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N26806

trans-β-Nitrostyrene

Name: <I>trans</I>-β-Nitrostyrene
Brand: ALDRICH

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

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24897584

MDL number:

MFCD00007402

Beilstein/REAXYS Number:

1210066

Assay:

99%

Form:

crystals

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Properties

Quality Level

100

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

Description

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

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

An unexpected promiscuous activity of 4-oxalocrotonate tautomerase: the cis-trans isomerisation of nitrostyrene.

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) ).

(S)-Proline-catalyzed nitro-Michael reactions: towards a better understanding of the catalytic mechanism and enantioselectivity.

Hui Yang et al.

Organic & biomolecular chemistry, 10(16), 3229-3235 (2012-03-10)

(S)-Proline-catalyzed nitro-Michael additions of aldehydes and ketones to β-nitrostyrene were investigated computationally (MP2/6-311+G**//M06-2X/6-31G**). Contrary to what is usually assumed in organocatalysis, the lowest-energy transition states of proline-catalyzed nitro-Michael reactions do not necessarily involve the carboxylic acid group of the proline

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