1,2,6-Hexanetriol supplier

Name
1,2,6-Hexanetriol
EINECS 203-424-6
CAS No. 106-69-4
Article Data46
CAS DataBase
Density 1.113 g/cm³
Solubility miscible with water
Melting Point 25-32 °C
Formula C₆H₁₄O₃
Boiling Point 323.1 °C at 760 mmHg
Molecular Weight 134.175
Flash Point 165.5 °C
Transport Information
Appearance clear light yellow coloured, viscous liquid
Safety 24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1,2,6-Trihydroxyhexane;NSC 404957;
PSA 60.69000
LogP -0.49780

Synthetic route

: 821-41-0
5-Hexen-1-ol

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
Stage #1: 5-Hexen-1-ol With formic acid; water; dihydrogen peroxide at 20 - 58℃; for 4h; Stage #2: With methanol; Marlon-AS3 at 60 - 70℃; under 760.051 Torr; for 4h; Product distribution / selectivity;	92%
Stage #1: 5-Hexen-1-ol With formic acid; water; dihydrogen peroxide at 20 - 58℃; for 4h; Stage #2: With butan-1-ol; Marlon-AS3 at 125 - 130℃; for 5h; Product distribution / selectivity;
Stage #1: 5-Hexen-1-ol With formic acid; water; dihydrogen peroxide at 20 - 58℃; for 4h; Stage #2: With ethanol; hexane-1-sulfonic acid Product distribution / selectivity;
Stage #1: 5-Hexen-1-ol With formic acid; water; dihydrogen peroxide at 20 - 58℃; for 4h; Stage #2: With ethanol; dodecansulfonic acid Product distribution / selectivity;
Stage #1: 5-Hexen-1-ol With formic acid; water; dihydrogen peroxide at 20 - 58℃; for 4h; Stage #2: With methanol; sulfuric acid Product distribution / selectivity;

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

A: 104-80-3, 1122-89-0, 2144-40-3, 81370-88-9, 81370-89-0
tetrahydrofuran-2,5-dimethanol

B: 106-69-4
hexane-1,2,6-triol

C: 10299-30-6
hexane-1,2,5-triol

D: 20221-50-5, 24211-51-6, 122923-46-0, 5581-21-5
1,2,5,6-hexanetetrol

Conditions

Conditions	Yield
With water; hydrogen In butan-1-ol at 129.84℃; under 20686.5 Torr; for 12h; Mechanism; Reagent/catalyst; Time; Solvent; pH-value; Sealed vessel; chemoselective reaction;	A 91% B n/a C n/a D n/a

...Expand

: 1883-75-6
2,5-bis-(hydroxymethyl)furan

A: 104-80-3, 1122-89-0, 2144-40-3, 81370-88-9, 81370-89-0
tetrahydrofuran-2,5-dimethanol

B: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With hydrogen In water; isopropyl alcohol at 110℃; under 36201.3 Torr; for 3h;	A 91% B 7%

: 14739-10-7
4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With ammonium nitrate; Montmorillonite-K10 for 0.05h; deprotection; microwave irradiation;	83%

: 91898-36-1
4-[4-(2-Methoxy-ethoxymethoxy)-butyl]-2,2-dimethyl-[1,3]dioxolane

A: 14739-10-7
4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol

B: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction;	A 54% B n/a

: 50-70-4
D-sorbitol

A: 106-69-4
hexane-1,2,6-triol

B: 140946-33-4
1,4,5-hexanetriol

C: 20221-50-5, 24211-51-6, 122923-46-0, 5581-21-5
1,2,5,6-hexanetetrol

D: 584-03-2
1,2-dihydroxybutane

Conditions

Conditions	Yield
With propylene glycol; hydrogen; copper In water at 210℃; under 93089.1 Torr; Concentration;	A 5.51% B 26.54% C 46.12% D 10.26%

