Product Name

  • Name

    1,4-Cyclohexanedimethanol

  • EINECS 203-268-9
  • CAS No. 105-08-8
  • Article Data52
  • CAS DataBase
  • Density 1.004 g/cm3
  • Solubility soluble in water
  • Melting Point 31.5 °C
  • Formula C8H16O2
  • Boiling Point 286.2 °C at 760 mmHg
  • Molecular Weight 144.214
  • Flash Point 161.1 °C
  • Transport Information
  • Appearance clear colourless viscous liquid
  • Safety 22-24/25-39-26
  • Risk Codes 36
  • Molecular Structure Molecular Structure of 105-08-8 (1,4-Cyclohexanedimethanol)
  • Hazard Symbols R36:;
  • Synonyms 1,4-Bis(hydroxymethyl)cyclohexane;1,4-Cyclohexamethylenebis methylol;1,4-Dimethylolcyclohexane;CHDM;CHDM-D;Cyclohex-1,4-ylenedimethanol;NSC 44508;Rikabinol DM;Sky CHDM;Vibracure A240;1,4-Cyclohexane dimethanol;
  • PSA 40.46000
  • LogP 0.77740

Synthetic route

cyclohexane-1,4-dicarboxylic acid
619-81-8, 619-82-9, 1076-97-7

cyclohexane-1,4-dicarboxylic acid

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With tin; hydrogen at 220℃; under 90009 Torr; for 0.75h; Temperature; Pressure;100%
With hydrogen In water at 230℃; under 15001.5 - 75007.5 Torr; Catalytic behavior; Reagent/catalyst; Autoclave;98.3%
With hydrogen In water at 230℃; under 63756.4 Torr; for 3h; Reagent/catalyst; Autoclave;95.8%
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In methanol at 200 - 240℃; under 30003 - 60006 Torr; for 8h;92%
With Cat.7; hydrogen at 180 - 250℃; under 52505.3 - 67506.8 Torr; Reagent/catalyst; Temperature; Pressure;
p-xylylene glycol
589-29-7

p-xylylene glycol

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With Ru/Al2O3; hydrogen In tetrahydrofuran at 60℃; under 7.50075 Torr; for 3.5h; Pressure; Autoclave;92%
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Stage #1: Bis(2-Hydroxyethyl)terephthalat With tin(II) chloride dihdyrate; ruthenium(III) chloride trihydrate; alumina; Cl6H6Pt(2-)*2H(1+)*6H2O; hydrogen In water at 180 - 260℃; under 37503.8 Torr; for 10h; Autoclave;
Stage #2: With sodium tetrahydroborate; sodium hydroxide at 500℃; for 5.5h; pH=9; Reagent/catalyst; Concentration; Temperature;
87.1%
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With C33H29FeMnN2O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In isopropyl alcohol at 75℃; under 37503.8 Torr; Autoclave;86%
Stage #1: dimethyl 1,4-cyclohexane dicarboxylate With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 0.5h;
Stage #2: With water In tetrahydrofuran
With hydrogen In methanol at 220℃; under 45004.5 Torr; Catalytic behavior; Time; Temperature; Green chemistry;
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen at 170 - 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 78.4%
bis(2-hydroxyethyl) cyclohexane-1,4-dicarboxylate

bis(2-hydroxyethyl) cyclohexane-1,4-dicarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In neat (no solvent) at 269.84℃; under 78757.9 Torr; for 10h; Reagent/catalyst; Pressure; Temperature; Autoclave;78%
ethyl 4-formylcyclohex-3-enecarboxylate

ethyl 4-formylcyclohex-3-enecarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 45004.5 Torr; for 12h; Reagent/catalyst;56%
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

C10H18O3

C10H18O3

E

C10H18O4

C10H18O4

Conditions
ConditionsYield
With hydrogen at 230℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 47.2%
D n/a
E n/a
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

E

1,4 dimethylcyclohexane
589-90-2

1,4 dimethylcyclohexane

Conditions
ConditionsYield
With hydrogen at 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 28.5%
D n/a
E n/a
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

C10H18O4

C10H18O4

E

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

F

1,4 dimethylcyclohexane
589-90-2

1,4 dimethylcyclohexane

Conditions
ConditionsYield
With hydrogen at 170 - 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 14.7%
D n/a
E n/a
F n/a
Bis(2-Hydroxyethyl)terephthalat
959-26-2

