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366463

Methyl nitroacetate

Name: Methyl nitroacetate
Brand: ALDRICH

98%

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About This Item

Linear Formula:

NO₂CH₂COOCH₃

CAS Number:

2483-57-0

Molecular Weight:

119.08

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24862657

EC Number:

219-622-0

Beilstein/REAXYS Number:

1758670

MDL number:

MFCD00075480

Assay:

98%

Form:

liquid

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Properties

Quality Level

100

assay

98%

form

liquid

refractive index

n20/D 1.425 (lit.)

bp

195-198 °C (lit.)

density

1.294 g/mL at 25 °C (lit.)

functional group

amine, ester, nitro

SMILES string

COC(=O)C[N+]([O-])=O

InChI

1S/C3H5NO4/c1-8-3(5)2-4(6)7/h2H2,1H3

InChI key

ALBSWLMUHHZLLR-UHFFFAOYSA-N

Description

Application

Methyl nitroacetate may be used:

in the preparation of aromatic and heteroaromatic linear (E)-α-nitro-arylpentenoates
to generate phenyliodonium ylide, used in the highly enantioselective and diastereoselective Cu(I)-catalyzed cyclopropanation of alkenes
in the preparation of methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate, via reaction with 4-nitrobenzylideneaniline

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 2

flash_point_f

221.0 °F - closed cup

flash_point_c

105 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Catalytic intermolecular allylic C-H alkylation.

Andrew J Young et al.

Journal of the American Chemical Society, 130(43), 14090-14091 (2008-10-04)

The first electrophilic Pd(II)-catalyzed allylic C H alkylation is reported, providing a novel method for formation of sp3-sp3 C C bonds directly from C H bonds. A wide range of aromatic and heteroaromatic linear (E)-alpha-nitro-arylpentenoates are obtained as single olefin

Experimental and theoretical studies of Diels-Alder reaction between methyl (Z)-2-nitro-3-(4-nitrophenyl)-2-propenoate and cyclopentadiene.

Jasinski R, et al.

Monatshefte fur Chemie / Chemical Monthly, 144(3), 327-335 (2013)

Expedient synthesis of cyclopropane alpha-amino acids by the catalytic asymmetric cyclopropanation of alkenes using iodonium ylides derived from methyl nitroacetate.

Benoît Moreau et al.

Journal of the American Chemical Society, 127(51), 18014-18015 (2005-12-22)

A highly enantioselective (up to 97.5% ee) and diastereoselective (95:5 dr trans/cis) Cu(I)-catalyzed cyclopropanation of alkenes using phenyliodonium ylide generated in situ from iodosobenzene and methyl nitroacetate is reported. The cyclopropanation took place with high enantioselectivity for a wide range

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Global Trade Item Number

SKU	GTIN
366463-5G	04061836684792
366463-1G	04061836677237