METHYL 3-FORMYL-4-HYDROXYBENZOATE
- Product Name
- METHYL 3-FORMYL-4-HYDROXYBENZOATE
- CAS No.
- 24589-99-9
- Chemical Name
- METHYL 3-FORMYL-4-HYDROXYBENZOATE
- Synonyms
- 5-carbomethoxysalicylaldehyde;METHYL 3-FORMYL-4-HYDROXYBENZOATE;5-(METHOXYCARBONYL)SALICYLALDEHYDE;Methyl 3-forMyl-4-hydroxybenzoate 97%;3-Formyl-4-hydroxybenzoesure-methylester;3-formyl-4-hydroxy-benzoicacimethylester;4-hydroxyisophthalaldehydeacidmethylester;4-hydroxy-isophthalaldehydicacimethylester;Benzoic acid, 3-forMyl-4-hydroxy-, Methyl ester;3-formyl-4-hydroxy-Benzoic acid methyl ester (9CI ACI)
- CBNumber
- CB7477924
- Molecular Formula
- C9H8O4
- Formula Weight
- 180.16
- MOL File
- 24589-99-9.mol
METHYL 3-FORMYL-4-HYDROXYBENZOATE Property
- Melting point:
- 80-84 °C
- Boiling point:
- 299.3±25.0 °C(Predicted)
- Density
- 1.310±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- form
- solid
- pka
- 6.56±0.18(Predicted)
- color
- Pale yellow
- InChI
- InChI=1S/C9H8O4/c1-13-9(12)6-2-3-8(11)7(4-6)5-10/h2-5,11H,1H3
- InChIKey
- ADSJCWKOKYOJSZ-UHFFFAOYSA-N
- SMILES
- C(OC)(=O)C1=CC=C(O)C(C=O)=C1
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-36/37/38
- Safety Statements
- 26
- WGK Germany
- 3
- RTECS
- DH1421520
- Hazard Note
- Harmful
- HS Code
- 29189900
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P270Do not eat, drink or smoke when using this product.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 673706
- Product name
- Methyl 3-formyl-4-hydroxybenzoate
- Purity
- 97%
- Packaging
- 1g
- Price
- $77.7
- Updated
- 2025/07/31
- Product number
- F1349
- Product name
- Methyl 3-Formyl-4-hydroxybenzoate
- Purity
- min. 95.0 %
- Packaging
- 1G
- Price
- $198
- Updated
- 2025/07/31
- Product number
- M305385
- Product name
- Methyl 3-formyl-4-hydroxybenzoate
- Packaging
- 10g
- Price
- $1175
- Updated
- 2021/12/16
- Product number
- CHM0030603
- Product name
- METHYL 3-FORMYL-4-HYDROXYBENZOATE
- Purity
- 95.00%
- Packaging
- 5G
- Price
- $1421.65
- Updated
- 2021/12/16
- Product number
- 1869AB
- Product name
- Methyl 3-formyl-4-hydroxybenzoate
- Packaging
- 1g
- Price
- $63
- Updated
- 2021/12/16
METHYL 3-FORMYL-4-HYDROXYBENZOATE Chemical Properties,Usage,Production
Uses
Methyl 3-Formyl-4-hydroxybenzoate is a useful synthetic intermediate in the synthesis of 1,2-Benzisoxazole-5-carboxylic Acid (B197900). Also a useful synthetic intermediate in the synthesis of Roflumilast (R639700); a selective phosphodiesterase 4 (PDE4) inhibitor and antiasthmatic in the treatment of chronic obstructive pulmonary disease.
Synthesis
50-00-0
99-76-3
24589-99-9
The general procedure for the synthesis of methyl 3-formyl-4-hydroxybenzoate from formaldehyde and methyl nipagin was as follows: methyl 4-hydroxybenzoate (3.00 g, 19.7 mmol) and magnesium chloride (2.81 g, 29.5 mmol) were dissolved in 100 mL of acetonitrile and mixed by stirring. Subsequently, triethylamine (TEA, 10.3 mL, 73.9 mmol) was slowly added via syringe. Next, paraformaldehyde (12.0 g, 133 mmol) was added all at once and the reaction mixture was heated to reflux. After keeping the reaction stirred under reflux conditions for 24 hours, it was cooled to room temperature. Upon completion of the reaction, the reaction was quenched by addition of about 100 mL of 1N hydrochloric acid (HCl) and the mixture was poured into ethyl acetate (EtOAc). The organic and aqueous layers were separated and the organic layer was washed with saturated brine. The aqueous layer was back-extracted with ethyl acetate (EtOAc). All organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated in vacuum by rotary evaporator. The crude product was purified by fast column chromatography. Pure grades collected and confirmed by thin layer chromatography (TLC) were concentrated under vacuum to give 2.06 g (58% yield) of the target product, methyl 3-formyl-4-hydroxybenzoate. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 11.54 (s, 1H), 10.27 (s, 1H), 8.21 (d, J = 2.4 Hz, 1H), 8.03 (dd, J = 8.8, 2.4 Hz, 1H), 7.07 (d, J = 8.8 Hz, 1H), 3.79 (s, 3H).
References
[1] Organic Syntheses, 2005, vol. 82, p. 64 - 68
[2] Journal of the American Chemical Society, 2009, vol. 131, # 43, p. 15608 - 15609
[3] Patent: US2008/300242, 2008, A1. Location in patent: Page/Page column 36
[4] Patent: WO2004/62661, 2004, A1. Location in patent: Page/Page column 35-36
[5] Tetrahedron Letters, 2016, vol. 57, # 52, p. 5914 - 5918
METHYL 3-FORMYL-4-HYDROXYBENZOATE Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from METHYL 3-FORMYL-4-HYDROXYBENZOATE manufacturers
- Product
- METHYL 3-FORMYL-4-HYDROXYBENZOATE 24589-99-9
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2018-08-09