Bis(2-Hydroxyethyl)terephthalat

A

4-methylbenzoic acid ethyl ester
94-08-6

4-methylbenzoic acid ethyl ester

B

para-xylene
106-42-3

para-xylene

C

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

D

C10H18O4

C10H18O4

Conditions
ConditionsYield
With hydrogen at 170 - 260℃; under 37503.8 Torr; for 8h; Autoclave;A n/a
B n/a
C 5.3%
D n/a
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

4-methyloxymethylhydroxymethylhydroxymethylcyclohexane
62172-89-8

4-methyloxymethylhydroxymethylhydroxymethylcyclohexane

D

bis(4-hydroxymethylcyclohexyl) ether

bis(4-hydroxymethylcyclohexyl) ether

Conditions
ConditionsYield
With hydrogen; Pt1Ru5; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 8h; Product distribution; Further Variations:; Catalysts; reaction times;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen; Ru5PtSn; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 24h;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

methyl 4-methyl-1-cyclohexanecarboxylate
51181-40-9

methyl 4-methyl-1-cyclohexanecarboxylate

D

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

Conditions
ConditionsYield
With hydrogen; Ru5PtSn; silica gel In ethanol at 119.85℃; under 30002.4 Torr; for 8h; Further byproducts given;
With hydrogen; Ru5PtSn; silica gel In ethanol at 119.85℃; under 15001.2 Torr; for 24h; Further byproducts given;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

A

dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

[4-(methoxymethyl)cyclohexyl]methanol
98955-27-2

[4-(methoxymethyl)cyclohexyl]methanol

D

bis(4-hydroxymethylcyclohexyl) ether

bis(4-hydroxymethylcyclohexyl) ether

Conditions
ConditionsYield
With hydrogen; Ru5PtSn; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 24h; Product distribution; Further Variations:; Catalysts; Temperatures; Pressures;
With hydrogen; Pt1Ru5; silica gel In ethanol at 99.85℃; under 15001.2 Torr; for 24h;
terephthalic acid
100-21-0

terephthalic acid

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 6 h / 260 - 280 °C / 4535.33 Torr
2: dimethyl 1,4-cyclohexane dicarboxylate; Pd/Al2O3; hydrogen / 1 h / 200 °C / 93849.2 Torr / Autoclave
3: (4-methylcyclohexyl)methanol; hydrogen / 5 h / 250 °C / 212036 Torr
View Scheme
Stage #1: terephthalic acid With palladium on activated charcoal; hydrogen In water at 230℃; under 60006 Torr;
Stage #2: at 230℃; Pressure; Temperature; Reagent/catalyst;
100 %Chromat.
With hydrogen In water at 20 - 230℃; under 60006 Torr; Catalytic behavior; Reagent/catalyst; Inert atmosphere;
terephthalic acid 1,4-bis(4-methylcyclohexyl)methyl ester
95623-88-4

terephthalic acid 1,4-bis(4-methylcyclohexyl)methyl ester

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethyl 1,4-cyclohexane dicarboxylate; Pd/Al2O3; hydrogen / 1 h / 200 °C / 93849.2 Torr / Autoclave
2: (4-methylcyclohexyl)methanol; hydrogen / 5 h / 250 °C / 212036 Torr
View Scheme
With hydrogen at 150℃; under 22502.3 Torr; Temperature; Pressure;
bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate
1420954-46-6

bis((4-methylcyclohexyl)methyl) cyclohexane-1,4-dicarboxylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With (4-methylcyclohexyl)methanol; hydrogen at 250℃; under 212036 Torr; for 5h;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

4-hydroxymethylcyclohexanecarboxylic acid methyl ester
13380-85-3

4-hydroxymethylcyclohexanecarboxylic acid methyl ester

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

Conditions
ConditionsYield
With hydrogen In methanol at 220℃; under 45004.5 Torr; Green chemistry;
With hydrogen In methanol at 219.84℃; under 37503.8 Torr; Reagent/catalyst; chemoselective reaction;
With hydrogen In isopropyl alcohol at 220℃; under 75007.5 Torr; for 10h; Reagent/catalyst; Autoclave;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

4-hydroxymethylcyclohexanecarboxylic acid methyl ester
13380-85-3

4-hydroxymethylcyclohexanecarboxylic acid methyl ester

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

D

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde
92385-32-5

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde

Conditions
ConditionsYield
With hydrogen at 220℃; under 45004.5 Torr; Catalytic behavior; Reagent/catalyst; Time; Overall yield = 98.7 %;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

B

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

C

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde
92385-32-5

4-(hydroxymethyl)-1-cyclohexanecarboxaldehyde

Conditions
ConditionsYield
With hydrogen at 220℃; under 45004.5 Torr; Catalytic behavior; Reagent/catalyst; Time; Overall yield = 67.4 %;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

