Conditions | Yield |
---|---|
With hydrogen; sodium ethanolate In 1,4-dioxane at 80℃; under 38002.6 Torr; for 16h; | 99% |
With C13H34BFeNOP2; hydrogen In tetrahydrofuran at 100℃; under 22502.3 Torr; for 18h; Autoclave; Inert atmosphere; | 96% |
With C15H29MnNO3P2(1+)*Br(1-); potassium tert-butylate; hydrogen In 1,4-dioxane at 110℃; under 22502.3 Torr; for 24h; Inert atmosphere; Autoclave; | 95% |
Conditions | Yield |
---|---|
With C48H43ClN2P2Ru; ammonium formate In water; toluene at 90℃; for 10h; Catalytic behavior; Schlenk technique; | 99% |
Stage #1: terephthalaldehyde, With [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu]; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 20℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride; water In methanol; toluene for 1h; Inert atmosphere; Reflux; | 97% |
With hydrogen In methanol at 130℃; under 11251.1 Torr; for 2h; Catalytic behavior; Autoclave; | 96.3% |
1,4-di(t-butyldimethylsiloxymethyl)benzene
p-xylylene glycol
Conditions | Yield |
---|---|
With low-loading and alkylated polystyrene-supported-SO3H In water at 40℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen In toluene at 80℃; under 30003 Torr; for 3h; | 99% |
With sodium tetrahydroborate In ethanol UV-irradiation; |
A
p-xylylene glycol
B
[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]methanol
Conditions | Yield |
---|---|
With MCM-41 In methanol for 8h; Ambient temperature; Yields of byproduct given; | A n/a B 97% |
With mesoporous silica MCM-41 In methanol at 20℃; for 8h; | A n/a B 97% |
Conditions | Yield |
---|---|
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 10h; Glovebox; Autoclave; | 97% |
With potassium borohydride; lithium chloride for 0.0833333h; microwave irradiation; | 85 % Chromat. |
Conditions | Yield |
---|---|
With [Zn(BH4)2(py)] In tetrahydrofuran for 7h; Heating; | 95% |
With zirconium(IV) borohydride In tetrahydrofuran at 25℃; for 1h; Reduction; | 91% |
Stage #1: terephthalic acid With sodium aminodiboranate In tetrahydrofuran at 20℃; Stage #2: With water | 90% |
With zinc(II) tetrahydroborate In tetrahydrofuran for 5h; Heating; | 70% |
Multi-step reaction with 2 steps 1: sulfuric acid / 3 h / 70 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere View Scheme |
p-xylylene glycol
Conditions | Yield |
---|---|
With sodium hydroxide In water Inert atmosphere; | 95% |
4-(hydroxylmethyl)benzaldehyde
p-xylylene glycol
Conditions | Yield |
---|---|
With formic acid; C20H29ClIrN4(1+)*Cl(1-) In water at 80℃; for 0.0833333h; | 95% |
With HNa*CHO2(1-); C63H72ClN3O5PRuS(1+)*Br(1-) In dimethylsulfoxide-d6; water-d2 at 37℃; for 12h; |
1,4-bis((methoxymethoxy)methyl)benzene
p-xylylene glycol
Conditions | Yield |
---|---|
phosphotungstic acid In ethanol for 3h; Heating; | 93% |
1,4-bis[(ethoxymethoxy)methyl]benzene
p-xylylene glycol
Conditions | Yield |
---|---|
phosphotungstic acid In ethanol for 2.5h; Heating; | 90% |
Conditions | Yield |
---|---|
Stage #1: 4-Carboxybenzaldehyde With sodium aminodiboranate In tetrahydrofuran at 20℃; Stage #2: With water | 90% |
With tributylphosphine; diphenylsilane; C45H25F12N7Ni2O9 In 1,4-dioxane at 100℃; for 16h; | 75% |
1,4-di(t-butyldimethylsiloxymethyl)benzene
A
p-xylylene glycol
B
[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]methanol
Conditions | Yield |
---|---|
With sodium tetrachloroaurate(III) dihydrate In methanol at 20℃; for 0.5h; | A n/a B 86% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 4.5h; Heating; | 84% |
With zinc(II) tetrahydroborate; N,N,N,N,-tetramethylethylenediamine In diethyl ether at 40℃; for 24h; | 75% |
terephthalaldehyde,
A
p-xylylene glycol
B
