2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol supplier

Name
2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol
EINECS 202-494-5
CAS No. 62147-49-3
Article Data4
CAS DataBase
Density 1.546 g/cm³
Solubility Soluble in ethanol, ethyl ether, acetone. Slightly soluble in water. Insoluble in ligroin.
Melting Point 70.00 - 80.00 ºC
Formula C6H12 O6
Boiling Point 448 °C at 760 mmHg
Molecular Weight 180.158
Flash Point 224.7 °C
Transport Information
Appearance white to off-white crystalline powder
Safety 26-36
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms 1,4-Dioxane-2,5-dimethanol,2,5-dihydroxy-, trans-
PSA 99.38000
LogP -2.60500

Synthetic route

: 56-81-5
glycerol

: 62147-49-3
1,3-dihydroxyacetone dimer

Conditions

Conditions	Yield
With C32H30N4O4Pd2(2+); p-benzoquinone In water; acetonitrile at 23℃; for 4h;	58%

: 50-00-0
formaldehyd

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 40031-31-0
erythrulose

C: 50-69-1, 58-86-6, 65-42-9, 147-81-9, 609-06-3, 1114-34-7, 1949-78-6, 5328-37-0, 10323-20-3, 20235-19-2, 24259-59-4, 25990-60-7, 34466-20-1, 41247-05-6, 53106-52-8, 55058-43-0, 80952-57-4
arabinose

D: 50-69-1, 58-86-6, 65-42-9, 147-81-9, 609-06-3, 1114-34-7, 1949-78-6, 5328-37-0, 10323-20-3, 20235-19-2, 24259-59-4, 25990-60-7, 34466-20-1, 41247-05-6, 53106-52-8, 55058-43-0, 80952-57-4
xylose

E: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

F: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

Conditions

Conditions	Yield
With triethylamine; thiazolium salt In N,N-dimethyl-formamide at 100℃; Mechanism; Product distribution; influence of amount of paraformaldehyde, paraformaldehyde:catalyst ratio, reaction temperature and time, other amine bases;

...Expand

: 50-00-0
formaldehyd

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 40031-31-0
erythrulose

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

D: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

Conditions

Conditions	Yield
With triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In N,N-dimethyl-formamide at 100℃; Further byproducts given;

...Expand

: 50-00-0
formaldehyd

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 50-69-1, 58-86-6, 65-42-9, 147-81-9, 609-06-3, 1114-34-7, 1949-78-6, 5328-37-0, 10323-20-3, 20235-19-2, 24259-59-4, 25990-60-7, 34466-20-1, 41247-05-6, 53106-52-8, 55058-43-0, 80952-57-4
arabinose

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

D: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

Conditions

Conditions	Yield
With triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In N,N-dimethyl-formamide at 100℃; Further byproducts given;

...Expand

: 50-00-0
formaldehyd

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 50-69-1, 58-86-6, 65-42-9, 147-81-9, 609-06-3, 1114-34-7, 1949-78-6, 5328-37-0, 10323-20-3, 20235-19-2, 24259-59-4, 25990-60-7, 34466-20-1, 41247-05-6, 53106-52-8, 55058-43-0, 80952-57-4
xylose

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

D: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

Conditions

Conditions	Yield
With triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In N,N-dimethyl-formamide at 100℃; Further byproducts given;

...Expand

: 50-00-0
formaldehyd

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

D: 95-43-2, 95-44-3, 533-49-3, 583-50-6, 1758-51-6, 7558-94-3, 29825-68-1, 29884-64-8, 38982-45-5
threose

Conditions

Conditions	Yield
With triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In N,N-dimethyl-formamide at 100℃; Further byproducts given;

...Expand

: 50-00-0
formaldehyd

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

D: 95-43-2, 95-44-3, 533-49-3, 583-50-6, 1758-51-6, 7558-94-3, 29825-68-1, 29884-64-8, 38982-45-5
erythrose

Conditions

Conditions	Yield
With triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In N,N-dimethyl-formamide at 100℃; Further byproducts given;

...Expand

: 141-46-8
Glycolaldehyde

A: 62147-49-3
1,3-dihydroxyacetone dimer

B: 40031-31-0
erythrulose

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
galactose

D: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
glucose

Conditions

Conditions	Yield
With triethylamine; 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride In N,N-dimethyl-formamide at 60℃; for 1h; Further byproducts given;

...Expand

: 50-99-7
D-glucose

A: 98-01-1
furfural

B: 62147-49-3
1,3-dihydroxyacetone dimer

C: 56-82-6
Glyceraldehyde

Conditions

Conditions	Yield
With niobium(V) oxide at 20℃; for 2h; Reagent/catalyst;

...Expand

: 58-86-6
D-xylose

A: 98-01-1
furfural

B: 62147-49-3
1,3-dihydroxyacetone dimer

C: 56-82-6
Glyceraldehyde

Conditions

Conditions	Yield
With erbium(III) oxide at 20℃; for 2h;

...Expand

: 57-48-7
D-Fructose

A: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

B: 62147-49-3
1,3-dihydroxyacetone dimer

C: 64-18-6
formic acid

D: 10326-41-7
D-Lactic acid

Conditions

Conditions	Yield
With dibutyltin dilaurate In water at 150℃; for 2h;	A 5.4 %Chromat. B 9.1 %Chromat. C 6 %Chromat. D 7.8 %Chromat.

