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16125

Sigma-Aldrich

Ethyl cis-3-bromoacrylate

≥99.0% (GC)

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About This Item

Fórmula empírica (notación de Hill):
C5H7BrO2
Número de CAS:
31930-34-4
Peso molecular:
179.01
Beilstein/REAXYS Number:
1902817
MDL number:
MFCD00674501
UNSPSC Code:
12352100
PubChem Substance ID:
57647549
NACRES:
NA.22

assay

≥99.0% (GC)

refractive index

n20/D 1.481

density

1.48 g/mL at 20 °C

storage temp.

2-8°C

SMILES string

CCOC(=O)\C=C/Br

InChI

1S/C5H7BrO2/c1-2-8-5(7)3-4-6/h3-4H,2H2,1H3/b4-3-

InChI key

UJTJVQIYRQALIK-ARJAWSKDSA-N

Application

Ethyl cis-3-bromoacrylate was used in the preparation of ethyl 2-amino-9-(2-deoxy-β-D-erythropentofuranosyl)-6,9-dihydro-6-oxo-1H-purine-1-acrylate. It was used in the synthesis of 3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,4-dihydropyrimido[1,2-a]purine-6,10-dione. It was employed as building block for the stereoselective preparation of cis-2-enoates.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Jozsef Szekely et al.
Nucleosides, nucleotides & nucleic acids, 27(2), 103-109 (2008-01-22)
Short, "one-pot" syntheses of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine are described. These syntheses proceed in improved yield and easier purification than previous syntheses and are well suited for the preparation of isotopically labeled nucleoside adducts for biomarker and
Michael B Otteneder et al.
Proceedings of the National Academy of Sciences of the United States of America, 103(17), 6665-6669 (2006-04-15)
3-(2-Deoxy-beta-D-erythro-pentofuranosyl)pyrimido[1,2-alpha]purin-10(3H)-one (M1dG) is a DNA adduct arising from the reaction of 2-deoxyguanosine with the lipid peroxidation product, malondialdehyde, or the DNA peroxidation product, base propenal. M1dG is mutagenic in bacteria and mammalian cells and is present in the genomic DNA
A.B. Smith et al.
Tetrahedron Letters, 26, 4419-4419 (1985)
X. Lu et al.
Tetrahedron Letters, 33, 2535-2535 (1992)
Alessio Grimaldi et al.
Communications biology, 3(1), 85-85 (2020-02-27)
Here, we developed an unbiased, functional target-discovery platform to identify immunogenic proteins from primary non-small cell lung cancer (NSCLC) cells that had been induced to apoptosis by cisplatin (CDDP) treatment in vitro, as compared with their live counterparts. Among the
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