Product Name

  • Name

    3-Hydroxypiperidine

  • EINECS 229-957-4
  • CAS No. 6859-99-0
  • Article Data22
  • CAS DataBase
  • Density 1.017 g/cm3
  • Solubility soluble in water
  • Melting Point 56-60 °C
  • Formula C5H11NO
  • Boiling Point 191.935 °C at 760 mmHg
  • Molecular Weight 101.148
  • Flash Point 104.475 °C
  • Transport Information UN 3263 8/PG 2
  • Appearance White to light yellow crystalline powder and lumps
  • Safety 26-36/37/39-45-27
  • Risk Codes 34-20/21/22-36/37/38
  • Molecular Structure Molecular Structure of 6859-99-0 (3-Hydroxypiperidine)
  • Hazard Symbols IrritantXi,CorrosiveC
  • Synonyms 3-Hydroxyhexahydropyridine;NSC 62082;Piperidin-3-ol;
  • PSA 32.26000
  • LogP 0.05950

Synthetic route

3-HYDROXYPYRIDINE

3-HYDROXYPYRIDINE

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

1-benzyl-3-hydroxypiperidine
14813-01-5

1-benzyl-3-hydroxypiperidine

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

Conditions
ConditionsYield
With hydrogen; palladium on carbon In tetrahydrofuran; methanol under 2585.81 Torr; for 16h;98%
5-chloro-2-hydroxypentylamine hydrochloride

5-chloro-2-hydroxypentylamine hydrochloride

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

Conditions
ConditionsYield
With sodium hydroxide In water at 10 - 50℃; for 7h;85%
5-bromo-2-hydroxypentylamine hydrobromide

5-bromo-2-hydroxypentylamine hydrobromide

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

Conditions
ConditionsYield
With sodium carbonate In water at 10 - 40℃; for 5h;80%
1-trimethylsilanyl-1,2,3,6-tetrahydro-pyridine
6612-51-7

1-trimethylsilanyl-1,2,3,6-tetrahydro-pyridine

A

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

B

4-HYDROXYPIPERIDINE
5382-16-1

4-HYDROXYPIPERIDINE

Conditions
ConditionsYield
A 75%
B 25%
3-hydroxypyridine hydrochloride
65520-06-1

3-hydroxypyridine hydrochloride

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

benzyl bromide
100-39-0

benzyl bromide

1-benzyl-3-hydroxypiperidine
14813-01-5

1-benzyl-3-hydroxypiperidine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;96%
With caesium carbonate In acetone; toluene at 20℃; for 24h;88%
In methanol for 2h; Heating;
With potassium carbonate; triethylamine In tetrahydrofuran; hexane; ethyl acetate
Multi-step reaction with 2 steps
1.1: potassium carbonate / toluene / 5 h / 40 - 50 °C
1.2: 2 h / 70 - 80 °C / Inert atmosphere
2.1: ethanol / tert-butyl methyl ether / 3 h / 10 - 20 °C
View Scheme
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

N-tert-butoxycarbonyl-3-piperidinol
85275-45-2

N-tert-butoxycarbonyl-3-piperidinol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With triethylamine In methanol at 20℃; for 15h;99%
With triethylamine In methanol at 20℃; for 15h;99%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

N-tert-butoxycarbonyl-3-piperidinol
85275-45-2

N-tert-butoxycarbonyl-3-piperidinol

Conditions
ConditionsYield
In dichloromethane at 20℃; for 15h;87%
With triethylamine In dichloromethane at 20℃; for 1h;83.6%
With triethylamine In tetrahydrofuran; dichloromethane12.66 g (87%)
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

propargyl bromide
106-96-7

propargyl bromide

1-(prop-2-yn-1-yl)piperidin-3-ol

1-(prop-2-yn-1-yl)piperidin-3-ol

Conditions
ConditionsYield
With caesium carbonate In acetone; toluene at 20℃; for 24h; Darkness;86%
With potassium carbonate In tetrahydrofuran for 6h; Reflux;67%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

4-Fluoronitrobenzene
350-46-9

4-Fluoronitrobenzene

1-(4-nitrophenyl)piperidin-3-ol
99841-68-6

1-(4-nitrophenyl)piperidin-3-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 6h;98%
With potassium carbonate In N-methyl-acetamide71%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

