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| CAS No.: | 672-13-9 |
|---|---|
| Name: | 2-Hydroxy-5-methoxybenzaldehyde |
| Article Data: | 87 |
| Molecular Structure: | |
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| Formula: | C8H8O3 |
| Molecular Weight: | 152.15 |
| Synonyms: | m-Anisaldehyde,6-hydroxy- (6CI,7CI,8CI);2-Formyl-4-methoxyphenol;2-Hydroxy-5-methoxybenzaldehyde;3-Methoxy-6-hydroxybenzaldehyde;4-Hydroxy-3-formylanisole;5-Methoxy-2-hydroxybenzaldehyde;5-Methoxysalicylaldehyde;NSC 30116; |
| EINECS: | 211-589-0 |
| Density: | 1.232 g/cm3 |
| Melting Point: | 4 °C(lit.) |
| Boiling Point: | 247.499 °C at 760 mmHg |
| Flash Point: | 108.071 °C |
| Solubility: | Miscible with chloroform. Slightly miscible with water. |
| Appearance: | clear yellow liquid |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-36-24/25 |
| PSA: | 46.53000 |
| LogP: | 1.21330 |
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| Conditions | Yield |
|---|---|
| Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Reflux; Stage #2: 4-methoxy-phenol In tetrahydrofuran Reflux; | 100% |
| Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran at 20 - 25℃; for 0.166667h; Stage #2: 4-methoxy-phenol In tetrahydrofuran Reflux; | 100% |
| Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran at 20℃; for 0.25h; Inert atmosphere; Stage #2: 4-methoxy-phenol In tetrahydrofuran for 16h; Inert atmosphere; Reflux; | 99% |
| Conditions | Yield |
|---|---|
| With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Inert atmosphere; | 98% |
| With aluminum (III) chloride In dichloromethane at 20℃; for 12h; Inert atmosphere; | 98% |
| With beryllium(II) chloride In toluene for 7h; | 95% |
| With aluminium(III) iodide; N,N-dimethyl-formamide dimethyl acetal In acetonitrile at 80℃; for 18h; | 47% |
| Stage #1: 2,5-dimethoxybenzaldehyde With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 4h; Stage #2: With water In dichloromethane at 0℃; |
- 41951-76-2
2-hydroxy-5-methoxybenzyl alcohol
- 672-13-9
2-hydroxy-5-methoxybenzaldehyde
| Conditions | Yield |
|---|---|
| With air; (acryl-TEMPO)-co-(allylamine-treated chlorophyll b-Co(III) complex) immobilized on SiO2-covered Fe3O4 magnetic nanoparticles In water at 25℃; for 0.416667h; | 96% |
| With oxygen In ethanol at 20℃; under 760.051 Torr; for 0.5h; Catalytic behavior; Green chemistry; | 95% |
| With dihydrogen peroxide at 20℃; for 3.6h; Catalytic behavior; Green chemistry; | 94% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide In water for 1h; Heating; | 72% |
| With sodium hydroxide Reimer-Tiemann reaction; Heating; | 65% |
| With sodium hydroxide at 70 - 80℃; for 0.5h; | 48% |
- 133503-46-5
1-(o-hydroxy-5-methoxyphenyl)-3-phenylpropargylic alcohol
A
- 672-13-9
2-hydroxy-5-methoxybenzaldehyde
B
- 886-66-8
1,4-diphenyl-1,3-butadiyne
| Conditions | Yield |
|---|---|
| With copper(II) acetate monohydrate In acetonitrile for 2h; Reflux; | A n/a B 72% |
- 224317-65-1
5-methoxy-2-(prop-2-yn-1-yloxy)benzaldehyde
A
- 672-13-9
2-hydroxy-5-methoxybenzaldehyde
| Conditions | Yield |
|---|---|
| With tetrabutylammonium tetrafluoroborate; tris(2,2'-bipyridine)nickel(II) tetrafluoroborate In N,N-dimethyl-formamide electrochem. reaction; magnesium rod anode, nickel foam grid cathode; | A 30% B 65% |
