Product Name

  • Name

    3-Pyridinemethanol

  • EINECS 202-864-6
  • CAS No. 100-55-0
  • Article Data158
  • CAS DataBase
  • Density 1.124 g/cm3
  • Solubility soluble in water
  • Melting Point -7.7 °C
  • Formula C6H7NO
  • Boiling Point 266 °C at 760 mmHg
  • Molecular Weight 109.128
  • Flash Point 97.5 °C
  • Transport Information
  • Appearance clear light yellow to yellow liquid
  • Safety 26-36-24/25
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 100-55-0 (3-Pyridinemethanol)
  • Hazard Symbols IrritantXi
  • Synonyms 3-(Hydroxymethyl)pyridine;3-Pyridinylmethanol;3-Pyridyl carbinal;3-Pyridylcarbinol;3-Pyridylmethanol;5-(Hydroxymethyl)pyridine;NSC 526046;Nicotinic alcohol;Nu-2121;Pyridine-3-carbinol;RO-1-5155;Roniacol;b-Picolyl alcohol;b-Pyridinecarbinol;b-Pyridylcarbinol;Nicotinyl alcohol;
  • PSA 33.12000
  • LogP 0.57390

Synthetic route

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With LaCu0.67Si1.33; hydrogen In methanol at 120℃; under 22502.3 Torr; for 9h; Autoclave;99%
With isopropyl alcohol at 300℃; for 3h;98%
With triethylamine; isopropyl alcohol; lithium bromide at 20℃; for 48h; Meerwein-Ponndorf-Verley reaction;97%
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen In tetrahydrofuran at 50℃; under 7500.75 Torr; for 5h; Schlenk technique; Inert atmosphere;98%
With sodium tetrahydroborate; sodium methylate In methanol at 25℃; for 3h; Reagent/catalyst; Inert atmosphere;98%
With 2-(Aminomethyl)pyridine; 1,3-bis-(diphenylphosphino)propane; potassium tert-butylate; hydrogen In 2-methyltetrahydrofuran at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst; Autoclave;95%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With sodium hydroxide In methanol; water at 240℃; for 2h; Autoclave; Inert atmosphere;94%
With acetic acid; sodium nitrite Diazotization;
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen In tetrahydrofuran at 100℃; under 38002.6 - 76005.1 Torr; for 10h; Glovebox; Autoclave;90%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 4h;87.4%
With C39H41FeMnN2O5P(1+)*Br(1-); hydrogen; potassium carbonate In ethanol at 90℃; under 37503.8 Torr; for 16h;80%
3-pyridylcarbinol-N-oxide
6968-72-5

3-pyridylcarbinol-N-oxide

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With methyloxorhenium(V)(2-(mercaptomethyl)thiophenolate) triphenylphosphine; triphenylphosphine In benzene at 20℃; for 1h;90%
With 1,1,2,2-tetrabutyl-1,2-dichloro distannane In tetrahydrofuran for 1h; Heating;85%
With gallium In water for 7h; Heating;84%
nicotinic acid
59-67-6

nicotinic acid

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With [Zn(BH4)2(py)] In tetrahydrofuran for 0.7h; Heating;90%
Multi-step reaction with 2 steps
1: Et3N / tetrahydrofuran / 0.5 h / 0 °C
2: Tulusion A-27 exchange resin supporting borohydride anion, Ni(OAc)2 / methanol / 1 h / 10 °C
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid
2: aluminum (III) chloride; sodium tetrahydroborate / tetrahydrofuran; toluene / 0 - 5 °C
View Scheme
6-chloronicotinylaldehyde
23100-12-1

6-chloronicotinylaldehyde

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With hydrogen; sodium acetate; palladium dichloride In methanol at 35℃; under 760.051 Torr; for 2h;88%
5-bromopyridine-3-carbaldehyde
113118-81-3

