Skip to Content
Merck
All Photos(3)

Key Documents

M29304

Sigma-Aldrich

N-Methylaniline

98%

Synonym(s):

Monomethylaniline

Sign Into View Organizational & Contract Pricing


About This Item

Linear Formula:
C6H5NHCH3
CAS Number:
Molecular Weight:
107.15
Beilstein:
741982
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

liquid

refractive index

n20/D 1.571 (lit.)

bp

196 °C (lit.)

mp

−57 °C (lit.)

density

0.989 g/mL at 25 °C (lit.)

SMILES string

CNc1ccccc1

InChI

1S/C7H9N/c1-8-7-5-3-2-4-6-7/h2-6,8H,1H3

InChI key

AFBPFSWMIHJQDM-UHFFFAOYSA-N

Looking for similar products? Visit Product Comparison Guide

Application

N-Methylaniline is a general reagent used:
  • In the preparation of phosphoramidite ligands for the rhodium-catalyzed asymmetric hydroboration.
  • As a formylating reagent in the C3-selective formylation of indoles.
  • In the synthesis of a rhodol-based fluorescent probe, HKGreen-3, for sensing peroxynitrite.
  • As a key starting material in the synthesis of AKT (protein kinase B) inhibitor-IV.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - STOT RE 2 Oral

Target Organs

Liver,spleen,Bone marrow

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

185.0 °F - closed cup

Flash Point(C)

85 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Efficient amide-directed catalytic asymmetric hydroboration.
Smith S M, et al.
Journal of the American Chemical Society, 130(12), 3734-3735 (2008)
Synthesis and biological evaluation of analogues of AKT (protein kinase B) inhibitor-IV.
Sun Q, et al.
Journal of Medicinal Chemistry, 54(5), 1126-1139 (2011)
HKGreen-3: a rhodol-based fluorescent probe for peroxynitrite.
Peng T and Yang D
Organic Letters, 12(21), 4932-4935 (2010)
Jonathan L Sessler et al.
Chemical communications (Cambridge, England), (14)(14), 1892-1894 (2005-03-30)
A novel porphyrin-fullerene dyad assembled through Watson-Crick hydrogen bonds is described; this system undergoes photoinduced electron transfer upon irradiation with visible light to produce a charge separated state that is substantially longer lived than that of previous dyads of this
Israel González et al.
Organic letters, 11(8), 1677-1680 (2009-04-10)
N-Methylanilines are readily synthesized in high yields through the copper(II)-promoted coupling of anilines and methylboronic acid. This method represents a new approach for the selective monomethylation of anilines, and it is the first reported example of a Chan-Lam coupling involving

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service