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111-27-3

Basic Information
CAS No.: 111-27-3
Name: Hexyl alcohol
Article Data: 637
Cas Database
Molecular Structure:
Molecular Structure of 111-27-3 (Hexyl alcohol)
Formula: C6H14O
Molecular Weight: 102.177
Synonyms: Epal 6;NSC 9254;Pentylcarbinol;n-Hexan-1-ol;n-Hexanol;n-Hexylalcohol;Hexylalcohol (8CI);1-Hexyl alcohol;1-Hydroxyhexane;Amylcarbinol;Caproyl alcohol;1-Hexanol;
EINECS: 203-852-3
Density: 0.817 g/cm3
Melting Point: -52 °C(lit.)
Boiling Point: 158.153 °C at 760 mmHg
Flash Point: 60 °C
Solubility: 6 g/L (25 ºC)
Appearance: Colourless liquid
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: 24/25
Transport Information: UN 2282 3/PG 3
PSA: 20.23000
LogP: 1.55900
Synthetic route
123-66-0

Ethyl hexanoate

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.5h;100%
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 15h; Glovebox; Autoclave;93%
With ethanol; ruthenium(bis[2‐(ethylsulfanyl)ethyl]amine)(dichloro)(triphenylphosphine); potassium tert-butylate In toluene at 80℃; for 16h; Catalytic behavior; Reagent/catalyst;89%
66-25-1

hexanal

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With Na-phosphate buffer; horse liver NADH; NAD; sodium formate; <(C5Me5)Rh(bpy-5-OAc)(H2O)>Cl2 at 25℃; for 30h; Product distribution; Mechanism; other ketones, other times, other temperatures, other enzymes;100%
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h; Product distribution; other aldehydes, ketones, carboxylic acids (also sodium salts), acid chlorides, esters, lactones, epoxides, amides, nitriles, nitrogen and sulfur compounds; var. temp., time and ratio of reagents;100%
With sodium aluminum tetrahydride In tetrahydrofuran at 0℃; for 0.0833333h;100%
106-70-7

methyl hexanoate

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C39H39N6ORu(1+)*Br(1-); potassium methanolate; hydrogen In tetrahydrofuran at 70℃; under 37503.8 Torr; for 4h; Reagent/catalyst;100%
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C30H26Cl2N3PRu; hydrogen; sodium ethanolate In toluene at 80℃; under 38002.6 Torr; for 16h; Catalytic behavior; Autoclave; Inert atmosphere; Schlenk technique;95%
82965-03-5

2,4,6-triisopropyl-benzenesulfonic acid n-hexylester

A

717-74-8

1,3,5-triisopropyl benzene

B

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide; toluene Product distribution; Mechanism; further solvents;A 100%
B 100%
6378-65-0

n-hexyl caproate

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
With C66H102N4OP2Ru; hydrogen In toluene at 105℃; under 22502.3 Torr; for 20h; Inert atmosphere; Glovebox;99%
With C31H26ClN2OPRu; hydrogen; sodium methylate In tetrahydrofuran at 80℃; for 2h;98%
626-77-7

propyl hexanoate

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With C56H70Cl3N10Ru2(1+)*F6P(1-); potassium tert-butylate; hydrogen In tetrahydrofuran; dodecane at 70℃; under 37503.8 Torr; for 16h; Inert atmosphere; Glovebox; Autoclave;100%
1927-63-5

2-hexyloxy-tetrahydro-pyran

111-27-3

hexan-1-ol

Conditions
ConditionsYield
silica-supported prop-1-ylsulfonic acid In methanol99.6%
With silica gel; iron(III) chloride for 45h; Ambient temperature;98.5%
ammonium cerium(IV) nitrate In alkaline aq. solution; acetonitrile at 70℃; for 2h; pH=8; Decomposition;94%
592-41-6

1-hexene

111-27-3

hexan-1-ol

Conditions
ConditionsYield
Stage #1: 1-hexene With 9-bora-bicyclo[3.3.1]nonane
Stage #2: With sodium peroxoborate tetrahydrate
99%
Stage #1: 1-hexene With borane-THF In tetrahydrofuran at 25℃; for 0.0138889h; Flow reactor;
Stage #2: With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran; ethanol; water at 20℃; for 0.00555556h; Flow reactor;
88%
With di-n-pentylbromoborane; alkaline H2O2; sodium hydride 1.) diglyme, room temperature, 7 h; further dialkylbromoboranes; Yield given. Multistep reaction;
82965-02-4

hexyl 2,4,6-trimethylbenzenesulfonate

A

108-67-8

1,3,5-trimethyl-benzene

B

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With lithium amalgam In N,N-dimethyl-formamide; toluene Product distribution; Mechanism; further solvents;A 85%
B 99%
1002-28-4

