2-Bromo-6-nitrotoluene
- Product Name
- 2-Bromo-6-nitrotoluene
- CAS No.
- 55289-35-5
- Chemical Name
- 2-Bromo-6-nitrotoluene
- Synonyms
- 1-BROMO-2-METHYL-3-NITROBENZENE;2-Bromo-6-nitrotoL;2-Bromo-6-Nitrotolune;6-BROMO-2-NITROTOLUENE;2-BROMO-6-NITROTOLUENE;Toluene, 2-bromo-6-nitro-;2-Bromo-6-nitrotoluene >2-BROMO-6-NITROTOLUENE 98+%;2-Bromo-6-nitrotoluene, 95%;2-methyi-3-nitrobromobenzene
- CBNumber
- CB2415725
- Molecular Formula
- C7H6BrNO2
- Formula Weight
- 216.03
- MOL File
- 55289-35-5.mol
2-Bromo-6-nitrotoluene Property
- Melting point:
- 38-40 °C (lit.)
- Boiling point:
- 143 °C/22 mmHg (lit.)
- Density
- 1.6841 (rough estimate)
- refractive index
- 1.6120 (estimate)
- Flash point:
- >110°C
- storage temp.
- Sealed in dry,Room Temperature
- form
- Low Melting Solid
- color
- Slightly beige to brown
- BRN
- 2502581
- InChI
- InChI=1S/C7H6BrNO2/c1-5-6(8)3-2-4-7(5)9(10)11/h2-4H,1H3
- InChIKey
- LYTNSGFSAXWBCA-UHFFFAOYSA-N
- SMILES
- C1(Br)=CC=CC([N+]([O-])=O)=C1C
- CAS DataBase Reference
- 55289-35-5(CAS DataBase Reference)
- NIST Chemistry Reference
- Benzene, 1-bromo-2-methyl-3-nitro-(55289-35-5)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-37/39-24/25
- RIDADR
- UN 2810 6.1/PG 1
- WGK Germany
- 3
- HS Code
- 29049090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 260053
- Product name
- 2-Bromo-6-nitrotoluene
- Purity
- 98%
- Packaging
- 25g
- Price
- $114
- Updated
- 2025/07/31
- Product number
- 260053
- Product name
- 2-Bromo-6-nitrotoluene
- Purity
- 98%
- Packaging
- 5g
- Price
- $59.8
- Updated
- 2023/06/20
- Product number
- B1878
- Product name
- 2-Bromo-6-nitrotoluene
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $46
- Updated
- 2025/07/31
- Product number
- B1878
- Product name
- 2-Bromo-6-nitrotoluene
- Purity
- >98.0%(GC)
- Packaging
- 25g
- Price
- $136
- Updated
- 2025/07/31
- Product number
- B697373
- Product name
- 1-Bromo-2-methyl-3-nitrobenzene
- Packaging
- 2.5g
- Price
- $65
- Updated
- 2021/12/16
2-Bromo-6-nitrotoluene Chemical Properties,Usage,Production
Chemical Properties
Beige solid
Uses
2-Bromo-6-nitrotoluene has been used:
- as starting reagent in total synthesis of N-acetyl methyl ester of (±)-clavicipitic acids
- in synthesis of carbazomadurin A, highly oxygenated neuronal cell protecting carbazole alkaloid
Synthesis Reference(s)
The Journal of Organic Chemistry, 49, p. 2657, 1984 DOI: 10.1021/jo00189a001
Synthesis
603-83-8
55289-35-5
1. Suspend 2-methyl-3-nitroaniline (45.6 g, 0.3 mol) in water (200 mL) and 40% aqueous hydrobromic acid (100 mL) and heat to reflux for 10 minutes. Cool to 0°C and slowly add aqueous sodium nitrite (20.7 g, 0.3 mol) (100 mL) dropwise, controlling the temperature to no more than 5°C. Continue stirring at 0-5°C for 30 min. 2. Slowly add the above diazonium salt solution to a stirred mixture of cuprous bromide (43.1 g, 0.3 mol) in hydrobromic acid (150 mL) and water (150 mL), and after stirring at room temperature for 30 minutes, heat the reaction to 70°C for 1 hour. The reaction solution was poured into ice water and extracted with dichloromethane (400 mL x 3), the organic phases were combined, washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. 3. The residue was purified by column chromatography (petroleum ether as eluent) to afford 1-bromo-2-methyl-3-nitrobenzene (58 g, 89% yield) as a light yellow solid. 4. 