2-Bromo-6-hydroxybenzaldehyde (HCID 11954768)

Names & identifiers

Preferred name: 2-Bromo-6-hydroxybenzaldehyde
IUPAC: 2-bromo-6-hydroxybenzaldehyde
English name: 2-Bromo-6-hydroxybenzaldehyde
Molecular formula: C7H5BrO2
Molecular weight: 201.02

Names & synonyms

2-BROMO-6-HYDROXYBENZALDEHYDE22532-61-2DTXSID30474659RefChem:257466DTXCID20425473696-195-0MFCD08234722Benzaldehyde, 2-bromo-6-hydroxy-6-bromo-2-hydroxybenzaldehydeCL8260AKOS005257158CS-W001122

Show more names

2-Bromo-6-hydroxybenzaldehyd3-BroMo-2-forMylphenol2-bromo-hydroxybenzaldehyde2-hydroxy-6-bromobenzaldehydeBenzaldehyde,2-broMo-6-hydroxy-3-Bromo-2-formylphenol, 6-Bromosalicylaldehyde

AB43626PS-5659SY024446EN300-116695Z12691757286-BROMOSALICYLALDEHYDE2-bromo-6-hydroxy-benzaldehyde6-Bromosalicylaldehyde; 2-Bromo-6-hydroxybenzaldehyde; 2-Hydroxy-6-bromobenzaldehyde; 6-Bromo-2-hydroxybenzaldehyde; 6-Bromosalicylaldehyde

Database identifiers

CAS: 22532-61-2
PubChem CID: 11954768
DTXSID: DTXSID30474659
EC Number: 696-195-0
Nikkaji: J1.399.370J

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 37.3 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 2
Rotatable bonds: 1
Heavy atoms: 10
Formal charge: 0
Complexity: 127

Physicochemical properties

Melting point: 50 · 50-52 °C
Boiling point: 243.4 · 243.4±20.0 °C(Predicted)
Density: 1.737 · 1.737±0.06 g/cm3(Predicted)
storage temp.: 2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility: DMSO (Slightly), Methanol (Slightly)
form: Solid
pka: 7.21 · 7.21±0.10(Predicted)
color: Light Yellow
InChI: InChI=1S/C7H5BrO2/c8-6-2-1-3-7(10)5(6)4-9/h1-4,10H
InChIKey: LQTXMBDCLHZDAM-UHFFFAOYSA-N
SMILES: C(=O)C1=C(O)C=CC=C1Br
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
HS Code: 2912210000 · 2912210000

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (66.7%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (33.3%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (33.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (33.3%): 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 3 reports by companies from 2 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 (100%)；Acute Tox. 4 (66.7%)；Skin Irrit. 2 (33.3%)；Eye Irrit. 2 (33.3%)；Acute Tox. 4 (100%)；STOT SE 3 (33.3%)

Safety data

hs_code: 2912210000
Signal word: Warning
Symbol(GHS): GHS07
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Applications

Uses2-Bromo-6-hydroxybenzaldehyde, is a substituted salicylaldehyde used in the synthesis of BIIB042, a γ-secretase modulator.

Preparation methods · 1 item

PreparationStep a: 2,6-Dibromobenzaldehyde, toluene, 1,3-propanediol, and concentrated sulfuric acid are heated to reflux and water is removed. After the reaction is complete, the mixture is cooled to room temperature, neutralized with sodium methoxide, and distilled under reduced pressure to obtain intermediate a;Step b: Intermediate a and tetrahydrofuran are cooled to -10℃ to 5℃, isopropyl Grignard reagent is added, Grignard exchange is completed, then trialkyl borate is added and the reaction is maintained at this temperature; hydrochloric acid is used to quench the reaction, organic solvent is used for extraction and separation, and the mixture is evaporated to dryness to obtain intermediate b;Step c: Intermediate b is added to an alcohol/water mixed solvent and a copper catalyst, and hydrogen peroxide is added for reaction; sodium thiosulfate solution is used to quench the reaction, extraction and separation are performed, organic solvent is added for slurrying, and filtration is used to obtain 2-bromo-6-hydroxybenzaldehyde.