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Merck

M29304

N-Methylaniline

98%

Synonym(s):

Monomethylaniline

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About This Item

Linear Formula:
C6H5NHCH3
CAS Number:
100-61-8
Molecular Weight:
107.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24896781
EC Number:
202-870-9
Beilstein/REAXYS Number:
741982
MDL number:
MFCD00008283
Assay:
98%
Form:
liquid

Key Documents

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InChI key

AFBPFSWMIHJQDM-UHFFFAOYSA-N

InChI

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

SMILES string

CNc1ccccc1

assay

98%

form

liquid

Quality Level

200

bp

196 °C (lit.)

mp

−57 °C (lit.)

density

0.989 g/mL at 25 °C (lit.)

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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.

signalword

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

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

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB7226
SDBB5848
SDBB4878
STBL0220
STBK0499

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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)
Efficient amide-directed catalytic asymmetric hydroboration.
Smith S M, et al.
Journal of the American Chemical Society, 130(12), 3734-3735 (2008)
HKGreen-3: a rhodol-based fluorescent probe for peroxynitrite.
Peng T and Yang D
Organic Letters, 12(21), 4932-4935 (2010)
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
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
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