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106-40-1

Basic Information
CAS No.: 106-40-1
Name: 4-Bromoaniline
Molecular Structure:
Molecular Structure of 106-40-1 (4-Bromoaniline)
Formula: C6H6BrN
Molecular Weight: 172.04
Synonyms: Aniline,p-bromo- (8CI);1-Amino-4-bromobenzene;benzenamine, 4-bromo-;Aniline, p-bromo-;p-Bromophenylamine;p-Bromoaniline;
EINECS: 203-393-9
Density: 1.594 g/cm3
Melting Point: 56-62 °C(lit.)
Boiling Point: 225.9 °C at 760 mmHg
Flash Point: 90.4 °C
Solubility: <0.1 g/100 mL at 23°C in water
Appearance: brown crystals
Hazard Symbols: HarmfulXn
Risk Codes: 21/22-36/37/38-20/21/22
Safety: 26-36/37-36/37/39
Transport Information: UN 2811 6.1/PG 3
PSA: 26.02000
LogP: 2.61250
Synthetic route
586-78-7

para-nitrophenyl bromide

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With copper(I) chloride; potassium borohydride In methanol for 0.166667h; Ambient temperature;100%
With sodium tetrahydroborate In methanol at 60℃; for 3h; Sealed tube;100%
With water; oxalic acid; titanium(IV) oxide for 3h; Wavelength; Irradiation; Inert atmosphere; Sealed tube; Green chemistry; chemoselective reaction;100%
108613-06-5

N-(4-bromophenyl)-1-tert-butyl-1,1-dimethylsilanamine

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With silica gel In ethanol; water at 20℃; for 2h;100%
62-53-3

aniline

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With oxygen; sodium bromide In dibutyl ether at 45℃; under 760.051 Torr; for 5h; Schlenk technique;99%
With N-Bromosuccinimide at 20℃; for 0.166667h; regioselective reaction;98%
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one for 0.0138889h; microwave irradiation;95%
2101-88-4

1-azido-4-bromobenzene

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 2h; Inert atmosphere;98%
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.166667h; Ambient temperature;97%
With borohydride supported on an ion exchange resin In methanol for 4h; Product distribution; Heating; other aryl azides and arylsulfonyl azides; var. temp. and times;96%
103-88-8

4-bromoacetanilide

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With 40% potassium fluoride/alumina at 85℃; for 0.0666667h; Microwave irradiation; Neat (no solvent);97%
With ammonium bromide; ethylenediamine at 70℃; for 5h; Microwave irradiation; Inert atmosphere; neat (no solvent);96%
With [RuCl2(2-(diphenylphosphino)-N-((6-((diphenylphosphino)methyl)pyridin-2-yl)methyl)ethan-1-amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 20h; Catalytic behavior; Autoclave; chemoselective reaction;95%
586-78-7

para-nitrophenyl bromide

A

62-53-3

aniline

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With platinum on carbon; hydrogen In methanol at 25℃; under 1500.15 Torr; for 24h; Catalytic behavior; Solvent; Temperature; Reagent/catalyst; Pressure;A 90%
B 5%
With isopropyl alcohol; sodium hydroxide for 12h; Inert atmosphere; Reflux; chemoselective reaction;A n/a
B 84%
With hydrogen In methanol at 30℃; under 22502.3 Torr; Reagent/catalyst;A n/a
B 83%
589-87-7

1,4-bromoiodobenzene

A

2101-88-4

1-azido-4-bromobenzene

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With sodium azide; copper; diisopropylamine; ascorbic acid In dimethyl sulfoxide at 80℃; for 14h;A 88%
B 7%
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
124397-40-6

(E)-N-(4-bromophenyl)-1-(p-tolyl)methanimine

109-77-3

malononitrile

A

2826-25-7

2-(4-methylbenzylidene)malononitrile

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With sodium dodecyl-sulfate In water at 25 - 30℃; for 0.2h;A 87%
B n/a

(4-bromo-phenyl)-carbamic acid 2,2,2-trichloro-ethyl ester

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With indium; ammonium chloride In ethanol for 2.5h; Heating;86%
1601-98-5

1,2-bis(4-bromophenyl)diazene

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With perchloric acid In isopropyl alcohol; acetonitrile at 25℃; for 0.583333h; pH=2; Inert atmosphere; Irradiation;86%
360791-98-6

