ChemicalBook > CAS DataBase List > METHYL 3-FORMYL-4-HYDROXYBENZOATE

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

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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

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Safety

Hazard Codes: Xn
Risk Statements: 22-36/37/38
Safety Statements: 26
WGK Germany: 3
RTECS: DH1421520
Hazard Note: Harmful
HS Code: 29189900

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 673706
Product name: Methyl 3-formyl-4-hydroxybenzoate
Purity: 97%
Packaging: 1g
Price: $77.7
Updated: 2025/07/31

TCI Chemical

Product number: F1349
Product name: Methyl 3-Formyl-4-hydroxybenzoate
Purity: min. 95.0 %
Packaging: 1G
Price: $198
Updated: 2025/07/31

TRC

Product number: M305385
Product name: Methyl 3-formyl-4-hydroxybenzoate
Packaging: 10g
Price: $1175
Updated: 2021/12/16

American Custom Chemicals Corporation

Product number: CHM0030603
Product name: METHYL 3-FORMYL-4-HYDROXYBENZOATE
Purity: 95.00%
Packaging: 5G
Price: $1421.65
Updated: 2021/12/16

AK Scientific

Product number: 1869AB
Product name: Methyl 3-formyl-4-hydroxybenzoate
Packaging: 1g
Price: $63
Updated: 2021/12/16

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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

Career Henan Chemical Co

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

24589-99-9, METHYL 3-FORMYL-4-HYDROXYBENZOATERelated Search:

Methyl3-(4-(dibromomethyl)phenyl)acrylate Methyl 2-hydroxy-4-phenylbenzoate methyl 3-(((tert-butoxycarbonyl)(methyl)amino)methyl)-1-methyl-1H-pyrazole-5-carboxylate methyl 3-bromo-4-(hexyloxy)benzoate METHYL 3,5-DIBROMO-4-HYDROXYBENZOATE methyl 3-ethynyl-2-(1H-indol-6-yl)benzoate METHYL 3-NITRO-1H-INDOLE-2-CARBOXYLATE 3-Cyano-2-methylBenzoic acid methyl ester methyl 3-ethyl-2-oxo-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazine-7-carboxylate OTAVA-BB 7070707015 Methyl 3-fluoro-6-oxo-1,6-dihydropyridine-2-carboxylate Propanoic acid, 3-(3-bromophenoxy)-, methyl ester 2-Pyridinecarboxylic acid, 3-(bromomethyl)-4-(difluoromethyl)-, methyl ester DIMETHYL 4-HYDROXYISOPHTHALATE ATRANORIN Dimethyl 4-methoxyisophthalate FUMARPROTOCETRARIC ACID PSOROMIC ACID

3-formyl-4-hydroxy-benzoicacimethylester

4-hydroxyisophthalaldehydeacidmethylester

4-hydroxy-isophthalaldehydicacimethylester

5-carbomethoxysalicylaldehyde

5-(METHOXYCARBONYL)SALICYLALDEHYDE

METHYL 3-FORMYL-4-HYDROXYBENZOATE

5-(Methoxycarbonyl)salicylaldehyde, 2-Hydroxy-5-(methoxycarbonyl)benzaldehyde, 2-Formyl-4-(methoxycarbonyl)phenol

Methyl 3-forMyl-4-hydroxybenzoate 97%

3-Formyl-4-hydroxybenzoesure-methylester

Benzoic acid, 3-forMyl-4-hydroxy-, Methyl ester

Benzoic acid, 3-formyl-4-hydroxy-, methyl ester (9CI, ACI)

3-formyl-4-hydroxy-Benzoic acid methyl ester (9CI ACI)

24589-99-9

Carbonyl Compounds

Building Blocks

Aldehydes

Organic Building Blocks