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N26806

Sigma-Aldrich

trans-β-Nitrostyrene

99%

Synonym(s):

trans-beta-Nitrostyrene, trans-1-Nitro-2-phenylethylene

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About This Item

Linear Formula:
C6H5CH=CHNO2
CAS Number:
5153-67-3
Molecular Weight:
149.15
Beilstein:
1210066
MDL number:
MFCD00007402
UNSPSC Code:
12352100
PubChem Substance ID:
24897584
NACRES:
NA.22

Assay

99%

form

crystals

bp

250-260 °C (lit.)

mp

55-58 °C (lit.)

storage temp.

2-8°C

SMILES string

[O-][N+](=O)\C=C\c1ccccc1

InChI

1S/C8H7NO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H/b7-6+

InChI key

PIAOLBVUVDXHHL-VOTSOKGWSA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bridging between organocatalysis and biocatalysis: asymmetric addition of acetaldehyde to β-nitrostyrenes catalyzed by a promiscuous proline-based tautomerase.
Ellen Zandvoort et al.
Angewandte Chemie (International ed. in English), 51(5), 1240-1243 (2011-12-23)
Ellen Zandvoort et al.
Chembiochem : a European journal of chemical biology, 13(13), 1869-1873 (2012-08-02)
Serendipitous switch: While exploring cis-nitrostyrene as a potential electrophile in Michael-type addition reactions catalysed by the enzyme 4-oxalocrotonate tautomerase (4-OT), it was unexpectedly found that 4-OT catalyses the isomerisation of cis-nitrostyrene to trans-nitrostyrene (k(cat) /K(m) = 1.9×10(3)  M(-1)  s(-1) ).
Junguk Park et al.
Biochemistry, 43(47), 15014-15021 (2004-11-24)
Protein tyrosine phosphatases (PTPs) catalyze the hydrolysis of phosphotyrosyl (pY) proteins to produce tyrosyl proteins and inorganic phosphate. Specific PTPs inhibitors provide useful tools for studying PTP function in signal transduction processes and potential treatment for human diseases such as
Catalytic asymmetric intermolecular Stetter reactions of enolizable aldehydes with nitrostyrenes: computational study provides insight into the success of the catalyst.
Daniel A DiRocco et al.
Angewandte Chemie (International ed. in English), 51(10), 2391-2394 (2012-01-28)
Jens Martin Werner et al.
Journal of pharmacological and toxicological methods, 57(2), 131-137 (2007-12-19)
Induction of apoptosis is perceived as the main intention of drug regimens for tumour therapy. Thus, the concentration- and time-dependence of drug-induced apoptosis should be carefully evaluated for experimental as well as for standard anti-tumour agents. A main feature of
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