...Expand

: 1,2-O,O-benzylidene-6-O-(tetrahydropyran-2-yl)hexane-1,2,6-triol

A: 106-69-4
hexane-1,2,6-triol

B: 91898-40-7
6-(2-tetrahydropyranyl)oxy-1,2-hexanediol

Conditions

Conditions	Yield
With zinc dibromide In dichloromethane at 20℃; for 7h;	A n/a B 11%

: 100-73-2
acrolein dimer

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With water; toluene-4-sulfonic acid anschliessende Hydrierung an Raney-Nickel bei pH 5;
Multi-step reaction with 2 steps 1: diluted aqueous sulfuric acid 2: Raney nickel; water / Hydrogenation View Scheme

: 3749-36-8
2-hydroxymethyl-3,4-dihydro-2H-pyran

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With hydrogenchloride Behandeln des Reaktionsgemisches mit Natriumboranat unter Zusatz von Kaliumcarbonat;

: 4437-40-5
6-oxo-tetrahydro-pyran-2-carboxylic acid

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

: 141-31-1
2-hydroxyadipaldehyde

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With water; nickel Hydrogenation;
With water; nickel Hydrogenation;

: 99116-04-8
5,6-dihydroxy-hexanal

: 106-69-4
hexane-1,2,6-triol

: 18294-84-3
2-acetoxy-adipic acid diethyl ester

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

: 89980-49-4
6-chloro-hexane-1,5-diol

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With potassium carbonate Heating;

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

A: 104-80-3, 1122-89-0, 2144-40-3, 81370-88-9, 81370-89-0
tetrahydrofuran-2,5-dimethanol

B: 1883-75-6
2,5-bis-(hydroxymethyl)furan

C: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
With hydrogen; Co/Ni catalyst (Co-0179/Ni C46-7-03) In water at 70 - 200℃; under 25858.1 Torr; Product distribution / selectivity;

...Expand

: 148254-22-2
4-[2-phenyl-(1,3-dioxolan-4-yl)]-butan-1-ol

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 65 percent / PPTS / CH2Cl2 / 12 h / 20 °C 2: ZnBr2 / CH2Cl2 / 7 h / 20 °C View Scheme

: 4-(1,4-dioxa-spiro[4.5]dec-2-yl)-butan-1-ol

: 106-69-4
hexane-1,2,6-triol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 84 percent / PPTS / CH2Cl2 / 12 h / 20 °C 2: ZnBr2 / CH2Cl2 / 6 h / 20 °C View Scheme

: 821-41-0
5-Hexen-1-ol

A: 106-69-4
hexane-1,2,6-triol

B copper oxide-chromium oxide: copper oxide-chromium oxide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOCl, KH2PO4 / H2O / 5 °C 2: aq. K2CO3 / Heating View Scheme

: 4500-29-2
N-cyclohexyl-diethanolamine

: 106-69-4
hexane-1,2,6-triol

: 104-80-3, 1122-89-0, 2144-40-3, 81370-88-9, 81370-89-0
tetrahydrofuran-2,5-dimethanol

A: 106-69-4
hexane-1,2,6-triol

B: 629-11-8
1,6-hexanediol

Conditions

Conditions	Yield
With hydrogen In water at 120℃; under 7500.75 - 60006 Torr; for 5h; Autoclave;

: 106-69-4
hexane-1,2,6-triol

: 100-72-1
Tetrahydropyran-2-methanol

Conditions

Conditions	Yield
trifluorormethanesulfonic acid In sulfolane at 125℃; for 0.5h;	100%
With aluminum oxide at 220 - 250℃; for 30h;	18%
With benzyltrichlorostannane at 105 - 135℃; for 3h;	70 % Turnov.
With trifluorormethanesulfonic acid In sulfolane at 125℃; for 0.5h;
With trifluorormethanesulfonic acid In sulfolane at 125℃; for 0.5h;

: 106-69-4
hexane-1,2,6-triol

: 67-64-1
acetone

: 14739-10-7
4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol

Conditions

Conditions	Yield
With toluene-4-sulfonic acid	100%
With toluene-4-sulfonic acid for 20h;	92%
With toluene-4-sulfonic acid Ambient temperature;	92%

