[ CAS No. 7469-77-4 ] {[proInfo.proName]}

Name: 7469-77-4|2-Methyl-1-naphthol|97%
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COA NMR CNMR HPLC LC-MS

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Product Details of [ 7469-77-4 ]

CAS No. :	7469-77-4	MDL No. :	MFCD00003964
Formula :	C₁₁H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SRJCJJKWVSSELL-UHFFFAOYSA-N
M.W :	158.20	Pubchem ID :	24055
Synonyms :

Calculated chemistry of [ 7469-77-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	50.94
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.02
Log Po/w (XLOGP3) :	3.18
Log Po/w (WLOGP) :	2.85
Log Po/w (MLOGP) :	2.83
Log Po/w (SILICOS-IT) :	2.98
Consensus Log Po/w :	2.77

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.44
Solubility :	0.0573 mg/ml ; 0.000362 mol/l
Class :	Soluble
Log S (Ali) :	-3.28
Solubility :	0.0838 mg/ml ; 0.00053 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.87
Solubility :	0.0212 mg/ml ; 0.000134 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 7469-77-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7469-77-4 ]

* 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.

Upstream synthesis route of [ 7469-77-4 ]
Downstream synthetic route of [ 7469-77-4 ]

[ 7469-77-4 ] Synthesis Path-Upstream 1~2

1
[ 7469-77-4 ]
[ 77-78-1 ]
[ 14093-86-8 ]

Reference： [1] Journal of the American Chemical Society, 1948, vol. 70, p. 2003
[2] Journal of the American Chemical Society, 1966, vol. 88, # 24, p. 5855 - 5864

2
[ 90-15-3 ]
[ 77-78-1 ]
[ 7469-77-4 ]
[ 14093-86-8 ]
[ 2216-69-5 ]

Reference： [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1982, vol. 21, # 5, p. 474

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Isomers

Technical Information

• Acidity of Phenols • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blanc Chloromethylation • Chan-Lam Coupling Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Conjugate Additions of p-Benzoquinones • Conversion of Amino with Nitro • Decomposition of Arenediazonium Salts to Give Phenols • Deprotonation of Methylbenzene • Diazo Coupling • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Halogenation of Phenols • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Kolbe-Schmitt Reaction • Nitration of Benzene • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Phenols • Pechmann Coumarin Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Reductive Removal of a Diazonium Group • Reimer-Tiemann Reaction • Reverse Sulfonation——Hydrolysis • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Nitro Group Conver to the Amino Function • Vilsmeier-Haack Reaction