2-(4-bromophenoxy)propanamide

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 140℃; for 3h; Green chemistry;86%
With potassium hydroxide at 140℃;126.5 mg
25203-36-5

methyl N-(4-bromophenyl)carbamate

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With sodium hydrogen telluride In N,N-dimethyl-formamide at 70 - 75℃; for 5h;85%
With water; hydrogen cation at 99.9℃; Rate constant;
120-72-9

indole

3340-78-1

2-phenyl-1,2,3,4-tetrahydroisoquinoline

586-78-7

para-nitrophenyl bromide

A

1-(1H-indol-3-yl)-2-phenyl-1, 2, 3, 4-tetrahydroisoquinoline

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With Co(dmgH)2Cl2; Eosin Y In water; acetonitrile at 20℃; for 48h; Inert atmosphere; Irradiation; Sealed tube;A 85%
B 94 %Spectr.
62-53-3

aniline

A

615-57-6

2,4-dibromo-aniline

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With tetra-N-butylammonium tribromide In chloroform for 0.05h;A 14%
B 84%
With tetra-N-butylammonium tribromide In chloroform at 20℃; for 0.05h; Product distribution; substituted anilines, 2-aminopyridine, other solvents, other reaction time, other reagent: tetraphenylphosphonium tribromide;A 16%
B 82%
With tetra-N-butylammonium tribromide In chloroform at 20℃; for 0.05h; other reagent: tetraphenylphosphonium tribromide;A 16%
B 82%

N,N',N''-tris(p-bromophenyl)phosphorous triamide

A

2,4-bis(p-bromoanilino)-1,3-bis(p-bromophenyl)-1,3,2,4-diazadiphosphetidine

B

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
In xylene for 2h; Heating;A 60.5%
B 83.5%
586-78-7

para-nitrophenyl bromide

A

1601-98-5

1,2-bis(4-bromophenyl)diazene

B

106-40-1

4-bromo-aniline

C

1215-42-5, 21650-67-9, 125367-64-8

4,4'-dibromoazoxybenzene

Conditions
ConditionsYield
With hydrazine hydrate; nickel(II) nitrate; zinc In tert-butyl alcohol for 0.333333h; Heating;A 6 % Chromat.
B 8%
C 82%
With hydrazine hydrate; nickel(II) nitrate; zinc In ethanol for 3h; Heating;A 13%
B 5%
C 79%
586-78-7

para-nitrophenyl bromide

A

106-40-1

4-bromo-aniline

B

92-87-5

p,p'-diaminobiphenyl

Conditions
ConditionsYield
With hydrazine hydrate In ethanol at 70℃; for 4h; chemoselective reaction;A 82%
B 7%
92159-87-0

benzyl (4-bromophenyl)carbamate

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction;81%
5391-88-8

1-(4-bromophenyl)ethanol

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 10h;81%
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 4h; Sealed tube;78%
86-98-6

4,7-dichloroquinoline

106-40-1

4-bromo-aniline

N-(4-bromophenyl)-7-chloroquinolin-4-amine

Conditions
ConditionsYield
In ethanol for 24h; Reflux;100%
for 0.166667h; microwave irradiation;95%
With ethanol
123-08-0

4-hydroxy-benzaldehyde

106-40-1

4-bromo-aniline

3382-65-8

4-hydroxybenzylidene-4'-bromoaniline

Conditions
ConditionsYield
for 24h; Ambient temperature;100%
In methanol at 20℃;90%
With sulfuric acid In neat (no solvent) Microwave irradiation; Sealed tube; Green chemistry;87%
124-63-0

methanesulfonyl chloride

106-40-1

4-bromo-aniline

4284-50-8

N-(4-bromophenyl)methanesulfonamide

Conditions
ConditionsYield
Stage #1: methanesulfonyl chloride; 4-bromo-aniline With triethylamine In dichloromethane at 0 - 20℃; for 3.08333h;
Stage #2: With methanol; ammonia; water In tetrahydrofuran at 20℃; for 16h;
100%
Stage #1: methanesulfonyl chloride; 4-bromo-aniline With triethylamine In dichloromethane at 0 - 20℃; for 3.08333h;
Stage #2: With ammonia; water In tetrahydrofuran; methanol at 20℃; for 16h;
100%
With pyridine In dichloromethane at 0 - 20℃; for 12h;98%
141-75-3

butyryl chloride

106-40-1

4-bromo-aniline

119199-11-0

N-(4-bromophenyl)butanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 5 - 20℃;100%
With triethylamine In chloroform at 20℃; for 0.0222222h; Flow reactor;82%
532-55-8