: 106-69-4
hexane-1,2,6-triol

: 76-83-5
trityl chloride

: 98289-12-4
1,2,6-hexanetriol 1,6-ditrityl ether

Conditions

Conditions	Yield
With pyridine for 64h; Ambient temperature;	94%

: 106-69-4
hexane-1,2,6-triol

: 124-63-0
methanesulfonyl chloride

: C9H20O9S3

Conditions

Conditions	Yield
In tetrahydrofuran; dichloromethane at 20℃; for 3h;	93%
With triethylamine In tetrahydrofuran; dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;

: 886577-76-0
2-isocyanato-2-methylpropane-1,3-diyl diacrylate

: 106-69-4
hexane-1,2,6-triol

: C28H40N2O13

Conditions

Conditions	Yield
With dibutyltin dilaurate In toluene for 3h;	92.3%

: 106-69-4
hexane-1,2,6-triol

: 13392-69-3
valeric acid

Conditions

Conditions	Yield
With oxygen; sodium methylate; silver trifluoromethanesulfonate In tetrahydrofuran; methanol at 37℃; under 760.051 Torr; Sealed tube;	92%

: 106-69-4
hexane-1,2,6-triol

: 100-39-0
benzyl bromide

: 195625-74-2
6-benzyloxy-hexane-1,5-diol

Conditions

Conditions	Yield
Stage #1: hexane-1,2,6-triol With di(n-butyl)tin oxide In toluene Reflux; Stage #2: benzyl bromide With tetrabutylammomium bromide In toluene at 20 - 90℃;	91%
Stage #1: hexane-1,2,6-triol With di(n-butyl)tin oxide In methanol for 2h; Heating; Stage #2: benzyl bromide With tetra-(n-butyl)ammonium iodide In benzene at 50℃; for 16h;	86%
Stage #1: hexane-1,2,6-triol With bis(tri-n-butyltin)oxide In toluene at 90℃; for 8h; Stage #2: benzyl bromide With tetrabutylammomium bromide In toluene at 90℃; for 5h;	63%
With tetrabutylammomium bromide; di(n-butyl)tin oxide 1) toluene, reflux, 6 h; 2) toluene, reflux, 5 h; Yield given. Multistep reaction;

: 106-69-4
hexane-1,2,6-triol

: 616-38-6
carbonic acid dimethyl ester

: 1262126-74-8
methyl 4-(2-oxo-1,3-dioxolan-4-yl)butyl carbonate

Conditions

Conditions	Yield
Stage #1: carbonic acid dimethyl ester With lanthanum(III) isopropoxide; 2-(2-methoxyethoxy)ethyl alcohol at 20℃; Stage #2: hexane-1,2,6-triol for 1h; Reflux; chemoselective reaction;	91%
With potassium carbonate at 80℃;	82%

: 106-69-4
hexane-1,2,6-triol

: 821-41-0
5-Hexen-1-ol

Conditions

Conditions	Yield
With rhenium(VII) oxide; triphenylphosphine at 165℃; for 1h; Reagent/catalyst; Concentration; Temperature;	91%
With rac-3-octanol at 170℃; for 1h;	38%

: 106-69-4
hexane-1,2,6-triol

: 77-76-9
2,2-dimethoxy-propane

: 14739-10-7
4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol

Conditions

Conditions	Yield
With camphor-10-sulfonic acid In acetone for 0.5h;	90%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 3h; Etherification; ketal formation;	57%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide Ambient temperature;

: 106-69-4
hexane-1,2,6-triol

: 707-07-3
orthobenzoic acid trimethyl ester

: Benzoic acid tetrahydro-pyran-2-ylmethyl ester

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 0℃; for 2h;	89%

: 106-69-4
hexane-1,2,6-triol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1,6-Bis-<(tert-butyldiphenylsilyl)oxy>-2-hexanol

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 5℃; for 18h;	87%

: 106-69-4
hexane-1,2,6-triol

: 3162-58-1
sulfur trioxide trimethylamine complex

: C6H14O12S3*3C3H9N

Conditions

Conditions	Yield
With N,N-dimethyl-formamide In 1,2-dichloro-ethane at 80℃; for 0.416667h; Inert atmosphere;	85.8%

