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A13127 2-Nitrobenzyl bromide, 98+%

CAS Number
3958-60-9
Synonyms
alpha-Bromo-2-nitrotoluene

Stock No. Size Price ($) Quantity Availability
A13127-06 5g 48.50
A13127-14 25g 162.00
A13127-22 100g 566.00
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2-Nitrobenzyl bromide, 98+%

MDL
MFCD00007184
EINECS
223-558-9

Chemical Properties

Formula
C7H6BrNO2
Formula Weight
216.04
Melting point
45-48°
Flash Point
>110°(230°F)
Storage & Sensitivity
Keep Cold.
Solubility
Insoluble in water.

Applications

2-Nitrobenzyl bromide is used in the preparation of S-2-nitrobenzyl-cysteine by reaction with L-cysteine. It is also used for the introduction of the 2-nitrobenzyl protecting group in organic synthesis. It plays an important role in the production of expectorant agent. Further, it is employed for caging unprotected cysteine-containing or thiophosphorylated peptides in aqueous solution. In addition to this, it is used in the preparation of (R)- and (S)-3-amino-3,4-dihydro-1H-quinolin-2-one.

Notes

Moisture sensitive. Incompatible with alcohols, bases, amines and oxidizing agents.

Literature References

Photosensitive protecting reagent for alcohols, acids, phenols etc: J. Am. Chem. Soc., 91, 5694 (1969); J. Org. Chem., 37, 2281, 2285 (1972); Compare 4,5-Dimethoxy-2-nitrobenzyl­ alcohol, L00719. Has also been recommended for the protection of the imidazole function in histidine containing peptides: J. Am. Chem. Soc., 97, 440 (1975). See Appendix 6. It has been investigated as a photocleavable protecting group for various N-heterocycles: Tetrahedron Lett., 39, 359 (1998). For reviews of photoremovable groups in organic synthesis, see: Synthesis, 1 (1980); Org. Photochem., 9, 225 (1987).

Lee, S. J.; Fowler, J. S.; Alexoff, D.; Schueller, M.; Kim, D.; Nauth, A.; Weber, C.; Kim, S. W.; Hooker, J. M.; Ma, L.; Qu, W. An efficient and practical synthesis of [2-11C]indole via superfast nucleophilic [11C]cyanation and RANEY® Nickel catalyzed reductive cyclization. Org. Biomol. Chem. 2015, 13 (46), 11235-11243.

Bathula, C.; Dangi, P.; Hati, S.; Agarwal, R.; Munshi, P.; Singh, A.; Singh, S.; Sen, S. Diverse synthesis of natural product inspired fused and spiro-heterocyclic scaffolds via ring distortion and ring construction strategies. New J. Chem. 2015, 39 (12), 9281-9292.

GHS Hazard and Precautionary Statements

Hazard Statements: H314

Causes severe skin burns and eye damage.

Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
638991
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2904.99
TSCA
No

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