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With C48H43ClN2P2Ru; ammonium formate In water; toluene at 90℃; for 9h; Catalytic behavior; Schlenk technique; | A 17% B 83% |
With hydrogen; palladium on activated charcoal In ethanol Ambient temperature; | A 3% B 74% |
With Grubbs catalyst first generation; potassium hydroxide In 1,4-dioxane at 80℃; for 20h; Cannizzaro reaction; | A 36% B 40% |
Conditions | Yield |
---|---|
With water; sodium carbonate In 1,4-dioxane at 80℃; for 3h; Solvent; Reagent/catalyst; Temperature; | 80% |
With water; sodium carbonate In 1,4-dioxane at 80℃; for 3h; Solvent; Temperature; Reagent/catalyst; | 80% |
With potassium carbonate | |
With water for 5h; Reflux; | |
With water; sodium formate at 140℃; under 3040.2 Torr; for 1h; Reagent/catalyst; Pressure; |
Conditions | Yield |
---|---|
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 4.5h; | 80% |
Stage #1: 4-(methoxycarbonyl)benzyl alcohol With diethoxymethylane; sodium triethylborohydride In diethyl ether; toluene at 20℃; for 8h; Inert atmosphere; Stage #2: With sodium hydroxide In methanol; diethyl ether; toluene at 20℃; for 2h; Reagent/catalyst; | 76% |
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran; 2-methyltetrahydrofuran at 45℃; under 3750.38 Torr; for 2.5h; Autoclave; | 63% |
Multi-step reaction with 4 steps 1: 100 percent 2: 88 percent / LiAlH4 / diethyl ether; diethyl ether / 1 h / Heating 3: 87 percent 4: 17 percent / 31percent aq. H2SiF6, Et3N / acetonitrile / 1 h / 0 °C View Scheme |
terephthalaldehyde,
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
p-xylylene glycol
Conditions | Yield |
---|---|
In methanol at 20℃; for 4h; Inert atmosphere; Glovebox; | 75% |
Conditions | Yield |
---|---|
Stage #1: terephthalic acid monoethyl ester With tetrabutylammonium borohydride; ethyl iodide In dichloromethane at 25℃; for 2h; Stage #2: With dihydrogen peroxide; sodium hydroxide In water at 0 - 25℃; for 0.333333h; | 75% |
4-chlorophenyl trifluoromethanesulfonate
p-xylylene glycol
Conditions | Yield |
---|---|
With sodium carbonate; bis(dibenzylideneacetone)-palladium(0); ruphos In 1,4-dioxane; water for 48h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux; | 73.1% |
4-Carboxybenzaldehyde
A
p-xylylene glycol
B
4-(hydroxylmethyl)benzaldehyde
Conditions | Yield |
---|---|
With phenylsilane; C34H30CoO6; potassium In tetrahydrofuran at 20℃; for 20h; Inert atmosphere; Schlenk technique; Glovebox; | A n/a B 73% |
Conditions | Yield |
---|---|
With carbon monoxide; hydrogen In tetrahydrofuran (N2), CO/H2 (1:1), in an autoclave, mixture heated at 70°C for 3.5 h, cooled, gases vented; filtered, solvent removed (reduced pressure), hexane added, filtered, solvent removed, IR, NMR, mass spectra; | A 71% B 69% |
Conditions | Yield |
---|---|
With C23H29Cl2N2OPRuS; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 37503.8 Torr; for 18h; Reagent/catalyst; Temperature; Inert atmosphere; Schlenk technique; Autoclave; | 71% |
4-<(tert-butyldimethylsiloxy)methyl><(triisopropylsiloxy)methyl>benzene
A
p-xylylene glycol
B
[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]methanol
C
(4-(((triisopropylsilyl)oxy)methyl)phenyl)methanol
Conditions | Yield |
---|---|
With fluorosilicic acid; triethylamine In acetonitrile at 0℃; for 1h; | A 17% B 7% C 70% |
Conditions | Yield |
---|---|
With hydrogen bromide; dihydrogen peroxide In 1,2-dichloro-ethane at 5℃; for 12h; Irradiation; | 70% |
Conditions | Yield |
---|---|
In sulfuric acid at 40℃; for 14h; electroreduction; | 68% |
1,4-benzenedicarboxylic acid dimethyl ester
A
p-xylylene glycol
B
4-(methoxycarbonyl)benzyl alcohol
Conditions | Yield |
---|---|
