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Basic Information
CAS No.: 589-29-7
Name: 1,4-Benzenedimethanol
Article Data: 109
Molecular Structure:
Molecular Structure of 589-29-7 (1,4-Benzenedimethanol)
Formula: C8H10O2
Molecular Weight: 138.166
Synonyms: p-Xylene-a,a'-diol (6CI,7CI,8CI);1,4-Bis(hydroxymethyl)benzene;1,4-Di(hydroxymethyl)benzene;1,4-Dimethylolbenzene;1,4-Xylylene glycol;4-(Hydroxymethyl)benzenemethanol;4-(Hydroxymethyl)benzyl alcohol;NSC 5097;Terephthalyl alcohol;p-(Hydroxymethyl)benzyl alcohol;p-Benzenedimethanol;p-Bis(hydroxymethyl)benzene;p-Xylene glycol;p-Xylylene glycol;p-Xylylene-a,a'-diol;p-Xylylenediol;a,a'-Dihydroxy-p-xylene;a,a'-p-Xylenediol;
EINECS: 209-641-2
Density: 1.18 g/cm3
Melting Point: 114-118 °C(lit.)
Boiling Point: 328.9 °C at 760 mmHg
Flash Point: 151.3 °C
Solubility: Soluble in ether, toluene, methanol and hot water.
Appearance: White needle crystal
Hazard Symbols: HarmfulXn
Risk Codes: 20/22
Safety: 22-24/25-9-7-23
PSA: 40.46000
LogP: 0.67120
Synthetic route
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
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%
623-27-8

terephthalaldehyde,

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
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%
139140-15-1

1,4-di(t-butyldimethylsiloxymethyl)benzene

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
With low-loading and alkylated polystyrene-supported-SO3H In water at 40℃; for 12h;99%
1571-08-0

methyl 4-formylbenzoate

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
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;

1-(tert-butyldimethylsilyloxymethyl)-4-triethylsilyloxymethylbenzene

A

589-29-7

p-xylylene glycol

B

118992-89-5

[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]methanol

Conditions
ConditionsYield
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%
636-09-9

diethyl terephthalate

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
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.
100-21-0

terephthalic acid

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
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

1,4-bis(pinacolborane ester)benzene

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
With sodium hydroxide In water Inert atmosphere;95%
52010-97-6

4-(hydroxylmethyl)benzaldehyde

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
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;
1058648-83-1

1,4-bis((methoxymethoxy)methyl)benzene

589-29-7

p-xylylene glycol

Conditions
ConditionsYield
phosphotungstic acid In ethanol for 3h; Heating;93%
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Specification

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