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520594

Sigma-Aldrich

2-Methyl-5-nitroindole

97%

Synonym(s):

NSC 131898

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About This Item

Empirical Formula (Hill Notation):
C9H8N2O2
CAS Number:
7570-47-0
Molecular Weight:
176.17
MDL number:
MFCD00090335
UNSPSC Code:
12352100
PubChem Substance ID:
24874150
NACRES:
NA.22

Assay

97%

form

solid

mp

172-176 °C (lit.)

SMILES string

Cc1cc2cc(ccc2[nH]1)[N+]([O-])=O

InChI

1S/C9H8N2O2/c1-6-4-7-5-8(11(12)13)2-3-9(7)10-6/h2-5,10H,1H3

InChI key

IDJGRXQMAHESOD-UHFFFAOYSA-N

Application

Reactant for preparation of:β
  • Cyanoindoles
  • Methanoindoles
  • Protein kinase C theta (PKCθ) inhibitors
  • Tubulin polymerization inhibitors
  • Peptide-mimetic protease-activated receptor-1 (PAR-1) antagonists
  • Cytosolic phospholipase A2α
  • Cyclooxygenase (COX) inhibitors
  • Serotonin 5-HT6 Receptor Ligands
  • Heterocyclic β-substituted alanine derivatives

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKBH6144V
09015MH
19412LA

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Syntheses Based on 2-Methyl-5-nitrogramine. Preparation of 2-Methyl-5-nitroindole-3-acetic Acid.
Noland WE and Rush KR.
The Journal of Organic Chemistry, 28(10), 2921-2922 (1963)
Nitration of Indoles. II. The Mononitration of Methylindoles1.
Noland WE, et al.
The Journal of Organic Chemistry, 28(9), 2262-2266 (1963)
Nitration of Indoles. III. Polynitration of 2-Alkylindoles1.
Noland WE, et al.
The Journal of Organic Chemistry, 30(10), 3457-3469 (1965)

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