2,5-Dihydroxybenzaldehyde
Gentisate aldehyde · GENTISALDEHYDE · NSC 72387 · GENTISINALDEHYDE · Cyanohydroquinone · GENTISIC ALDEHYDE · ForMylhydroquinone · 2,5-Dihydroxybenzald
Identifiers & Physical Properties
| CAS No. | 1194-98-5 |
|---|---|
| Molecular formula | C7H6O3 |
| Average molar mass | 138.12 g/mol |
| Monoisotopic mass | 138.03169405 g/mol |
| SMILES | O=Cc1cc(O)ccc1O |
| InChIKey | CLFRCXCBWIQVRN-UHFFFAOYSA-N |
| PubChem CID | 70949 |
| ChEMBL | CHEMBL243186 |
| ChEBI | CHEBI:28508 |
| EC No. | 214-789-6 |
| DTXSID | DTXSID1061601 |
Chemical & Physical Properties
| XLogP | 1.2 |
|---|---|
| Topological polar surface area | 57.5 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 1 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 124 |
| LogP (partition coefficient) | 0.54 |
| Solubility | 1.38E+04 mg/L @ 25 °C (exp)13.8g/l soluble |
| Melting point | 100.00 to 103.00 °C. @ 760.00 mm Hg97-99 °C (lit.) |
| Physical Description | Solid |
| Collision Cross Section | 119.54 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Boiling point | 213.5°C (rough estimate) |
| Density | 1.2667 (rough estimate) |
| Refractive index | 1.4797 (estimate) |
| Storage conditions | Store below +30°C. |
| pKa (acidity coefficient) | 8.89±0.18(Predicted) |
| Physical state | Crystalline Powder |
| Color | Yellow to khaki-green |
| Sensitivity | Air Sensitive |
| BRN | 1363961 |
| InChI | 1S/C7H6O3/c8-4-5-3-6(9)1-2-7(5)10/h1-4,9-10H |
| InChIKey | CLFRCXCBWIQVRN-UHFFFAOYSA-N |
| SMILES | Oc1ccc(O)c(C=O)c1 |
| LogP (partition coefficient) | 0.540 |
| CAS DataBase Reference | 1194-98-5(CAS DataBase Reference) |
| FDA UNII | 0Q83HDS90W |
| NIST Chemistry Reference | 2,5-Dihydroxybenzaldehyde(1194-98-5) |
| EPA Substance Registry System | Benzaldehyde, 2,5-dihydroxy- (1194-98-5) |
| UNSPSC Code | 12352114 |
| NACRES | NA.22 |
| GHS pictogram | GHS07 |
| Signal word | Warning |
| GHS hazard statements | H315-H317-H319-H335 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
| Hazard symbols | Xi |
| Risk statements (R) | 36/37/38-43 |
| Safety statements (S) | 26-36/37/39-37/39-26,37/39-36 |
| Water hazard class (WGK) | 3 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Customs code | 29124990 |
| Storage class | 13 - Non Combustible Solids |
| Hazard class | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
Safety & Regulations
| GHS classification | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatory information | Benzaldehyde, 2,5-dihydroxy-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29124990 |
| Risk statements (R) | 36/37/38-43 |
| Signal word | Warning |
| GHS pictogram | GHS07 |
| Hazard symbols | Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-36/37/39-37/39-26,37/39-36 |
| Storage class | 13 - Non Combustible Solids |
| GHS hazard statements | H315-H317-H319-H335 |
| Hazard class | Eye Irrit. 2Skin Irrit. 2Skin Sens. 1STOT SE 3 |
| GHS precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 |
Applications & Uses
Description
2,5-Dihydroxybenzaldehyde is a building block. It has been used in the synthesis of 2,4-dimethylbenzoylhydrazones with antileishmanial and antioxidant activity.
Uses
2,5-Dihydroxybenzaldehyde (cas# 1194-98-5) is a compound useful in organic synthesis.
Preparation & Synthesis
Preparation
Add 80 mmol of dry paraformaldehyde to a mixture of 12 mmol of the phenol derivative and 2.5 mmol of MgO nanocrystalline (0.1 g). Expose the resulting mixture under microwave irradiation with a power of 650 W. Monitor the progress of the reaction by thin layer chromatography (TLC) developed by n-hexane : ethyl acetate (8 : 2). Add 100 mL of sulfuric acid (15% w/w) to the reaction mixture and heated at 50 °C for 15 min. Cool the reaction mixture to room temperature. Extract the product by dichloromethane (2 x 50 mL). Dry the organic layer over anhydrous magnesium sulphate. Evaporate the solution resulting from filtration to obtain the crude product. Purify the other product by column chromatography using n-hexane : ethyl acetate (95 : 5 to 70 : 30).