isopropyloxazoline

(Rp)-2-(tert-Butylthio)-1-(diphenylphosphino)ferrocene 98%

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(Rp)-2-(tert-Butylthio)-1-(diphenylphosphino)ferrocene

(R)-N-Methyl-N-diphenylphosphino-1-[(S)-2-diphenylphosphino)ferrocenyl]ethylamine ≥96%

682322

(R)-N-Methyl-N-diphenylphosphino-1-[(S)-2-diphenylphosphino)ferrocenyl]ethylamine

(4S)-(+)-4-[4-(tert-butyl)phenyl]-α-[(4S)-4-[4-(tert-butyl)phenyl]-2-oxazolidinylidene]-2-oxazolineacetonitrile 97%

682772

(4S)-(+)-4-[4-(tert-butyl)phenyl]-α-[(4S)-4-[4-(tert-butyl)phenyl]-2-oxazolidinylidene]-2-oxazolineacetonitrile

assay

97%

assay

98%

assay

≥96%

assay

97%

form

solid

form

solid

form

solid

form

solid

functional group

ether, phosphine

functional group

phosphine, thioether

functional group

amine, phosphine

functional group

ether, nitrile

optical activity

[α]20/D 366°, c = 0.1 in chloroform

optical activity

-

optical activity

-

optical activity

[α]22/D +349°, c = 2% in chloroform

mp

158-162 °C

mp

146-149 °C

mp

108.7-113.6 °C

mp

257-261 °C

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

General description

1,3-Dinitrobenzene can undergo reductive degradation by alkaline ascorbic acid to produce 1,3-phenylenediamine.[1]

Application

1,3-Dinitrobenzene can be used as a reactant to synthesize:      
  • 2′,6′- dinitrobiphenyl-4-ol and 1-nitrodibenzofuran via copper-catalyzed regioselective cross-coupling reaction with 4-iodophenol and 2-iodophenol respectively.[2]      
  • 1H-indazole derivatives by reacting with various N-tosylhydrazones in the presence of a base catalyst.[3]      
  • 3-(1H-Tetrazol-1-yl)benzenamine by reacting with triethyl orthoformate and NaN3 in the presence of a three-functional redox catalytic system.[4]

Signal Word

Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

302.0 °F - closed cup

Flash Point(C)

150 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves
  • Specification Sheet

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    Certificates of Analysis (COA)

    Lot/Batch Number
    MKCN0773
    MKCM4488
    MKCL8178
    MKCH5604
    MKCH2920

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    Min Luo et al.
    Biochemistry, 54(35), 5513-5522 (2015-08-12)
    Aldehyde dehydrogenase 7A1 (ALDH7A1) is part of lysine catabolism and catalyzes the NAD(+)-dependent oxidation of α-aminoadipate semialdehyde to α-aminoadipate. Herein, we describe a structural study of human ALDH7A1 focused on substrate recognition. Five crystal structures and small-angle X-ray scattering data
    Laura A Jansen et al.
    Annals of neurology, 75(1), 22-32 (2013-10-15)
    A high incidence of structural brain abnormalities has been reported in individuals with pyridoxine-dependent epilepsy (PDE). PDE is caused by mutations in ALDH7A1, also known as antiquitin. How antiquitin dysfunction leads to cerebral dysgenesis is unknown. In this study, we
    Haiyong Wang et al.
    Tumour biology : the journal of the International Society for Oncodevelopmental Biology and Medicine, 35(12), 12665-12670 (2014-09-13)
    Although the entire etiology of esophageal squamous cell carcinoma (ESCC) is still unclear, alcohol drinking has been identified as a major environmental risk factor. The aldehyde dehydrogenase (ALDH) superfamily members are major enzymes involved in the alcohol-metabolizing pathways. Accumulating evidences
    Diana Andrejeva et al.
    BMC cancer, 18(1), 1180-1180 (2018-11-30)
    Changes in cellular metabolism are now recognized as potential drivers of cancer development, rather than as secondary consequences of disease. Here, we explore the mechanism by which metabolic changes dependent on aldehyde dehydrogenase impact cancer development. ALDH7A1 was identified as

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