Benzoyl isothiocyanate

106-40-1

4-bromo-aniline

19249-89-9

1-benzoyl-3-(4-bromophenyl)thiourea

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1.2h;100%
In acetone82%
at 75℃; for 2h; Reflux;72%
98-59-9

p-toluenesulfonyl chloride

106-40-1

4-bromo-aniline

32857-48-0

N-(4-bromophenyl)-4-methylbenzenesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane for 2h; Inert atmosphere;100%
With triethylamine In dichloromethane at 4℃;100%
With pyridine In dichloromethane at 20℃; for 16h;99%
64-18-6

formic acid

106-40-1

4-bromo-aniline

2617-78-9

N-(4-bromophenyl)formamide

Conditions
ConditionsYield
In toluene Reflux;100%
With sodium formate at 20℃; for 2.75h; Neat (no solvent);99%
With zinc(II) oxide at 70℃; for 0.333333h;98%
106-40-1

4-bromo-aniline

3623-23-2

4-bromonitrosobenzene

Conditions
ConditionsYield
With Oxone In dichloromethane; water at 20℃; for 4h;100%
With oxone||potassium monopersulfate triple salt In dichloromethane; water at 20℃;100%
With dihydrogen peroxide In methanol; water at 20℃; for 2h; Catalytic behavior; Sealed tube; chemoselective reaction;94%
108-24-7

acetic anhydride

106-40-1

4-bromo-aniline

103-88-8

4-bromoacetanilide

Conditions
ConditionsYield
With cadmium(II) oxide at 80℃; for 0.166667h; Neat (no solvent); Microwave irradiation;100%
In dichloromethane at 20℃; Inert atmosphere;100%
In dichloromethane at 0 - 20℃; Inert atmosphere;100%
120-14-9

3,4-dimethoxy-benzaldehyde

106-40-1

4-bromo-aniline

82363-27-7

3,4-dimethoxybenzal-4-bromoaniline

Conditions
ConditionsYield
In toluene Heating;100%
In methanol at 20℃;76%
106-40-1

4-bromo-aniline

589-87-7

1,4-bromoiodobenzene

Conditions
ConditionsYield
Stage #1: 4-bromo-aniline With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Inert atmosphere;
Stage #2: With potassium iodide In ethyl acetate for 0.5h;
100%
With sulfuric acid; potassium iodide; sodium nitrite In water at -5 - 60℃; Inert atmosphere;92%
Stage #1: 4-bromo-aniline With sulfuric acid; silica gel; sodium nitrite at 20℃; grinding; Neat (no solvent);
Stage #2: With water at 20℃; grinding; Neat (no solvent);
Stage #3: With potassium iodide at 20℃; for 0.166667h; Sandmeyer reaction; grinding; Neat (no solvent);
87%
556-61-6

methyl thioisocyanate

106-40-1

4-bromo-aniline

61449-55-6

1-(4-bromophenyl)-3-methyl-thiourea

Conditions
ConditionsYield
at 20℃; for 24h; Addition; solid-phase reaction;100%
In ethanol for 1h; Heating;
106-40-1

4-bromo-aniline

98-80-6

phenylboronic acid

92-67-1

4-Aminobiphenyl

Conditions
ConditionsYield
With potassium carbonate In methanol at 75℃; for 0.0833333h; Catalytic behavior; Suzuki-Miyaura Coupling; Microwave irradiation;100%
With C22H21Cl4N4O3Pd2S(1-)*C16H36N(1+); potassium carbonate In water at 75℃; for 2h; Reagent/catalyst; Suzuki Coupling; Schlenk technique;99%
With sodium carbonate; palladium In ethanol; water at 20 - 83℃; for 0.366667h; Concentration; Suzuki Coupling; Microwave irradiation;99%
106-40-1