...Expand

: 57-48-7
D-Fructose

A: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

B: 62147-49-3
1,3-dihydroxyacetone dimer

C: 64-18-6
formic acid

D: 64-19-7
acetic acid

E: 78-98-8
2-oxopropanal

Conditions

Conditions	Yield
With n-butylstannoic acid In water at 150℃; for 2h;	A 5.4 %Chromat. B 10.2 %Chromat. C 6.8 %Chromat. D 7.4 %Chromat. E 5.2 %Chromat.

...Expand

: 57-48-7
D-Fructose

A: 67-47-0
5-hydroxymethyl-2-furfuraldehyde

B: 62147-49-3
1,3-dihydroxyacetone dimer

Conditions

Conditions	Yield
With dibutyltin dilaurate In water at 150℃; for 2h;	A 5.2 %Chromat. B 6.7 %Chromat.

: 62147-49-3
1,3-dihydroxyacetone dimer

: 18162-48-6
tert-butyldimethylsilyl chloride

: 127382-65-4
1,3-bis-O-(tert-butyldimethylsilyl)-1,3-dihydroxy-2-propanone

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane for 18h;	100%
With triethylamine In dichloromethane at 20℃; for 12h;	99%
With 1H-imidazole In N,N-dimethyl-formamide for 3h; Ambient temperature;	98%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 53293-00-8
hex-5-ynoic acid

: 2-oxopropane-1,3-diyl bis(hex-5-ynoate)

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;	100%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 108-24-7
acetic anhydride

: 6946-10-7
1,3-diacetoxyacetone

Conditions

Conditions	Yield
In pyridine for 14h; Ambient temperature;	98%
With pyridine	85%
With pyridine at 20℃;	80%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 2463-63-0
3-Butyl-acrolein

: 1186656-01-8
(1R,3aS,6R,6aR)-6-butylhexahydrofuro[3,4-c]furan-1,3a-diol

Conditions

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 20℃; optical yield given as %ee; enantioselective reaction;	98%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 122-51-0
orthoformic acid triethyl ester

: 18294-29-6
2,5-diethoxy-2,5-bis(hydroxymethyl)-1,4-dioxane

Conditions

Conditions	Yield
sulfuric acid In ethanol 1.) reflux, 30 min, 2.) 4 days;	97%
Stage #1: orthoformic acid triethyl ester With sulfuric acid In ethanol for 0.5h; Reflux; Inert atmosphere; Stage #2: 1,3-dihydroxyacetone dimer In ethanol at 0 - 4℃;	97%
With toluene-4-sulfonic acid In ethanol for 24h;	74%
sulfuric acid 1) ethanol, 30 min., reflux, 2) 4 deg C, 24 h; Yield given. Multistep reaction;
With sulfuric acid In ethanol

: 62147-49-3
1,3-dihydroxyacetone dimer

: potassium sulphocyanide

: 100-46-9
benzylamine

: 98412-23-8
1-benzyl-2-mercapto-5-hydroxymethyl-imidazole

Conditions

Conditions	Yield
With acetic acid In butan-1-ol for 50h; Ambient temperature;	97%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 3287-99-8, 39110-74-2
benzylamine hydrochloride

: 333-20-0
potassium thioacyanate

A: 98412-23-8
1-benzyl-2-mercapto-5-hydroxymethyl-imidazole

: 4-benzyl-3a-methyl-3a,4,6,6a-tetrahydro-2H-imidazo[4,5-d][1,3]oxazole-2(3H),5-dithione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 55℃; for 18h; Product distribution; Further Variations:; Solvents; Marckwald imidazole synthesis;	A 97% B 2.8%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 17061-61-9
4-methoxybenzylamine hydrochloride

: 470690-99-4
[2-mercapto-1-(4-methoxybenzyl)-1H-imidazol-5-yl]methanol

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 55℃; for 18h; Product distribution; Further Variations:; Solvents; Marckwald imidazole synthesis;	97%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 6728-26-3
(E)-2-Hexenal

: 1186655-96-8
(1R,3aS,6R,6aR)-6-propylhexahydrofuro[3,4-c]furan-1,3a-diol

Conditions

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 20℃; for 16h; optical yield given as %ee; enantioselective reaction;	96%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 53448-07-0, 71277-05-9, 2463-77-6
2-undecenal