With dichloro(benzene)ruthenium(II) dimer; 2-((di-p-tolylphosphino)methyl)-1-methyl-1H-imidazole; potassium tert-butylate; hydrogen In tetrahydrofuran at 100℃; under 37503.8 Torr; for 4.5h; | A 67% B 13% |
With dichlorido-bis[(2-diphenylphosphino)ethyl]amine-cobalt(II); hydrogen; sodium methylate In 1,4-dioxane at 120℃; under 37503.8 Torr; for 48h; Autoclave; | |
With tris((2-(diphenylphosphino)ethyl)amino)ruthenium monocarbonyl; hydrogen; phenol In toluene under 45004.5 Torr; for 18h; Glovebox; Inert atmosphere; Heating; Autoclave; | A 9 %Spectr. B 88 %Spectr. |
ethyl 4-(aminocarbonyl)benzoate
p-xylylene glycol
Conditions | Yield |
---|---|
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique; | 63% |
(C7H7(CH3)2CHOHC2CH2O)2C6H4
dicobalt octacarbonyl
p-xylylene glycol
Conditions | Yield |
---|---|
Stage #1: (C7H7(CH3)2CHOHC2CH2O)2C6H4; dicobalt octacarbonyl In dichloromethane at 20℃; Nicholas Reaction; Inert atmosphere; Stage #2: p-xylylene glycol With boron trifluoride diethyl etherate In dichloromethane at -78 - 20℃; Nicholas Reaction; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With manganese(IV) oxide; molecular sieve In hexane for 3h; Heating; | 99% |
With dihydrogen peroxide In water at 100℃; for 5.5h; chemoselective reaction; | 99% |
With 1-methyl-1H-imidazole; copper(I) oxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 25℃; for 24h; | 99% |
Conditions | Yield |
---|---|
With ammonium hydroxide; iodine at 60℃; for 2h; | 99% |
With ammonium hydroxide; iodine at 60℃; for 2h; | 99% |
Stage #1: p-xylylene glycol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: p-xylylene glycol With monopotassium naphthalene In tetrahydrofuran at 22℃; for 2h; Stage #2: oxirane In tetrahydrofuran at 40℃; for 20h; Stage #3: With acetic acid In tetrahydrofuran | 99% |
(C7H7(CH3)2CHOHC2CH2O)2C6H4
dicobalt octacarbonyl
p-xylylene glycol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In 1,4-dioxane; dichloromethane ligand reacted with Co complex in CH2Cl2, treated with 1,4-benzenedimethanol in dioxane at room temp.; | 99% |
Conditions | Yield |
---|---|
With dibutyltin dilaurate In N,N-dimethyl-formamide at 20℃; for 3h; | 99% |
Conditions | Yield |
---|---|
Stage #1: p-xylylene glycol With monopotassium naphthalene In tetrahydrofuran at 22℃; for 2h; Stage #2: oxirane In tetrahydrofuran at 40℃; for 24h; Stage #3: With acetic acid In tetrahydrofuran | 98% |
p-xylylene glycol
chromium(0) hexacarbonyl
tricarbonyl[C6H4(CH2OH)2]chromium(0)
Conditions | Yield |
---|---|
In tetrahydrofuran; dibutyl ether the mixt. of Cr(CO)6 and the alcohol in dibutyl ether and THF was heated under reflux with stirring at between 180 and 240°C for 20-48 hunder N2; filtered, washed with THF, concd., filtered, dried in vac., dissolved in THF, filtered, concd. in vac. (N2 atm.); elem. anal.; | 98% |
In tetrahydrofuran; dibutyl ether N2 atmosphere; refluxing (26 h); crystn. on cooling (ice bath), filtration off, chromy., recrystn. (CH2Cl2/hexane); elem. anal.; | 90% |
Conditions | Yield |
---|---|
With Silphos; bromine In acetonitrile for 0.166667h; Heating; | 97% |
With hydrogen bromide bei der Destillation; |
Conditions | Yield |
---|---|
With diethylene glycol dimethyl ether at 70℃; for 0.583333h; Sonication; | 97% |
With C24H33IrN4O3; water; sodium hydroxide for 18h; Reflux; | 96% |
With sodium hypochlorite; water at 25℃; for 0.5h; | 94% |
Conditions | Yield |
---|---|
With hydrogen; nickel In sodium hydroxide at 20℃; | 96% |
Multi-step reaction with 2 steps 1: pyridine 2: 76 percent / H2 / Pd/C(ethylenediamine) / methanol / 1 h / 20 °C View Scheme | |
With hydrogen In ethanol; water at 170℃; under 15001.5 Torr; for 12h; Autoclave; Sealed tube; Green chemistry; | 97.8 %Chromat. |
Conditions | Yield |
---|---|
