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345016

Sigma-Aldrich

2-Methyl-5-nitrobenzonitrile

97%

Synonym(s):

5-Nitro-o-tolunitrile

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About This Item

Linear Formula:
O2NC6H3(CH3)CN
CAS Number:
939-83-3
Molecular Weight:
162.15
MDL number:
MFCD00017040
UNSPSC Code:
12352100
PubChem Substance ID:
24861288
NACRES:
NA.22

assay

97%

mp

103.5-107.5 °C (lit.)

solubility

ethanol: soluble(lit.)

functional group

nitrile
nitro

SMILES string

Cc1ccc(cc1C#N)[N+]([O-])=O

InChI

1S/C8H6N2O2/c1-6-2-3-8(10(11)12)4-7(6)5-9/h2-4H,1H3

InChI key

XOSDYLFXPMFRGF-UHFFFAOYSA-N

General description

2-Methyl-5-nitrobenzonitrile is an aralkyl nitrile.[1] It is formed by nitration of o-toluonitrile with NO2+BF4-.[1] Crystal structure of 2-methyl-5-nitrobenzonitrile is stabilized by van der Waals interactions.[2]

Application

2-Methyl-5-nitrobenzonitrile was used in the preparation of 5-(2-methyl-5-nitrophenyl)-1H-tetrazole.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBB0505
82796KJ
MKAA2331
10307TH
05314LE

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Wen-Xian Liang et al.
Acta crystallographica. Section E, Structure reports online, 64(Pt 6), o972-o972 (2008-01-01)
In the title compound, C(8)H(6)N(2)O(2), the nitro group is rotated by 10.2 (2)° out of the plane of the benzene ring. The crystal structure is stabilized by van der Waals inter-actions.
Jing Dai et al.
Acta crystallographica. Section E, Structure reports online, 64(Pt 10), o1944-o1944 (2008-01-01)
In the title compound, C(8)H(7)N(5)O(2), the benzene ring makes a dihedral angle of 45.7 (2)° with the tetra-zole ring. In the crystal structure, the mol-ecules are linked into a chain running along the a axis by N-H⋯N hydrogen bonds, and the
Recent aspects of nitration: New preparative methods and mechanistic studies (A Review).
Olah GA, et al.
Proceedings of the National Academy of Sciences of the USA, 79(14), 4487-4494 (1982)

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