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6-Chlorohexanol

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Name

6-Chlorohexanol

EINECS 217-925-2
CAS No. 2009-83-8 Density 1.001 g/cm3
PSA 20.23000 LogP 1.77790
Solubility Melting Point 129-130ºC
Formula C6H13ClO Boiling Point 212.8 °C at 760 mmHg
Molecular Weight 136.62 Flash Point 98.9 °C
Transport Information UN 2810 Appearance clear colorless to pale yellow liquid
Safety 26-36/37-36/37/39 Risk Codes 20/21-36/38-36/37/38-20/21/22
Molecular Structure Molecular Structure of 2009-83-8 (6-Chlorohexanol) Hazard Symbols HarmfulXn,img src=/images/Xi.gif alt=Irritant >Xi
Synonyms

1-Chloro-6-hydroxyhexane;6-Chloro-1-hexanol;6-Chloro-1-hexano;Hexamethylene chlorohydrin;omega-Chlorohexanol;1-Hexanol, 6-chloro-;6-Chlorohexan-1-ol;4-01-00-01704 (Beilstein Handbook Reference);1-Chloro-6-hexanol;

 

6-Chlorohexanol Synthetic route

629-11-8

1,6-hexanediol

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With tetrachloromethane; hexacarbonyl molybdenum at 120℃; for 8h;98%
With 1,3,5-trichloro-2,4,6-triazine In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Solvent; Temperature; Large scale;95.2%
With hydrogenchloride; copper(l) chloride In toluene at 100℃; for 24h;66%
59431-24-2

1-(tert-butyl-dimethylsilyloxy)-6-chloro-hexane

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With titanium tetrachloride; ethyl acetate In dichloromethane at 30℃; for 0.166667h;94%
10297-06-0

1-chloro-5-hexyne

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With formic acid; F6P(1-)*C16H22N3Ru(1+); water In 1-methyl-pyrrolidin-2-one at 25℃; for 48h; Inert atmosphere; Sealed tube;92%
With 1-hydroxytetraphenylcyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II); Ru(Cp)(PPh2PytBu)2(MeCN)PF6; water In isopropyl alcohol at 80℃; for 3h; Inert atmosphere; regioselective reaction;85%
With [2,2]bipyridinyl; formic acid; (η5-cyclopentadienyl) (η6-naphthalene)ruthenium hexafluorophosphate; water In tetrahydrofuran at 55℃; for 48h;80%
Multi-step reaction with 4 steps
1.1: n-butyllithium / hexane; diethyl ether / 1 h / -78 °C / Inert atmosphere
1.2: 6 h / 20 °C / Inert atmosphere
2.1: palladium 10% on activated carbon; hydrogen; water / methanol / 0.5 h / 20 °C / 760.05 Torr / Inert atmosphere
3.1: dichloromethane / 6 h / -20 °C / Inert atmosphere
4.1: potassium fluoride; potassium hydrogencarbonate; dihydrogen peroxide; tetrabutyl ammonium fluoride / tetrahydrofuran; water / 2 h / 40 °C
View Scheme
629-11-8

1,6-hexanediol

A

2009-83-8

6-chloro-1-hexanol

B

2163-00-0

1,6-dichlorohexane

Conditions
ConditionsYield
With tetrachloromethane; triphenylphosphine In acetonitrile Product distribution; Mechanism;A 48%
B 39%
With hydrogenchloride at 92 - 96℃;
With hydrogenchloride
629-11-8

1,6-hexanediol

A

6294-17-3

1-bromo-6-chlorohexane

B

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; zinc(II) chlorideA n/a
B 34%
4224-62-8

6-chlorohexanoic acid

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
592-90-5

oxepane

A

2009-83-8

6-chloro-1-hexanol

B

108291-44-7

13-chloro-7-oxatridecane-1-ol

Conditions
ConditionsYield
With water; titanium tetrachloride 1.) 60 - 70 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given;
928-89-2

6-chlorohexene

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With hydrogenchloride; dimethylsulfide borane complex; diethylzinc; oxygen; zinc dibromide; zinc 1.) ether, 2 h at 0 deg C then 8 h at r.t., 2.) hexane, 30 min at 0 deg C then 15 min, 3.) THF, perfluorohexanes, -78 deg C, 4.) ether, 3 h; Yield given. Multistep reaction;
Yield given. Multistep reaction;
With potassium tri(isopropoxy)borohydride; n-octylthexylchloroborane at 0℃;89 % Chromat.
928-89-2

