| Identification | More | [Name]
2-Nitrobenzyl bromide | [CAS]
3958-60-9 | [Synonyms]
2-(BROMOMETHYL)NITROBENZENE
2-NITROBENZYL BROMIDE
A-BROMO-O-NITROTOLUENE
ALPHA-BROMO-2-NITROTOLUENE
ALPHA-BROMO-O-NITROTOLUENE
NITROBENZYL-2 BROMIDE
O-NITROBENZYL BROMIDE
1-(Bromomethyl)-2-nitrobenzene
1-Bromomethyl-2-nitro-benzene
Benzene, 1-(bromomethyl)-2-nitro-
-Bromo-2-mitrotoluene
o-Nitrobenaylbromide
α-Bromo-2-nitrotoluene
a-Bromo-2-nitrotoluene
2-Nitrobenzyl bromide, 98+%
2-Nitrobenzyl
à-bromo-2-nitrotoluene
2-Benzyl bromide
1-Nitro-2-(bromomethyl)benzene | [EINECS(EC#)]
223-558-9 | [Molecular Formula]
C7H6BrNO2 | [MDL Number]
MFCD00007184 | [Molecular Weight]
216.03 | [MOL File]
3958-60-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [Melting point ]
44-46 °C (lit.) | [Boiling point ]
265.51°C (rough estimate) | [density ]
1.6841 (rough estimate) | [refractive index ]
1.6120 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly) | [form ]
Crystals or Crystalline Powder | [color ]
Yellow to light brown | [Water Solubility ]
insoluble | [Detection Methods]
GC | [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) | [Storage Precautions]
Moisture sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS05,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H314-H335 | [Precautionary statements ]
P260-P280-P303+P361+P353-P305+P351+P338+P310 | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [F ]
4.8-19-21 | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29049085 | [Storage Class]
8A - Combustible corrosive hazardous materials | [Hazard Classifications]
Eye Dam. 1
Skin Corr. 1B |
| Hazard Information | Back Directory | [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. | [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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