: 1186656-05-2
(1R,3aS,6R,6aR)-6-octylhexahydrofuro[3,4-c]furan-1,3a-diol

Conditions

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 20℃; optical yield given as %ee; enantioselective reaction;	96%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 3287-99-8, 39110-74-2
benzylamine hydrochloride

: 333-20-0
potassium thioacyanate

: 98412-23-8
5-hydroxymethyl-1-phenylmethylimidazoline-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	96%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 2620-49-7
3,4-methylenedioxybenzylamine hydrochloride

: 1-(benzo[d][1,3]dioxol-5-ylmethyl)-5-(hydroxymethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	95%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 104-88-1
4-chlorobenzaldehyde

: 78-39-7
Triethyl orthoacetate

: 4,6-bis((Z)-4-chlorobenzylidene)-2-ethoxy-2-methyl-1,3-dioxan-5-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydroxyacetone dimer With acetic acid In 1,4-dioxane at 60℃; for 0.166667h; Inert atmosphere; Stage #2: Triethyl orthoacetate In 1,4-dioxane at 60℃; for 8h; Stage #3: 4-chlorobenzaldehyde With pyrrolidine In 1,4-dioxane at 20℃; Claisen-Schmidt Condensation;	95%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: potassium sulphocyanide

: 74-89-5
methylamine

: 143122-18-3
5-hydroxymethyl-2-mercapto-1-methyl-1H-imidazole

Conditions

Conditions	Yield
With acetic acid In butan-1-ol for 50h; Ambient temperature;	93%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 7409-30-5
p-nitrobenzylamine

: 333-20-0
potassium thioacyanate

: 114772-19-9
1-(4-Nitrobenzyl)-2-Mercapto-5-Hydroxymethylimidazole

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 55℃; for 18h; Product distribution; Further Variations:; Solvents; Marckwald imidazole synthesis;	92%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 2548-87-0, 20664-46-4, 2363-89-5
2-octen-1-al

: 1186656-02-9
(1R,3aS,6R,6aR)-6-pentylhexahydrofuro[3,4-c]furan-1,3a-diol

Conditions

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 20℃; optical yield given as %ee; enantioselective reaction;	92%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 73728-66-2
(2,4-dichlorophenyl)methanamine hydrochloride

: 1-(2,4-dichlorobenzyl)-5-(hydroxymethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	92%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 3858-78-4
n-butylamine hydrochloride

: 1-butyl-5-(hydroxymethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	92%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 35660-94-7
(E)-2-methylbut-2-enoyl chloride

: 1,3-ditigloyloxyacetone

Conditions

Conditions	Yield
With pyridine In benzene at 0 - 20℃; for 2h;	91%

: 62147-49-3
1,3-dihydroxyacetone dimer

: 10406-25-4
4-aminobenzyl cyanide

: 333-20-0
potassium thioacyanate

: 252882-62-5
1-(4-cyanobenzyl)-2-mercapto-5-hydroxymethylimidazole

Conditions

Conditions	Yield
In water; acetonitrile at 55℃; for 18h; Product distribution; Further Variations:; Solvents; Marckwald imidazole synthesis;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 26177-44-6
4-bromobenzylamine hydrochloride

: 312936-77-9
1-(4-Bromobenzyl)-2-Mercapto-5-Hydroxymethylimidazole

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 55℃; for 18h; Product distribution; Further Variations:; Solvents; Marckwald imidazole synthesis;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 3287-99-8, 39110-74-2
benzylamine hydrochloride

: 333-20-0
potassium thioacyanate

: 98412-23-8
1-benzyl-2-mercapto-5-hydroxymethyl-imidazole

Conditions

Conditions	Yield
In butan-1-ol at 7℃; for 0.5h; Sonication;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 17061-61-9
4-methoxybenzylamine hydrochloride

: 5-(hydroxymethyl)-1-(4-methoxybenzyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 2,6-difluorobenzylamine hydrochloride

: 1-(2,6-difluorobenzyl)-5-(hydroxymethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 333-20-0
potassium thioacyanate

: 86188-24-1
2-(thien-2-yl)-ethylamine hydrochloride

: 5-(hydroxymethyl)-1-(2-(thiophen-2-yl)ethyl)-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 593-51-1
methylamine hydrochloride