2,4-Dinitrofluorobenzene
70-34-8

2,4-Dinitrofluorobenzene

1-(2,4-dinitrophenyl)piperidine-3-ol
1012966-07-2

1-(2,4-dinitrophenyl)piperidine-3-ol

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 6h;91%
With potassium carbonate In dimethyl sulfoxide at 20℃; for 24h;86%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

1-(phenylsulfonyl)piperidin-3-ol
1021372-74-6

1-(phenylsulfonyl)piperidin-3-ol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 5h; Inert atmosphere;99%
With triethylamine In dichloromethane
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

4-Fluorobenzoic acid
456-22-4

4-Fluorobenzoic acid

(4-fluoro-phenyl)-(3-hydroxy-piperidin-1-yl)-methanone
851883-00-6

(4-fluoro-phenyl)-(3-hydroxy-piperidin-1-yl)-methanone

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; benzotriazol-1-ol In dichloromethane at 20℃;53%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-[1,3,5]triazine-2,4-diamine
502767-50-2

6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-[1,3,5]triazine-2,4-diamine

1-[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazine-2-yl]-piperidin-3-ol
676360-88-6

1-[4-(3-chloro-4-methoxy-phenylamino)-6-cycloheptylamino-[1,3,5]triazine-2-yl]-piperidin-3-ol

Conditions
ConditionsYield
With sodium hydroxide In benzene21%
Stage #1: 3-hydroxypiperazine With sodium hydroxide In benzene for 2h; Heating / reflux;
Stage #2: 6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-[1,3,5]triazine-2,4-diamine In benzene at 25℃; for 6h; Heating / reflux;		21%
Stage #1: 3-hydroxypiperazine With sodium hydroxide In benzene for 2h; Heating / reflux;
Stage #2: 6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-[1,3,5]triazine-2,4-diamine In benzene at 25℃; for 6h; Heating / reflux;		21%
Stage #1: 3-hydroxypiperazine With sodium hydroxide In benzene for 2h; Heating / reflux;
Stage #2: 6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-[1,3,5]triazine-2,4-diamine In benzene at 25℃; for 6h; Heating / reflux;		21%
Stage #1: 3-hydroxypiperazine With sodium hydroxide In benzene for 2h; Heating / reflux;
Stage #2: 6-chloro-N2-(3-chloro-4-methoxy-phenyl)-N4-cycloheptyl-[1,3,5]triazine-2,4-diamine In benzene at 25℃; for 6h; Heating / reflux;		21%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

cyclohexylcarbamic acid 2,2,2-trifluoroethyl ester

cyclohexylcarbamic acid 2,2,2-trifluoroethyl ester

3-hydroxypiperidine-1-carboxylic acid cyclohexylamide
606131-61-7

3-hydroxypiperidine-1-carboxylic acid cyclohexylamide

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 100℃; for 4h;75%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

(S)-5-chloro-N-(3-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine
1401462-29-0

(S)-5-chloro-N-(3-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

1-(7-(3-((S)-2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidin-3-ol hydrochloride

1-(7-(3-((S)-2-methylpyrrolidin-1-yl)phenylamino)thiazolo[5,4-d]pyrimidin-5-yl)piperidin-3-ol hydrochloride

Conditions
ConditionsYield
Stage #1: 3-hydroxypiperazine; (S)-5-chloro-N-(3-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine With caesium carbonate; XPhos; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;
Stage #2: With hydrogenchloride In water for 0.166667h;		51.8%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

dichloro(1,5-cyclooctadiene)palladium(II)
12107-56-1

dichloro(1,5-cyclooctadiene)palladium(II)

