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4-Bromobenzoic acid

HCID 11464
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
586-76-5
Standard SMILES
O=C(O)c1ccc(Br)cc1
InChIKey
TUXYZHVUPGXXQG-UHFFFAOYSA-N
Molecular formula
C7H5BrO2
Average molar mass
201.02 g/mol
Monoisotopic mass
199.94729

Overview

4-bromobenzoic acid appears as colorless to red crystals. (NTP, 1992)

Names & identifiers

Preferred name
4-Bromobenzoic acid
IUPAC
4-bromobenzoic acid
English name
4-Bromobenzoic acid
Molecular formula
C7H5BrO2
Molecular weight
201.02

Names & synonyms

4-Bromobenzoic acid586-76-5P-BROMOBENZOIC ACIDBenzoic acid, 4-bromo-p-CarboxybromobenzeneBenzoic acid, p-bromo-p-Bromobenzenecarboxylic acid4-Brom-benzoesaeure4-carboxybromobenzene4-bromobenzenecarboxylic acidEINECS 209-581-7NSC 17582
Show more names
4-bromo-benzoicaci4-Bromobenzoic aicdBenzoicacid,4-bromo-'LGC' (4008)Homarine HCL4-BrombenzoesureAKOS BBS-00003716p-bromo-benzoicaci
BROMOBENZOIC ACID, P-BRN 1906923AI3-08859NSC-175824-09-00-01017 (Beilstein Handbook Reference)6992P6102ODTXSID7060413CHEBI:60698

Database identifiers

CAS
586-76-5
PubChem CID
11464
DTXSID
DTXSID7060413
ChEMBL
CHEMBL22051
ChEBI
CHEBI:60698
UNII
6992P6102O
EC Number
209-581-7
Nikkaji
J43.481G

Properties

Computed structural propertiesFilling in

XLogP
2.9
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
10
Formal charge
0
Complexity
128

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Benzoic Acid Derivatives
SpringerMaterials PropertiesCrystal structure
LogP2.86
Melting Point473.9 °F (NTP, 1992)
Physical Description · 2 items

4-bromobenzoic acid appears as colorless to red crystals. (NTP, 1992)

Solid; [Merck Index] Colorless to red solid; [CAMEO] Beige powder; [Aldrich MSDS]

Physicochemical properties

Melting point
252 · 252-254 °C (lit.)
Boiling point
116 °C · 116 °C(Press: 15-16 Torr)
Density
1 · 1,894 g/cm3
refractive index
1.608 · 1.6080 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (95.2%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P262, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 63 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Chemical: Benzoic acid, 4-bromo-

Benzoic acid, 4-bromo-: Does not have an individual approval but may be used under an appropriate group standard

Health HazardsACUTE/CHRONIC HAZARDS: Explodes above its melting point. (NTP, 1992)
Hazards SummaryAn irritant; Harmful by ingestion; [Aldrich MSDS]
Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 item

Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Chemistry & industry

Uses & manufacturing

UsesUsed to detect strontium in organic syntheses; [Merck Index]
General Manufacturing InformationBenzoic acid, 4-bromo-: ACTIVE
Applications · 2 items

Uses4-Bromobenzoic acid was used to study the metabolic fate of 2-,3-and 4-bromo benzoic acids in rat hepatocytes incubation using high temperature liquid chromatography. It was used in bromine-specific detection of the metabolites of 2-,3-and 4-bromobenzoic acid in the urine and bile of rats by inductively coupled plasma mass spectrometry. It is also used as an intermediate for the synthesis of agrochemicals, pharmaceutical, chemical intermediates and liquid crystals.

General DescriptionColorless to red crystals.

Preparation methods · 1 item

Preparation4-Bromobenzoic acid is obtained by the reaction of p-bromotoluene with glacial acetic acid as the molten agent and oxygen as the oxidant, utilising a liquid-phase oxidation catalytic method under the action of a catalyst. The catalyst is a combination of acetic acid cobalt, manganese acetate, and bromide compounds.

