2,6-Dihydroxybenzaldehyde

Base Information

• Chemical Name: 2,6-Dihydroxybenzaldehyde
• CAS No.: 387-46-2
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 2912499000
• European Community (EC) Number: 812-673-5
• UNII: K89FJ2AWV2
• DSSTox Substance ID: DTXSID40437750
• Nikkaji Number: J5.715K
• Wikidata: Q27121982
• Metabolomics Workbench ID: 57368
• ChEMBL ID: CHEMBL3274337
• Mol file: 387-46-2.mol

Synonyms:2,6-dihydroxybenzaldehyde;387-46-2;Benzaldehyde, 2,6-dihydroxy-;Ranjal;resorcinol-formaldehyde;6-Hydroxysalicylaldehyde;K89FJ2AWV2;CHEBI:50206;MFCD08061915;UNII-K89FJ2AWV2;YSWG240;SCHEMBL311198;CHEMBL3274337;DTXSID40437750;DGXAGETVRDOQFP-UHFFFAOYSA-N;BCP16333;AKOS006227711;CS-W001105;DS-17274;SY013806;FT-0659071;EN300-861906;F10457;A824267;Q27121982;Z1198175863

Chemical Property of 2,6-Dihydroxybenzaldehyde

Chemical Property:

• Vapor Pressure: 0.065mmHg at 25°C
• Melting Point: 154-155 ºC
• Refractive Index: 1.674
• Boiling Point: 223.343 °C at 760 mmHg
• PKA: 7.66±0.10(Predicted)
• Flash Point: 103.154 °C
• PSA: 57.53000
• Density: 1.41 g/cm³
• LogP: 0.91030
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 114

Purity/Quality:

98% ^*data from raw suppliers

2,6-Dihydroxybenzaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C(=C1)O)C=O)O
• Uses: 2,6-Dihydroxybenzaldehyde is a reactant used in the synthesis of cinnamides as potent cholinesterase inhibitors.

Technology Process of 2,6-Dihydroxybenzaldehyde

There total 30 articles about 2,6-Dihydroxybenzaldehyde 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: 82.0%

5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9) → 2,6-dihydroxybenzaldehyde (387-46-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 ℃; for 6h; Inert atmosphere;

DOI:10.1055/s-0030-1259300

Reference yield: 65.6%

2,6-bis(1-ethoxyethoxy)benzaldehyde → 2,6-dihydroxybenzaldehyde (387-46-2)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 16h; pH=0.7 - 0.8;

Reference yield: 62.0%

5-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-benzo[1,3]dioxin-4-one (888958-29-0) → 2,6-dihydroxybenzaldehyde (387-46-2) + 5-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-one (154714-19-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jo0601664

upstream raw materials:

6-methoxysalicylaldehyde

3-formyl-2, 4-dihydroxybenzoic acid

2,6-dimethoxybenzaldehyde

chloroform

Downstream raw materials:

2,6-diacetoxy-benzaldehyde

2,6-bis(4-methoxycarbonylbenzyloxy)benzaldehyde

2,6-bis(4-bromobenzyloxy)benzaldehyde

2,6-bis(2,3,4,5,6-pentafluorobenzyloxy)benzaldehyde

Refernces

• 1、 Huang, Xihua,Liu, Jie,Sheng, Jianfei,Song, Xianheng,Du, Zhibo,Li, Mingkang,Zhang, Xuejing,Zou, Yong. "Decarboxylation of α,β-unsaturated aromatic lactones: Synthesis of: E-ortho -hydroxystilbenes from 3-arylcoumarins or isoaurones". supporting information. p. 804 - 808. Retrieved 2018/03/06.
• 2、 Alberti, Mariza N.,Polyhach, Yevhen,Tzirakis, Manolis D.,T?dtli, Laura,Jeschke, Gunnar,Diederich, Fran?ois. "Exploring the Strength of the H-Bond in Synthetic Models for Heme Proteins: The Importance of the N?H Acidity of the Distal Base". supporting information. p. 10194 - 10202. Retrieved 2016/07/19.