Conditions | Yield |
---|---|
With sodium In diethyl ether; tert-butyl alcohol Inert atmosphere; Reflux; | 97% |
With sodium; tert-butyl alcohol In tetrahydrofuran at 20℃; | 96.5% |
With ethanol; sodium In benzene Inert atmosphere; Reflux; | 96% |
9,9-dichloro-1,4-dihydro-4a,8a-methanonaphthalene
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
In ethylene glycol at 120℃; for 0.0833333h; | 85% |
Conditions | Yield |
---|---|
With manganese(II) chloride dihydrate; lithium In tetrahydrofuran at 25℃; for 1h; Birch reaction; Inert atmosphere; regioselective reaction; | 83% |
Multi-step reaction with 3 steps 1: NaBH4,m-dicyanobenzene / acetonitrile; H2O / 7 h / Irradiation 2: 100 percent / silica gel 3: 59 percent / NaBH4,m-dicyanobenzene / acetonitrile; H2O / 16 h / Irradiation View Scheme |
Conditions | Yield |
---|---|
With tert-Amyl alcohol; ethylenediamine In tetrahydrofuran at 0 - 5℃; for 1h; Birch reduction; Inert atmosphere; | A 83% B n/a |
Conditions | Yield |
---|---|
With propylamine Irradiation; | A 80% B 20% |
With potassium amide In tetrahydrofuran; ammonia at -78℃; for 0.5h; Product distribution; var. alkali amides; | A 9 % Chromat. B 80 % Chromat. |
1,4-Dihydroxy-Δ2,6-hexalin
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With pyridine; trichlorophosphate for 72h; Ambient temperature; | 62% |
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 0.5h; | 60% |
Conditions | Yield |
---|---|
With manganese(II) chloride dihydrate; lithium In tetrahydrofuran at 25℃; for 1h; Birch reaction; Inert atmosphere; regioselective reaction; | 50% |
phenylium
buta-1,3-diene
A
naphthalene
B
1,2-Dihydronaphthalene
C
(E)-1-Phenyl-1,3-butadiene
D
1,4-dihydronaphthalene
E
3-Methylindene
Conditions | Yield |
---|---|
With oxygen; trimethylamine under 30 Torr; Mechanism; Product distribution; also with 3H-labelled compound, nuclear decay of a tritium atom, further pressures, additives; | A 9% B 3% C 3% D 4% E 4% |
Conditions | Yield |
---|---|
With ethanol; sodium |
1-amino-5,8-dihydronaphthalene
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
und Behandeln mit alkal.Natriumstannit-Loesung.Diazotization; |
2,3-dibromo-1,2,3,4-tetrahydro-naphthalene
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With ethanol; zinc |
Conditions | Yield |
---|---|
With diethyl ether; ethanol |
Conditions | Yield |
---|---|
With ethanol; sodium |
Conditions | Yield |
---|---|
With iodosylbenzene; Fe(III)prorphyrinate (SbF-)3 salt In various solvent(s) Mechanism; |
naphthalene
A
tetralin
B
1,2-Dihydronaphthalene
C
1,4-dihydronaphthalene
D
1,2,3,3',4,4'-hexahydro-2,2'-binaphthyl
E
1,1',2,2',3,4-hexahydro-2,2'-binaphthyl
Conditions | Yield |
---|---|
With ammonia; lithium In diethyl ether at -33℃; for 0.5h; Product distribution; Mechanism; other metals, var. time; |
Conditions | Yield |
---|---|
With methanol; lithium at 27℃; Product distribution; other metals (Na, K) and proton donor (H2O); | |
With ethanol; sodium 1) 2h 2) 3h, 170 deg C; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; | |
With sodium tetrahydroborate; triethylamine In methanol; diethylene glycol dimethyl ether Irradiation; Further byproducts given; | A 3 % Spectr. B 17 % Spectr. |
1,4-epoxy-1,4-dihydronaphthalene
A
isotetraline
B
tetralin
C
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran Heating; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran Rate constant; Heating; in presence of compefitor; | |
With ammonia; lithium; tert-butyl alcohol In tetrahydrofuran Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
1,2-Dihydronaphthalene
A
naphthalene
B
tetralin
C
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With potassium amide In tetrahydrofuran; ammonia at -78℃; for 0.5h; 1) THF, NH3, -78 degC, 30 min; Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 80 % Chromat. |
Conditions | Yield |
---|---|