Upstream & downstream products

Upstream raw materials

Oxygen4-Bromotoluene

Downstream products

ETHYL 4-ACETYLBENZOATE4-Carboxylphenylboronic acid pinacol ester

Related reactions

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HRID 36028As reactantuspto-grants-1995_05
HRID 37148 reaction equation
HRID 37148As reactantuspto-grants-1995_05
HRID 51711 reaction equation
HRID 51711As reactantuspto-grants-2004_03
HRID 71720 reaction equation
HRID 71720As reactantuspto-grants-2014_09
HRID 72977 reaction equation
HRID 72977As reactantuspto-grants-2014_09
HRID 73004 reaction equation
HRID 73004As reactantuspto-grants-2014_09
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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5 % · ethanol: soluble5%
form
Crystals or Powder
pka
3.96 · 3.96(at 25℃)
color
White to beige to pink-brownish
Water Solubility
SOLUBLE IN HOT WATER
Merck
14 · 14,1408
BRN
1906923 · 1906923
Stability
Stable. Incompatible with strong oxidizing agents.
Cosmetics Ingredients Functions
SKIN CONDITIONING
InChI
1S/C7H5BrO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10)
InChIKey
TUXYZHVUPGXXQG-UHFFFAOYSA-N
SMILES
OC(=O)c1ccc(Br)cc1
CAS DataBase Reference
586 · 586-76-5(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
6992 P6102O · 6992P6102O
NIST Chemistry Reference
4 · Benzoic acid, 4-bromo-(586-76-5)
EPA Substance Registry System
4 · 4-Bromobenzoic acid (586-76-5)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302
Precautionary statements
264 · P264-P270-P301+P312-P501
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37/38-36-37/38
Safety Statements
26 · 26-36-24/25-22-37/39
WGK Germany
3 · 3
RTECS
4448050 · DG4448050
Hazard Note
Irritant
TSCA
TSCA listed
HS Code
29163900 · 29163900
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 Oral · Acute Tox. 4 Oral
Air and Water ReactionsNo rapid reaction with air. No rapid reaction with water.
Hazard Classes and CategoriesAcute Tox. 4 (95.2%)

Safety & protection

Fire FightingA fire in your laboratory involving this chemical should be extinguished with a dry chemical, carbon dioxide or halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter.

Safety data

wgk
3
tsca
TSCA listed
rtecs
DG4448050
hs_code
29163900
risk_code
22-36/37/38-36-37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
hazard_note
Irritant
safety_code
26-36-24/25-22-37/39
Storage Class
11 - Combustible Solids
Hazard statements
H302
Hazard Classifications
Acute Tox. 4 Oral
Precautionary statements
P264-P270-P301+P312-P501
4-(3-TERT-BUTYL-1,2,4-OXADIAZOL-5-YL)PHENYLBORONIC ACID
3-TERT-BUTYL-5-(4-BROMOPHENYL)-1,2,4-OXADIAZOLE
Methyl 4-bromo-3-nitrobenzoate
Methyl 2-bromobenzoate
4-ETHYNYL-BENZOIC ACID
4-BROMO-4'-METHOXYBENZOPHENONE
2-(4-bromophenyl)-1,3,4-oxadiazole
4'-tert-Butyl[1,1'-biphenyl]-4-carboxylic acid
4-AZIDOBENZOIC ACID
4-AMINOCARBONYLPHENYLBORONIC ACID, PINACOL ESTER
4-N-HEPTYLBENZOIC ACID
4,4'-Bis(hydroxymethyl)biphenyl
4-(TRIFLUOROACETYL)TOLUENE
3-Bromo-4-(trifluoromethyl)benzoic acid
4-(Methylamino)benzoic acid

Additional notes

DefinitionChEBI: A bromobenzoic acid carrying a single bromo subsituent at the 4-position.