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Basic information
- CAS
42860-02-6- Standard SMILES
O=C(O)c1cc(Cl)cc(Br)c1- InChIKey
PBRRUJWXRUGGAW-UHFFFAOYSA-N- Molecular formula
- C7H4BrClO2
- Average molar mass
- 235.46 g/mol
- Monoisotopic mass
- 233.90832
Names & identifiers
- Preferred name
- 3-Bromo-5-chlorobenzoic acid
- IUPAC
- 3-bromo-5-chlorobenzoic acid
- English name
- 3-BROMO-5-CHLOROBENZOIC ACID
- Molecular formula
- C7H4BrClO2
- Molecular weight
- 235.46
Names & synonyms
3-Bromo-5-chlorobenzoic acid42860-02-6DTXSID10275020RefChem:93194DTXCID80226468630-135-63-Bromo-5-ChlorobenzoicAcidMFCD06797227Benzoic acid, 3-bromo-5-chloro-5-bromo-3-chlorobenzoic acidSCHEMBL560354CL8073
Show more names
CBPABenzoic acid,3-broMo-5-chloro-3-Bromo-5-chlorobenzoic Acid >3-Bromo-5-chlorobenzoic acid 98%3-BROMO-5-CHLOROBENZOIC ACID ISO 9001：2015 REACH
AKOS015834263CS-W004992AB29578PS-7659SY024815B4191EN300-1074643-bromo-5-chloro-benzoic Acid
Database identifiers
- CAS
42860-02-6- PubChem CID
- 33128
- DTXSID
DTXSID10275020- EC Number
- 630-135-6
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
- 11
- Formal charge
- 0
- Complexity
- 163
Physicochemical properties
- Melting point
- 190 · 190-192
- Boiling point
- 332 · 332.0±27.0 °C(Predicted)
- Density
- 1.809 · 1.809
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- soluble in Methanol
- form
- powder to crystal
- pka
- 3.44 · 3.44±0.10(Predicted)
- color
- White to Light yellow
- InChI
- InChI=1S/C7H4BrClO2/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3H,(H,10,11)
- InChIKey
- PBRRUJWXRUGGAW-UHFFFAOYSA-N
- SMILES
- C(O)(=O)C1=CC(Cl)=CC(Br)=C1
- CAS DataBase Reference
- 42860 · 42860-02-6
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
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
Warning
H302 (37.5%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (12.5%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (87.5%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (87.5%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (12.5%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (75%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 8 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (37.5%)；Skin Irrit. 2 (87.5%)；Eye Irrit. 2 (87.5%)；STOT SE 3 (75%)
Safety data
- hs_code
- 2916399090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Harmful/Irritant/Keep Cold
- Hazard statements
- H315-H319
Chemistry & industry
Applications
Uses3-Bromo-5-chlorobenzoic acid, as an aromatic bromic acid, can be used to synthesize inhibitors of phosphodiesterase PDE4 and cholinergic receptors (mACHRs), and can also be used to synthesize drugs for the treatment of type 2 diabetes.
Preparation methods
PreparationPreparation of 3-bromo-5-chlorobenzoic acid (diazotization, diazonium salt conversion) In a 250 mL four-necked flask equipped with a thermometer, dropping funnel, and reflux condenser, 11.2 g (0.045 mol) of 2-amino-3-bromo-5-chlorobenzoic acid and 12 mL of 98% concentrated sulfuric acid were added sequentially. After stirring and dissolving, 5.4 g of 30% sodium nitrite aqueous solution was slowly added dropwise while controlling the reaction temperature at 10℃. After the addition was completed, the reaction was kept at this temperature for 1 h. In another 250 mL four-necked flask equipped with a thermometer and reflux condenser, 2.4 g (0.04 mol) of copper powder and 50 mL of ethanol were added. The above reaction solution was added dropwise under reflux, and the addition was completed within 30 min. Reflux was continued for 1 h. After slightly cooling, the reaction apparatus was changed to a distillation apparatus to distill and recover most of the ethanol. After cooling, the reaction solution was poured into ice water, and 9.8 g of yellow solid precipitated. Recrystallization from anhydrous ethanol yielded 7.2g of white 3-bromo-5-chlorobenzoic acid crystals (purity 99.6%) with a melting range of 190.0–192.0℃ (literature value [1] 189–190℃), and a total yield of 41.7% (based on 2-amino-3-bromo-5-chlorobenzoic acid). Maintaining the holding time unchanged, appropriately increasing the temperature of the diazotization reaction helps to increase the product yield. However, when the temperature is further increased to 10℃, the product yield decreases instead. This is because the diazotization reaction is an electrophilic substitution reaction. 2-amino-3-bromobenzoic acid is relatively weak, and appropriately increasing the temperature can accelerate the diazotization reaction rate. However, excessively high reaction temperatures will cause nitrous acid and diazonium salts to decompose, which in turn decreases the product yield. Therefore, the suitable diazotization reaction temperature is 5℃.
Suppliers100 total
Related reactions
9 records
Compound notes
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