4-bromo-aniline

107-12-0

propiononitrile

N-(4-bromo-phenyl)-propionamidine

Conditions
ConditionsYield
With aluminium trichloride In toluene at 107℃; for 1.5h;100%
1493-27-2

ortho-nitrofluorobenzene

106-40-1

4-bromo-aniline

58476-59-8

4-bromo-N-(2-nitrophenyl)benzenamine

Conditions
ConditionsYield
In dimethyl sulfoxide at 100℃; for 48h; Inert atmosphere; Schlenk technique;100%
With potassium fluoride at 170 - 180℃; for 30h;92%
With potassium fluoride at 150℃; for 18h; Inert atmosphere;90%
106-40-1

4-bromo-aniline

4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-diazonium nitrate

3-(4-bromophenyl)-1-(4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine-3-yl)triazene

Conditions
ConditionsYield
With trimethylamine at 20℃; under 375.03 Torr; for 12h;100%
1849-54-3

3-hydroxypyridine-4-carboxaldehyde

106-40-1

4-bromo-aniline

4-{[(E)-4-Bromo-phenylimino]-methyl}-pyridin-3-ol

Conditions
ConditionsYield
In toluene Heating;100%
In toluene for 5h; Heating;82%
37517-81-0

3-chloro-3-oxopropanoic acid methyl ester

106-40-1

4-bromo-aniline

669000-20-8

methyl 3-((4-bromophenyl)amino)-3-oxopropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
Stage #1: 4-bromo-aniline With triethylamine In ethyl acetate at 10℃;
Stage #2: 3-chloro-3-oxopropanoic acid methyl ester at 17℃; for 0.75h;
122.75 g

N-(2-ethylhexyl)-1,7-(3',5'-di-tert-butoxyphenoxy)perylene-3,4-dicarboxyanydride-9,10-dicarboxyimide

106-40-1

4-bromo-aniline

C66H69BrN2O6

Conditions
ConditionsYield
With 1H-imidazole In toluene for 3h; Reflux;100%
106-40-1

4-bromo-aniline

151169-74-3

2,3-dichlorobenzeneboronic acid

1148126-14-0

2',3'-dichlorobiphenyl-4-amine

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; triphenylphosphine In toluene for 24h; Suzuki coupling; Inert atmosphere; Reflux;100%
762-42-5

dimethyl acetylenedicarboxylate

106-40-1

4-bromo-aniline

106509-83-5

dimethyl 2-(4-bromophenylamino)maleate

Conditions
ConditionsYield
at 20℃; for 0.133333h; Milling; Inert atmosphere;100%
In methanol at 70℃; for 24h; Michael addition;79%
1258500-12-7

1-(2,5-dimethyl-1H-pyrrol-1-yl)prop-2-en-1-one

106-40-1

4-bromo-aniline

1258500-19-4

N-(3-(2,5-dimethyl-1H-pyrrol-1-yl)-3-oxoprop-1-yl)-4-bromoaniline

Conditions
ConditionsYield
In water at 50℃; for 24h; Michael condensation;100%
32315-10-9

bis(trichloromethyl) carbonate

106-40-1

4-bromo-aniline

2493-02-9

4-bromophenyl isocyanate

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
Stage #1: bis(trichloromethyl) carbonate; 4-bromo-aniline In dichloromethane at 20℃; for 0.5h;
Stage #2: With triethylamine In dichloromethane at -35 - 20℃; for 2h;
93%
With triethylamine In toluene for 7h; Reflux; Cooling with ice;72%
14371-10-9

(E)-3-phenylpropenal

106-40-1

4-bromo-aniline

(1E,2E)-N-(4-bromophenyl)-3-phenylprop-2-en-1-imine

Conditions
ConditionsYield
In neat (no solvent) for 0.25h;100%
106-40-1

4-bromo-aniline

107-12-0

propiononitrile

C9H11BrN2

Conditions
ConditionsYield
With aluminum (III) chloride In toluene at 100℃; for 0.0833333h;100%
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    Product name: 4-Bromoaniline CAS NO: 106-40-1 MF: C6H6BrN MW: 172.02 EINECS NO: 203-393-9 Melting point: 56-62 °C(lit.) Bolling point: 230-250 °C solubility : ethanol: soluble0.5g/10 mL, clear, colorless to almost colorless H

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    4-Bromoaniline 106-40-1

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    106-40-1

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    MSDS/COA Download

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    106-40-1

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    106-40-1

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    106-40-1

    MSDS/COA Download

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    106-40-1

    4-Bromoaniline CAS NO.106-40-1

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  • 4-Bromoaniline CAS 106-40-1

