[ CAS No. 5060-65-1 ]

Name: 5060-65-1|Naphthalene-2,6-dicarbaldehyde|97%
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Quality Control of [ 5060-65-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 5060-65-1 ]

CAS No. :	5060-65-1	MDL No. :	MFCD00462585
Formula :	C₁₂H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQDQMRZGMILNMQ-UHFFFAOYSA-N
M.W :	184.19	Pubchem ID :	816772
Synonyms :

Calculated chemistry of [ 5060-65-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	54.72
TPSA :	34.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.51
Log Po/w (XLOGP3) :	1.54
Log Po/w (WLOGP) :	2.46
Log Po/w (MLOGP) :	1.76
Log Po/w (SILICOS-IT) :	3.28
Consensus Log Po/w :	2.11

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.35
Solubility :	0.825 mg/ml ; 0.00448 mol/l
Class :	Soluble
Log S (Ali) :	-1.87
Solubility :	2.51 mg/ml ; 0.0136 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.97
Solubility :	0.0197 mg/ml ; 0.000107 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 5060-65-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 5060-65-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 5060-65-1 ]

[ 5060-65-1 ] Synthesis Path-Downstream 1~56

1
[ 5060-65-1 ]
[ 33895-27-1 ]
[ 42049-92-3 ]

Reference： [1]Laarhoven,W.H.; Cuppen,H.J.M. [Recueil des Travaux Chimiques des Pays-Bas, 1973, vol. 92, p. 553 - 563]

2
[ 5060-65-1 ]
[ 25075-81-4 ]
<2(4)>(2,6)-Naphthalenophantetraen [ No CAS ]

Reference： [1]Tanner,D. et al. [Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1979, vol. 33, p. 443 - 448]

3
[ 4542-77-2 ]
[ 5060-65-1 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1973,vol. 92,p. 553 - 563

4
[ 91-63-4 ]
[ 5060-65-1 ]
[ 113308-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride Heating;

Reference： [1]Vernigor, E. M.; Koz'menko, M. V.; Lebedev, S. A.; Luk'yanets, E. A.; Savvina, L. P.; Shalaev, V. K. [Chemistry of Heterocyclic Compounds, 1987, vol. 23, # 6, p. 677 - 680][Khimiya Geterotsiklicheskikh Soedinenii, 1987, vol. 23, # 6, p. 820 - 823]

5
[ 95-21-6 ]
[ 5060-65-1 ]
[ 75220-93-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;

Reference： [1]Vernigor, E. M.; Shalaev, V. K.; Novosel'tseva, L. P.; Luk'yanets, E. A.; Ustenko, A. A.; et al. [Chemistry of Heterocyclic Compounds, 1980, vol. 16, # 5, p. 464 - 468][Khimiya Geterotsiklicheskikh Soedinenii, 1980, # 5, p. 604 - 608]

6
[ 120-75-2 ]
[ 5060-65-1 ]
[ 74862-11-6 ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;

7
[ 3969-09-3 ]
[ 5060-65-1 ]
[ 74862-10-5 ]

Yield	Reaction Conditions	Operation in experiment
31%	With potassium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;

8
[ 5060-65-1 ]
[ 111-40-0 ]
2,5,8,19,22,25-hexaaza<9,9>(2,6)naphthalenophane-1,8,18,25-tetraene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In acetonitrile for 36h; Ambient temperature;

Reference： [1]Dhaenens, Michel; Lehn, Jean-Marie; Vigneron, Jean-Pierre [Journal of the Chemical Society. Perkin transactions II, 1993, # 7, p. 1379 - 1381]

9
[ 5060-65-1 ]
[ 20686-65-1 ]
[ 74872-71-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 464 - 468
Khimiya Geterotsiklicheskikh Soedinenii,1980,p. 604 - 608

10
[ 5060-65-1 ]
[ 20686-66-2 ]
[ 74872-70-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;

11
[ 5060-65-1 ]
[ 85-15-4 ]
[ 74862-09-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;