5-bromopyridine-3-carbaldehyde

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With hydrogen; sodium acetate; palladium dichloride In methanol at 35℃; under 760.051 Torr; for 2h;83%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With TEA; magnesium bromide In dichloromethane at 20℃; for 48h; Cannizzaro reaction;A 82%
B n/a
With N,N,N',N'-tetramethylguanidine In water at 20℃; for 7h; Cannizzaro reaction;A 44%
B 41%
With barium dihydroxide; formaldehyd at 100 - 110℃; for 0.0333333h; Irradiation;A 97 % Chromat.
B 3 % Chromat.
With aluminum oxide; sodium hydroxide; water for 0.00416667h; Irradiation; Yield given; Yields of byproduct given;
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

A

3-picolyl bromide
69966-55-8

3-picolyl bromide

B

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

C

3-(isoamyloxymethyl)pyridine

3-(isoamyloxymethyl)pyridine

Conditions
ConditionsYield
With bromine; isopentyl nitrite In dichloromethane Product distribution / selectivity;A 81%
B 11%
C 3%
With bromine; isopentyl nitrite In tetrahydrofuran Product distribution / selectivity;A 79%
B 11%
C 3%
With bromine; isopentyl nitrite In chloroform Product distribution / selectivity;A 67%
B 18%
C 3%
...Expand
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

5-carbamoyl 4,7-dihydro thieno<2,3-b>pyridine
108460-23-7

5-carbamoyl 4,7-dihydro thieno<2,3-b>pyridine

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

5-Carbamoyl-7-methyl-thieno[2,3-b]pyridin-7-ium; perchlorate

5-Carbamoyl-7-methyl-thieno[2,3-b]pyridin-7-ium; perchlorate

Conditions
ConditionsYield
With magnesium(II) perchlorate; water In acetonitrile at 65℃;A 80%
B n/a
With magnesium(II) perchlorate; water In acetonitrile at 65℃;A 80%
B n/a
With magnesium(II) perchlorate; water In acetonitrile at 65℃; Product distribution; water-sensitivity;
...Expand
6-bromonicotinaldehyde
149806-06-4

6-bromonicotinaldehyde

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With hydrogen; sodium acetate; palladium dichloride In methanol at 35℃; under 760.051 Torr; for 4h;78%
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

nicotinamide
98-92-0

nicotinamide

Conditions
ConditionsYield
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃;A 21%
B 74%
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

1-Benzyl-1,4-dihydronicotinamide
952-92-1

1-Benzyl-1,4-dihydronicotinamide

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

3-(aminocarbonyl)-1-(phenylmethyl)pyridinium perchlorate
15519-25-2

3-(aminocarbonyl)-1-(phenylmethyl)pyridinium perchlorate

Conditions
ConditionsYield
With magnesium(II) perchlorate In acetonitrile at 65℃;A 70%
B n/a
With magnesium(II) perchlorate In acetonitrile at 65℃; Product distribution;
...Expand
3-pyridylcarbinol-N-oxide
6968-72-5

3-pyridylcarbinol-N-oxide

A

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

B

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With 1,1'-bis(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In acetonitrile at 150℃; for 1h; Microwave irradiation; chemoselective reaction;A 20%
B 66%
nicotinamide
98-92-0

nicotinamide

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With C24H20ClN2OPRu; potassium tert-butylate; hydrogen In tetrahydrofuran at 110℃; under 10640.7 Torr; for 36h; Inert atmosphere; Schlenk technique;63%
With {Ru(H)(BH4)(CO)(3-(di-tert-butylphosphino)-N-((1-methyl-1H-imidazol-2-yl)methyl)propylamine)}; hydrogen In isopropyl alcohol at 150℃; under 37503.8 Torr; for 18h; Autoclave;95 %Chromat.
With C16H25MnN3O3P(1+)*Br(1-); potassium tert-butylate; hydrogen In tert-Amyl alcohol; cyclohexane at 140℃; under 37503.8 Torr; for 24h; Inert atmosphere; Autoclave;55 %Chromat.
C14H15NO2

