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1,6-Hexanediol

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Name

1,6-Hexanediol

EINECS 211-074-0
CAS No. 629-11-8 Density 0.963 g/cm3
PSA 40.46000 LogP 0.53140
Solubility water: 0.1 g/mL, clear, colorless Melting Point 38-42 °C(lit.)
Formula C6H14O2 Boiling Point 239.7 °C at 760 mmHg
Molecular Weight 118.176 Flash Point 101.7 °C
Transport Information N/A Appearance white waxy flakes
Safety 36/37-24/25-23 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 629-11-8 (1,6-Hexanediol) Hazard Symbols N/A
Synonyms

hexane-1,6-diol;HDO;4-01-00-02556 (Beilstein Handbook Reference);.omega.-Hexanediol;Hexamethylenediol;alpha,omega-Hexanediol;1,6-Dihydroxyhexane;.alpha.,.omega.-Hexanediol;Hexamethylene Glycol;

Article Data 267

1,6-Hexanediol Synthetic route

124-04-9

Adipic acid

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With hydrogen In water at 160℃; under 22502.3 Torr; for 18h; Molecular sieve; chemoselective reaction;100%
With hydrogen In water at 130℃; under 37503.8 Torr; for 18h; Pressure; Reagent/catalyst; Autoclave;89%
With hydrogen In water at 120℃; under 35409.9 Torr; for 2.5h; Reagent/catalyst; Pressure; Temperature;88%
627-93-0

hexanedioic acid dimethyl ester

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With ethanol; [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II) at 100℃; for 24h; Inert atmosphere; Sealed tube; Darkness;99%
With water; hydrogen under 37503.8 Torr;95%
With hydrogen; copper-comprising catalyst at 195 - 210℃; under 45004.5 Torr; Product distribution / selectivity; Gas phase;90%
502-44-3

hexahydro-2H-oxepin-2-one

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With C21H35BrMnN2O2P; hydrogen; potassium hydride; 1,3,5-trimethyl-benzene In toluene at 100℃; under 15001.5 Torr; for 36h; Autoclave; Inert atmosphere;98%
With C21H35BrMnN2O2P; hydrogen; potassium hydride In toluene at 100℃; under 15001.5 Torr; for 36h;98%
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 0.5h; Ambient temperature;95%

1-triethylsilyloxy-6-[β-(trimethylsilyl)ethoxymethyloxy]hexane

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 10h; Heating;98%
91988-83-9

6-tert-butoxyhexan-1-ol

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With sodium iodide; cerium(III) chloride In acetonitrile at 70℃; for 3h;98%
279245-42-0

6-[β-(trimethylsilyl)ethoxymethoxy]hexan-1-ol

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With magnesium bromide In diethyl ether; nitromethane at 20℃; for 5h; Hydrolysis;95%

1-(tert-butyldimethylsilyloxy)-6-[β-(trimethylsilyl)ethoxymethoxy]hexane

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With carbon tetrabromide In methanol for 10h; Heating;95%
With zinc dibromide In methanol; dichloromethane for 10h; Hydrolysis;72%
Multi-step reaction with 2 steps
1: 99 percent / TBAF / tetrahydrofuran / 1.5 h / 0 °C
2: 95 percent / MgBr2*Et2O / diethyl ether; nitromethane / 5 h / 20 °C
View Scheme
874796-87-9

1-(tert-butyldimethylsilyloxy)-6-(triethylsilyloxy)-hexane

A

629-11-8

1,6-hexanediol

B

103202-59-1

6-(tert-butyldimethylsilyl)oxyhexan-1-ol

Conditions
ConditionsYield
With carbonochloridic acid 1-chloro-ethyl ester In methanol at 20℃; for 0.025h; Product distribution; Further Variations:; Reagents;A 3%
B 95%
33875-22-8

2-(5-oxopentyl)-1,3-dioxolane

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With water; hydrogen at 80 - 180℃; under 15001.5 - 30003 Torr; for 4h; Autoclave; Acidic conditions;95%
209973-05-7

N-(6-hydroxyhexyloxy)phthalimide

629-11-8

1,6-hexanediol

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 2h; Heating;93%

1,6-Hexanediol Consensus Reports

Reported in EPA TSCA Inventory.

