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

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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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 107794
Product name: 2-Nitrobenzyl bromide
Purity: 98%
Packaging: 5g
Price: $40.94
Updated: 2025/07/31

Sigma-Aldrich

Product number: 107794
Product name: 2-Nitrobenzyl bromide
Purity: 98%
Packaging: 25g
Price: $136
Updated: 2025/07/31

TCI Chemical

Product number: N0404
Product name: 2-Nitrobenzyl Bromide
Purity: >98.0%(GC)
Packaging: 5g
Price: $40
Updated: 2025/07/31

TCI Chemical

Product number: N0404
Product name: 2-Nitrobenzyl Bromide
Purity: >98.0%(GC)
Packaging: 25g
Price: $139
Updated: 2025/07/31

Usbiological

Product number: 285028
Product name: 2-Nitrobenzyl bromide
Packaging: 250g
Price: $545
Updated: 2021/12/16

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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

2-Nitrotoluene 2,2'-Azobis(2-methylpropionitrile) Carbon tetrachloride

Preparation Products

2-NITRO-ALPHA-TOLUENESULFONYL CHLORIDE

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View Lastest Price from 2-Nitrobenzyl bromide manufacturers

Henan Aochuang Chemical Co.,Ltd.

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

Hebei Chuanghai Biotechnology Co,.LTD

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

Hebei Fengqiang Trading Co., LTD

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

3958-60-9, 2-Nitrobenzyl bromideRelated Search:

2-Nitrobenzyl alcohol 2-Nitrodiphenylamine 2-Nitrophenylacetic acid 2-Nitrobenzaldehyde 2-Nitrobenzoic acid 2-Nitrophenol Sodium Salt 2-NITRO-4-(TRIFLUOROMETHYL)BENZYL BROMIDE 2,4-DINITROBENZYL BROMIDE 2-FLUORO-6-NITROBENZYL BROMIDE,2-Fluoro-6-nitrobenzyl bromide 98% 4-Methoxy-2-nitrobenzyl bromide 2-Nitrobenzyl bromide 4,5-DIMETHOXY-2-NITROBENZYL BROMIDE,4,5-dimenoxy-2-nitrobenzyl bromide,4,5-Dimethoxy-2-nitrobenzyl bromide 95% 4-Bromomethyl-3-nitrobenzoic acid Methyl 2-bromomethyl-3-nitrobenzoate 4-BROMO-2-NITROBENZYL BROMIDE 3-FLUORO-4-NITROBENZYL BROMIDE 4-Nitrobenzyl bromide 4-Methoxy-3-nitrobenzyl bromide

1-(Bromomethyl)-2-nitrobenzene

1-Bromomethyl-2-nitro-benzene

Benzene, 1-(bromomethyl)-2-nitro-

-Bromo-2-mitrotoluene

o-Nitrobenaylbromide

2-NITROBENZYL BROMIDE

2-(BROMOMETHYL)NITROBENZENE

A-BROMO-O-NITROTOLUENE

ALPHA-BROMO-O-NITROTOLUENE

ALPHA-BROMO-2-NITROTOLUENE

O-NITROBENZYL BROMIDE

NITROBENZYL-2 BROMIDE

a-Bromo-2-nitrotoluene

2-Nitrobenzyl bromide, 98+%

2-Nitrobenzyl

α-Bromo-2-nitrotoluene

à-bromo-2-nitrotoluene

2-Benzyl bromide

1-Nitro-2-(bromomethyl)benzene

2-Nitrobenzyl bromide,97%

2-Nitrobenzyl bromid

1-(Bromomethyl)-2-nitrobenzene, alpha-Bromo-2-nitrotoluene

2-Nitrobenzyl broMide, 97% 5GR

2-Nitrobenayl broMide

2-Nitrobenzyl BroMide, 98.0%(GC)

LIXI-011

α-Bromo-2-nitrotoluene alpha-Bromo-o-nitrotoluene

2-Nitrobenzyl bromide, 98%, for synthesis

2-NitrobenzylBromide&gt

Rizatriptan EP Impurity3

3958-60-9

958-60-9

BENZYL HALIDE

Nitrogen Compounds

Organic Building Blocks

Nitro Compounds

DNA / RNA Synthesis

Protecting Agents for Hydroxyl Group (DNA/RNA Synthesis)

Building Blocks

Biochemistry

Nucleosides, Nucleotides & Related Reagents

Protecting Agents for Hydroxyl and Amino Groups

Protecting Agents, Phosphorylating Agents & Condensing Agents

Aromatic Halides (substituted)

ADVANCED INT.