Conditions | Yield |
---|---|
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% |
1-(tert-butyl-dimethylsilyloxy)-6-chloro-hexane
6-chloro-1-hexanol
Conditions | Yield |
---|---|
With titanium tetrachloride; ethyl acetate In dichloromethane at 30℃; for 0.166667h; | 94% |
1-chloro-5-hexyne
6-chloro-1-hexanol
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
With tetrachloromethane; triphenylphosphine In acetonitrile Product distribution; Mechanism; | A 48% B 39% |
With hydrogenchloride at 92 - 96℃; | |
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride; sodium hydroxide; zinc(II) chloride | A n/a B 34% |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; diethyl ether |
Conditions | Yield |
---|---|
With water; titanium tetrachloride 1.) 60 - 70 deg C, 24 h; Yield given. Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
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. |
Conditions | Yield |
---|---|
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; |
A
5-Hexen-1-ol
B
6-chloro-1-hexanol
C
6-(N,N-dimethylamino)-1-hexanol
D
6-(dimethylamino)-1-methoxyhexane
Conditions | Yield |
---|---|
at 220℃; Product distribution; |
hydrogenchloride
1,6-hexanediol
A
6-chloro-1-hexanol
B
1,6-dichlorohexane
Conditions | Yield |
---|---|
unter kontinuierlicher Extraktion mit Toluol; |
hydrogenchloride
1,6-hexanediol
A
6-chloro-1-hexanol
B
1,13-dichloro-7-oxatridecane
C
13-chloro-7-oxatridecane-1-ol
D
1,6-dichlorohexane
Conditions | Yield |
---|---|
at 92 - 96℃; weitere Produkte: 6.6'-Dihydroxy-dihexylaether und Hexamethylenglykol-bis-<6-hydroxy-hexyl>-aether; |
(6-chlorohex-1-yn-1-yl)triethylsilane
6-chloro-1-hexanol
Conditions | Yield |
---|---|
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 |
6-chloro-1-hexanol
Conditions | Yield |
---|---|
With potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; water at 40℃; for 2h; Fleming-Tamao Oxidation; |
6-chloro-1-hexanol
Conditions | Yield |
---|---|
With potassium fluoride; tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; water at 40℃; for 2h; Fleming-Tamao Oxidation; |
6-chloro-1-hexanol
Conditions | Yield |
---|---|
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 |
3,4-dihydro-2H-pyran
6-chloro-1-hexanol
(chloro-6' hexyloxy)-2 tetrahydropyranne
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
In ethanol for 15h; Heating; | 100% |
6-chloro-1-hexanol
p-toluenesulfonyl chloride
4-methylbenzenesulfonic acid 6-chlorohexyl ester
Conditions | Yield |
---|---|
With pyridine at 0 - 15℃; | 100% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 87% |
With dmap; triethylamine In dichloromethane for 3h; Ambient temperature; |
Conditions | Yield |
---|---|
With magnesium oxide; lithium trifluoromethanesulfonate; lithium tetrakis(pentafluorophenyl)borate In dichloromethane; cyclohexane at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
for 5h; Heating; | 100% |
6-chloro-1-hexanol
6-azidohexan-1-ol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 49h; Inert atmosphere; | 100% |
6-chloro-1-hexanol
1-iodohexan-6-ol
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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; |
6-chloro-1-hexanol
6-chloro-1-hexyl acetate
Conditions | Yield |
---|---|
With pyridine; acetic anhydride In diethyl ether; water | 99% |
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 4h; | 99% |
Conditions | Yield |
---|---|
With potassium iodide at 100℃; for 72h; Autoclave; | 99% |
With potassium iodide at 100℃; for 72h; Autoclave; | 99% |
Conditions | Yield |
---|---|
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% |
chloro-trimethyl-silane
6-chloro-1-hexanol
trimethylsilyl 6-chloro-1-hexyl ether
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 50℃; | 98% |
6-chloro-1-hexanol
ethyl vinyl ether
acetaldehyde ethyl 6-chlorohexyl acetal
Conditions | Yield |
---|---|
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; |
6-chloro-1-hexanol
4-amino-o-xylene
N-(6'-hydroxyhexyl)-3,4-dimethylaniline
Conditions | Yield |
---|---|
With triethylamine at 110℃; for 5h; | 98% |
With triethylamine for 6h; Reflux; | 57% |
With triethylamine at 110℃; for 5h; |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With potassium carbonate In nitrogen; water; N,N-dimethyl-formamide | 98% |
Conditions | Yield |
---|---|
With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 12h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With dibutyltin dilaurate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In neat liquid at 20℃; for 24h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
In water at 25℃; for 8h; | 97% |
With methanol |
Conditions | Yield |
---|---|
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; |
6-chloro-1-hexanol
tert-butylchlorodiphenylsilane
6-(tert-butyldiphenylsilyloxy)hexyl chloride
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane | 97% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 87% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h; |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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% |
6-chloro-1-hexanol
methanesulfonyl chloride
6-chlorohexyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 14h; | 96% |
With triethylamine In benzene | 91.1% |
With triethylamine for 0.25h; Substitution; |
Conditions | Yield |
---|---|
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 |
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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