: 333-20-0
potassium thioacyanate

: 5-(hydroxymethyl)-1-methyl-1H-imidazole-2(3H)-thione

Conditions

Conditions	Yield
With acetic acid In water; acetonitrile at 60℃; for 16h;	90%

...Expand

: 1445-45-0
Trimethyl orthoacetate

: 62147-49-3
1,3-dihydroxyacetone dimer

: 1122-91-4
4-bromo-benzaldehyde

: 4,6-bis((Z)-4-bromobenzylidene)-2-methoxy-2-methyl-1,3-dioxan-5-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydroxyacetone dimer With acetic acid In 1,4-dioxane at 60℃; for 0.166667h; Inert atmosphere; Stage #2: Trimethyl orthoacetate In 1,4-dioxane at 60℃; for 8h; Stage #3: 4-bromo-benzaldehyde With pyrrolidine In 1,4-dioxane at 20℃; Claisen-Schmidt Condensation;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 78-39-7
Triethyl orthoacetate

: 100-10-7
4-dimethylamino-benzaldehyde

: 4,6-bis((Z)-4-(dimethylamino)benzylidene)-2-ethoxy-2-methyl-1,3-dioxan-5-one

Conditions

Conditions	Yield
Stage #1: 1,3-dihydroxyacetone dimer With acetic acid In 1,4-dioxane at 60℃; for 0.166667h; Inert atmosphere; Stage #2: Triethyl orthoacetate In 1,4-dioxane at 60℃; for 8h; Stage #3: 4-dimethylamino-benzaldehyde With pyrrolidine In 1,4-dioxane at 20℃; Claisen-Schmidt Condensation;	90%

...Expand

: 62147-49-3
1,3-dihydroxyacetone dimer

: 591-51-5
phenyllithium

: (S)- 5,6-dihydro-6-(2-phenylethyl)-2H-pyran-2-one

: (2aS,2a1R,4aS,6S,7aS)-6-phenethyl-4a-phenyltetrahydro-2H,6H-1,4,5-trioxacyclopenta[cd]inden-2a(3H)-ol

Conditions

Conditions	Yield
Stage #1: phenyllithium; (S)- 5,6-dihydro-6-(2-phenylethyl)-2H-pyran-2-one In tetrahydrofuran; dibutyl ether at -78℃; for 0.25h; Stage #2: 1,3-dihydroxyacetone dimer With camphor-10-sulfonic acid In tetrahydrofuran; dibutyl ether; N,N-dimethyl-formamide at -78 - 0℃; for 2h;	90%

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: 62147-49-3
1,3-dihydroxyacetone dimer

: 123-73-9
crotonaldehyde

: 1186655-98-0
(1R,3aS,6R,6aR)-6-methylhexahydrofuro[3,4-c]furan-1,3a-diol

Conditions

Conditions	Yield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 20℃; optical yield given as %ee; enantioselective reaction;	89%

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol Chemical Properties

IUPAC Name: 2,5-bis(hydroxymethyl)-1,4-dioxane-2,5-diol
Empirical Formula: C₆H₁₂O₆
Molecular Weight: 180.1559g/mol
EINECS: 202-494-5
Structure of 1,4-Dioxane-2,5-dimethanol,2,5-dihydroxy-, (2R,5S)-rel- (CAS NO.62147-49-3):

Index of Refraction: 1.549
Molar Refractivity: 37.1 cm³
Molar Volume: 116.5 cm³
Polarizability: 14.71×10^-24cm³
Surface Tension: 84.9 dyne/cm
Density: 1.546 g/cm³
Flash Point: 224.7 °C
Enthalpy of Vaporization: 81.51 kJ/mol
Melting Point: 75-80 °C(lit.)
Boiling Point: 448 °C at 760 mmHg
Vapour Pressure: 6.59E-10 mmHg at 25°C
Sensitive: Hygroscopic
Stability: Stable. Incompatible with strong oxidizing agents. Protect from moisture.
Physical Appearance: Off-whitepowde
Product Categories: Dioxanes;Dioxanes & Dioxolanes
Canonical SMILES: C1C(OCC(O1)(CO)O)(CO)O
InChI: InChI=1S/C6H12O6/c7-1-5(9)3-12-6(10,2-8)4-11-5/h7-10H,1-4H2
InChIKey: KEQUNHIAUQQPAC-UHFFFAOYSA-N

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: UC1645000

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol Specification

1,4-Dioxane-2,5-dimethanol,2,5-dihydroxy-, (2R,5S)-rel- , its cas register number is 62147-49-3. It also can be called 1,3-Dihydroxyacetone Dimer ; 2,5-Bis(hydroxymethyl)-1,4-dioxane-2,5-diol ; 2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol ; 2,5-Dihydroxydioxane-2,5-dimethanol . 1,4-Dioxane-2,5-dimethanol,2,5-dihydroxy-, (2R,5S)-rel- (CAS NO.62147-49-3) is irritating to eyes, respiratory system and skin.

Product Name

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol

Synthetic route

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol Chemical Properties

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol Safety Profile

2,5-Dihydroxy-1,4-dioxane-2,5-dimethanol Specification

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