: 64-18-6
formic acid

: 106-69-4
hexane-1,2,6-triol

: 65909-61-7
hex-5-enyl formate

Conditions

Conditions	Yield
at 20 - 240℃; Inert atmosphere;	84%

: 106-69-4
hexane-1,2,6-triol

: 103-71-9
phenyl isocyanate

: 110101-24-1
1-O-(phenylcarbamoyl)-1,2,6-hexanetriol

Conditions

Conditions	Yield
With Zn naphthenate In N,N-dimethyl-formamide for 1h;	80%

: 106-69-4
hexane-1,2,6-triol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 163799-48-2
1,6-Bis<(tert-butyldimethylsilyl)oxy>-2-hexanol

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 5℃; for 18h;	79%

: 106-69-4
hexane-1,2,6-triol

: 616-38-6
carbonic acid dimethyl ester

: 4427-86-5
4-(4-hydroxybutyl)-1,3-dioxolan-2-one

Conditions

Conditions	Yield
With potassium carbonate at 80℃;	79%
With potassium carbonate at 80℃; for 15h;	79%
With potassium carbonate at 80℃; for 15h;	79%
With potassium carbonate at 80℃; for 15h;	79%

: 106-69-4
hexane-1,2,6-triol

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 4-[2-(4-Methoxyphenyl)-[1,3]-dioxolan-4-yl]butan-1-ol

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In N,N-dimethyl-formamide at 50℃; for 20h;	76%

: 106-69-4
hexane-1,2,6-triol

: 98289-14-6
1,6-dihydroxy-2-hexanone

Conditions

Conditions	Yield
Stage #1: hexane-1,2,6-triol With dimethyltin dichloride In methanol Stage #2: With tetraethylammonium bromide In methanol at 0℃; Electrolysis;	76%
With bromine; oxygen; dimethyltin dichloride; potassium carbonate In water at 0℃; for 2h; Darkness; Green chemistry;	60%
Multi-step reaction with 3 steps 1: 94 percent / pyridine / 64 h / Ambient temperature 2: 73.9 percent / chromium trioxide, pyridine / CH2Cl2 / 0.28 h / Ambient temperature 3: 62 percent / trifluoroacetic acid / H2O; dioxane / 2 h / 55 °C View Scheme
Multi-step reaction with 3 steps 1: 94 percent / pyridine / 64 h / Ambient temperature 2: 73.9 percent / chromium trioxide, pyridine / CH2Cl2 / 0.28 h / Ambient temperature 3: 45 percent / 80percent acetic acid / Heating View Scheme

: 106-69-4
hexane-1,2,6-triol

: 98-59-9
p-toluenesulfonyl chloride

: toluene-4-sulfonic acid 2,6-dihydroxy-hexyl ester

Conditions

Conditions	Yield
With triethylamine; fluorous tin oxide (C6F13CH2CH2)2SnO In dichloromethane at 20℃; for 1h; Martinelli catalytic sulfonylation;	74%

: 106-69-4
hexane-1,2,6-triol

: 146803-41-0
N-(fluorenylmethyloxycarbonyl)-L-alaninal

: 1449315-29-0
C24H29NO5

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 5h; Solvent; Time;	73%

: 106-69-4
hexane-1,2,6-triol

: 98-59-9
p-toluenesulfonyl chloride

: C20H26O7S2

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -20℃; Inert atmosphere; Schlenk technique;	73%

: 106-69-4
hexane-1,2,6-triol

: 106-89-8
epichlorohydrin

: 1,2,6-hexanetriol triglycidyl ether

Conditions

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 5h;	72%

: 106-69-4
hexane-1,2,6-triol

: 1125-88-8
benzaldehyde dimethyl acetal

: 148254-22-2
4-[2-phenyl-(1,3-dioxolan-4-yl)]-butan-1-ol

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In N,N-dimethyl-formamide at 55℃; for 24h;	72%

: 106-69-4
hexane-1,2,6-triol

: 81683-96-7
6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

Conditions

Conditions	Yield
With dihydridotetrakis(triphenylphosphine)ruthenium; acetone In toluene at 180℃;	71%
With acetone; dihydridotetrakis(triphenylphosphine)ruthenium In toluene at 180℃; for 3h;	71 % Chromat.