3-hexyn-1-ol

A

928-96-1

(Z)-3-Hexen-1-ol

B

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With hydrogen; copper-palladium; silica gel In ethanol at 25℃; under 760 Torr; Kinetics;A 99%
B n/a
With hydrogen In methanol at 30℃; under 760.051 Torr; for 3h;A 99%
B 1%
With hydrogen In methanol at 20℃; under 150.015 - 900.09 Torr; for 0.0116667h; Inert atmosphere; Schlenk technique; Green chemistry;A n/a
B n/a
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    Product Name: 1-Hexanol CAS: 111-27-3 MF: C6H14O MW: 102.17 EINECS: 203-852-3 by Plant (Food/Spice/Herb) Mol File: 111-27-3.mol 1-Hexanol Structure 1-Hexanol Chemical Properties Melting point -52 °C (lit.) Boiling point

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Specification

The Hexyl alcohol with CAS registry number of 111-27-3 is also called 1-Hydroxyhexane. The IUPAC name is hexan-1-ol. Its EINECS registry number is 203-852-3. In addition, the molecular formula is C6H14O and the molecular weight is 102.17. It belongs to the classes of Alkanols; Monofunctional & alpha,omega-Bifunctional Alkanes; Monofunctional Alkanes. And it is Colorless transparent liquid, with fruit fragrance, and slightly soluble in water, but miscible with ether and ethanol. What's more, it should be stored in a cool, ventilated and dry place.It is harmful if swallowed. You shoulad avoid contact with skin and eyes.

Physical properties about Hexyl alcohol are:
(1)ACD/LogP: 1.86; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.858; (4)ACD/LogD (pH 7.4): 1.858; (5)ACD/BCF (pH 5.5): 15.195; (6)ACD/BCF (pH 7.4): 15.195; (7)ACD/KOC (pH 5.5): 244.051; (8)ACD/KOC (pH 7.4): 244.051; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 20.23 Å2; (13)Index of Refraction: 1.416; (14)Molar Refractivity: 31.381 cm3; (15)Molar Volume: 125.082 cm3; (16)Polarizability: 12.44 ×10-24cm3; (17)Surface Tension: 27.947 dyne/cm; (18)Density: 0.817 g/cm3; (19)Flash Point: 60 °C; (20)Enthalpy of Vaporization: 44.5 kJ/mol; (21)Boiling Point: 158.153 °C at 760 mmHg; (22)Vapour Pressure: 0.947 mmHg at 25°C.

Preparation of Hexyl alcohol:
Hexyl alcohol can be prepared by magnesium butylbromide and epoxyethane. The magnesium butylbromide can be prepared by bromobutane and magnesium. In the presence of catalyst iodine, you can make the bromine butane solution react with magnesium flocks under stirring. The reaction process must be controlled backflowing and without water. And you should control the dropping speed of bromine butane solution. After finish dropping, access the epoxy ethane at the cooling condition and control the speed in order to maintain the reaction temperature at 10 °C.
Hexyl alcohol can be prepared by magnesium butylbromide and epoxyethane

Uses of Hexyl alcohol:
Hexyl alcohol can be used in making preservatives and sleeping pills in medicine industry and manufacturing the plastic, synthetic lubricants, spices and medicine, etc. It also can be used as solvent of dye, all kinds of rubber, special printing ink, oil and natural resins. In addition, it can be used for analysis reagent and help solvent of nitric acid cellulose. Moreover, it can be used in baking goods, pudding and meat products.

You can still convert the following datas into molecular structure:
(1)SMILES: CCCCCCO;
(2)InChI: InChI=1/C6H14O/c1-2-3-4-5-6-7/h7H,2-6H2,1H3;
(3)InChIKey: ZSIAUFGUXNUGDI-UHFFFAOYAO.

The toxicity data of Hexyl alcohol is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LC inhalation > 1060ppm/6H (1060ppm)   Food and Cosmetics Toxicology. Vol. 13, Pg. 695, 1975.
mammal (species unspecified) LD50 unreported 2442mg/kg (2442mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 51(5), Pg. 61, 1986.
mouse LC inhalation > 1060ppm/6H (1060ppm)   Food and Cosmetics Toxicology. Vol. 13, Pg. 695, 1975.
mouse LD50 intravenous 103mg/kg (103mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 135, Pg. 330, 1962.
mouse LD50 oral 1950mg/kg (1950mg/kg)   Hygiene and Sanitation Vol. 31(1-3), Pg. 310, 1966.
rabbit LD50 skin 3100uL/kg (3.1mL/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.
rat LD inhalation > 1060ppm/6H (1060ppm)   Food and Cosmetics Toxicology. Vol. 13, Pg. 695, 1975.
rat LD50 oral 720mg/kg (720mg/kg) LIVER: FATTY LIVER DEGERATION

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BLOOD: OTHER CHANGES
South African Medical Journal. Vol. 43, Pg. 795, 1969.