4-Hydroxy-3-(hydroxymethyl)benzaldehyde

Base Information

• Chemical Name: 4-Hydroxy-3-(hydroxymethyl)benzaldehyde
• CAS No.: 54030-32-9
• Molecular Formula: C8H8 O3
• Molecular Weight: 152.15
• Hs Code.: 2912499000
• European Community (EC) Number: 862-829-1
• UNII: VS48HCI63J
• DSSTox Substance ID: DTXSID10202371
• Nikkaji Number: J588.625B
• Wikidata: Q27291995
• Mol file: 54030-32-9.mol

Synonyms:4-Hydroxy-3-(hydroxymethyl)benzaldehyde;54030-32-9;BENZALDEHYDE, 4-HYDROXY-3-(HYDROXYMETHYL)-;BRN 2251439;4-Hydroxy-3-hydroxymethylbenzaldehyde;UNII-VS48HCI63J;VS48HCI63J;Oprea1_353947;SCHEMBL4371754;DTXSID10202371;AKOS006370930;SB84676;SS-5147;3-(hydroxymethyl)-4-hydroxybenzaldehyde;LS-25068;CS-0453503;EN300-138017;Q27291995;Z1198723368

Chemical Property of 4-Hydroxy-3-(hydroxymethyl)benzaldehyde

Chemical Property:

• Vapor Pressure: 0.000609mmHg at 25°C
• Melting Point: 142-145 °C
• Boiling Point: 300.9°Cat760mmHg
• PKA: 7.74±0.18(Predicted)
• Flash Point: 150°C
• PSA: 57.53000
• Density: 1.342g/cm³
• LogP: 0.69700
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 135

Purity/Quality:

99%+, ^*data from raw suppliers

4-Hydroxy-3-(hydroxymethyl)benzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=O)CO)O
• Uses: 4-Hydroxy-3-(hydroxymethyl)benzaldehyde is an impurity of Albuterol (A514501) which is a β2-adrenoceptor agonist, a bronchodilator and a tocolytic. 4-Hydroxy-3-(hydroxymethyl)benzaldehyde is also used in the preparation of Cinnamyl alcohol-like compounds which can be used for treatment of free radical generated related diseases inlcuding auto-immunodeficiency diseases. It is also used as a reagent in the synthesis of 5-Diacetoxymethyl-cycloSal-d4TMP which is a prototype of enzymatically activated cycloSal-pronucleotides that may possess antiviral activities against HIV.

Technology Process of 4-Hydroxy-3-(hydroxymethyl)benzaldehyde

There total 8 articles about 4-Hydroxy-3-(hydroxymethyl)benzaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

3-(chloromethyl)-4-hydroxybenzaldehyde (53412-47-8) → 4-hydroxy-3-(hydroxymethyl)benzaldehyde (54030-32-9)

Guidance literature:

With calcium carbonate; In tetrahydrofuran; at 20 ℃; for 13h;

DOI:10.1055/s-2005-871927

Reference yield: 85.0%

2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-carboxaldehyde (54030-33-0) → 4-hydroxy-3-(hydroxymethyl)benzaldehyde (54030-32-9)

Guidance literature:

With hydrogenchloride; In methanol; water; at 50 ℃; for 2h; Inert atmosphere;

Reference yield: 55.0%

5-formyl-2-hydroxybenzaldehyde (3328-70-9) → 4-hydroxy-3-(hydroxymethyl)benzaldehyde (54030-32-9)

Guidance literature:

5-formyl-2-hydroxybenzaldehyde; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; C₆H₁₃ClO₂Si; triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; regioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201800544

upstream raw materials:

3-(chloromethyl)-4-hydroxybenzaldehyde

2,2-dimethyl-4H-benzo[d][1,3]dioxin-6-carboxaldehyde

6-bromo-2,2-dimethyl-4H-benzo[1,3]dioxine

5-bromo-2-hydroxybenzyl alcohol

Downstream raw materials:

[(R)-2-(2,2-Dimethyl-4H-benzo[1,3]dioxin-6-yl)-2-((2R,6S)-6-methyl-tetrahydro-pyran-2-yloxy)-ethyl]-[6-(4-phenyl-butoxy)-hexyl]-amine

(R)-(-)-salmeterol

acetate salt of salbutamol

curcumin

Refernces

• 1、 -. "BIOFILM FORMATION INHIBITOR". Paragraph 0054. . Retrieved 2019/01/06.
• 2、 Guo, Zong-Liang,Deng, Yan-Qiu,Zhong, Shi,Lu, Gui. "Enantioselective synthesis of (R)-salmeterol employing an asymmetric Henry reaction as the key step". scheme or table. p. 1395 - 1399. Retrieved 2011/11/06.