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2,4,6-TRIBROMOANILINE
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Name

2,4,6-TRIBROMOANILINE

 EINECS 205-700-1
CAS No. 147-82-0 Density 2.35
PSA 26.02000 LogP 4.13750
Solubility insoluble AUTOIGNITION Melting Point 119 - 122 C
Formula C6H4 Br3 N Boiling Point 300 C
Molecular Weight 329.816 Flash Point 132.9 °C
Transport Information 25kgs Appearance White crystal
Safety Moderately toxic by intraperitoneal route. When heated to decomposition it emits very toxic fumes of Br− and NOx. See also BROMIDES and ANILINE. Risk Codes R23/24/25;R33   
Molecular Structure Molecular Structure of 147-82-0 (2,4,6-Tribromoaniline) Hazard Symbols
Synonyms

Aniline,2,4,6-tribromo- (6CI,7CI,8CI); 2,4,6-Tribromoaniline;2,4,6-Tribromobenzenamine; NSC 2216; sym-Tribromoaniline

Article Data 175

2,4,6-TRIBROMOANILINE Synthetic route

106-40-1

4-bromo-aniline

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane bromide; calcium carbonate In methanol at 20℃; for 0.166667h;95%
Stage #1: 4-bromo-aniline With sulfuric acid In water for 0.0833333h; Green chemistry;
Stage #2: With sodium bromate; sodium bromide In water at 20℃; for 4h; Green chemistry;		94%
With trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane; hydrogen bromide In water at 20℃; for 0.7h;93%
615-36-1

2-bromoaniline

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With methanol; P-benzyltriphenylphosphonium tribromide; sodium hydrogencarbonate In dichloromethane for 0.116667h; Ambient temperature;94%
With dibromamine-T In acetonitrile at 20℃; for 0.166667h;90%
62-53-3

aniline

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With hydrogenchloride; dihydrogen peroxide; sodium bromide In water at 15℃; for 2h;99.9%
With hydrogen bromide; sodium bromide In chloroform; water at 0℃; Electrochemical reaction;98%
With bromine; acetic acid at 20℃; for 1h;98%
106-40-1

4-bromo-aniline

A

615-57-6

2,4-dibromo-aniline

B

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With sodium perborate; ammonium heptamolybdate; potassium bromide In acetic acid at 20℃; for 2.25h; Bromination;
With sodium persulfate; copper(ll) sulfate pentahydrate; sodium bromide In water; acetonitrile at 7 - 25℃; for 24h; Overall yield = 79 percent; Overall yield = 1.44 g; regioselective reaction;A 79 %Chromat.
B 21 %Chromat.
615-36-1

2-bromoaniline

A

615-57-6

2,4-dibromo-aniline

B

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With sodium persulfate; copper(ll) sulfate pentahydrate; sodium bromide In water; acetonitrile at 7 - 25℃; for 24h; Overall yield = 76 percent; Overall yield = 1.38 g; regioselective reaction;A 83 %Chromat.
B 17 %Chromat.
615-57-6

2,4-dibromo-aniline

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With bromine In tetrachloromethane at 20 - 40℃;99%
Bromierung;
62-53-3

aniline

A

615-57-6

2,4-dibromo-aniline

B

147-82-0

2,4,6-tribromoaniline

C

106-40-1

4-bromo-aniline

Conditions
ConditionsYield
Stage #1: aniline With n-butyllithium In diethyl ether; hexane at -78℃; for 1h;
Stage #2: With poly[4-(dibutyliodostannyl)butyl]styrene In diethyl ether; hexane at 20℃; for 18h;
Stage #3: With bromine In diethyl ether; hexane; dichloromethane at -78 - 20℃; for 2h;		A n/a
B n/a
C 76%
With bromine; acetic acid In tetrachloromethane for 0.0833333h; Ambient temperature; other reagent: bromine;A 41%
B 31%
C 21%
With bromine In tetrachloromethane for 0.0833333h; Product distribution; Mechanism; Ambient temperature; other aromatic compounds, other reagents: bromodimethylsulfonium bromide, bromodimethylsulfonium bromide/acetic acid, bromine/acetic acid, other solvents, other reaction temperature and time;A 33%
B 30%
C 19%
118-92-3

anthranilic acid

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With 1-benzyl-1-aza-4-azoniabicyclo<2.2.2>octane bromide; calcium carbonate In methanol at 20℃; for 0.416667h;90%
106-40-1

4-bromo-aniline

1972-28-7

diethylazodicarboxylate

A

4114-28-7

diethyl hydrazodicarboxylate

B

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With ZrBr4 In dichloromethane at 20℃; for 1.5h;A n/a
B 83%
121-57-3

4-aminobenzene sulfonic acid

147-82-0

2,4,6-tribromoaniline

Conditions
ConditionsYield
With water; bromine
With water; bromine
With bromine; acetic acid

2,4,6-TRIBROMOANILINE Chemical Properties

2,4,6-TRIBROMOANILINE's Molecular formula: C6H4Br3N
2,4,6-TRIBROMOANILINE's Molar mass: 329.81
EINECS: 205-700-1
density: 2.35 
Flash Point: 300°C
Boiling Point: 300 °C(lit.)
Melting point: 120-122 °C(lit.)
Appearance: White crystals or powder
Synonyms: TRIBROMOANILINE;1,4,6-tribromobenzenamine;AKOS BBS-00003575;ANILINE TRIBROMIDE;AKOS B028948;2,4,6-TRIBROMOBENZENAMINE;2,4,6-TRIBROMOANILINE;2,4,6-Tribomoaniline

2,4,6-TRIBROMOANILINE Uses

2,4,6-TRIBROMOANILINE is used for pharmaceutical intermediates, chemical flame retardants etc.

2,4,6-TRIBROMOANILINE Toxicity Data With Reference

1.   

ipr-mus LD50:500 mg/kg

   NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
2.    RTECS  BZ0175000

2,4,6-TRIBROMOANILINE Consensus Reports

Reported in EPA TSCA Inventory.

2,4,6-TRIBROMOANILINE Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits very toxic fumes of Br− and NOx. See also BROMIDES and ANILINE.
Hazard Codes  T,Xi,Xn 
RIDADR  UN 2811 6.1/PG 2
WGK Germany  3
Hazard Note  Irritant
Risk Statements  23/24/25-33-36/37/38-20/21/22
Safety Statements  28-36/37/39-45-36/37-28A-26
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