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Yield	Reaction Conditions	Operation in experiment
94.7%	With sulfuric acid; dihydrogen peroxide; In water; at 36 - 40℃; for 6h;Green chemistry;	Connected to a stirrer, thermometer, a 500 ml four-necked flask with a water separator and a reflux condenser. Add 100 grams of 1,2-dichloromethane,15.9 g (0.1 mol) of <strong>[7469-77-4]2-methyl-1-naphthol</strong>,1.2 grams of 95percent concentrated sulfuric acid, heated, Keep the internal temperature between 36-40 °C,15.0 g (0.31 mol) of a 70percent aqueous hydrogen peroxide solution was added dropwise, and water was separated. The total volume in the flask was kept constant, and the mixture was stirred at 40 ° C for 6 hours. Add 50 grams of saturated sodium chloride solution, Hot layering, The aqueous layer was extracted 3 times with 1,2-dichloromethane. 50 grams each time.The organic phases are combined and the 1,2-dichloromethane is recovered by distillation. obtained 16.3 g of 2-methyl-1,4-naphthoquinone, The yield was 94.7percent and the GC purity was 99.3percent.
74.1 - 88%	With 10-molybdo-2-vanadophosphoric acid; In hexane; at 50℃; for 2 - 3.5h;Conversion of starting material;	1 gram of <strong>[7469-77-4]2-methyl-1-naphthol</strong> is dissolved in 100 ml of n- hexane, through which nitrogen has been bubbled beforehand. 100 g of solution of heteropolycompound 0.4M, (density 1.48 g/ml) having the composition H5PMo10V2040 (for the sake of simplicity, the molecules of - water of crystallization and hydration are mot shown), are placed in a 500-ml reactor and heated to the temperature of 50 C under vigorous agitation, while nitrogen is bubbled through. The molar ratio between heteropolycompound and substrate is equal to 4. By means of a suitable funnel, the solution of 2-methyl-l-naphthol is dripped at a constant rate, with the reactor kept at 50 C and under a nitrogen head, into the solution of heteropolycompound, under continual agitation. The drip time is equal to approximately 2 hours. At the end the reaction mixture is kept under agitation for another 10 minutes. The mixture is cooled to 20 C and the two phases are separated according to the procedure described hereafter. The light organic phase is washed with water (the wash water is collected in the heavy aqueous phase) in order to remove the traces of heteropolycompound, while the heavy aqueous phase is washed with n- hexane and then collected in the light phase. The organic phase is anhydrified with Na2S04, filtered and evaporated until a yellow solid product is obtained. The heavy phase is treated further with chloroform and evaporated until a reddish residue is obtained. The two solid residues were dried in a stove at 40 C for 12 hours and then analyzed to determine the content of menadione by HPLC and GC.The concentration of the heteropolycompound-in the aqueous solution is equal to 1. 09percent vanadium by weight; the solution is then treated with poure O2 at atmospheric pressure and at the temperature of 100 °C (step 2). After 13 hours of treatment, the value of alphaV is determined again and is found to be equal to 25.5+/-2.0 percent. At this point the solution is concentrated by removing the solvent at the temperature of 100 °C, until a concentration of heteropolycompound equal to approximately 2.5 percent by weight of vanadium is obtained. The aqueous solution is replenished with fresh heteropolycompound in an amount that corresponds to the amount used to determine the value of alphaV Clearly, if this operation is not necessary this determination is not performed. The synthesis stage is then repeated, using the same aqueous solution containing the regenerated heteropolycompound, which has an alphaV equal to 25.5+/-2.0, and repeating the procedure as in step 1 (step 3). The result is a yield value in 2-methyl-1,4-naphthoquinone equal to 79.2percent, for a total conversion of the reagent 2-methyl-l-naphthol. The value alphaV is then determined again and is found to be equal to 67.22. 0percent. The aqueous solution, is then subjected to a reoxidation treatment again, as in step 2 (step 4). The aqueous solution containing the partially regenerated heteropolycompound (initial alphaV equal to 25.5+/-2.0 percent) reused again (steps 5 onward). The result is a yield in menadione equal to 78.0percent, with a ratio between weight of menadione and weight of resins equal to 4.3 and a degree of reduction alphaV at the end of the reaction equal to 66.7+/-2.0percent.[(SYNTHESIS OF 2-METHYL-1,] 4-naphthoquinone with [H5PMOLOV2040 TNDER] pressure at high temperature) The reduction procedure (step 1) described in Example 1 is repeated, but step 2 is performed at high pressure (10 atmospheres of pure [02)] in an autoclave at [120 °C.] After 12 hours of treatment, the value [ALPHA;V ] is equal to 12percent. The value of the yield in [2-METHYL-1,] 4-naphthoquinone is equal to 75.9percent, with a menadione/resins ratio equal to 5.63 at the [3RD] cycle. If step [2] is instead performed in the same conditions used in Example [1,] at least 150 hours of treatment are needed in order to reach [A VALUE OF OCV] lower than [5percent.] The procedure described in Example 1 is repeated, except that the dripping time of the solution containing the reagent in the aqueous solution is equal to 210 minutes. The result is a significant increase in the yield in 2- methyl-1, 4-naphthoquinone, which is equal to 88 percent.The procedure described in Example 1 is repeated, except that a ratio between heteropolycompound and substrate equal to 2 instead of 4 is used. The result is a menadione yield equal to 74. [1percent,] with a ratio between weight of menadione and weight of resins equal to 5.7 and with total conversion of the substrate. The value of alphaV is equal to 88.9+/-2.0percent.
	With phosphovanadomolybdic acid; In hexane; at 50℃; for 2h;Conversion of starting material;	The reduction procedure described in Example 1 is repeated, except that a heteropolycompound having the composition H4PMo11V040, with a molar ratio of 4 between the heteropolycompound and the substrate, is used. The resulting menadione yield is equal to 67.3percent, with a ratio between weight of menadione and weight of resins equal to 3.2 and with total conversion of the substrate. The value of alphaV is equal to 81.8+/-2.0percent. This test demonstrates that it is possible to use a heteropolycompound containing a single atom of V by formula, and that it can be reduced almost completely. In these conditions, however, the resulting yield is considerably lower than the yield obtained in Exarnple 1. The treatment of concentration of the aqueous solution containing the reduced heteropolycompound was then performed until a solution containing 1.19percent V was obtained. This was then subjected to the treatment of reoxidation with oxygen, and after 29 hours of treatment a degree of reduction alphaV equal to 77.0+/-2. 0percent was reached; extension of the treatment in the same conditions did not provide further variations of the degree of reduction. This test demonstrates that the catalyst containing a single atom of V by molecular formula can be used as oxidizer, but is then found to be an ineffective reducing agent for molecular oxygen, and therefore is less effective than the compound containing 2 atoms of V by molar formula