: 106-69-4
hexane-1,2,6-triol

: 107-02-8
acrolein

: 2421-08-1
4-(4-Hydroxy-butyl)-2-vinyl-1,3-dioxolan

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 1h; Reflux;	60%

1,2,6-Hexanetriol Consensus Reports

Reported in EPA TSCA Inventory.

1,2,6-Hexanetriol Specification

The IUPAC name of 1,2,6-Hexanetriol is hexane-1,2,6-triol. With the CAS registry number 106-69-4, it is also named as 1,2,6-Trihydroxyhexane. The product's categories are industrial / fine chemicals. In addition, it is clear light yellow coloured, viscous liquid which is miscible with water, lower aliphatic alcohols, glycerol, partly soluble in acetone, and insoluble in benzene and ethyl acetate. This chemical is stable, combustible and incompatible with strong oxidizing agents, acid anhydrides, acid chlorides. Furthermore, people should avoid contact with skin and eyes. 1,2,6-Hexanetriol can be obtained by acrolein dimer through hydrolysis and hydrogenation.

The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.75; (4)ACD/LogD (pH 7.4): -1.75; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 2.65; (8)ACD/KOC (pH 7.4): 2.65; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.483; (13)Molar Refractivity: 34.4 cm³; (14)Molar Volume: 120.4 cm³; (15)Polarizability: 13.64×10^-24 cm³; (16)Surface Tension: 48.8 dyne/cm; (17)Enthalpy of Vaporization: 65.48 kJ/mol; (18)Vapour Pressure: 2.12E-05 mmHg at 25°C; (19)Rotatable Bond Count: 5; (20)Exact Mass: 134.094294; (21)MonoIsotopic Mass: 134.094294; (22)Topological Polar Surface Area: 60.7; (23)Heavy Atom Count: 9.

Uses of 1,2,6-Hexanetriol: It is used as solvent and coupling agent for polyamide resin plasticizer, wetting agent of tobacco and special hydraulic fluid. And it is also used as raw material in the production of alkyd resins, celluloid, polyurethane and synthetic rubber. In addition, it reacts with isocyanatobenzene to get 1-O-(phenylcarbamoyl)-1,2,6-hexanetriol. This reaction needs reagent Zn naphthenate and solvent dimethylformamide. The reaction time is 1 hours. The yield is 80%.

People can use the following data to convert to the molecule structure.
1. SMILES: OCCCCC(O)CO;
2. InChI: InChI=1/C6H14O3/c7-4-2-1-3-6(9)5-8/h6-9H,1-5H2.

The following are the toxicity data which has been tested.

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	oral	11400mg/kg (11400mg/kg)		Shell Chemical Company. Unpublished Report. Vol. -, Pg. 5, 1961.
mouse	LD50	subcutaneous	5800mg/kg (5800mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 28, Pg. 276, 1972.
rabbit	LD50	skin	> 20mL/kg (20mL/kg)		Union Carbide Data Sheet. Vol. 7/13/1971,
rat	LD50	intraperitoneal	10gm/kg (10000mg/kg)	GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS LIVER: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 15, Pg. 282, 1969.
rat	LD50	intravenous	5600mg/kg (5600mg/kg)	GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS LIVER: OTHER CHANGES	Toxicology and Applied Pharmacology. Vol. 15, Pg. 282, 1969.
rat	LD50	oral	15500mg/kg (15500mg/kg)		"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 731, 1969.
rat	LD50	subcutaneous	10900mg/kg (10900mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	Shikoku Igaku Zasshi. Shikoku Medical Journal. Vol. 28, Pg. 276, 1972.

Product Name

1,2,6-Hexanetriol

Synthetic route

1,2,6-Hexanetriol Consensus Reports

1,2,6-Hexanetriol Specification

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