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

C30H31Cl2NOP2Pd

C30H31Cl2NOP2Pd

Conditions
ConditionsYield
Stage #1: 3-hydroxypiperazine; chloro-diphenylphosphine With triethylamine In toluene at -78 - 20℃; for 2.5h; Schlenk technique; Inert atmosphere;
Stage #2: dichloro(1,5-cyclooctadiene)palladium(II) In toluene for 4h; Reflux; Schlenk technique; Inert atmosphere;		88%
...Expand
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

dichloro( 1,5-cyclooctadiene)platinum(ll)
12080-32-9

dichloro( 1,5-cyclooctadiene)platinum(ll)

chloro-diphenylphosphine
1079-66-9

chloro-diphenylphosphine

C30H31Cl2NOP2Pt

C30H31Cl2NOP2Pt

Conditions
ConditionsYield
Stage #1: 3-hydroxypiperazine; chloro-diphenylphosphine With triethylamine In toluene at -78 - 20℃; for 2.5h; Schlenk technique; Inert atmosphere;
Stage #2: dichloro( 1,5-cyclooctadiene)platinum(ll) In toluene for 4h; Reflux; Schlenk technique; Inert atmosphere;		87%
...Expand
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

4-(5-chloro-6-nitrothiazolo[4,5-b]pyridin-2-yl)morpholine

4-(5-chloro-6-nitrothiazolo[4,5-b]pyridin-2-yl)morpholine

1-(2-morpholino-6-nitrothiazolo[4,5-b]pyridin-5-yl)piperidin-3-ol

1-(2-morpholino-6-nitrothiazolo[4,5-b]pyridin-5-yl)piperidin-3-ol

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;83.33%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;83.33%
(5-Bromo-2-methylpentane-2-sulfonyl)benzene
794533-95-2

(5-Bromo-2-methylpentane-2-sulfonyl)benzene

3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

1-(4-benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine
794533-72-5

1-(4-benzenesulfonyl-4-methylpentyl)-3-hydroxypiperidine

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 18h;98%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

N-trifluoroacetyl-3-hydroxypiperidine
73193-62-1

N-trifluoroacetyl-3-hydroxypiperidine

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 8h;85%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

5-chloro-2-nitroaniline
1635-61-6

5-chloro-2-nitroaniline

5-(3'-hydroxypiperidin-1'-yl)-2-nitroaniline

5-(3'-hydroxypiperidin-1'-yl)-2-nitroaniline

Conditions
ConditionsYield
With potassium carbonate In ISOPROPYLAMIDE at 120 - 130℃; for 21h; Inert atmosphere;86%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

2-chloro-5-(trifluoromethyl)-pyrazine
799557-87-2

2-chloro-5-(trifluoromethyl)-pyrazine

1-(5-(trifluoromethyl)pyrazin-2-yl)piperidin-3-ol
1420466-40-5

1-(5-(trifluoromethyl)pyrazin-2-yl)piperidin-3-ol

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; L-proline In dimethyl sulfoxide at 65℃; for 48h; Sealed tube;94%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

N-(3-bromopropyl)-4-nitro-1H-pyrazole
1152518-79-0

N-(3-bromopropyl)-4-nitro-1H-pyrazole

1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)piperidin-3-ol
1422982-43-1

1-(3-(4-nitro-1H-pyrazol-1-yl)propyl)piperidin-3-ol

Conditions
ConditionsYield
With caesium carbonate In water; N,N-dimethyl-formamide at 20℃; for 12h;95%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

tert-butyl 4-{[4-amino-6-formyl-5-(7-methoxy-5-methyl-1-benzothiophen-2-yl)pyrrolo[2,1-f]-[1,2,4]triazin-7-yl]methyl}piperazine-1-carboxylate
1443531-81-4

tert-butyl 4-{[4-amino-6-formyl-5-(7-methoxy-5-methyl-1-benzothiophen-2-yl)pyrrolo[2,1-f]-[1,2,4]triazin-7-yl]methyl}piperazine-1-carboxylate

rac-1-{[4-amino-5-(7-methoxy-5-methyl-1-benzothiophen-2-yl)-7-(piperazin-1-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methyl}piperidin-3-ol trihydrochloride

rac-1-{[4-amino-5-(7-methoxy-5-methyl-1-benzothiophen-2-yl)-7-(piperazin-1-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-6-yl]methyl}piperidin-3-ol trihydrochloride

Conditions
ConditionsYield
Stage #1: 3-hydroxypiperazine; tert-butyl 4-{[4-amino-6-formyl-5-(7-methoxy-5-methyl-1-benzothiophen-2-yl)pyrrolo[2,1-f]-[1,2,4]triazin-7-yl]methyl}piperazine-1-carboxylate With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 60℃; for 2h;
Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃;		100%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

