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2-Bromoaniline
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Name

2-Bromoaniline

 EINECS 210-421-3
CAS No. 615-36-1 Density 1.594 g/cm3
PSA 26.02000 LogP 2.61250
Solubility soluble in alcohol and ether, insoluble in water Melting Point 29 °C
Formula C6H6BrN Boiling Point 227 °C at 760 mmHg
Molecular Weight 172.024 Flash Point 91.1 °C
Transport Information UN 2811 6.1/PG 3 Appearance clear yellow to red-brown liquid after melting
Safety 36/37-45-61-36/37/39-26 Risk Codes 23/24/25-33-52/53-36/37/38-20/21/22
Molecular Structure Molecular Structure of 615-36-1 (2-Bromoaniline) Hazard Symbols ToxicT, HarmfulXn,
Synonyms

Aniline,o-bromo- (8CI);2-Amino-1-bromobenzene;2-Bromobenzenamine;2-Bromophenylamine;NSC 7086;o-Aminobromobenzene;o-Bromoaniline;

Article Data 223

2-Bromoaniline Synthetic route

577-19-5

2-nitrophenyl bromide

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With hydrogen In tetrahydrofuran; water at 120℃; under 22502.3 Torr; for 4h; Autoclave;99%
With hydrazine In ethanol at 80℃; for 0.333333h; Catalytic behavior; chemoselective reaction;99.6%
With hydrogen In water at 120℃; under 15001.5 Torr; for 5h; Green chemistry; chemoselective reaction;99%
583-53-9

1,2-dibromobenzene

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With 2-((dicyclohexylphosphino)methyl)-1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium iodide; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;99%
With 2-(di-tert-butylphosphino)-1-mesityl-4,5-diphenyl-1H-imidazole; ammonia; palladium diacetate; sodium t-butanolate In 1,4-dioxane at 120℃; under 7500.75 Torr; for 24h; Autoclave; Inert atmosphere;> 99 %Chromat.
2593-27-3

2-bromo-N-hydroxybenzamide

615-36-1

2-bromoaniline

Conditions
ConditionsYield
Stage #1: o-bromo-N-hydroxybenzamide With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 50℃; for 2h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃;		99%
With sodium hydroxide In dimethyl sulfoxide at 80℃; for 1.5h; Lossen rearrangement;
Stage #1: o-bromo-N-hydroxybenzamide With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.0833333h;
577-19-5

2-nitrophenyl bromide

A

62-53-3

aniline

B

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With hydrazine hydrate In toluene at 20℃; for 3h; Inert atmosphere;A n/a
B 97%
With hydrogenchloride; zinc(II) chloride In benzene Ambient temperature; electrolysis; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With water; zinc at 250℃; for 0.3h; Reduction; Title compound not separated from byproducts;
With 5%-palladium/activated carbon; hydrazine hydrate In methanol at 80℃; for 0.0833333h; Overall yield = 95 %;
With hydrogen In toluene at 110℃; under 7500.75 Torr; for 0.75h; Autoclave;
10113-38-9

N-(2-bromophenyl)formamide

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 110℃; under 15001.5 Torr; for 3h; Catalytic behavior;97%
With sodium hydroxide In ethanol; water at 40℃; Kinetics;
3302-39-4

1-azido-2-bromobenzene

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With ammonium hydroxide at 90℃; for 1.25h;96%
With D-glucose; potassium hydroxide In water at 85℃; for 0.166667h; Green chemistry; chemoselective reaction;85%
With tributylgermanium hydride; thiophenol In toluene for 0.5h; Heating;5%
15426-16-1

bis-(2-bromo-phenyl)-diazene

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With aminomethyl polystyrene resin formic acid salt; zinc In methanol at 20℃; for 0.25h;94%
With formic acid; zinc In methanol at 20℃; for 0.116667h;93%
With ammonium formate; nickel In methanol at 20℃; for 0.116667h;93%
15426-16-1

(E)-1,2-bis(2-bromophenyl)diazene

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With nickel; hydrazinium monoformate In methanol for 0.116667h; Heating;93%
62-53-3

aniline

A

106-40-1

4-bromo-aniline

B

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With dihydrogen peroxide; potassium bromide In water; acetonitrileA 87%
B 12%
With pyridinium hydrobromide perbromide In tetrahydrofuran for 0.25h; Product distribution; other aromatic amines;A 84%
B n/a
With N-Bromosuccinimide; silver hexafluoroantimonate; 1-methylthiotriptycene In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique; Overall yield = 95 percentSpectr.;A 76%
B n/a
244205-40-1

(2-bromophenyl)boronic acid

615-36-1

2-bromoaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide; air In methanol at 20℃; for 16h;87%
With copper(I) oxide; ammonium hydroxide; oxygen; sodium hydroxide In water at 25℃; for 15h;78%
With sodium hydroxide; hydroxylamine-O-sulfonic acid In acetonitrile at 20℃; for 16h;70%

2-Bromoaniline Specification

The IUPAC name of this chemical is 2-bromoaniline. With the CAS registry number 615-36-1, it is also named as Benzenamine, 2-bromo-. The product's categories are Amines; Blocks; Bromides; Anilines, Aromatic Amines and Nitro Compounds; Miscellaneous; Anilines, Amides & Amines; Bromine Compounds; C2 to C6; Nitrogen Compounds. It is clear yellow to red-brown liquid after melting which is soluble in alcohol and ether, insoluble in water. Additionally, this chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.19; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.19; (4)ACD/LogD (pH 7.4): 2.19; (5)#H bond acceptors: 1; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 1; (8)Index of Refraction: 1.625; (9)Molar Refractivity: 38.17 cm3; (10)Molar Volume: 107.8 cm3; (11)Polarizability: 15.13×10-24 cm3; (12)Surface Tension: 47.7 dyne/cm; (13)Enthalpy of Vaporization: 46.35 kJ/mol; (14)Vapour Pressure: 0.0795 mmHg at 25°C; (15)Exact Mass: 170.968362; (16)MonoIsotopic Mass: 170.968362; (17)Topological Polar Surface Area: 26; (18)Heavy Atom Count: 8; (19)Complexity: 74.9.

Preparation of 2-Bromoaniline: It can be obtained by nitrophenylamine with diazotization, bromination and deoxidation.

Uses of 2-Bromoaniline: It is used as intermediate in organic synthesis. For example: it can react with benzoyl chloride to get benzoic acid-(2-bromo-anilide). This reaction needs reagent N,N-Dimethylaniline at temperature of 100 °C. The reaction time is 45 min. The yield is 95%.

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. And it is also harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 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. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) Avoid release to the environment. Refer to special instructions / safety data sheets.

People can use the following data to convert to the molecule structure.
1. SMILES:Nc1ccccc1Br
2. InChI:InChI=1/C6H6BrN/c7-5-3-1-2-4-6(5)8/h1-4H,8H2
3. InChIKey:AOPBDRUWRLBSDB-UHFFFAOYAG

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