12
[ 5060-65-1 ]
[ 139693-30-4 ]
[1-(3,5-Di-tert-butyl-phenyl)-meth-(Z)-ylidene]-[6-([1-(3,5-di-tert-butyl-phenyl)-meth-(Z)-ylidene]-amino}-methyl)-naphthalen-2-ylmethyl]-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene for 10h; Heating;

Reference： [1]Ashton, Peter R.; Fyfe, Matthew C. T.; Martinez-Diaz, M.-Victoria; Menzer, Stephan; Schiavo, Cesare; Stoddart, J. Fraser; White, Andrew J. P.; Williams, David J. [Chemistry - A European Journal, 1998, vol. 4, # 8, p. 1523 - 1534]

13
[ 5060-65-1 ]
[ 153277-56-6 ]
[ 220273-43-8 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at -78℃; Yield given;

Reference： [1]Adamczyk, Maciej; Reddy, Rajarathnam E. [Tetrahedron Asymmetry, 1998, vol. 9, # 22, p. 3919 - 3921]

Yield	Reaction Conditions	Operation in experiment
	/BRN= 387156/;

15
[ 840-65-3 ]
[ 5060-65-1 ]
[ 7567-87-5 ]
[ 55343-77-6 ]
[ 157383-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bis(2-methoxyethoxy)aluminium dihydride; N-methylaniline In tetrahydrofuran at 5℃;

Reference： [1]Hagiya, Kazutake; Mitsui, Sunao; Taguchi, Hiroaki [Synthesis, 2003, # 6, p. 823 - 828]

16
[ 558-13-4 ]
[ 5060-65-1 ]
[ 610283-01-7 ]

Yield	Reaction Conditions	Operation in experiment
58%	With triphenylphosphine In dichloromethane at 20℃; for 1h;

Reference： [1]Hwang, Gil Tae; Son, Hyung Su; Ku, Ja Kang; Kim, Byeang Hyean [Journal of the American Chemical Society, 2003, vol. 125, # 37, p. 11241 - 11248]

17
[ 5859-93-8 ]
[ 5060-65-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With pyridinium chlorochromate In dichloromethane at 49.84℃; for 4h; Inert atmosphere;
58%	With pyridinium chlorochromate In dichloromethane at 20℃;
54%	With C₁₁H₁₇N₂O₂; potassium <i>tert</i>-butylate; copper(ll) bromide In water; acetonitrile at 20℃;

50%	With pyridinium chlorochromate In dichloromethane at 49.84℃; for 4h; Inert atmosphere;
	With pyridinium chlorochromate

Reference： [1]Xie, Gao-Yi; Jiang, Long; Lu, Tong-Bu [Dalton Transactions, 2013, vol. 42, # 39, p. 14092 - 14099]
[2]Hwang, Gil Tae; Son, Hyung Su; Ku, Ja Kang; Kim, Byeang Hyean [Journal of the American Chemical Society, 2003, vol. 125, # 37, p. 11241 - 11248]
[3]Location in patent: scheme or table Gartshore, Christopher J.; Lupton, David W. [Advanced Synthesis and Catalysis, 2010, vol. 352, # 18, p. 3321 - 3328]
[4]García-Simón, Cristina; Monferrer, Alba; Garcia-Borràs, Marc; Imaz, Inhar; Maspoch, Daniel; Costas, Miquel; Ribas, Xavi [Chemical Communications, 2019, vol. 55, # 6, p. 798 - 801]
[5]Panahi, Farhad; Mahmoodi, Ali; Ghodrati, Sajjad; Eshghi, Fazlolah [RSC Advances, 2020, vol. 11, # 1, p. 168 - 176]

18
[ 110-91-8 ]
[ 5060-65-1 ]
2,6-bis(dimorpholinomethyl)naphthalene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	at 20℃; for 12h;

Reference： [1]Winter, Andreas; Hummel, Johanna; Risch, Nikolaus [Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 4862 - 4871]

19
[ 5060-65-1 ]
C₂₀H₂₄N₂O₂⁽²⁺⁾*2Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 69 percent / 12 h / 20 °C 2: acetyl chloride / diethyl ether / 12 h / 20 °C