C14H15NO2

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With sodium hydrogen sulfate; eosin; dihydrogen peroxide In water; acetonitrile for 48h; Irradiation;57%
3-Chloropyridine
626-60-8

3-Chloropyridine

potassium (acetoxymethyl)trifluoroborate

potassium (acetoxymethyl)trifluoroborate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With sodium carbonate; bis(dibenzylideneacetone)-palladium(0); ruphos In 1,4-dioxane; water for 48h; Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;51.9%
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

A

3-picolyl bromide
69966-55-8

3-picolyl bromide

B

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With bromine; acetic acid; sodium nitrite In dichloromethane Product distribution / selectivity;A 44%
B 49%
3-pyridylcarbinol-N-oxide
6968-72-5

3-pyridylcarbinol-N-oxide

N,N-Dimethylthiocarbamoyl chloride
16420-13-6

N,N-Dimethylthiocarbamoyl chloride

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

C9H12N2O2S

C9H12N2O2S

Conditions
ConditionsYield
In acetonitrile at 81℃; for 4h;A 47%
B 9%
...Expand
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

methyl methoxyacetate
6290-49-9

methyl methoxyacetate

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

C

methyl α-methoxy-β-(β-pyridyl)acrylate
136138-66-4

methyl α-methoxy-β-(β-pyridyl)acrylate

Conditions
ConditionsYield
With sodium methylate In toluene for 2h; Heating;A n/a
B 10%
C 31%
...Expand
3-Chloropyridine
626-60-8

3-Chloropyridine

sodium [(2,2-dimethyl)propionyloxy]methyl trifluoroborate

sodium [(2,2-dimethyl)propionyloxy]methyl trifluoroborate

A

3-(pivaloxymethyl)pyridine
859842-81-2

3-(pivaloxymethyl)pyridine

B

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With potassium phosphate; water; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In 1,4-dioxane at 20 - 100℃; for 14.25h;A 12%
B 14%
...Expand
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Br(1-)*C9H21N2O(1+)
1342295-75-3

Br(1-)*C9H21N2O(1+)

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

nicotinic acid
59-67-6

nicotinic acid

trans-N,N-diethyl-3-(pyridin-3-yl)oxirane-2-carboxamide

trans-N,N-diethyl-3-(pyridin-3-yl)oxirane-2-carboxamide

Conditions
ConditionsYield
Stage #1: Br(1-)*C9H21N2O(1+) With sodium hydroxide In dichloromethane; water at 0℃; for 0.0833333h; Inert atmosphere;
Stage #2: 3-pyridinecarboxaldehyde In dichloromethane; water at 0 - 25℃; for 24h; Inert atmosphere; diastereoselective reaction;		A n/a
B n/a
C 10%
...Expand
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With hydrogenchloride; palladium on activated charcoal Hydrogenation;
3-bromomethyl-pyridine; picrate

3-bromomethyl-pyridine; picrate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With water Zerlegen des entstandenen 3-Oxymethyl-pyridin-pikrats mit Natronlauge;
pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

3-Methylpyridine
108-99-6

3-Methylpyridine

Conditions
ConditionsYield
With tin(IV) oxide In isopropyl alcohol at 300℃; for 0.5h;A 5 % Chromat.
B 35 % Chromat.
2-Methyl-benzoic acid pyridin-3-ylmethyl ester
77934-69-1

2-Methyl-benzoic acid pyridin-3-ylmethyl ester

A

ortho-methylbenzoic acid
118-90-1

ortho-methylbenzoic acid

B

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With water in alkaline medium In acetone Rate constant; Ambient temperature;
nicotinyl 6-aminonicotinate

nicotinyl 6-aminonicotinate

A

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

B

6-aminonicotinic acid
3167-49-5

6-aminonicotinic acid

Conditions
ConditionsYield
With phosphate buffer In water at 65℃; Rate constant; Thermodynamic data; pH 5.17, ΔS, activation energy, other pH, solvent effect;
3-nitrooxymethylpyridine
13469-94-8

