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107794

Sigma-Aldrich

2-Nitrobenzyl bromide

98%

Sinonimo/i:

α-Bromo-2-nitrotoluene

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About This Item

Formula condensata:
O2NC6H4CH2Br
Numero CAS:
3958-60-9
Peso molecolare:
216.03
Beilstein:
638991
Numero CE:
223-558-9
Numero MDL:
MFCD00007184
Codice UNSPSC:
12352100
ID PubChem:
24846780
NACRES:
NA.22

Saggio

98%

Forma fisica

solid

Punto di fusione

44-46 °C (lit.)

Gruppo funzionale

bromo

Stringa SMILE

[O-][N+](=O)c1ccccc1CBr

InChI

1S/C7H6BrNO2/c8-5-6-3-1-2-4-7(6)9(10)11/h1-4H,5H2
HXBMIQJOSHZCFX-UHFFFAOYSA-N

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Applicazioni

2-Nitrobenzyl bromide was used for caging unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution. It can be used in the synthesis of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one.

Azioni biochim/fisiol

2-Nitrobenzyl bromide reacts with L-cysteine to form S-2-nitrobenzyl-cysteine which was used for modification of ultra-low-gelling-temperature (ULGT) agarose.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314

Classi di pericolo

Eye Dam. 1 - Skin Corr. 1B

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

230.0 °F - closed cup

Punto d’infiammabilità (°C)

110 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
STBK6371
STBK4666
STBJ8925
STBJ4110
STBH3553

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Kyoung-Ho Park et al.
International journal of molecular sciences, 20(16) (2019-08-21)
A kinetic study was carried out on the solvolysis of o-nitrobenzyl bromide (o-isomer, 1) and p-nitrobenzyl bromide (p-isomer, 3), and o-nitrobenzoyl chloride (o-isomer, 2) in a wide range of solvents under various temperatures. In all of the solvents without aqueous
Ying Luo et al.
Nature materials, 3(4), 249-253 (2004-03-23)
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A practical synthesis of (R)-and (S)-3-amino-3, 4-dihydro-1H-quinolin-2-one.
Hulin B and Lopaze MG.
Tetrahedron Asymmetry, 15(12), 1957-1958 (2004)
P Pan et al.
FEBS letters, 405(1), 81-85 (1997-03-17)
Photoreleasable molecules are important in studies of various biological phenomena, especially cell signaling. Here we report a generally applicable approach for 'caging' unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution with 2-nitrobenzyl bromides. Photolysis of the caged peptides was achieved
William L Scott et al.
Journal of combinatorial chemistry, 11(1), 14-33 (2008-12-25)
Distributed Drug Discovery (D(3)) proposes solving large drug discovery problems by breaking them into smaller units for processing at multiple sites. A key component of the synthetic and computational stages of D(3) is the global rehearsal of prospective reagents and
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