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577-19-5

Basic Information
CAS No.: 577-19-5
Name: Benzene,1-bromo-2-nitro-
Article Data: 129
Cas Database
Molecular Structure:
Molecular Structure of 577-19-5 (Benzene,1-bromo-2-nitro-)
Formula: C6H4BrNO2
Molecular Weight: 202.007
Synonyms: 2-Bromo-1-nitrobenzene;2-Bromonitrobenzene;2-Nitro-1-bromobenzene;2-Nitrobromobenzene;2-Nitrophenyl bromide;NSC 403836;o-Bromonitrobenzene;o-Nitrobromobenzene;o-Nitrophenyl bromide;
EINECS: 209-409-0
Density: 1.719 g/cm3
Melting Point: 40-42 °C(lit.)
Boiling Point: 261 °C at 760 mmHg
Flash Point: 87.8 °C
Solubility: insoluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: HarmfulXn, IrritantXi
Risk Codes: 20/21/22-36/37/38
Safety: 36/37-36/37/39-26-22
Transport Information: UN 3459 6.1/PG 3
PSA: 45.82000
LogP: 2.88050
Synthetic route
552-16-9

ortho-nitrobenzoic acid

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With bromine; dibromoisocyanuric acid In dichloromethane at 20℃; for 24h; Reagent/catalyst; Concentration; UV-irradiation;100%
With Bromotrichloromethane; trichloroisocyanuric acid; bromine In tetrachloromethane at 10 - 120℃; for 18h; Temperature; Reagent/catalyst; Concentration; Photolysis;97%
With [bis(acetoxy)iodo]benzene; bromine In various solvent(s) for 22h; bromodecarboxylation; Heating; irradiation;51%
6319-40-0

4-bromo-3-nitrobenzoic acid

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With sulfolane; sodium hydrogencarbonate at 195℃; for 2h;92%

2-nitrobenzenediazonium o-benzenedisulfonamide

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper In acetonitrile at 20℃; for 0.75h; Substitution;89%
With tetrabutylammomium bromide In acetonitrile at 60℃; for 0.75h; Substitution;83%
244205-40-1

(2-bromophenyl)boronic acid

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With Iron(III) nitrate nonahydrate In toluene at 80℃; for 18h; Inert atmosphere;87%
With copper(I) oxide; ammonium hydroxide; oxygen; sodium nitrite In water at 25℃; for 36h;44%

C14H10Br2F3IO4S

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With sodium nitrite In 1,2-dichloro-ethane at 20 - 80℃; Schlenk technique;85%
88-74-4

2-nitro-aniline

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With tert.-butylnitrite; tetrabutylammomium bromide; copper(I) bromide; 10-camphorsulfonic acid In acetonitrile at 20℃; for 24h; Reagent/catalyst; Time; Solvent;83%
With potassium nitrite; hydrogen bromide; dimethyl sulfoxide In water at 35℃; for 0.25h;78%
With tert.-butylnitrite; tetrabutylammomium bromide; toluene-4-sulfonic acid; copper(ll) bromide In acetonitrile at 20℃; for 1h;76%
609-73-4

o-nitroiodobenzene

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With aluminum oxide; copper(I) bromide In various solvent(s) at 150℃; for 8h;80%
5570-19-4

2-nitrophenylboronic acid

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
With sodium nitrite In acetonitrile at 80℃; for 20h; Sealed tube;80%
98-95-3

nitrobenzene

577-19-5

2-nitrophenyl bromide

Conditions
ConditionsYield
Stage #1: nitrobenzene With acetic acid at 0℃;
Stage #2: With bromine at 20℃; for 12h;
78.9%
With bromine; acetic acid at 0 - 20℃; for 12h;78.9%
With hydrogen bromide; dimethyl sulfoxide for 21h; Ambient temperature;67%
108-86-1

bromobenzene

A

577-19-5

2-nitrophenyl bromide

B

586-78-7

para-nitrophenyl bromide

Conditions
ConditionsYield
With nitric acid at 50℃; for 3h;A 20.9%
B 78.2%
With Iron(III) nitrate nonahydrate; phosphorus pentoxide In neat (no solvent) at 20℃; for 6h; Milling; Green chemistry; Overall yield = 93 percent;A 25%
B 68%
With thionyl chloride; bismuth subnitrate In dichloromethane at 20℃; for 9h;A 18%
B 60%
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Specification

The IUPAC name of 2-Nitrobromobenzene is 1-bromo-2-nitrobenzene. With the CAS registry number 577-19-5, it is also named as Benzene, 1-bromo-2-nitro-. The product's categories are Aromatic Hydrocarbons (substituted) & Derivatives; Benzene Derivates; Miscellaneous; Bromine Compounds; Nitro Compounds; Nitrogen Compounds; Organic Building Blocks. It is white to light yellow crystal powder which is easily soluble in ethanol, soluble in ether and benzene, insoluble in water. What's more, it is stable, combustible and incompatible with strong bases, strong oxidizing agents. When heated to decomposition it emits toxic vapors of NOx and Br. So the storage environment should be well- ventilated, low-temperature and dry. Keep 2-Nitrobromobenzene separate from oxidants and food additives.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.52; (4)ACD/LogD (pH 7.4): 2.52; (5)ACD/BCF (pH 5.5): 48.44; (6)ACD/BCF (pH 7.4): 48.44; (7)ACD/KOC (pH 5.5): 559.63; (8)ACD/KOC (pH 7.4): 559.63; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.605; (13)Molar Refractivity: 40.48 cm3; (14)Molar Volume: 117.4 cm3; (15)Polarizability: 16.05×10-24 cm3; (16)Surface Tension: 50.5 dyne/cm; (17)Enthalpy of Vaporization: 47.86 kJ/mol; (18)Vapour Pressure: 0.0192 mmHg at 25°C; (19)Exact Mass: 200.942541; (20)MonoIsotopic Mass: 200.942541; (21)Topological Polar Surface Area: 45.8; (22)Heavy Atom Count: 10; (23)Complexity: 134.

Preparation of 2-Nitrobromobenzene: It can be obtained by o-nitroaniline. The mixture of o-nitroaniline and sulfuric acid is cooled to 0-5 °C. Adding sodium nitrite solution slowly under stirring. When the reaction makes potassium iodide starch test paper turn blue, we stops. The obtained diazonium salt solution adds to 40 °C CuBr solution while stirring. After cooling, it is extracted with diethyl ether. The extract is washed by lye, hydrochloric acid and water. Then we can get the product after the recovery of ether. The yield is 70%.

Uses of 2-Nitrobromobenzene: It is used in organic synthesis. It also can react with 2-methylamino-benzoic acid to get N-methyl-N-(2-nitro-phenyl)-anthranilic acid. This reaction needs reagents potassium carbonate, copper powder and isoamyl alcohol.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure.
1. SMILES:O=[N+]([O-])c1ccccc1Br
2. InChI:InChI=1/C6H4BrNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H 
3. InChIKey:ORPVVAKYSXQCJI-UHFFFAOYAL