1,1'-Methylenedi-2-naphthol

Base Information

• Chemical Name: 1,1'-Methylenedi-2-naphthol
• CAS No.: 1096-84-0
• Molecular Formula: C21H16 O2
• Molecular Weight: 300.357
• Hs Code.: 2907199090
• European Community (EC) Number: 214-145-4
• NSC Number: 402620,5992
• UNII: WSE97K4L90
• DSSTox Substance ID: DTXSID8074447
• Nikkaji Number: J61.683D
• Wikidata: Q27292809
• Pharos Ligand ID: RQ12U8FP4C3D
• ChEMBL ID: CHEMBL447347
• Mol file: 1096-84-0.mol

Synonyms:1,1'-methylenedi-2-naphthol;Squaxon;Squoxin;ST1859

Chemical Property of 1,1'-Methylenedi-2-naphthol

Chemical Property:

• Appearance/Colour: light pink to light brown crystalline powder
• Melting Point: 181-190 °C (dec.)(lit.)
• Refractive Index: 1.5680 (estimate)
• Boiling Point: 543.4°Cat760mmHg
• PKA: 8.91±0.50(Predicted)
• Flash Point: 258.6°C
• PSA: 40.46000
• Density: 1.283g/cm³
• LogP: 4.99500
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 300.115029749
• Heavy Atom Count: 23
• Complexity: 359

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,1''-Methylenedi-2-naphthol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C=CC(=C2CC3=C(C=CC4=CC=CC=C43)O)O

Technology Process of 1,1'-Methylenedi-2-naphthol

There total 71 articles about 1,1'-Methylenedi-2-naphthol 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: 99.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + β-naphthol (135-19-3) → bis(2-hydroxy-1-naphthyl)methane (1096-84-0)

Guidance literature:

With hydrogen bromide; In water; acetonitrile; at 20 ℃; for 5h;

DOI:10.1039/c3ra45898a

Reference yield: 91.8%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + β-naphthol (135-19-3) → 1-hydroxymethyl-2-naphthol (5386-25-4) + bis(2-hydroxy-1-naphthyl)methane (1096-84-0)

Guidance literature:

In acetic acid; at 90 ℃; for 2h;

DOI:10.1002/jlcr.838

Reference yield: 81.0%

methanol (67-56-1) + β-naphthol (135-19-3) → bis(2-hydroxy-1-naphthyl)methane (1096-84-0)

Guidance literature:

With potassium tert-butylate; C₃₇H₃₆Cl₂NPRuS₂; at 135 ℃; for 36h; Sealed tube; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.joc.1c01185

upstream raw materials:

ethanol

hexamethylenetetramine

β-naphthol

di-2-naphthoxymethane

Downstream raw materials:

bis-(2-benzoyloxy-[1]naphthyl)-methane

C₂₈H₂₀ClO₄P

C₂₈H₂₀ClO₄P

C₂₉H₂₃O₄P

Refernces

• 1、 Angelini, Giancarlo,Ursini, Ornella,Minetti, Patrizia,Celona, Diana,De Angelis, Francesco. "Simplified synthesis of 1,1′[14C]-methylene-di (2-naphthol). A radiochemical and kinetic approach". . p. 543 - 556. Retrieved 2004.
• 2、 Merijan,Gardner. "". . p. 3965. Retrieved 1965.
• 3、 Baghel, Garima Singh,Chinta, Jugun Prakash,Rao, Chebrolu P.. "Synthesis, characterization of the amido-conjugates of 1,1′- methylene-bis(2-naphthol) and recognition of Cu2+ in aqueous acetonitrile". . p. 2397 - 2404. Retrieved 2012.
• 4、 Woodgate, Paul D.,Horner, Gillian M.,Maynard, N. Paul,Rickard, Clifton E.F.. "Synthesis of dioxazaborocines from N-substituted-bis(2-hydroxyaryl)aminomethylamines". . p. 180 - 193. Retrieved 1999.
• 5、 Monti,Castillo. "". . p. 3764,3767. Retrieved 1970.
• 6、 Rao, P. Venkateshwara,Rao, Chebrolu Pulla,Wegelius, Elina K.,Kolehmainen, Erkki,Rissanen, Kari. "Reactivity of cis-bis(acetylacetonato)dichlorotitanium(IV) towards hydroxy-containing ligands: Isolation and characterisation of products". . p. 4469 - 4474. Retrieved 1999.
• 7、 Kumar, Sandeep,Mehta, Shilpika Bali. "One-step novel synthesis of methylene bisphenols and methylene bisnaphthols using Lewis acid mediated rearrangement". . . Retrieved 2021/12/20.
• 8、 Biswas, Nandita,Srimani, Dipankar. "Ru-Catalyzed Selective Catalytic Methylation and Methylenation Reaction Employing Methanol as the C1 Source". . p. 10544 - 10554. Retrieved 2021/07/31.