3-nitrooxymethylpyridine

A

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

B

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
ConditionsYield
With sodium methylate In methanol for 3h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
ConditionsYield
With 10% Ru/C; oxygen In toluene at 90℃; under 760.051 Torr; for 24h;100%
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide for 0.25h; Ambient temperature;99%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; oxygen; copper(I) bromide dimethylsulfide complex In chlorobenzene at 80℃; for 8h;99%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-Picolyl chloride
3099-31-8

3-Picolyl chloride

Conditions
ConditionsYield
With thionyl chloride In dichloromethane Reflux;100%
With thionyl chloride for 0.583333h; Cooling with ice; Reflux;72.5%
With 1-methyl-pyrrolidin-2-one; benzenesulfonyl chloride In 1,2-dichloro-ethane at 80℃; for 1.5h;41%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

1-(2,2-diethoxyethyl)-4-(imidazol-1-yl)carbonyl-5-aminopyrazole
222055-82-5

1-(2,2-diethoxyethyl)-4-(imidazol-1-yl)carbonyl-5-aminopyrazole

5-amino-1-(2,2-diethoxy-ethyl)-1H-pyrazole-4-carboxylic acid pyridin-3-ylmethyl ester
222055-89-2

5-amino-1-(2,2-diethoxy-ethyl)-1H-pyrazole-4-carboxylic acid pyridin-3-ylmethyl ester

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.166667h;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

N-(3-methoxyphenylsulfonyl)-D-valine benzyl ester

N-(3-methoxyphenylsulfonyl)-D-valine benzyl ester

C25H28N2O5S
952596-21-3

C25H28N2O5S

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

C13H12Cl3NO4

C13H12Cl3NO4

6-methyl 1-pyridin-3-ylmethyl 3,4-dihydroquinoline-1,6(2H)-dicarboxylate
953435-15-9

6-methyl 1-pyridin-3-ylmethyl 3,4-dihydroquinoline-1,6(2H)-dicarboxylate

Conditions
ConditionsYield
at 20℃; for 8h;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-iodo-7-methoxy-4,4-dimethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-6-ol
760991-59-1

3-iodo-7-methoxy-4,4-dimethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-6-ol

3-iodo-7-methoxy-4,4-dimethyl-6-(pyridin-3-ylmethoxy)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydroindeno[1,2-c]pyrazole
760991-63-7

3-iodo-7-methoxy-4,4-dimethyl-6-(pyridin-3-ylmethoxy)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1,4-dihydroindeno[1,2-c]pyrazole

Conditions
ConditionsYield
With di-tert-butyl-diazodicarboxylate; Ph3P on solid support In tetrahydrofuran at 20℃;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

C14H18BrNO4
1174637-69-4

C14H18BrNO4

C20H25N2O5(1+)*Br(1-)

C20H25N2O5(1+)*Br(1-)

Conditions
ConditionsYield
In neat (no solvent) at 25℃; for 0.05h; Sonication;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

C14H18BrNO3

C14H18BrNO3

C20H25N2O4(1+)*Br(1-)

C20H25N2O4(1+)*Br(1-)

Conditions
ConditionsYield
In neat (no solvent) at 25℃; for 0.05h; Sonication;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

1-bromo-4-methoxy-10-methyl-6H-benzo[c]chromen-6-one

1-bromo-4-methoxy-10-methyl-6H-benzo[c]chromen-6-one

pyridin-3-ylmethyl (R)-6'-bromo-2'-hydroxy-3'-methoxy-6-methyl-[1,1'-biphenyl]-2-carboxylate

pyridin-3-ylmethyl (R)-6'-bromo-2'-hydroxy-3'-methoxy-6-methyl-[1,1'-biphenyl]-2-carboxylate

