Basic information
- Standard SMILES
COc1ccc(C(=O)CBr)cc1- InChIKey
XQJAHBHCLXUGEP-UHFFFAOYSA-N- Molecular formula
- C9H9BrO2
- Average molar mass
- 229.07 g/mol
- Monoisotopic mass
- 227.97859163
Names & identifiers
- Preferred name
- Bromomethyl 4-methoxyphenyl ketone
- IUPAC
- 2-bromo-1-(4-methoxyphenyl)ethanone
- English name
- 2-Bromo-4'-methoxyacetophenone
- Molecular formula
- C9H9BrO2
- Molecular weight
- 229.07
Names & synonyms
2632-13-52-Bromo-1-(4-methoxyphenyl)ethanoneEthanone, 2-bromo-1-(4-methoxyphenyl)-p-Methoxyphenacyl bromide4-Methoxyphenacyl bromideBromomethyl 4-methoxyphenyl ketonePV5M69J53HEINECS 220-118-8NSC-129010DTXSID20180934NSC 1290104Methoxyphenacyl bromide
Show more names
2-BROMO-1-(4-METHOXYPHENYL)ETHAN-1-ONEPTP Inhibitor II4-methoxy phenecyl bromidePTP inhibitor 1AKOS BBS-000008172-Bromo-4-methoxyTIMTEC-BB SBB0077774-METHOXYPHENACYL BR2-Bromo-4'-methoxyac
RefChem:5703662Bromo4'methoxyacetophenoneomegaBromo4methoxyacetophenoneDTXCID60103425Ethanone, 2bromo1(4methoxyphenyl)220-118-8InChI=1/C9H9BrO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H2-Bromo-4'-methoxyacetophenone
Database identifiers
- CAS
2632-13-5- PubChem CID
- 4965
- DTXSID
DTXSID20180934- ChEMBL
CHEMBL103009- UNII
- PV5M69J53H
- EC Number
- 220-118-8
- Nikkaji
- J192.152E
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 151
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Aromatic Ketones, Halogenated
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionOff-white crystalline powder with an irritating odor; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 69 · 69-71 °C(lit.)
- Boiling point
- 215.8 °C · 215.8°C (rough estimate)
- Density
- 1.4921 · 1.4921 (rough estimate)
- refractive index
- 1.55 · 1.5500 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Crystals or Crystalline Powder
- color
- Off-white to light brown
- Water Solubility
- It is soluble in DMSO, water (partly miscible), most organic solvents, and methanol.
- BRN
- 743112 · 743112
- InChI
- InChI=1S/C9H9BrO2/c1-12-8-4-2-7(3-5-8)9(11)6-10/h2-5H,6H2,1H3
- InChIKey
- XQJAHBHCLXUGEP-UHFFFAOYSA-N
- SMILES
- C(=O)(C1=CC=C(OC)C=C1)CBr
- CAS DataBase Reference
- 2632 · 2632-13-5(CAS DataBase Reference)
- FDA UNII
- 5 M69J53H · PV5M69J53H
- NIST Chemistry Reference
- 2 · Ethanone, 2-bromo-1-(4-methoxyphenyl)-(2632-13-5)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 314 · H314-H335
- Precautionary statements
- 260 · P260-P271-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 3 · Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- Hazard Codes
- C,Xi
- Risk Statements
- 34 · 34-36/37-36/37/38
- Safety Statements
- 26 · 26-27-28-36/37/39-45-37/39
- RIDADR
- 3261 · UN 3261 8/PG 2
- WGK Germany
- 3 · 3
- F
- 8 · 8-9-19-21
- Hazard Note
- Corrosive
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29147090 · 29147090
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 Skin · Eye Dam. 1Skin Corr. 1BSTOT SE 3
Safety & regulation
GHS classification
GHS Classification
Danger
H314 (95.9%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
P260, P261, P264, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P319, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 49 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information2-Bromo-4methoxyacetophenone: Does not have an individual approval but may be used under an appropriate group standard
Hazards SummaryCauses burns and lachrymation; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; [Alfa Aesar MSDS] See 4-Acetylanisole.
Hazard Classes and CategoriesSkin Corr. 1B (95.9%)
Toxicology
Adverse EffectsDermatotoxin - Skin burns.
Safety data
- F
- 8-9-19-21
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- ridadr
- UN 3261 8/PG 2
- hs_code
- 29147090
- risk_code
- 34-36/37-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- C,Xi
- hazard_note
- Corrosive
- safety_code
- 26-27-28-36/37/39-45-37/39
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H314-H335
- Hazard Classifications
- Eye Dam. 1Skin Corr. 1BSTOT SE 3
- Precautionary statements
- P260-P271-P280-P301+P330+P331-P303+P361+P353-P305+P351+P338
Chemistry & industry
Applications
Uses2-Bromo-4'-methoxyacetophenone, is used as a cell-permeable, covalent and potent protein tyrosine phosphatase inhibitor.
Uses2-Bromo-4'-methoxyacetophenone is a α-haloacetophenone derivatives tested for inhibition of protein tyrosine phosphatases SHP-1 and PTP1B.
Preparation methods
PreparationObtained by reaction of N-bromosuccinimide (NBS) with 4-methoxyacetophenone in the presence of trimethylsilyl trifluoromethanesulfonate (TMS-OTf) in acetonitrile at r.t. for 24 h (87%).
Upstream & downstream products
Upstream raw materials
Downstream products
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