With propylamine for 4h; Product distribution; Irradiation; |
1,2-Dihydronaphthalene
A
styrene
B
naphthalene
C
tetralin
D
1,4-dihydronaphthalene
E
1-indene
Conditions | Yield |
---|---|
silicon tetrafluoride Product distribution; Irradiation; |
benzo[2,3]bicyclo[3.1.0]hexane
A
naphthalene
B
1,2-Dihydronaphthalene
C
1,2-divinylbenzene
D
1,4-dihydronaphthalene
E
2-methylene-2,3-dihydro-1H-indene
Conditions | Yield |
---|---|
at 500 - 900℃; under 0.1 Torr; Product distribution; Mechanism; |
1,4-dihydronaphthalen-1-yltrimethylsilane
A
tetralin
B
1,2-Dihydronaphthalene
C
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In acetonitrile at 25℃; for 0.5h; var. reag; time, temp; and solv.; | A 10 % Chromat. B 4 % Chromat. C 84 % Chromat. |
With potassium hydroxide In various solvent(s) at 85℃; for 24h; var. reag, time, temp. and solv.; | A 9 % Chromat. B 85 % Chromat. C 4 % Chromat. |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 1h; var. reag; time, temp; and solv.; | A 9 % Chromat. B 5 % Chromat. C 84 % Chromat. |
1,4-dihydronaphthalen-1-yltrimethylsilane
A
1,4-dihydronaphthalene
B
1-methyl-1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; methyl iodide In tetrahydrofuran at 0℃; for 2h; | A 52 % Chromat. B 48 % Chromat. |
With tetrabutyl ammonium fluoride; methyl iodide In tetrahydrofuran at -78℃; for 2h; | A 4 % Chromat. B 96 % Chromat. |
8,9-dehydro-<4>(2,7)troponophane
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
at 200℃; |
tert-butyl 1-indanperacetate
A
tetralin
B
1,2-Dihydronaphthalene
C
1-methyl-1,2,3,4-tetrahydronaphthalene
D
1,4-dihydronaphthalene
E
2-methyltetralin
Conditions | Yield |
---|---|
at 427℃; under 0.01 Torr; Product distribution; flash vacuum pyrolysis, other reaction temperatures; | A 26.1 % Chromat. B 26.0 % Chromat. C 16.2 % Chromat. D 4.74 % Chromat. E 5.64 % Chromat. |
tert-butyl tetralin-2-percarboxylate
A
tetralin
B
1,2-Dihydronaphthalene
C
1-methyl-1,2,3,4-tetrahydronaphthalene
D
1,4-dihydronaphthalene
E
2-methyltetralin
Conditions | Yield |
---|---|
at 427℃; under 0.01 Torr; Product distribution; flash vacuum pyrolysis, other reaction temperatures; | A 28.4 % Chromat. B 29.3 % Chromat. C 12.7 % Chromat. D 6.02 % Chromat. E 4.75 % Chromat. |
(1,4-dihydro-1-naphthyl)bis(4-methoxyphenyl)phosphine
A
1,4-dihydronaphthalene
B
bis(4-methoxyphenyl)phosphine
Conditions | Yield |
---|---|
With ammonia; sodium at -78℃; for 4h; |
Z-4-chloro-1-phenyl-2-butene
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With aluminium trichloride In Petroleum ether for 5h; Ambient temperature; |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; | 100% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 5h; Heating; | 100% |
With tert.-butylhydroperoxide; hexacarbonyl molybdenum In dichloromethane; benzene for 5h; Heating; | 79% |
Conditions | Yield |
---|---|
With N,N'-Dimethylurea; tris(pyrrolidino)phosphine oxide; lithium bromide In tetrahydrofuran Electrochemical reaction; | 98% |
1,4-dihydronaphthalene
4-methoxyphenylboronic acid
1,2,3,4-tetrahydro-1-(4-methoxyphenyl)naphthalene
Conditions | Yield |
---|---|
With nickel(II) triflate; methanol; potassium phosphate; 1,3-diaminocyclohexane In toluene at 80℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction; | 98% |
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 60℃; for 12h; Inert atmosphere; | 97% |
With manganese; 6,6'-dimethyl-2,2'-bipyridine; phosphonic acid diethyl ester; nickel dibromide In chloroform at 35℃; for 24h; | 76% |
With diethyl ether; ammonia; sodium at -70 - -60℃; anschliessende Behandlung mit Aethanol; |
Conditions | Yield |
---|---|
With methanol; manganese(IV) oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone In nitromethane at 20℃; for 24h; Inert atmosphere; | 96% |
With N,N'-di-tert-butyldiaziridinone; triphenylphosphine; copper(l) chloride In dichloromethane-d2 at 65℃; for 12h; Inert atmosphere; | 69% |
