1,8-dihydroxy-2-naphthaldehyde

Base Information

• Chemical Name: 1,8-dihydroxy-2-naphthaldehyde
• CAS No.: 858457-19-9
• Molecular Formula: C11H8O3
• Molecular Weight: 188.17900
• Mol file: 858457-19-9.mol

Synonyms:2-Naphthalenecarboxaldehyde,1,8-dihydroxy;1,8-dihydroxy-2-naphthaldehyde;2-formyl-1,8-naphthalenediol;1,8-Dihydroxy-[2]naphthaldehyd;

Chemical Property of 1,8-dihydroxy-2-naphthaldehyde

Chemical Property:

• Melting Point: 139-140℃
• Boiling Point: 389.5±22.0 °C(Predicted)
• PKA: 5.15±0.50(Predicted)
• PSA: 57.53000
• Density: 1.424±0.06 g/cm3(Predicted)
• LogP: 2.06350

Purity/Quality:

98% ^*data from raw suppliers

1,8-Dihydroxy-2-naphthaldehyde 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,8-dihydroxy-2-naphthaldehyde

There total 4 articles about 1,8-dihydroxy-2-naphthaldehyde 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: 98.0%

2-formyl-1,8-bis(methoxymethoxy)naphthalene (865873-39-8) → 1,8-dihydroxy-2-naphthaldehyde (858457-19-9)

Guidance literature:

With hydrogenchloride; In dichloromethane; isopropyl alcohol; at 0 ℃; for 6h;

DOI:10.1039/b507579c

Reference yield:

1,8-bis(methoxymethoxy)naphthalene (172915-62-7) → 1,8-dihydroxy-2-naphthaldehyde (858457-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi; TMEDA / hexane; diethyl ether / 6 h / 0 °C

1.2: 88 percent / hexane; diethyl ether / 0 - 20 °C

2.1: 98 percent / HCl / propan-2-ol; CH₂Cl₂ / 6 h / 0 °C

With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In diethyl ether; hexane; dichloromethane; isopropyl alcohol;

DOI:10.1039/b507579c

Reference yield:

1,8-dihydroxynaphthalene (569-42-6) → 1,8-dihydroxy-2-naphthaldehyde (858457-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C

2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / diethyl ether / 6 h / 20 °C

2.2: 0 - 20 °C

3.1: hydrogenchloride / dichloromethane; isopropyl alcohol; water / 6 h / 0 °C

With hydrogenchloride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1021/jacs.5b08562

upstream raw materials:

1,8-dihydroxynaphthalene

2-formyl-1,8-bis(methoxymethoxy)naphthalene

1,8-bis(methoxymethoxy)naphthalene

Downstream raw materials:

2-(phenyl)imino-1,8-dihydroxynaphthalene

C₂₃H₂₅NO₂

Refernces

• 1、 Peng, Chia-Yu,Shen, Jiun-Yi,Chen, Yi-Ting,Wu, Pei-Jhen,Hung, Wen-Yi,Hu, Wei-Ping,Chou, Pi-Tai. "Optically Triggered Stepwise Double-Proton Transfer in an Intramolecular Proton Relay: A Case Study of 1,8-Dihydroxy-2-naphthaldehyde". . p. 14349 - 14357. Retrieved 2015/11/27.