Conditions
ConditionsYield
With C29H28F6N4OS at 20℃; for 3h; enantioselective reaction;100%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

acetic anhydride
108-24-7

acetic anhydride

3-(acetoxymethyl)pyridine
10072-09-0

3-(acetoxymethyl)pyridine

Conditions
ConditionsYield
With 4-N,N-dimethylaminopyridinium saccharinate at 25℃; for 0.5h; Inert atmosphere; Neat (no solvent);99%
With 4-N,N-dimethylaminopyridinium saccharinate In neat (no solvent) at 25℃; for 0.5h; Reagent/catalyst;99%
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere;99%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

10,11-(methylenedioxy)-7-(chloromethyl)-(20S)-camptothecin
149882-14-4

10,11-(methylenedioxy)-7-(chloromethyl)-(20S)-camptothecin

7-{[3-(hydroxymethyl)pyridiniumyl]methyl}-10,11-(methylenedioxy)-(20S)-camptothecin chloride

7-{[3-(hydroxymethyl)pyridiniumyl]methyl}-10,11-(methylenedioxy)-(20S)-camptothecin chloride

Conditions
ConditionsYield
for 16h; Ambient temperature;99%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

methyl iodide
74-88-4

methyl iodide

1-methyl-3-(hydroxymethyl)pyridinium perchlorate

1-methyl-3-(hydroxymethyl)pyridinium perchlorate

Conditions
ConditionsYield
Stage #1: 3-hydroxymethylpyridin; methyl iodide at 0℃; for 3h;
Stage #2: With silver perchlorate In methanol at 0℃; for 1h;		99%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-Pyridinecarboxylic acid 3-pyridinylmethyl ester
49673-77-0

3-Pyridinecarboxylic acid 3-pyridinylmethyl ester

Conditions
ConditionsYield
With iodine; potassium carbonate In tert-butyl alcohol at 20℃; for 19h;99%
With RuH(CO)Cl(PPh3)(κ2-CP); caesium carbonate In toluene at 110℃; for 26h; Schlenk technique; Glovebox; Inert atmosphere;87%
With silver(I) hexafluorophosphate; oxygen; palladium diacetate; potassium carbonate; 1,2-bis[di(t-butyl)phosphinomethyl]benzene In toluene at 110℃; under 750.075 Torr; for 20h; chemoselective reaction;75%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

pyridine-3-carbonitrile
100-54-9

pyridine-3-carbonitrile

Conditions
ConditionsYield
Stage #1: 3-hydroxymethylpyridin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite In dichloromethane at 20℃; for 1h; Inert atmosphere;
Stage #2: With ammonia; iodine In dichloromethane; water at 20℃; for 2h; Inert atmosphere;		99%
With ammonia; oxygen In tert-Amyl alcohol; water at 100℃; under 3750.38 Torr; for 4h; Autoclave; High pressure;99%
With potassium phosphate; ammonium formate In acetonitrile at 115℃; for 16h; Sealed tube; Green chemistry;91%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

nicotinic acid
59-67-6

nicotinic acid

Conditions
ConditionsYield
With tert-butyldimethylsilyl chloride In methanol; water at 20℃; for 0.5h; Reagent/catalyst; Green chemistry;99%
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 12h; pH=9.8 - 10.1; Electrolysis;96%
With ferrous(II) sulfate heptahydrate; Oxone In water at 20℃; for 0.5h; Sonication; Green chemistry;94%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

1-(benzyloxy)-4-bromo-3-fluorobenzene
185346-79-6

1-(benzyloxy)-4-bromo-3-fluorobenzene

3-[5-(benzyloxy)-2-bromophenoxymethyl]pyridine
1355091-47-2

3-[5-(benzyloxy)-2-bromophenoxymethyl]pyridine

Conditions
ConditionsYield
Stage #1: 3-hydroxymethylpyridin In 1-methyl-pyrrolidin-2-one; mineral oil at 20℃; for 0.5h;
Stage #2: 4-(benzyloxy)-1-bromo-2-fluorobenzene In 1-methyl-pyrrolidin-2-one; mineral oil at 100℃; for 0.5h;		99%
Stage #1: 3-hydroxymethylpyridin With sodium hydride In 1-methyl-pyrrolidin-2-one at 20℃; for 0.5h;
Stage #2: 4-(benzyloxy)-1-bromo-2-fluorobenzene at 100℃; for 0.25h;
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

