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4-BROMOBENZOIC ACID
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Name

4-BROMOBENZOIC ACID

 EINECS 209-581-7
CAS No. 586-76-5 Density 1.701 g/cm3
PSA 37.30000 LogP 2.14730
Solubility soluble in hot water Melting Point 252-254 °C(lit.)
Formula C7H5BrO2 Boiling Point 299.8 °C at 760 mmHg
Molecular Weight 201.019 Flash Point 135.1 °C
Transport Information N/A Appearance White to light yellow crystal powder
Safety 26-36-24/25-22-37/39 Risk Codes 22-36/37/38-36-37/38
Molecular Structure Molecular Structure of 586-76-5 (4-Bromobenzoic acid) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

p-Carboxybromobenzene;4-Bromobenzene carboxylic acid;p-Bromobenzoicacid;p-Bromobenzenecarboxylic acid;Benzoic acid, 4-bromo-;4-09-00-01017 (Beilstein Handbook Reference);Benzoic acid, p-bromo-;p-Bromobenzoic acid;

Article Data 548

4-BROMOBENZOIC ACID Synthetic route

106-38-7

para-bromotoluene

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With sodium chromate(VI); sulfuric acid100%
With tert.-butylhydroperoxide; water at 20℃; for 14h; Inert atmosphere;99%
With sulfuric acid; ozone; acetic acid; manganese(II) acetate at 16℃; for 1.25h; Product distribution / selectivity;98%
619-42-1

4-methoxycarbonylphenyl bromide

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With aluminum oxide; potassium hydroxide In toluene for 22h; Product distribution; Ambient temperature;100%
Stage #1: 4-methoxycarbonylphenyl bromide With sodium hydroxide In tetrahydrofuran; water at 20℃;
Stage #2: With hydrogenchloride In water at 0℃; pH=2;		100%
With iodine; aluminium In acetonitrile at 80℃; for 18h;99%
113445-97-9

1-isocyanato-1-phenyl-2,2,2-trifluoroethyl 4-bromobenzoate

106-54-7

p-Chlorothiophenol

A

586-76-5

4-Bromobenzoic acid

B

118364-61-7

1-phenyl-1-(4-chlorophenylthio)-2,2,2-trifluoroethyl isocyanate

Conditions
ConditionsYield
In benzene 1.) 20 deg C, 12 h, 2.) reflux, 3 h;A 100%
B 87%
201230-82-2

carbon monoxide

589-87-7

1,4-bromoiodobenzene

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With amphiphilic resin-supported phosphine-palladium; water; potassium carbonate at 25℃; under 760 Torr; for 12h; hydroxycarbonylation;100%
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;93%
With water; palladium diacetate; potassium carbonate at 20℃; under 760.051 Torr; for 6h;91%
99-90-1

para-bromoacetophenone

98-80-6

phenylboronic acid

immobilized 4-bromobenzoic acid

immobilized 4-bromobenzoic acid

A

92-91-1

biphenyl-4-acetaldehyde

B

586-76-5

4-Bromobenzoic acid

C

92-92-2

biphenyl-4-carboxylic acid

Conditions
ConditionsYield
Stage #1: para-bromoacetophenone; phenylboronic acid; immobilized 4-bromobenzoic acid With potassium carbonate In water; N,N-dimethyl-formamide
Stage #2: With potassium hydroxide In ethanol; water		A 100%
B 19%
C 81%
...Expand
124-38-9

carbon dioxide

106-37-6

1.4-dibromobenzene

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With magnesium In tetrahydrofuran at -78℃; for 0.5h;99%
1122-91-4