With iron(III) trifluoromethanesulfonate; C65H77N5O4S2 In 1,2-dichloro-ethane at 75℃; under 760.051 Torr; for 8h; Inert atmosphere; | 35% |
1,4-dihydronaphthalene
cis-1,2,3,4-tetrahydro-naphthalene-2,3-diol
Conditions | Yield |
---|---|
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; acetone at 20℃; for 36h; | 92% |
With potassium permanganate; dihydrogen peroxide In water; acetone at 0℃; for 2h; Temperature; Inert atmosphere; Green chemistry; | 85% |
With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide In acetone; tert-butyl alcohol at 20℃; for 16h; | 83% |
1,4-dihydronaphthalene
tris(p-bromophenyl)amine radical cation
A
naphthalene
trans-2,3-Dibrom-1,2,3,4-tetrahydronaphthalin
trans-2-Brom-3-chlor-1,2,3,4-tetrahydronaphthalin
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 3h; Rate constant; Kinetics; Mechanism; other bases, temperatures, times and solvents; | A 92% B n/a C n/a |
1,4-dihydronaphthalene
(2α,3β)-2-Hydroxy-3-bromo-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With tetrahydrofuran; N-Bromosuccinimide In water Inert atmosphere; | 90% |
With N-Bromosuccinimide; water In dimethyl sulfoxide at 5℃; for 0.75h; | 73% |
With N-Bromosuccinimide; water |
methanol
Phenylselenyl chloride
1,4-dihydronaphthalene
trans-2-methoxy-3-phenylseleno-1,2,3,4-tetrahydronaphthalene
Conditions | Yield |
---|---|
With triethylamine at 25℃; for 20h; | 90% |
With triethylamine at 20 - 25℃; for 2h; Yield given; |
Conditions | Yield |
---|---|
Stage #1: 1,4-dihydronaphthalene With bromine In tetrachloromethane at 0 - 20℃; for 0.5h; Stage #2: silver(I) acetate With acetic acid at 80℃; for 6h; Stage #3: With potassium hydroxide In methanol for 8h; | 89% |
para-iodoanisole
1,4-dihydronaphthalene
1,2,3,4-tetrahydro-1-(4-methoxyphenyl)naphthalene
Conditions | Yield |
---|---|
With 6,6'-dimethyl-2,2'-bipyridine; cesium fluoride; nickel dichloride In tetrahydrofuran at 22 - 26℃; for 14h; Inert atmosphere; Sealed tube; regioselective reaction; | 87% |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere; | 85% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24h; Prilezhaev Epoxydation (mCPBA); | 75% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 24h; |
1,4-dihydronaphthalene
Methyl thioglycolate
methyl (1,2,3,4-tetrahydro-2-naphthyl)acetate
Conditions | Yield |
---|---|
With {Au(dppm)}2Cl2; triphenylphosphine In acetonitrile Irradiation; | 85% |
1,4-dihydronaphthalene
(E)-4-(2-bromo-vinyl)-anisole
Conditions | Yield |
---|---|
With lithium methanolate; C12H12N2*Ni(2+)*2Br(1-); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In N,N-dimethyl acetamide at -10℃; for 12h; Inert atmosphere; regioselective reaction; | 85% |
1,4-dihydronaphthalene
methyl 4-iodobenzoate
methyl 4-(1,2,3,4-tetrahydronaphthalen-1-yl)benzoate
Conditions | Yield |
---|---|
With dimethylsulfide borane complex; (6,6’-dimethyl-2,2'-bipyridine)nickel(II) dibromide; lithium methanolate In N,N-dimethyl acetamide at -19℃; for 12h; Inert atmosphere; Sealed tube; Glovebox; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-fluorobis(benzenesulfon)imide In toluene at 20℃; Schlenk technique; Inert atmosphere; | 84% |
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide In acetone at 20℃; for 16h; | 83% |
3,6-diphenyl-1,2,4,5-tetrazine
1,4-dihydronaphthalene
1,4-diphenyl-5,10-dihydrobenzophthalazine
Conditions | Yield |
---|---|
In ethylene glycol at 120℃; for 1h; | 81% |
chloroform
1,4-dihydronaphthalene
1,1-dichloro-1a,2,7,7a-tetrahydro-1H-cyclopropa[b]naphthalene
Conditions | Yield |
---|---|
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In ethanol; water at 0 - 60℃; | 81% |
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride | 70% |
With sodium hydroxide In water | 46% |
With cetyltrimethylammonim bromide; sodium hydroxide In ethanol; water at 0 - 25℃; Inert atmosphere; | 27% |