B

1,4-cyclohexanedicarboxaldehyde
33424-83-8

1,4-cyclohexanedicarboxaldehyde

Conditions
ConditionsYield
With hydrogen at 180℃; under 30003 Torr; Temperature; Pressure; Concentration;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

4-hydroxymethylcyclohexanecarboxylic acid methyl ester
13380-85-3

4-hydroxymethylcyclohexanecarboxylic acid methyl ester

B

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

Conditions
ConditionsYield
With hydrogen In isopropyl alcohol at 220℃; under 75007.5 Torr; for 10h; Reagent/catalyst; Pressure; Autoclave;
dimethyl 1,4-cyclohexane dicarboxylate
94-60-0

dimethyl 1,4-cyclohexane dicarboxylate

A

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

B

(4-methylcyclohexyl)methanol
34885-03-5

(4-methylcyclohexyl)methanol

Conditions
ConditionsYield
With hydrogen In isopropyl alcohol at 220℃; under 75007.5 Torr; for 10h; Reagent/catalyst; Pressure; Autoclave;
L-leucine
61-90-5

L-leucine

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

L,L-leucine 1,4-cyclohexanedimethanol diester
893447-84-2

L,L-leucine 1,4-cyclohexanedimethanol diester

Conditions
ConditionsYield
Stage #1: L-leucine; bis-1,4-(hydroxymethyl)cyclohexane With toluene-4-sulfonic acid In toluene at 150℃; for 30h; Heating / reflux;
Stage #2: With sodium hydrogencarbonate In water; toluene at 60℃;
100%
L-leucine
61-90-5

L-leucine

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

L,L-leucine 1,4-cyclohexanedimethanol diester
893447-84-2

L,L-leucine 1,4-cyclohexanedimethanol diester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene at 20 - 150℃; for 30h; Heating / reflux;100%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

acetic anhydride
108-24-7

acetic anhydride

1,4-cyclohexanedimethylene diacetate
6308-18-5

1,4-cyclohexanedimethylene diacetate

Conditions
ConditionsYield
With pyridine at 125℃; for 3.5h; Reagent/catalyst; Large scale;99%
With pyridine at 125℃; for 3.5h; Large scale;99%
5-Norbornene-2-carboxaldehyde
5453-80-5, 19926-90-0

5-Norbornene-2-carboxaldehyde

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

5-norbornene-2-(4-hydroxymethyl)cyklohexylmethoxymethanol

5-norbornene-2-(4-hydroxymethyl)cyklohexylmethoxymethanol

Conditions
ConditionsYield
sodium hydride at 20℃; for 10h;93%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde
59274-95-2

7-oxa-bicyclo[2.2.1]hept-5-ene-2-carbaldehyde

oxabicyclo[2.2.1]-hept-5-ene-2-(4-hydroxymethyl)cyclohexylmethoxy methanol

oxabicyclo[2.2.1]-hept-5-ene-2-(4-hydroxymethyl)cyclohexylmethoxy methanol

Conditions
ConditionsYield
sodium hydride at 20℃; for 10h;93%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

aniline
62-53-3

aniline

C20H26N2
1352050-49-7

C20H26N2

Conditions
ConditionsYield
With Pt-Sn/γ-Al2O3 In o-xylene at 145℃; for 24h; Inert atmosphere;93%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

cyclohexane-1,4-dimethyl chloride
824-93-1

cyclohexane-1,4-dimethyl chloride

Conditions
ConditionsYield
With pyridine; thionyl chloride Chlorination; Heating;92%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

phenyl chloroformate
1885-14-9

phenyl chloroformate

1,4-cyclohexanedimethanol diphenyl dicarbonate
22563-70-8

1,4-cyclohexanedimethanol diphenyl dicarbonate

Conditions
ConditionsYield
With pyridine; dmap In tetrahydrofuran at 0 - 20℃;90.2%
2-Isocyanatoethyl methacrylate
30674-80-7

2-Isocyanatoethyl methacrylate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C15H25NO5

C15H25NO5

Conditions
ConditionsYield
With dibutyltin dilaurate In toluene for 5h;90.1%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

acetyl chloride
75-36-5

acetyl chloride

1,4-cyclohexanedimethylene diacetate
6308-18-5

1,4-cyclohexanedimethylene diacetate

Conditions
ConditionsYield
With pyridine; dmap In chloroform at 0 - 20℃;87%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