4-((4-(4-(trifluoromethoxy)phenyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoic acid

4-((4-(4-(trifluoromethoxy)phenyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoic acid

(3-hydroxypiperidin-1-yl)(4-((4-(6-(trifluoromethoxy)pyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)methanone

(3-hydroxypiperidin-1-yl)(4-((4-(6-(trifluoromethoxy)pyridin-3-yl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)phenyl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;89%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

benzenesufonyl hydrazide
80-17-1

benzenesufonyl hydrazide

1-(phenylsulfonyl)piperidin-3-ol
1021372-74-6

1-(phenylsulfonyl)piperidin-3-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667h;95%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

p-bromophenylsulfonyl hydrazide
2297-64-5

p-bromophenylsulfonyl hydrazide

1-(4-bromophenylsulfonyl)piperidin-3-ol

1-(4-bromophenylsulfonyl)piperidin-3-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667h;92%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

2-nitrobenzenesulfonyl hydrazide
5906-99-0

2-nitrobenzenesulfonyl hydrazide

1-(2-nitrophenylsulfonyl)piperidin-3-ol
1023119-86-9

1-(2-nitrophenylsulfonyl)piperidin-3-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667h;92%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

toluene-4-sulfonic acid hydrazide
1576-35-8

toluene-4-sulfonic acid hydrazide

1-(p-toluenesulfonyl)-piperidin-3-ol
220384-68-9

1-(p-toluenesulfonyl)-piperidin-3-ol

Conditions
ConditionsYield
With tert.-butylhydroperoxide; iodine In water at 20℃; for 0.0166667h;96%
3-hydroxypiperazine
6859-99-0

3-hydroxypiperazine

acryloyl chloride
814-68-6

acryloyl chloride

1-(3-hydroxypiperidin-1-yl)-2-propen-1-one

1-(3-hydroxypiperidin-1-yl)-2-propen-1-one

Conditions
ConditionsYield
With triethylamine In dichloromethane at -10℃; for 2h;85.1%

3-Hydroxypiperidine Specification

The 3-Hydroxypiperidine, with the CAS registry number 6859-99-0, is also known as Piperidin-3-ol. It belongs to the product categories of Fine Chemical & Intermediates; Alcohols and Derivatives; Pyrans, Piperidines &Piperazines; Piperidine. Its EINECS number is 229-957-4. This chemical's molecular formula is C5H11NO and molecular weight is 101.15. What's more, its systematic name is 3-Piperidinol.

Physical properties of 3-Hydroxypiperidine are: (1)ACD/LogP: -0.357; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.42; (4)ACD/LogD (pH 7.4): -2.51; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 2; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 32.26 Å2; (13)Index of Refraction: 1.475; (14)Molar Refractivity: 27.997 cm3; (15)Molar Volume: 99.474 cm3; (16)Polarizability: 11.099×10-24cm3; (17)Surface Tension: 33.7 dyne/cm; (18)Density: 1.017 g/cm3; (19)Flash Point: 104.475 °C; (20)Enthalpy of Vaporization: 49.823 kJ/mol; (21)Boiling Point: 191.935 °C at 760 mmHg; (22)Vapour Pressure: 0.13 mmHg at 25°C.

Uses of 3-Hydroxypiperidine: it can be used to produce 3-hydroxy-piperidine-1-carbonyl chloride at the temperature of -65 °C. It will need reagent triethylamine and solvent CH2Cl2 with the reaction time of 15 hours. The yield is about 87%.

3-Hydroxypiperidine can be used to produce 3-hydroxy-piperidine-1-carbonyl chloride at the temperature of -65 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is harmful by inhalation, in contact with skin and if swallowed. It is irritating to eyes, respiratory system and skin. It can cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective clothing, gloves and eye/face protection. You should take off immediately all contaminated clothing. In case of accident or if you feel unwell, you need to seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: OC1CCCNC1
(2)Std. InChI: InChI=1S/C5H11NO/c7-5-2-1-3-6-4-5/h5-7H,1-4H2
(3)Std. InChIKey: BIWOSRSKDCZIFM-UHFFFAOYSA-N 

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