Stage #1: p-xylylene glycol With monopotassium naphthalene In tetrahydrofuran at 22℃; for 2h; Stage #2: oxirane In tetrahydrofuran at 40℃; for 64h; Stage #3: With acetic acid In tetrahydrofuran | 96% |
Dimethoxymethane
p-xylylene glycol
{4-[(methoxymethoxy)methyl]phenyl}methanol
Conditions | Yield |
---|---|
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00972222h; Microwave irradiation; | 96% |
Conditions | Yield |
---|---|
With ruthenium(II) bis(triphenylphosphine) dichloride at 190℃; for 14h; Inert atmosphere; Schlenk technique; | 96% |
p-xylylene glycol
sodium acetate
1,4-bis(hydroxymethyl)benzene diacetate
Conditions | Yield |
---|---|
In water at 100℃; for 8h; | 96% |
Conditions | Yield |
---|---|
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 12h; Heating; | 95.3% |
With dicyclohexyl-carbodiimide |
p-xylylene glycol
p-bis(iodomethyl)benzene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; cesium iodide In acetonitrile at 20℃; for 0.416667h; | 95% |
With Silphos; iodine In acetonitrile for 0.0833333h; Heating; | 95% |
With tetrachlorosilane; sodium iodide In chloroform; acetonitrile at 20℃; for 5h; | 88% |
With hydrogen iodide |
Conditions | Yield |
---|---|
With pyridine | 95% |
p-xylylene glycol
chloromethyl methyl ether
1,4-bis((methoxymethoxy)methyl)benzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at -20 - 20℃; | 95% |
Conditions | Yield |
---|---|
With 12-tungstophosphoric acid immobilized on [bmim][FeCl4] at 75 - 82℃; for 0.00972222h; Microwave irradiation; | 95% |
The 1,4-Benzenedimethanol is an organic compound with the formula C8H10O2. The IUPAC name of this chemical is [4-(hydroxymethyl)phenyl]methanol. With the CAS registry number 589-29-7, it is also named as 1,4-Dimethylolbenzene. The product's categories are Benzhydrols, Benzyl & Special Alcohols; Benzene derivates; Fluorenes, etc. (reagent for high-performance polymer research); Functional Materials; Reagent for High-Performance Polymer Research. Besides, it is an organic synthesis intermediate. It is also used for production of soluble polyphenylene.
Physical properties about 1,4-Benzenedimethanol are: (1)ACD/LogP: -0.15; (2)ACD/LogD (pH 5.5): -0.15; (3)ACD/LogD (pH 7.4): -0.15; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 19.76; (7)ACD/KOC (pH 7.4): 19.76; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 4; (11)Polar Surface Area: 18.46 Å2; (12)Index of Refraction: 1.583; (13)Molar Refractivity: 39.15 cm3; (14)Molar Volume: 117 cm3; (15)Polarizability: 15.52×10-24cm3; (16)Surface Tension: 51.9 dyne/cm; (17)Density: 1.18 g/cm3; (18)Flash Point: 151.3 °C; (19)Enthalpy of Vaporization: 60.3 kJ/mol; (20)Boiling Point: 328.9 °C at 760 mmHg; (21)Vapour Pressure: 7.43E-05 mmHg at 25°C.
Preparation: this chemical can be prepared by terephthalic acid dimethyl ester. This reaction will need reagent Zn(BH4)2, cyclohexene and solvent tetrahydrofuran. The reaction time is 2 hours by heating. The yield is about 70%.
Uses of 1,4-Benzenedimethanol: it can be used to produce p-tolyl-methanol at temperature of 20 °C. It will need reagent H2 and solvent aq. NaOH. The yield is about 96%.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation and if swallowed. Please keep container tightly closed. When you are using it, do not breathe dust/gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with skin and eyes.
You can still convert the following datas into molecular structure:
(1)SMILES: OCc1ccc(cc1)CO
(2)InChI: InChI=1/C8H10O2/c9-5-7-1-2-8(6-10)4-3-7/h1-4,9-10H,5-6H2
(3)InChIKey: BWVAOONFBYYRHY-UHFFFAOYAM
(4)Std. InChI: InChI=1S/C8H10O2/c9-5-7-1-2-8(6-10)4-3-7/h1-4,9-10H,5-6H2
(5)Std. InChIKey: BWVAOONFBYYRHY-UHFFFAOYSA-N
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