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100-11-8 - 4-Nitrobenzyl bromide, 97+% - alpha-Bromo-4-nitrotoluene - A15236 - Alfa Aesar

A15236 4-Nitrobenzyl bromide, 97+%

CAS Number
100-11-8
Synonyms
alpha-Bromo-4-nitrotoluene

Size Price ($) Quantity Availability
25g 33.39
100g 98.10
500g 373.16
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4-Nitrobenzyl bromide, 97+%

MDL
MFCD00007373
EINECS
202-820-6

Chemical Properties

Formula
C7H6BrNO2
Formula Weight
216.04
Melting point
97-101°
Solubility
It hydrolyzes in water. Soluble in alcohol and ether.

Applications

4-Nitrobenzyl bromide is used in the synthesis of di and tri-substituted azoles. It is also used in the preparation of N6-Benzyladenosine-5’-uronamides as selective A3 adenosine agonists.

Notes

Stable under recommended storage conditions. Incompatible with oxidizing agents, amines, bases and alcohols.

Literature References

Josef Prousek. The course of reaction of 4-nitrobenzyl bromide and 5-nitrofurfuryl bromide with bases: Operation of anion-radical mechanism. Collect. Czech. Chem. Commun. 1982, 47,(5), 1334-1338.

 

Paul G.Bulger; Ian F.Cottrell; Cameron J.Cowden; Antony J.Davies; Ulf-H Dolling. An investigation into the alkylation of 1,2,4-triazole. Tetrahedron Letters. 2000, 41,(8), 1297-1301.

Has been used as a protecting reagent for the carboxyl group in peptide synthesis: Helv. Chim. Acta, 42, 972 (1959); see 4-Nitrobenzyl­ chloride, A15749, and Appendix 6. Has also been used in ß-lactam synthesis. Cleavage by sodium sulfide avoids hydrogenolysis problems otherwise encountered with these sulfur-containing nuclei: J. Org. Chem., 43, 1243 (1978).

For the protection of alcohols, introduction of the group by the use of silver oxide has been recommended. Selective cleavage can be accomplished with DDQ (2,3-Dichloro-5,6-dicyanobenzoquinone, A11879) or by anodic oxidation. Many other benzyl-type protecting groups are unaffected by these conditions: Tetrahedron Lett., 31, 389 (1990). Indium metal in the presence of ammonium chloride is an effective deprotection system for 4-nitrobenzyl ethers and esters: J. Chem. Soc., Perkin 1, 955 (2001).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

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

Other References

Beilstein
742796
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2904.90
TSCA
Yes
RTECS
XS7967000

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