Yield	Reaction Conditions	Operation in experiment
96%	Conversion of starting material;	The catalyst is prepared as described in Example 9, but instead of being subjected to a heat treatment at 450 °C in air, it undergoes a treatrnent at 600 °C in air for 3 hours. After this treatment, the catalyst shows the following improvements with respect to the sample described in Example 9: shorter time required to reach stable performance and distinctly higher catalytic performance than the catalyst described in Example 9, especially in terms of selectivity: 1-naphthol conversion 100percent, selectivity to 2-methyL-l-naphthol equal to 96percent.
94%	Conversion of starting material;	The catalyst described in Example 9, once the stable catalytic performance cited in the example has been reached, is subjected to treatment in a current of N2 at 450 °C for 3 hours. After this treatment, the performance is as follows : 1-naphthol conversion 98percent, selectivity to 2-methyl-1-naphthol 96percent. The treatment therefore produces, with respect to the stationary situation described in Example 9, a slight decrease of conversion but a considerable increase in selectivity. The yield of the chosen product (given by the product of conversion and selectivity) is therefore distinctly higher than the yield obtained before said treatment. The same result is achieved if the pretreatment is performed on the fresh catalyst, i. e., after calcinations in air.
93%	Conversion of starting material;	The catalyst described in Example 10, after reaching the stable catalytic performance cited in the example, is subjected to a treatment in N2 current at 450 °C for 3 hours. After this treatment, the performance is as follows: 1- naphthol conversion 98percent, selectivity to 2-methyl-1-naphthol 95percent. The treatment therefore leads, with respect to the stationary situation described in Example 10, to a negligible decrease in conversion but to a substantial increase in selectivity. The yield in the chosen product (determined by the product of conversion and selectivity) is therefore distinctly higher, in this case also, than before this treatment.

90%	Conversion of starting material;	A catalyst is prepared according to the method described above and is finally subjected to thermal treatment im air at 450 °C. The sample is characterized by a Mg/Fe ratio, expressed as atomic ratio between the two elements, equal to 0.25.The conversion of 1-naphthol is found to increase and is now equal to 98percent. Despite the high conversion, there is also high selectivity to 2-methyl-1-naphthol , which is equal to 92percent..
83%	Conversion of starting material;	A catalyst is prepared according to the method described above, and is finally subjected to heat treatment in air at 450 °C. However, differently from the catalysts described in Exarnples 7-13, the catalyst is also subjected to a preliminary treatment at the same temperature in a nitrogen current before starting the reactivity tests. The sample is characterized by a Mg/Fe ratio, expressed as atomic ratio between the two elements, equal to 2.0. Conversion of 1-naphthol equal to 92percent is observed. Selectivity to 2-methyl- 1-naphthol is equal to 90percent.
81%	Conversion of starting material;	A catalyst is prepared according to the method described above and is finally subjected to thermal treatment im air at 450 °C. The sample is characterized by a Mg/Fe ratio, expressed as atomic ratio between the two elements, equal to 0.75. . A further increase of 1-naphthol conversion is observed conversion is now equal to 100percent. However, there is a slight decrease in selectivity to 2-methyl-1-naphthol, which is now equal to 81percent.
77%	Conversion of starting material;	A catalyst is prepared according to the method described above and is finally subjected to thermal treatment im air at 450 °C. The sample is characterized by a Mg/Fe ratio, expressed as atomic ratio between the two elements, equal to 1.50. .Conversion of 1-naphthol equal to 99percent is observed.
63%	Conversion of starting material;	A catalyst is prepared according to the method described above and is finally subjected to thermal treatment im air at 450 °C. The sample is characterized by a Mg/Fe ratio, expressed as atomic ratio between the two elements, equal to 0.05. Conversion of the 1-naphthol is equal-to 74percent, while selectivity to 2-methyl-1-naphthol is equal to 85percent.
30%	ferric oxide; magnesium oxide;Conversion of starting material;	A catalyst is prepared by using the following method: first Mg and Fe hydroxates are precipitated separately; then, they are filtered separately and dried at 90 °C. The two precipitates are then simply mixed so as to have a Mg/Fe atomic ratio equal to 0.25, and the mixture is treated as usual at 450 °C]for 8 hours in air. The catalyst yields the following performance : conversion 36percent, selectivity 84percent. Accordingly, the catalyst is less active than the corresponding sample prepared with the coprecipitation method.

Yield	Reaction Conditions	Operation in experiment
		Thus, there can be hydroxylated a lot of derivatives of phenol, e.g.,...isopropyl-4'-methylphenylether, 1-hydroxynaphthalene,2-hydroxynaphthalene, 1-methoxynaphthaline, 1-hydroxy-2-methylnaphthalene, 1-hydroxy-4-methylnaphthalene, 2-hydroxy-1-methylnaphthalene, 2-hydroxy-6-methylnaphthalene, ...
		Examples of the naphthols include1-naphthol,2-naphthol,methyl-1-naphthol,methyl-2-naphthol,chloro-1-naphthol,chloro-2-naphthol,bromo-1-naphthol,bromo-2-naphthol,1-naphtholsulfonic acid,...

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