1-Bromo-2-methyl-3-nitrobenzene (37.0 g, 0.17 mol), N-bromosuccinimide (61 g, 0.34 mol) and azobisisobutyronitrile (0.7 g, 4.2 mmol) were refluxed in carbon tetrachloride (500 mL) overnight. The filtrate was filtered and concentrated to give the red liquid crude product 1-bromo-2-(bromomethyl)-3-nitrobenzene (53 g), which was used directly in the next step. 5. The crude product 1-bromo-2-(bromomethyl)-3-nitrobenzene (53 g) was stirred with a solution of sodium acetate (32.8 g, 0.4 mol) in N,N-dimethylformamide (300 mL) at 70 °C overnight. The reaction solution was diluted with water, extracted with ethyl acetate, the organic phases were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. 6. The residue was purified by column chromatography (petroleum ether/ethyl acetate=20/1) to give white solid 2-bromo-6-nitrobenzyl acetate (24.0 g, two-step overall yield 51%). 7. Under nitrogen protection, nitrogen was bubbled into a solution of 2-bromo-6-nitrobenzyl acetate (24.5 g, 0.089 mol) in 1,4-dioxane (500 mL) for 20 min, potassium acetate (38.4 g, 0.358 mol), [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (3.65 g, 4.5 mmol) and bis(pinacolato) alcoholato)diboron (34.1 g, 0.13 mol) and stirred at 95 °C for 20 hours. After cooling and concentration under reduced pressure, the residue was partitioned with ethyl acetate and water, the organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. 8. The residue was purified by column chromatography (petroleum ether/ethyl acetate=20/1) to afford 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-nitrobenzenemethanol as a white solid (11.0 g, 38% yield). lC-MS (ESI) m/z 322 [M+1]+ (calculated value 321.1). 9. To a solution of 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-nitrobenzenemethanol (11.0 g, 0.034 mol) in methanol (350 mL) was added an aqueous solution of 5N sodium hydroxide (17 mL, 0.085 mol) and refluxed under nitrogen protection for 24 hours. Concentrate under reduced pressure and dissolve in tetrahydrofuran (200 mL), add 5N hydrochloric acid (60 mL, 0.3 mol) and stir at 40°C for 16 hours. After cooling, it was diluted with ethyl acetate and poured into brine, the organic phase was separated, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. 10. The residue was recrystallized in a mixed solvent of ethyl acetate and petroleum ether to give 4-nitrobenzo[c][1,2]oxaborol-1(3H)-ol as a yellow solid (5.0 g, 81% yield).LC-MS (ESI) m/z 180 [M+1]+ (calculated value 179.0).1H NMR (300MHz, DMSO-d6): δ 9.59 ( s, 1H), 8.33 (d, 1H), 8.14 (d, 1H), 7.71 (t, 1H), 5.37 (s, 2H). 11. A solution of 4-nitrobenzo[c][1,2]oxaborol-1(3H)-ol (2.7 g, 0.015 mol) in methanol (150 mL) was hydrogenated by addition of palladium/carbon (1.0 g) overnight at atmospheric pressure and room temperature to afford the target product, 2-bromo-6-nitrotoluene (1.5 g, 66% yield). lc-MS (ESI) m/z 150 [M+1 ]+ (calculated value 149.1).1H NMR (300MHz, DMSO-d6): δ 8.92 (s, 1H), 7.02 (t, 1H), 6.90 (d, 1H), 6.62 (d, 1H), 4.99 (s, 2H), 4.77 (s, 2H).
References
[1] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 10162 - 10173
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2048 - 2054
[3] Archiv der Pharmazie, 2015, vol. 348, # 4, p. 266 - 274
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 17, p. 2013 - 2021
[5] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 1011,1016, 1025
2-Bromo-6-nitrotoluene Preparation Products And Raw materials
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View Lastest Price from 2-Bromo-6-nitrotoluene manufacturers
- Product
- 2-Bromo-6-nitrotoluene 55289-35-5
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 20 mt
- Release date
- 2024-11-25
- Product
- 1-Bromo-2-methyl-3-nitrobenzene 55289-35-5
- Price
- US $122.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2024-01-11
- Product
- 2-Bromo-6-nitrotoluene 55289-35-5
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99.99%
- Supply Ability
- 50000tons
- Release date
- 2023-08-04