2-Nitrobenzyl bromide Chemical Properties

Melting point:

44-46 °C (lit.)

Boiling point:

265.51°C (rough estimate)

Density 

1.6841 (rough estimate)

refractive index 

1.6120 (estimate)

Flash point:

>230 °F

storage temp. 

Inert atmosphere,2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)

form 

Crystals or Crystalline Powder

color 

Yellow to light brown

Water Solubility 

insoluble

BRN 

638991

Stability:

Hygroscopic

InChI

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

InChIKey

HXBMIQJOSHZCFX-UHFFFAOYSA-N

SMILES

C1(CBr)=CC=CC=C1[N+]([O-])=O

CAS DataBase Reference

3958-60-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Nitrobenzyl bromide(3958-60-9)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

4.8-19-21

HazardClass 

8

PackingGroup 

II

HS Code 

29049085

MSDS

• Language:English Provider:2-Nitrobenzyl bromide
• Language:English Provider:SigmaAldrich
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2-Nitrobenzyl bromide Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

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.

Uses

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.

Biochem/physiol Actions

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.

Synthesis

In a 5000 L bromination reactor, 300 kg of dichloroethane, 226 kg of o-nitrotoluene and 27 kg of azobisisobutyronitrile were added sequentially. After stirring for 20 minutes, the mixed solution was transferred to a high tank and set aside; the bromination reactor was then refilled. To the reactor, 300 kg of dichloroethane and 226 kg of o-nitrotoluene were added, mixed thoroughly, then 889.03 kg of 40% hydrobromic acid was added, and the mixture was stirred at 72 to 75°C. The mixture was then transferred to the high tank and set aside for 20 minutes. From the high tank, the mixed solution was slowly added to the bromination reactor with 448.26 kg of 30% hydrogen peroxide at a 1:4 dropwise rate. After dropwise addition, the reaction was continued for 2 hours. After completion of the reaction, it was cooled to room temperature and analyzed by HPLC. The feedstock conversion was over 99.0% and no by-products such as dibrominated products were detected. The molar ratio of o-nitrotoluene, 40% hydrobromic acid and 30% hydrogen peroxide in the reaction was 1:1.2:1.2. After static partitioning, the upper aqueous phase was separated; the lower organic phase was washed with 600 L of water, and the solvent was removed by distillation under reduced pressure, and finally washed with cold dichloroethane to obtain a white 2-nitrobenzyl bromide solid product in 98.5% yield.

References

[1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[2] Patent: CN107778181, 2018, A. Location in patent: Paragraph 0008; 0028; 0029
[3] Patent: CN108440301, 2018, A. Location in patent: Page/Page column 0038-0058
[4] Patent: CN108203384, 2018, A. Location in patent: Paragraph 0022; 0023; 0024; 0025; 0026; 0027
[5] Patent: EP2308868, 2011, A1. Location in patent: Page/Page column 18

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