6-chlorohexene

A

2009-83-8

6-chloro-1-hexanol

B

111-27-3

hexan-1-ol

Conditions
ConditionsYield
With sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; sodium iodide 1.) diglyme, 25 deg C, electrolysis, 2.) 25 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given;

chlorure de trimethylammonio-6 hexanol-1

A

821-41-0

5-Hexen-1-ol

B

2009-83-8

6-chloro-1-hexanol

C

1862-07-3

6-(N,N-dimethylamino)-1-hexanol

D

58390-19-5

6-(dimethylamino)-1-methoxyhexane

Conditions
ConditionsYield
at 220℃; Product distribution;
7647-01-0

hydrogenchloride

629-11-8

1,6-hexanediol

CuCl

CuCl

A

2009-83-8

6-chloro-1-hexanol

B

2163-00-0

1,6-dichlorohexane

Conditions
ConditionsYield
unter kontinuierlicher Extraktion mit Toluol;
7647-01-0

hydrogenchloride

629-11-8

1,6-hexanediol

A

2009-83-8

6-chloro-1-hexanol

B

91692-23-8

1,13-dichloro-7-oxatridecane

C

108291-44-7

13-chloro-7-oxatridecane-1-ol

D

2163-00-0

1,6-dichlorohexane

Conditions
ConditionsYield
at 92 - 96℃; weitere Produkte: 6.6'-Dihydroxy-dihexylaether und Hexamethylenglykol-bis-<6-hydroxy-hexyl>-aether;
928-51-8

4-Chloro-1-butanol

2009-83-8

6-chloro-1-hexanol

1446713-43-4

(6-chlorohex-1-yn-1-yl)triethylsilane

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: palladium 10% on activated carbon; hydrogen; water / methanol / 0.5 h / 20 °C / 760.05 Torr / Inert atmosphere
2: dichloromethane / 6 h / -20 °C / Inert atmosphere
3: potassium fluoride; potassium hydrogencarbonate; dihydrogen peroxide; tetrabutyl ammonium fluoride / tetrahydrofuran; water / 2 h / 40 °C
View Scheme

C12H22ClF3O2Si

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; water at 40℃; for 2h; Fleming-Tamao Oxidation;

C10H23ClOSi

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
With potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; water at 40℃; for 2h; Fleming-Tamao Oxidation;

(6-chlorohexyl)triethylsilane

2009-83-8

6-chloro-1-hexanol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dichloromethane / 6 h / -20 °C / Inert atmosphere
2: potassium fluoride; potassium hydrogencarbonate; dihydrogen peroxide; tetrabutyl ammonium fluoride / tetrahydrofuran; water / 2 h / 40 °C
View Scheme
110-87-2

3,4-dihydro-2H-pyran

2009-83-8

6-chloro-1-hexanol

2009-84-9

(chloro-6' hexyloxy)-2 tetrahydropyranne

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dichloromethane at 21℃; for 18h;100%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 1.5h;99%
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 21h;98.5%
2009-83-8

6-chloro-1-hexanol

17356-08-0

thiourea

6-hydroxy-1-hexylthiouronium chloride

Conditions
ConditionsYield
In ethanol for 15h; Heating;100%
2009-83-8

6-chloro-1-hexanol

98-59-9

p-toluenesulfonyl chloride

71042-21-2

4-methylbenzenesulfonic acid 6-chlorohexyl ester

Conditions
ConditionsYield
With pyridine at 0 - 15℃;100%
With dmap; triethylamine In dichloromethane at 0 - 20℃;87%
With dmap; triethylamine In dichloromethane for 3h; Ambient temperature;
2009-83-8

6-chloro-1-hexanol

55791-06-5

benzyl mesylate

53821-21-9

6-(benzyloxy)-1-chlorohexane

Conditions
ConditionsYield
With magnesium oxide; lithium trifluoromethanesulfonate; lithium tetrakis(pentafluorophenyl)borate In dichloromethane; cyclohexane at 20℃; for 24h;100%
110-86-1

pyridine

2009-83-8

6-chloro-1-hexanol

6-hydroxyhexyl-1-pyridinium chloride

Conditions
ConditionsYield
for 5h; Heating;100%
2009-83-8

6-chloro-1-hexanol

146292-90-2

6-azidohexan-1-ol

Conditions
ConditionsYield
With sodium azide In dimethyl sulfoxide at 50℃; for 24h;100%
With sodium azide In water for 16h; Heating;96.7%
With sodium azide In N,N-dimethyl-formamide at 90℃; Inert atmosphere;95%
2009-83-8

6-chloro-1-hexanol

118-41-2

Eudesmic acid

6-chlorohexyl 3,4,5-trimethoxybenzoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 49h; Inert atmosphere;100%
2009-83-8

6-chloro-1-hexanol

40145-10-6

1-iodohexan-6-ol

Conditions
ConditionsYield
With sodium iodide In acetone Reflux;99%
With sodium iodide In acetone 1.) room temperature, 48 h, 2.) reflux, 5 h;97%
With potassium iodide In butanone for 48h; Heating;74%
2009-83-8