With cetyltrimethylammonim bromide; sodium hydroxide In ethanol; water at 0 - 25℃; for 2h; Inert atmosphere; | 27% |
1,4-dihydronaphthalene
A
(1R,2S)-1,2-dihydronaphthalene-1,2-diol
B
(R)-1-hydroxy-1,4-dihydronaphthalene
C
(-)-(S)-2-hydroxy-1,2-dihydronaphthalene
Conditions | Yield |
---|---|
for 0.5h; Pseudomonas putida UV4; | A 10% B 81% C 9% |
for 23h; Pseudomonas putida UV4; | A 90 % Spectr. B n/a C n/a |
Conditions | Yield |
---|---|
With 6,6'-dimethyl-2,2'-bipyridine; nickel(II) bromide trihydrate; di-tert-butyl dicarbonate; propyl bromide; sodium iodide; magnesium chloride; zinc In N,N-dimethyl acetamide at 30℃; for 24h; regioselective reaction; | 81% |
1-bromo-4-methoxy-benzene
1,4-dihydronaphthalene
1,2,3,4-tetrahydro-1-(4-methoxyphenyl)naphthalene
Conditions | Yield |
---|---|
With manganese; 6,6'-dimethyl-2,2'-bipyridine; nickel(II) perchlorate hexahydrate; propyl bromide In N,N-dimethyl acetamide at 25℃; for 32h; Inert atmosphere; Sealed tube; regioselective reaction; | 77% |
1,4-dihydronaphthalene
diphenyl diselenide
silver(I) trifluoromethanethiolate
Conditions | Yield |
---|---|
Stage #1: 1,4-dihydronaphthalene; diphenyl diselenide; silver(I) trifluoromethanethiolate In acetonitrile at 20℃; for 0.25h; Schlenk technique; Inert atmosphere; Stage #2: With boron trifluoride diethyl etherate In acetonitrile at 20℃; for 1h; Schlenk technique; Inert atmosphere; | 77% |
1-(1,1,1-trifluoroprop-2-en-2-yl)-4-methoxybenzene
1,4-dihydronaphthalene
Conditions | Yield |
---|---|
With 6,6'-dimethyl-2,2'-bipyridine; nickel(II) bromide trihydrate; Triethoxysilane; tetrabutylammomium bromide; lithium fluoride; triphenylphosphine In N,N-dimethyl acetamide at 60℃; for 24h; Inert atmosphere; Sealed tube; chemoselective reaction; | 73% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; palladium diacetate; toluene-4-sulfonic acid In water; acetonitrile at 20℃; for 6h; Wacker Oxidation; chemoselective reaction; | 72% |
The Naphthalene,1,4-dihydro-, with CAS registry number 612-17-9, has the systematic name of 1,4-dihydronaphthalene. And its IUPAC name is the same one. Besides this, it is also called Delta2-dialin. And the chemical formula of this chemical is C10H10. What's more, its EINECS is 210-297-0.
Physical properties of Naphthalene,1,4-dihydro-: (1)ACD/LogP: 3.53; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.53; (4)ACD/LogD (pH 7.4): 3.53; (5)ACD/BCF (pH 5.5): 283.34; (6)ACD/BCF (pH 7.4): 283.34; (7)ACD/KOC (pH 5.5): 1981.36; (8)ACD/KOC (pH 7.4): 1981.36; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.572; (14)Molar Refractivity: 42.64 cm3; (15)Molar Volume: 129.5 cm3; (16)Polarizability: 16.9×10-24cm3; (17)Surface Tension: 39.5 dyne/cm; (18)Density: 1.004 g/cm3; (19)Flash Point: 70.7 °C; (20)Enthalpy of Vaporization: 42.95 kJ/mol; (21)Boiling Point: 211.5 °C at 760 mmHg; (22)Vapour Pressure: 0.264 mmHg at 25°C.
Preparation: this chemical can be prepared by naphthalene. This reaction will need reagent sodium and solvent ethanol.
Uses of Naphthalene,1,4-dihydro-: it can be used to produce (+-)-trans-3-bromo-1,2,3,4-tetrahydro-[2]naphthol. This reaction will need reagents H2O, N-bromo-succinimide.
When you are using this chemical, please be cautious about it as the following:
The Naphthalene,1,4-dihydro- is highly flammable, so keep it away from sources of ignition. And you should keep its container tightly closed and in a well-ventilated place. When use this chemical, wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)SMILES: c1ccc2c(c1)C/C=C\C2
(2)InChI: InChI=1/C10H10/c1-2-6-10-8-4-3-7-9(10)5-1/h1-6H,7-8H2
(3)InChIKey: FUPIVZHYVSCYLX-UHFFFAOYAN
(4)Std. InChI: InChI=1S/C10H10/c1-2-6-10-8-4-3-7-9(10)5-1/h1-6H,7-8H2
(5)Std. InChIKey: FUPIVZHYVSCYLX-UHFFFAOYSA-N
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