| Conditions | Yield |
|---|---|
| Reimer-Tiemann reaction; | 60% |
| Multi-step reaction with 2 steps 1: 40 percent / BF3*Et2O / CH2Cl2 / 14 h / Ambient temperature 2: 47 percent / H2O, HgO, BF3*Et2O / tetrahydrofuran / 1 h / Ambient temperature View Scheme |
- 80210-54-4
2-[1,3]Dithiolan-2-yl-4-methoxy-phenol
- 672-13-9
2-hydroxy-5-methoxybenzaldehyde
| Conditions | Yield |
|---|---|
| With boron trifluoride diethyl etherate; water; mercury(II) oxide In tetrahydrofuran for 1h; Ambient temperature; | 47% |
- 100-97-0
hexamethylenetetramine
- 150-76-5
4-methoxy-phenol
A
- 672-13-9
2-hydroxy-5-methoxybenzaldehyde
B
- 73289-61-9
2-hydroxy-5-methoxyisophthaldehyde
| Conditions | Yield |
|---|---|
| In trifluoroacetic acid for 24h; | A n/a B 32% |
| Conditions | Yield |
|---|---|
| in ein zuvor auf 165grad erhitztes Gemisch von Glycerin und Borsaeure bei 150grad und Behandeln des Reaktionsgemisches mit wss.H2SO4 bei 115grad; | |
| With toluene-4-sulfonic acid In acetic acid for 5h; Duff Aldehyde Synthesis; Reflux; Inert atmosphere; |
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Specification
The 2-Hydroxy-5-methoxybenzaldehyde with cas registry number of 672-13-9 is clear yellow liquid which is sensitive to air. This chemical is also known as 5-Methoxysalicylaldehyde. Its systematic name is called Benzaldehyde, 2-hydroxy-5-methoxy-. And its IUPAC name is named as 2-hydroxy-5-methoxybenzaldehyde. This chemical belongs to the following categories: Aromatic Aldehydes & Derivatives (substituted); Benzaldehyde; Adehydes, Acetals & Ketones; Anisoles, Alkyloxy Compounds & Phenylacetates; Phenols. It has the EINECS registry number of 211-589-0.
The physical properties about this chemical are: (1)ACD/LogP: 1.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): 1.5 ; (5)#H bond acceptors: 3; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 3; (8)Index of Refraction: 1.587; (9)Molar Refractivity: 41.56 cm3; (10)Molar Volume: 123.5 cm3; (11)Surface Tension: 47.3 dyne/cm; (12)Density: 1.231 g/cm3; (13)Flash Point: 108.1 °C; (14)Enthalpy of Vaporization: 50.43 kJ/mol; (15)Boiling Point: 247.5 °C at 760 mmHg; (16)Vapour Pressure: 0.0162 mmHg at 25°C ; (17)Refractive index: 1.577-1.579.
Preparation of 2-Hydroxy-5-methoxybenzaldehyde: it can be made by 4-methoxy-phenol with 60% yield.
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Uses of 2-Hydroxy-5-methoxybenzaldehyde: this chemical can react with nitroethene to give 6-methoxy-3-nitro-2H-chromene by using reagent n-Bu2NH and solvent CHCl3 at temperature 80 ℃. The reaction time is about 24 hours with 72% yield.
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When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Therefore, wear suitable protective clothing during using it to avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)SMILES: O=Cc1cc(ccc1O)OC;
(2)InChI: InChI=1/C8H8O3/c1-11-7-2-3-8(10)6(4-7)5-9/h2-5,10H,1H3;
(3)InChIKey: FZHSPPYCNDYIKD-UHFFFAOYAD
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 125mg/kg (125mg/kg) | BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA | "Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 228, 1954. |