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Sigma-Aldrich

2,4-Dimethoxybenzylamine

98%

Synonym(s):

(2,4-Dimethoxyphenyl)methanamine, 1-(2,4-Dimethoxyphenyl)methanamine, 2,4-Dimethoxybenzenemethanamine, 2,4-Dimethyloxybenzylamine, [(2,4-Dimethoxyphenyl)methyl]amine

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About This Item

Linear Formula:
(CH3O)2C6H3CH2NH2
CAS Number:
20781-20-8
Molecular Weight:
167.21
MDL number:
MFCD00052393
UNSPSC Code:
12352100
PubChem Substance ID:
24867094
NACRES:
NA.22

assay

98%

refractive index

n20/D 1.549 (lit.)

bp

140 °C/1 mmHg (lit.)

density

1.113 g/mL at 25 °C (lit.)

SMILES string

COc1ccc(CN)c(OC)c1

InChI

1S/C9H13NO2/c1-11-8-4-3-7(6-10)9(5-8)12-2/h3-5H,6,10H2,1-2H3

InChI key

QOWBXWFYRXSBAS-UHFFFAOYSA-N

General description

2,4-Dimethoxybenzylamine can be preprepared by reduction (NaBH4 , BF3.OEt2, THF) of 2,4-dimethoxybenzonitrile.

Application

2,4-Dimethoxybenzylamine is an amine nucleophile used to investigate the 1,4- reactivity of 5-bromo-2-indene-1-one. It may be used in the following studies:
  • As an ammonia equivalent in the concise synthesis of a series of 2,4,5-trisubstituted oxazoles, via a tandem Ugi/Robinson-Gabriel reaction sequence.
  • Total synthesis of (-)-muraymycin (MRY) D2 and its epimer, the antibacterial nucleoside natural product.
  • Two-step synthesis of amide derivatives of uracil polyoxin C (UPOC) methyl ester using the Ugi reaction.
  • Synthesis of N-hydroxythiourea.
  • Synthesis of anti-HIV-1 agents.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

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

Certificates of Analysis (COA)

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Shinichi Imamura et al.
Chemical & pharmaceutical bulletin, 52(1), 63-73 (2004-01-08)
A novel lead compound, N-(3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [(125)I]RANTES and CCR5-expressing CHO cells. The IC(50) value of 1 was 1.9 microM. In an effort to improve the binding affinity of 1, a
Tetsuya Tanino et al.
The Journal of organic chemistry, 75(5), 1366-1377 (2010-02-11)
Full details of the first total synthesis of (-)-muraymycin (MRY) D2 and its epimer, the antibacterial nucleoside natural product, are described. Key strategic elements of the approach include the preparation of the urea dipeptide moiety found in the muraymycins containing
Keith J Stanger et al.
Journal of combinatorial chemistry, 8(3), 435-439 (2006-05-09)
We describe parallel/combinatorial, solid-phase, supported synthesis of diverse hydroxamates using a common intermediate, an N-derivatized, O-linked hydroxylamine. The method allows the concurrent synthesis of both N-alkyl and N-H hydroxamates and is compatible with a wide range of chemical transformations. The
M Sato et al.
Journal of medicinal chemistry, 19(2), 336-337 (1976-02-01)
The synthesis of the title compound (1) was accomplished by the conversion of 2,4-dimethoxybenzylamine (2) into an isothiocyanate (3) using thiocarbonyl diimidazole. Treatment of 3 with hydroxylamine and removal of the DMB group with trifluoroacetic acid gave 1. N-Hydroxythiourea (1)
Andrew Plant et al.
The Journal of organic chemistry, 74(13), 4870-4873 (2009-05-22)
A simple, two-step synthesis of amide derivatives of uracil polyoxin C (UPOC) methyl ester using the Ugi reaction is described. The four components employed in the Ugi reaction are 2',3'-isopropylidine-protected uridine-5'-aldehyde, 2,4-dimethoxybenzylamine, an isoxazolecarboxylic acid, and the convertible isonitrile N-(2-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)carbonitrile.
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