Reference： [1]Winter, Andreas; Hummel, Johanna; Risch, Nikolaus [Journal of Organic Chemistry, 2006, vol. 71, # 13, p. 4862 - 4871]

20
[ 1141-38-4 ]
[ 5060-65-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 84 percent / DIBAL / toluene / 0 °C 2: 58 percent / PCC / CH₂Cl₂ / 20 °C
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride 2: pyridinium chlorochromate

Reference： [1]Hwang, Gil Tae; Son, Hyung Su; Ku, Ja Kang; Kim, Byeang Hyean [Journal of the American Chemical Society, 2003, vol. 125, # 37, p. 11241 - 11248]
[2]Panahi, Farhad; Mahmoodi, Ali; Ghodrati, Sajjad; Eshghi, Fazlolah [RSC Advances, 2020, vol. 11, # 1, p. 168 - 176]

21
[ 5060-65-1 ]
(3,5-Di-tert-butyl-benzyl)-{6-[(3,5-di-tert-butyl-benzylamino)-methyl]-naphthalen-2-ylmethyl}-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: toluene / 10 h / Heating 2: NaBH₄ / methanol / 8 h / Heating

22
[ 5060-65-1 ]
2,5,8,19,22,25-hexaaza<9,9>(2,6)naphthalenophane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / acetonitrile / 36 h / Ambient temperature 2: NaBH₄ / methanol / 0.75 h / Heating

Reference： [1]Dhaenens, Michel; Lehn, Jean-Marie; Vigneron, Jean-Pierre [Journal of the Chemical Society. Perkin transactions II, 1993, # 7, p. 1379 - 1381]

23
[ 5060-65-1 ]
3,4-diaminobenzamidine monohydrochloride [ No CAS ]
C₂₆H₂₀N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With p-benzoquinone In ethanol; water for 12h;	1 The above dialdehyde (0. 184 g, 0. 001 MOLE), 4-amidino1, 2-PHENYLENEDIAMINE HYDROCHLORIDE HEMIHYDRATE (0. 39 g, 0. 002 mole) and 0. 216 G (0. 002 mole) 1, 4-BENZOQUINONE in ethanol was REFLUXED for 12 H and after standard work-up was converted to its HYDROCHLORIDE SALT, 0. 43 G (70%) ; M. P. >300°C ; 1H-NMR (DMSO-D6) : 8. 87 (S, 2H), 8. 42 (D, 2H, J=8. 4HZ), 8. 28 (D, 2H, J=8. 4HZ), 8. 23 (S, 2H), 7. 86 (D, 2H, J=8. 4HZ), 7. 74 (D, 2H, J=8. 4HZ) ; FAB MS : m/e 445(M++1); 13CNMR(DMSO-d6) : 166. 7, 145. 2, 141. 2, 138. 4, 134. 3, 130. 6, 127. 9, 127. 1, 125. 5, 123. 6, 122. 9, 116. 5, 115. 8 ; ANAL. CALC. for C26H20N8.4HCl.1.5H2O. C, 52. 89 ; H, 4. 40 : N, 18. 98. Found : C, 52. 51 ; H, 4. 53 ; N, 18. 86.

Reference： [1]Current Patent Assignee: UNIVERSITY SYSTEM OF GEORGIA - WO2005/33065, 2005, A1 Location in patent: Page/Page column 38

24
[ 31656-49-2 ]
[ 5060-65-1 ]