6-chloro-1-hexanol

75-50-3

trimethylamine

chlorure de trimethylammonio-6 hexanol-1

Conditions
ConditionsYield
In water; acetonitrile at 70℃; for 18h; Inert atmosphere;99%
In water; acetonitrile for 36h; Heating / reflux;62%
In water; acetonitrile for 36h; Reflux;62%
In water; acetonitrile at 70℃; for 14h;
In toluene at 70℃; for 24h; Inert atmosphere;
2009-83-8

6-chloro-1-hexanol

40200-18-8

6-chloro-1-hexyl acetate

Conditions
ConditionsYield
With pyridine; acetic anhydride In diethyl ether; water99%
2009-83-8

6-chloro-1-hexanol

108-24-7

acetic anhydride

40200-18-8

6-chloro-1-hexyl acetate

Conditions
ConditionsYield
With pyridine at 0 - 20℃; for 4h;99%
598-56-1

N,N-dimethyl-ethanamine

2009-83-8

6-chloro-1-hexanol

N-ethyl-N-(6-hydroxyhexyl)-N,N-dimethylammonium chloride

Conditions
ConditionsYield
With potassium iodide at 100℃; for 72h; Autoclave;99%
With potassium iodide at 100℃; for 72h; Autoclave;99%
2009-83-8

6-chloro-1-hexanol

75-89-8

2,2,2-trifluoroethanol

1341666-66-7

C8H15F3O2

Conditions
ConditionsYield
Stage #1: 2,2,2-trifluoroethanol With sodium
Stage #2: 6-chloro-1-hexanol In diethylene glycol dimethyl ether at 120℃; for 5h;
Stage #3: With hydrogenchloride In water pH=1 - 2; Product distribution / selectivity;
98.9%
75-77-4

chloro-trimethyl-silane

2009-83-8

6-chloro-1-hexanol

34714-00-6

trimethylsilyl 6-chloro-1-hexyl ether

Conditions
ConditionsYield
With triethylamine In ethyl acetate at 0 - 10℃; for 8h; Temperature; Green chemistry;98.6%
With triethylamine In tert-butyl methyl ether at 2℃; Temperature; Inert atmosphere;94.2%
With triethylamine In diethyl ether for 0.25h;93%
2009-83-8

6-chloro-1-hexanol

1666-13-3

diphenyl diselenide

78998-75-1

6-(phenylselanyl)hexan-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 50℃;98%
2009-83-8

6-chloro-1-hexanol

109-92-2

ethyl vinyl ether

51732-22-0

acetaldehyde ethyl 6-chlorohexyl acetal

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 0 - 15℃; for 3h;98%
With toluene-4-sulfonic acid for 1h;88%
With trichlorophosphate
With toluene-4-sulfonic acid at 0 - 10℃; for 3h;
2009-83-8

6-chloro-1-hexanol

95-64-7

4-amino-o-xylene

189748-84-3

N-(6'-hydroxyhexyl)-3,4-dimethylaniline

Conditions
ConditionsYield
With triethylamine at 110℃; for 5h;98%
With triethylamine for 6h; Reflux;57%
With triethylamine at 110℃; for 5h;
2009-83-8

6-chloro-1-hexanol

501-52-0

3-Phenylpropionic acid

6-chlorohexyl 3-phenylpropanoate

Conditions
ConditionsYield
With sulfonated polypyrene In n-heptane at 110℃; for 1h;98%
fluorous ammonium triflate In toluene at 80℃; for 3h;97%
Stage #1: 3-Phenylpropionic acid With 1-methyl-1H-imidazole; p-toluenesulfonyl chloride In acetonitrile at 0 - 5℃; for 0.5h;
Stage #2: 6-chloro-1-hexanol In acetonitrile at 0 - 5℃; for 2h; Further stages.;
95%
2009-83-8

6-chloro-1-hexanol

89639-61-2

p-methylthiolphenol

4-Methylphenyl-6'-hydroxyhexyl sulfide

Conditions
ConditionsYield
With potassium carbonate In nitrogen; water; N,N-dimethyl-formamide98%
2009-83-8

6-chloro-1-hexanol

54945-19-6

4-hydroxy-4'-methoxybenzil

1220040-72-1

C21H24O5

Conditions
ConditionsYield
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere;98%
2009-83-8

6-chloro-1-hexanol

2778-42-9

1,3-bis(1-isocyanato-1-methylethyl)benzene

bis(6-chlorohexyl) (1,3-phenylenebis(propane-2,2-diyl))dicarbamate

Conditions
ConditionsYield
With dibutyltin dilaurate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;98%
2009-83-8

6-chloro-1-hexanol

60-34-4

methylhydrazine

6-(1-methylhydrazinyl)hexan-1-ol

Conditions
ConditionsYield
In neat liquid at 20℃; for 24h; Inert atmosphere;98%
2009-83-8