(R)-1-C-(1-Cyclohexen-5-yl)carbaldehyde
60631-76-7

(R)-1-C-(1-Cyclohexen-5-yl)carbaldehyde

cyclohexylmethyl alcohol
100-49-2

cyclohexylmethyl alcohol

acetal oligomer

acetal oligomer

Conditions
ConditionsYield
With N,N-dimethyl acetamide; toluene-4-sulfonic acid at 140℃; for 20h;85%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

chlorophosphoric acid diphenyl ester
2524-64-3

chlorophosphoric acid diphenyl ester

1,4-cyclohexanedimethanol bis(diphenyl phosphate)
476371-27-4

1,4-cyclohexanedimethanol bis(diphenyl phosphate)

Conditions
ConditionsYield
With magnesium chloride In methanol; hexane82.2%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

C17H20O5
1033761-69-1

C17H20O5

C42H52O10

C42H52O10

Conditions
ConditionsYield
With dmap; 2,6-di-tert-butyl-4-methyl-phenol; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;81%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

cyclohexane-1,4-dicarbonitrile
10534-13-1

cyclohexane-1,4-dicarbonitrile

Conditions
ConditionsYield
With 1,10-Phenanthroline; ammonia; oxygen In 1,4-dioxane at 30 - 60℃; under 3750.38 Torr; for 12h; Pressure; Temperature; Reagent/catalyst; Solvent;80.5%
maleic anhydride
108-31-6

maleic anhydride

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

(Z)-2-butenedioic-acid-1,4-cyclohexanediylbis(methylene) ester
551929-43-2

(Z)-2-butenedioic-acid-1,4-cyclohexanediylbis(methylene) ester

Conditions
ConditionsYield
In acetonitrile at 50℃; for 72h;80%
In acetonitrile at 50℃; for 72h;80%
4-(hydroxymethyl)cyclohexane-1-carboxylic acid
13380-84-2

4-(hydroxymethyl)cyclohexane-1-carboxylic acid

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

[4-(hydroxymethyl)cyclohexyl]methyl 4-(hydroxymethyl)cyclohexane-1-carboxylate

[4-(hydroxymethyl)cyclohexyl]methyl 4-(hydroxymethyl)cyclohexane-1-carboxylate

Conditions
ConditionsYield
Stage #1: bis-1,4-(hydroxymethyl)cyclohexane With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 4-(hydroxymethyl)cyclohexane-1-carboxylic acid In dimethyl sulfoxide at 20℃; for 5h;
80%
Stage #1: bis-1,4-(hydroxymethyl)cyclohexane With dmap; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 4-(hydroxymethyl)cyclohexane-1-carboxylic acid In dimethyl sulfoxide at 20℃; for 5h;
80%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

2-(diphenylmethoxy)-pyridine

2-(diphenylmethoxy)-pyridine

(4-(benzhydryloxymethyl)cyclohexyl)methanol

(4-(benzhydryloxymethyl)cyclohexyl)methanol

Conditions
ConditionsYield
With iron(III) chloride In 1,2-dichloro-ethane at 70℃; for 10h;78%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

(4-chlorophenyl)(phenyl)carbamic chloride
1187856-44-5

(4-chlorophenyl)(phenyl)carbamic chloride

(4-(hydroxymethyl)cyclohexyl)methyl (4-chlorophenyl)(phenyl)carbamate

(4-(hydroxymethyl)cyclohexyl)methyl (4-chlorophenyl)(phenyl)carbamate

Conditions
ConditionsYield
With pyridine at 120℃; for 18h;78%
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

1,5-dioxa-3,3-bis(ethoxycarbonyl)-8,8,10,10-tetramethyl-9-azaspiro<5.5>undecane
110844-29-6

1,5-dioxa-3,3-bis(ethoxycarbonyl)-8,8,10,10-tetramethyl-9-azaspiro<5.5>undecane

8,8,10,10-Tetramethyl-1,5-dioxa-9-azaspiro-[5.5]undecane-3,3-dicarboxylic acid
110839-53-7

8,8,10,10-Tetramethyl-1,5-dioxa-9-azaspiro-[5.5]undecane-3,3-dicarboxylic acid

Conditions
ConditionsYield
In dichloromethane; acetic acid77%
Isopropenyl acetate
108-22-5