Yield	Reaction Conditions	Operation in experiment
72.3%		To A stirred solution of 3. 5 G (0. 02 mole) of 2, 6- DICYANONAPHTHALENE in 75 ML CH2Cl2 under N2 was added DIBAL (4. 26 g, 30 ML, 1 M solution in CYCLOHEXANE) in 10 min., after 15 min. stirring, it was heated at 45C for 45 min. The cooled reaction mixture (ice-bath) was decomposed with 2N H2S04 (50 ML) while stirring continued for 1 H, CH2Cl2 layer was separated, washed with water, NAHCOS, water and dried over NA2S04 and filtered and cone. in vac. triturated with hexane and filtered and dried to yield 2. 66 G (72. 3%) pale crystalline solid, M. P. 173-4C ; H-NMR (DMSO-D6) : 10. 18 (S, 1H), 10. 17 (S, 1H), 8. 57 (S, 2H), 8. 23 (D, 2H, J=8. 4HZ), 7. 96 (D, 2H, J=8. 4HZ) ; 13CNMR (DMSO-D6) : 192. 5, 135. 6, 134. 9, 133. 0, 130. 2, 123. 4 ; MS : M/E 184(M+).

Reference： [1]Patent: WO2005/33065,2005,A1 .Location in patent: Page/Page column 37-38

25
β-cycloperanyltriphenylphosphonium bromide [ No CAS ]
hexane-gave [ No CAS ]
[ 5060-65-1 ]
[ 7732-18-5 ]
(E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1.89 g (42%)	With potassium <i>tert</i>-butylate; acetic acid In tetrahydrofuran; hexane; ethyl acetate; <i>tert</i>-butyl alcohol	1 Preparation of (E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthaldehyde EXAMPLE 1 Preparation of (E)-6-[2-(2,6,6-trimethyl-1-cyclohexen-1-yl)ethenyl]-2-naphthaldehyde A mixture of 2.74 g (14.7 mmol) of 2,6-naphthalenedicarboxaldehyde and 7.00 g (14.6 mmol) of β-cycloperanyltriphenylphosphonium bromide in 40 mL of dry THF and 5.5 mL of dry t-BuOH was stirred and cooled in a -20° C. bath. Then 1.65 g (14.7 mmol) of t-BuOK in 18 mL of t-BuOH was added over a period of 4 min. The resultant tannish orange mixture was stirred at ambient temperature for 21 h and then diluted with 200 mL of hexane and 100 mL of H2 O containing 2 drops of HOAc. The aqueous layer was extracted with 100 mL of hexane. The organic extracts were washed with two 50-mL portions of H2 O and brine, dried (MgSO4), and concentrated at reduced pressure to a yellow oil and solid which--after extraction with 100-mL portions of hexane and 5% EtOAc/hexane--gave 5.7 g of yellow oil and some solid. This material was chromatographed on 300 g of silica gel. Elution with 600 mL of hexane followed by 5% EtOAc/hexane gave two fractions of 1.7 g and 1.4 g. The first fraction was rechromatographed on 100 g of silica gel eluted in the same manner to afford 0.7 g of yellow oil, which was combined with the second fraction. These combined fractions were purified by preparative LC with 3% EtOAc/hexane to give 1.89 g (42%) of viscous yellow oil, which solidified on cooling, mp 35°-37° C.

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - US4456618, 1984, A

26
[ 5060-65-1 ]
N,N-dibutyl-4-iodobenzamide [ No CAS ]
C₄₂H₅₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N,N-dibutyl-4-iodobenzamide With cyclopentylmagnesium bromide In tetrahydrofuran at 0℃; Stage #2: 2,6-naphthalenedicarbaldehyde In tetrahydrofuran at 0 - 20℃;

Reference： [1]Location in patent: experimental part Chen, Jun-Chun; Lee, Tse-Shi; Lin, Chih-Hsiu [Chemistry - A European Journal, 2008, vol. 14, # 9, p. 2777 - 2787]

27
[ 1129492-00-7 ]
[ 24424-99-5 ]
[ 5060-65-1 ]
[ 1129492-03-0 ]

Yield	Reaction Conditions	Operation in experiment
378 mg	Stage #1: N-(3-tert-butoxycarbonylaminopropyl)-N,N-bis(2-aminoethyl)amine; 2,6-naphthalenedicarbaldehyde In acetonitrile at 20℃; for 120h; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol; dichloromethane at 20℃; for 2h; Stage #3: di-<i>tert</i>-butyl dicarbonate With dmap at 20℃; for 18h;