  • Casno:

    106-40-1

    MSDS/COA Download

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  • p-Bromoaniline

  • Casno:

    106-40-1

    p-Bromoaniline

    Min.Order: 1 Metric Ton

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    106-40-1

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    106-40-1

    4-Bromoaniline

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  • Casno:

    106-40-1

    4-Bromoaniline 106-40-1

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    106-40-1

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    106-40-1

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  • Casno:

    106-40-1

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  • Casno:

    106-40-1

    4-Bromoaniline

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    Business Type:Lab/Research institutions

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  • Casno:

    106-40-1

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  • Casno:

    106-40-1

    4-Bromoaniline

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    106-40-1

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  • Casno:

    106-40-1

    4-Bromoaniline

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  • Casno:

    106-40-1

    p-Bromo Aniline

    Min.Order: 1 Kilogram

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    106-40-1

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    Business Type:Lab/Research institutions

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    106-40-1

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    106-40-1

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  • Casno:

    106-40-1

    4-Bromoaniline

    Min.Order: 1 Gram

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    106-40-1

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  • Casno:

    106-40-1

    4-Bromoaniline

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  • Casno:

    106-40-1

    4-Bromoaniline

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Chemistry

Molecular Structure of 4-Bromoaniline (CAS NO.106-40-1):

IUPAC Name: 4-bromoaniline 
Empirical Formula: C6H6BrN 
Molecular Weight: 172.02
Form: crystalline
Color: white to light yellow
Water Solubility: <0.1 g/100 mL at 23 °C
Merck: 14,1404
BRN: 742031
H bond acceptors: 1
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 3.24 Å2
Index of Refraction: 1.625
Molar Refractivity: 38.17 cm3
Molar Volume: 107.8 cm3
Surface Tension: 47.7 dyne/cm
Density: 1.594 g/cm3
Flash Point: 90.4 °C
Melting point: 56-62 °C(lit.)
Enthalpy of Vaporization: 46.24 kJ/mol
Boiling Point: 225.9 °C at 760 mmHg
Vapour Pressure: 0.0843 mmHg at 25°C
InChI
InChI=1/C6H6BrN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
Smiles
c1(ccc(Br)cc1)N
EINECS: 203-393-9
Stability: Stable. Combustible. Incompatible with strong oxidizing agents, peroxides, acids, acid chlorides, acid anhydrides, chloroformates. May be air sensitive.
Product Categories: Fine chemical & intermediates; Anilines, Aromatic Amines and Nitro Compounds; Amines; Phenyls & Phenyl-Het; API intermediates; Anilines, Amides & Amines; Bromine Compounds; Anilines (Building Blocks for Liquid Crystals); Bifunctional Compounds (Building Blocks for Liquid Crystals); Building Blocks for Liquid Crystals; Functional Materials; Phenyls & Phenyl-Het; C2 to C6; Nitrogen Compounds

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 248mg/kg (248mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.
mouse LD50 oral 289mg/kg (289mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 44(12), Pg. 19, 1979.
rat LD50 oral 456mg/kg (456mg/kg)   Ceskoslovenska Hygiena. Czechoslovak Hygiene. Vol. 23, Pg. 168, 1978.

Consensus Reports

 4-Bromoaniline (CAS NO.106-40-1) is reported in EPA TSCA Inventory.

Safety Profile

Poison by ingestion and intraperitoneal routes. Mutation data reported. When heated to decomposition it emits toxic fumes of Br and NOx.
Hazard Codes: HarmfulXn
Risk Statements: 21/22-36/37/38-20/21/22
R21/22:Harmful in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36/37-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: BW9280000
F: 8-9-23
Hazard Note: Harmful
HazardClass: 6.1
PackingGroup: III
HS Code: 29214210

Specification

  4-Bromoaniline , with CAS number of 106-40-1, can be called 4-Bromanilinu ; 4-Bromo-aniline ; Aniline, p-bromo- ; Benzenamine, 4-bromo- ; p-Bromophenylamine ; p-Bromoaniline . It is a crystalline, 4-Bromoaniline (CAS NO.106-40-1) is sensitive to prolonged exposure to air. Vapor may form highly reactive mixtures in air . Insoluble in water, with highly reactive mixtures in air. Flash point data are not available for 4-Bromoaniline, but 4-Bromoaniline is probably combustible.