6-chloro-1-hexanol

5188-07-8

sodium thiomethoxide

98433-41-1

6-(methylthio)hexan-1-ol

Conditions
ConditionsYield
In water at 25℃; for 8h;97%
With methanol
2009-83-8

6-chloro-1-hexanol

115-11-7

isobutene

1001-73-6

1-(tert-butoxy)-6-chlorohexane

Conditions
ConditionsYield
With sulfuric acid In dichloromethane for 5h;97%
With Amberlyst H-15 In hexane for 8h; Ambient temperature;95%
With Amberlyst H-15 In hexane for 8h; Ambient temperature;81%
With sulfuric acid In dichloromethane for 20h; Ambient temperature;70%
Amberlyst H-15 In hexane Ambient temperature; Yield given;
2009-83-8

6-chloro-1-hexanol

58479-61-1

tert-butylchlorodiphenylsilane

195451-92-4

6-(tert-butyldiphenylsilyloxy)hexyl chloride

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane97%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;87%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h;
2009-83-8

6-chloro-1-hexanol

6294-17-3

1-bromo-6-chlorohexane

Conditions
ConditionsYield
Stage #1: 6-chloro-1-hexanol With diisopropyl-carbodiimide; copper(II) bis(trifluoromethanesulfonate) In tetrahydrofuran at 100℃; for 0.0833333h; microwave irradiation;
Stage #2: With Acetyl bromide In tetrahydrofuran at 150℃; for 0.0833333h; microwave irradiation; Further stages.;
96%
With phosphorus tribromide
2009-83-8

6-chloro-1-hexanol

4224-62-8

6-chlorohexanoic acid

Conditions
ConditionsYield
Stage #1: 6-chloro-1-hexanol With Oxone; sodium ortho-iodobenzenesulfonate In acetonitrile at 70℃; for 1h;
Stage #2: With water In acetonitrile for 5h;
96%
With oxone; C18H10F17IO3; tetra(n-butyl)ammonium hydrogensulfate In nitromethane; water at 70℃; for 12h;92%
With 2-hydroxypyridin; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 72h;85%
2009-83-8

6-chloro-1-hexanol

124-63-0

methanesulfonyl chloride

93847-88-2

6-chlorohexyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 14h;96%
With triethylamine In benzene91.1%
With triethylamine for 0.25h; Substitution;
2009-83-8

6-chloro-1-hexanol

540-38-5

4-Iodophenol

436865-00-8

4-(6-hydroxyhexyloxy)iodobenzene

Conditions
ConditionsYield
Stage #1: p-Iodophenol With potassium hydroxide In ethanol for 1h; Heating;
Stage #2: 6-chloro-1-hexanol In ethanol for 24h; Heating;
96%
With potassium carbonate; sodium iodide In dimethyl sulfoxide at 50℃; for 24h;76%
With potassium carbonate In isopropyl alcohol for 60h; Reflux;11.6 g

6-Chlorohexanol Specification

The 6-Chlorohexanol, with the CAS registry number 2009-83-8, is also known as 1-Chloro-6-hydroxyhexane; 6-Chloro-1-hexanol; Hexamethylene chlorohydrin.It belongs to the product categories of omega-Chloroalkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;OLED materials,pharm chemical,electronic. This chemical's molecular formula is C6H13ClO and molecular weight is 136.62. Its EINECS number is 217-925-2. What's more,Its systematic name is 6-Chlorohexan-1-ol.

Physical properties about 6-Chlorohexanol are: (1)ACD/LogP: 1.754; (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): 12.67; (6)ACD/BCF (pH 7.4): 12.67; (7)ACD/KOC (pH 5.5): 214.33; (8)ACD/KOC (pH 7.4): 214.33; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Index of Refraction: 1.444; (13)Molar Refractivity: 36.23 cm3; (14)Molar Volume: 136.467 cm3; (15)Surface Tension: 32.5800018310547 dyne/cm; (16)Density: 1.001 g/cm3; (17)Flash Point: 98.889 °C; (18)Enthalpy of Vaporization: 52.238 kJ/mol; (19)Boiling Point: 212.82 °C at 760 mmHg; (20)Vapour Pressure: 0.0379999987781048 mmHg at 25°C;

The 6-Chlorohexanol is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin .When you use it, wear suitable protective clothing, gloves and eye/face protection.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES:ClCCCCCCO;
(2)Std. InChI:InChI=1S/C6H13ClO/c7-5-3-1-2-4-6-8/h8H,1-6H2;
(3)Std. InChIKey:JNTPTNNCGDAGEJ-UHFFFAOYSA-N.

The toxicity data of 6-Chlorohexanol as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal > 100mg/kg (100mg/kg)   Journal of Organic Chemistry. Vol. 21, Pg. 739, 1956.

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