2-Nitrobenzyl bromide
- Product Name
- 2-Nitrobenzyl bromide
- CAS No.
- 3958-60-9
- Chemical Name
- 2-Nitrobenzyl bromide
- Synonyms
- 1-(Bromomethyl)-2-nitrobenzene;2-Nitrobenzyl;LIXI-011;2-Benzyl bromide;o-Nitrobenaylbromide;2-Nitrobenzyl bromid;2-NITROBENZYL BROMIDE;-Bromo-2-mitrotoluene;O-NITROBENZYL BROMIDE;NITROBENZYL-2 BROMIDE
- CBNumber
- CB9478950
- Molecular Formula
- C7H6BrNO2
- Formula Weight
- 216.03
- MOL File
- 3958-60-9.mol
2-Nitrobenzyl bromide Property
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H314Causes severe skin burns and eye damage
H335May cause respiratory irritation
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
N-Bromosuccinimide Price
- Product number
- 107794
- Product name
- 2-Nitrobenzyl bromide
- Purity
- 98%
- Packaging
- 5g
- Price
- $40.94
- Updated
- 2025/07/31
- Product number
- 107794
- Product name
- 2-Nitrobenzyl bromide
- Purity
- 98%
- Packaging
- 25g
- Price
- $136
- Updated
- 2025/07/31
- Product number
- N0404
- Product name
- 2-Nitrobenzyl Bromide
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $40
- Updated
- 2025/07/31
- Product number
- N0404
- Product name
- 2-Nitrobenzyl Bromide
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $139
- Updated
- 2025/07/31
- Product number
- B685690
- Product name
- 1-(Bromomethyl)-2-nitrobenzene
- Packaging
- 5g
- Price
- $55
- Updated
- 2021/12/16
2-Nitrobenzyl bromide Chemical Properties,Usage,Production
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
88-72-2
3958-60-9
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
2-Nitrobenzyl bromide Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 2-Nitrobenzyl bromide manufacturers
- Product
- 2-Nitrobenzyl bromide 3958-60-9
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 1Ton
- Release date
- 2022-10-19
- Product
- 2-Nitrobenzyl bromide 3958-60-9
- Price
- US $9.00/KG
- Min. Order
- 1KG
- Purity
- 99.9
- Supply Ability
- 1 ton
- Release date
- 2024-08-21
- Product
- 2-Nitrobenzyl bromide 3958-60-9
- Price
- US $100.00/kg
- Min. Order
- 1kg
- Purity
- 99
- Supply Ability
- 5000
- Release date
- 2023-06-15