4-bromo-benzaldehyde

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With tert.-butylhydroperoxide; di-tert-butyl peroxide; silica-supported selenamide In water; tert-butyl alcohol at 75℃; for 7h;99%
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h;99%
With sheep hemoglobin; oxygen In water at 20℃; under 760.051 Torr; for 150h; pH=7.0; Catalytic behavior; Darkness; Green chemistry; Enzymatic reaction; chemoselective reaction;99%
24523-45-3, 41097-38-5

bis-(4-bromo-benzylidene)-hydrazine

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 20h; Heating;99%
With [bis(acetoxy)iodo]benzene In tetrahydrofuran at 20℃; for 4h; Green chemistry;80%
19350-68-6

p-bromobenzaldehyde tosylhydrazone

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With silica-supported selenamide; dihydrogen peroxide In tetrahydrofuran at 55℃; for 42h;99%
With poly(diselanediyl-1,2-phenylene); dihydrogen peroxide In tetrahydrofuran for 10h; Heating;90%
124-38-9

carbon dioxide

183677-71-6

2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane

586-76-5

4-Bromobenzoic acid

Conditions
ConditionsYield
With potassium tert-butylate; copper(l) chloride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In tetrahydrofuran at 70℃; under 760.051 Torr; for 24h;99%
With (1,3-bis(2,6-diisopropyl-4-(morpholinomethyl)phenyl)imidazolidin-2-ylidene)copper(I) bromide; potassium tert-butylate In tetrahydrofuran under 760.051 Torr; for 24h; Inert atmosphere; Schlenk technique; Reflux; Green chemistry;94%
Stage #1: carbon dioxide; 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane With copper(l) iodide; 5,5-bis(4,5-dihydrooxazol-2-yl)nonane; cesium fluoride In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 10h;
Stage #2: With hydrogenchloride; water In N,N-dimethyl-formamide		86%
Stage #1: carbon dioxide; 2-(4-bromophenyl)-5,5-dimethyl-1,3,2-dioxaborinane With potassium tert-butylate; silver(I) acetate; triphenylphosphine In 1,4-dioxane at 100℃; under 15201 Torr; for 8h; Inert atmosphere; Autoclave;
Stage #2: With hydrogenchloride In tetrahydrofuran; water Inert atmosphere;		71%

4-BROMOBENZOIC ACID Chemical Properties

Synonyms:4-bromo-Benzoic acid;  p-Bromobenzoic acid;  p-bromo-benzoic acid; 4-bromobenzoic acid.
MF: C7H5BrO2
MW: 201.02
EINECS: 209-581-7
4-BROMOBENZOIC ACID,its melting point is about  252-254 °C(lit.);density is 1,894 g/cm3 ,soluble in hot water.Appearance is white to light yellow crystal powder.4-BROMOBENZOIC ACID is soluble in ethanol, ethyl ether, acetone and hot water.
   Following is the molecular structure of 4-BROMOBENZOIC ACID:
  

4-BROMOBENZOIC ACID Uses

4-BROMOBENZOIC ACID can be used in organic intermediates.

4-BROMOBENZOIC ACID Toxicity Data With Reference

1.   

orl-mus LD50:1059 mg/kg

   GISAAA    Gigiena i Sanitariya. 44 (12)(1979),19.
2.   

ipr-mus LD50:536 mg/kg

   GISAAA    Gigiena i Sanitariya. 44 (12)(1979),19.

RTECS : DG4448050

4-BROMOBENZOIC ACID Consensus Reports

Reported in EPA TSCA Inventory.

4-BROMOBENZOIC ACID Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits toxic vapors of Br−.

Hazard Codes : Xn,Xi (Harmful,Irritant)
Risk Statements :
 R22:Harmful if swallowed
 R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements  :
 S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
 S36:Wear suitable protective clothing
 S24/25: Avoid contact with skin and eyes
 S22:Do not breathe dust
 S37/39 :Wear suitable gloves and eye/face protection

4-BROMOBENZOIC ACID Specification

  HANDLING and STORAGE about 4-BROMOBENZOIC ACID:

  Handling:
  Wash thoroughly after handling.
  Remove contaminated clothing and wash before reuse.
  Minimize dust generation and accumulation.
  Avoid ingestion and inhalation.
  Avoid contact with eyes, skin, and clothing.
  Keep container tightly closed.Use with adequate ventilation.
  Storage:Store in a tightly closed container. Store in a cool, dry,well-ventilated area away from incompatible substances.

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