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366463

Sigma-Aldrich

Methyl nitroacetate

98%

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About This Item

Linear Formula:
NO2CH2COOCH3
CAS Number:
2483-57-0
Molecular Weight:
119.08
Beilstein/REAXYS Number:
1758670
EC Number:
219-622-0
MDL number:
MFCD00075480
UNSPSC Code:
12352100
PubChem Substance ID:
24862657
NACRES:
NA.22

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.)

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

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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

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

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

Certificates of Analysis (COA)

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Sigma-Aldrich

360554

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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)
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
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
[Experimental establishment of the maximum permissible concentration of the methyl and ethyl esters of nitroacetic acid].
G I Sidorin et al.
Gigiena truda i professional'nye zabolevaniia, (7)(7), 49-51 (1980-07-01)

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