Isopropenyl acetate

bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

A

1,4-cyclohexanedimethylene diacetate
6308-18-5

1,4-cyclohexanedimethylene diacetate

B

diisopropenyl 1,4-cyclohexanedimethanol ether

diisopropenyl 1,4-cyclohexanedimethanol ether

C

C13H22O3

C13H22O3

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; sodium carbonate In toluene at 100℃; for 6h;A n/a
B 75%
C n/a
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

trans-1,4-Cyclohexanedimethanol
3236-48-4

trans-1,4-Cyclohexanedimethanol

Conditions
ConditionsYield
With Ni/NiO-diatomite at 200℃; for 3h; Reagent/catalyst; Autoclave; Inert atmosphere;72.6%
Multi-step reaction with 2 steps
1: 52.1 percent / 140 - 165 °C
2: 46.3 percent / aq. NaOH / 10 h / Heating
View Scheme
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

[4-(p-toluenesulfonyloxymethyl)cyclohexyl]methanol
109004-13-9

[4-(p-toluenesulfonyloxymethyl)cyclohexyl]methanol

Conditions
ConditionsYield
With pyridine; dmap; triethylamine In dichloromethane at 20℃; for 3h;72%
In pyridine at 20℃; for 36h;61%
With pyridine In dichloromethane186 g
bis-1,4-(hydroxymethyl)cyclohexane
105-08-8

bis-1,4-(hydroxymethyl)cyclohexane

ethyl 3-diazoindole-2-carboxylate
89607-68-1

ethyl 3-diazoindole-2-carboxylate

3-(4-hydroxymethyl-cyclohexylmethoxy)-3H-indole-2-carboxylic acid ethyl ester

3-(4-hydroxymethyl-cyclohexylmethoxy)-3H-indole-2-carboxylic acid ethyl ester

Conditions
ConditionsYield
dirhodium tetraacetate In dichloromethane at 85℃; for 3h; Substitution; O-H insertation;72%

1,4-Cyclohexanedimethanol Consensus Reports

1,4-BIS(HYDROXYMETHYL)CYCLOHEXANE is reported in EPA TSCA Inventory.

1,4-Cyclohexanedimethanol Specification

The 1,4-Bis(hydroxymethyl)cyclohexane is an organic compound with the formula C8H16O2. The IUPAC name of this chemical is [4-(hydroxymethyl)cyclohexyl]methanol. With the CAS registry number 105-08-8, it is also named as Cyclohexan-1,4-diyldimethanol. The product's category is Alkohols. Besides, it is clear colourless viscous liquid, which should be stored in a cool and well-ventilated place. It is used in the manufacture of polyester fiber, polyester electrical appliances, unsaturated polyester resin, polyester glaze, polyurethane foam.

Physical properties about 1,4-Bis(hydroxymethyl)cyclohexane are: (1)ACD/LogP: 0.36; (2)ACD/LogD (pH 5.5): 0.36; (3)ACD/LogD (pH 7.4): 0.36; (4)ACD/BCF (pH 5.5): 1.1; (5)ACD/BCF (pH 7.4): 1.1; (6)ACD/KOC (pH 5.5): 37.33; (7)ACD/KOC (pH 7.4): 37.33; (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: 1.47; (13)Molar Refractivity: 40.12 cm3; (14)Molar Volume: 143.5 cm3; (15)Polarizability: 15.9×10-24cm3; (16)Surface Tension: 40.5 dyne/cm; (17)Density: 1.004 g/cm3; (18)Flash Point: 161.1 °C; (19)Enthalpy of Vaporization: 60.96 kJ/mol; (20)Boiling Point: 286.2 °C at 760 mmHg; (21)Vapour Pressure: 0.000303 mmHg at 25°C.

Preparation: this chemical can be prepared by trans-1,4-bis-acetoxymethyl-cyclohexane. This reaction will need reagent methanolic potassium carbonate at ambient temperature. The yield is about 100%.



Uses of 1,4-Bis(hydroxymethyl)cyclohexane: it can be used to produce trans-1,4-Bis(chloromethyl)-cyclohexane. It will need reagent CCl4, Ph3P. The yield is about 64%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: OCC1CCC(CO)CC1
(2)InChI: InChI=1/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2
(3)InChIKey: YIMQCDZDWXUDCA-UHFFFAOYAS
(4)Std. InChI: InChI=1S/C8H16O2/c9-5-7-1-2-8(6-10)4-3-7/h7-10H,1-6H2
(5)Std. InChIKey: YIMQCDZDWXUDCA-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 1600mg/kg (1600mg/kg)   Kodak Company Reports. Vol. 21MAY1971,
mouse LDLo intraperitoneal 1600mg/kg (1600mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 194, 1969.
rat LD50 oral 3200mg/kg (3200mg/kg)   Kodak Company Reports. Vol. 21MAY1971,
rat LDLo intraperitoneal 800mg/kg (800mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 194, 1969.

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