1,6-Hexanediol Standards and Recommendations

1,6-HEXANEDIOL (629-11-8): 96.0% min
C6 DIOLS: 99.0% min
ACID NUMBER: 0.1 max (mg KOH/g)
COLOR, APHA: 20 max
WATER: 0.1% MAX

1,6-Hexanediol Specification

Introduction of 1,6-Hexanediol
The 1,6-Hexanediol, with the cas registry number 629-11-8, has the IUPAC name of hexane-1,6-diol. Being a kind of white acicular crystal, it is hygroscopic, and is soluble in water and ethanol while insoluble in benzene. Besides, its product categories are including Industrial/Fine Chemicals; alpha,omega-Alkanediols; alpha,omega-Bifunctional Alkanes; Monofunctional & alpha,omega-Bifunctional Alkanes; Optimization Reagents; Protein Structural Analysis; X-Ray Crystallography. It is widely applied in many ways. It could be used in producing polyurethane, unsaturated polyester, plasticizer, hardening agent of gelatinizing agent, and ameliorant of lubricating oil; It could also be used in producing in pesticide cinerin, organic peroxides, musk, polyvinyl plastics cross-linking agent, and polyether rubber.
 
The characteristics of this chemical are as follows:
(1)# of Rule of 5 Violations: 0; (2)ACD/LogD (pH 5.5): -0.07; (3)ACD/LogD (pH 7.4): -0.07; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 21.88; (7)ACD/KOC (pH 7.4): 21.88; (8)#H bond acceptors: 2; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 7; (11)Polar Surface Area: 40.46; (12)Index of Refraction: 1.449; (13)Molar Refractivity: 32.91 cm3; (14)Molar Volume: 122.5 cm3; (15)Polarizability: 13.04 ×10-24 cm3; (16)Surface Tension: 37.9 dyne/cm; (17)Density: 0.963 g/cm3; (18)Flash Point: 101.7 °C; (19)Enthalpy of Vaporization: 55.39 kJ/mol; (20)Boiling Point: 239.7 °C at 760 mmHg; (21)Vapour Pressure: 0.00693 mmHg at 25°C; (22)Exact Mass: 118.09938; (23)MonoIsotopic Mass: 118.09938; (24)Topological Polar Surface Area: 40.5; (25)Heavy Atom Count: 8; (26)Formal Charge: 0; (27)Complexity: 31.5.

Structure Descriptors of
1,6-Hexanediol:
(1)Canonical SMILES: C(CCCO)CCO
(2)InChI: InChI=1S/C6H14O2/c7-5-3-1-2-4-6-8/h7-8H,1-6H2
(3)InChIKey: XXMIOPMDWAUFGU-UHFFFAOYSA-N 5. Preparation of 
 
Toxicity of 1,6-Hexanediol are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1738mg/kg (1738mg/kg)   Toxicology and Applied Pharmacology. Vol. 49, Pg. 385, 1979.
 
rabbit LD50 skin > 10gm/kg (10000mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
 
rat LD50 oral 3730mg/kg (3730mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 313, 1974.
 

Preparation of 1,6-Hexanediol:
The production method of 1,6-Hexanediol is as below: go through the catalytic reduction of the Dimethyl adipate for synthesis with the existence of Sodium Metal and ethanol to get the products or have the catalytic reduction of 2,4diyne-1,6-diol to get this chemical.

Safety information of 1,6-Hexanediol:
When you are dealing with this chemical, you should be very careful and then take some measures to protect yourself. It is irritating to eyes, respiratory system and skin, so you should wear suitable protective clothing and gloves while using. And then avoid contacting with skin and eyes and remember not to breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). 

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