acetophenone
98-86-2

acetophenone

1-phenyl-3-(pyridin-3-yl)propan-1-one
39976-56-2

1-phenyl-3-(pyridin-3-yl)propan-1-one

Conditions
ConditionsYield
With titanium(IV) oxide; potassium hydroxide In toluene at 100℃; for 10h; Sealed tube; Irradiation;99%
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); caesium carbonate In toluene at 140℃; for 20h; Inert atmosphere; Sealed tube;89%
With C38H43IrN2PS2(1+)*CF3O3S(1-); caesium carbonate In tert-Amyl alcohol at 120℃; for 24h; Schlenk technique; Inert atmosphere;86%
pyridin-3-ylamine
462-08-8

pyridin-3-ylamine

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

N-(pyridin-3-ylmethyl)pyridin-3-amine
78675-94-2

N-(pyridin-3-ylmethyl)pyridin-3-amine

Conditions
ConditionsYield
With potassium hydroxide at 130℃; for 25h; Schlenk technique; Inert atmosphere;99%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

methyl iodide
74-88-4

methyl iodide

3-(Hydroxymethyl)-1-methylpyridinium iodide
6457-55-2

3-(Hydroxymethyl)-1-methylpyridinium iodide

Conditions
ConditionsYield
In toluene for 1h; Heating;98%
In dichloromethane at 20℃; for 12h;90%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

pivaloyl chloride
3282-30-2

pivaloyl chloride

3-(pivaloxymethyl)pyridine
859842-81-2

3-(pivaloxymethyl)pyridine

Conditions
ConditionsYield
With TEA In ethyl acetate at 0℃; for 3h;98%
With triethylamine In dichloromethane at 0 - 25℃;
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

3-<(trimethylsilyloxy)methyl>pyridine
85719-72-8

3-<(trimethylsilyloxy)methyl>pyridine

Conditions
ConditionsYield
With potassium fluoride incorporated on clinoptilolite nanoparticles In dichloromethane at 20℃; for 0.666667h; chemoselective reaction;98%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In acetonitrile at 20℃; for 0.25h;90%
With polyvinylpolypyrrolidonium tribromide In acetonitrile at 20℃; for 0.25h;60%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

p-aminomethylbenzoic acid
56-91-7

p-aminomethylbenzoic acid

4-benzoic acid
241809-79-0

4-benzoic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; sodium chloride; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide98%
Stage #1: 3-hydroxymethylpyridin With 1,1'-carbonyldiimidazole In tetrahydrofuran at 10 - 20℃; for 1h;
Stage #2: p-aminomethylbenzoic acid With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In tetrahydrofuran at 20℃; for 5h;
Stage #3: With hydrogenchloride; water pH=5;		91%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

4-pentynoic acid
6089-09-4

4-pentynoic acid

2-pyridinylmethyl 4-pentynoate
1268158-83-3

2-pyridinylmethyl 4-pentynoate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; Inert atmosphere;98%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

N,N-diisopropylphosphoramide dichloride
921-26-6

N,N-diisopropylphosphoramide dichloride

bis(pyridin-3-ylmethyl) diisopropylphosphoramidite

bis(pyridin-3-ylmethyl) diisopropylphosphoramidite

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 0 - 20℃;98%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

2-methylquinoline
91-63-4

2-methylquinoline

2-(2-(pyridin-3-yl)ethyl)quinolone
21203-10-1

2-(2-(pyridin-3-yl)ethyl)quinolone

Conditions
ConditionsYield
With [Mn(HN(C2H4PiPr2)2)(CO)2Br]; potassium tert-butylate In tert-Amyl alcohol at 140℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique; Glovebox;98%
With cesium hydroxide In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 24h;92%
With ruthenium(III) chloride trihydrate; potassium tert-butylate In 1,4-dioxane at 130℃; for 24h; Inert atmosphere;65%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

acetophenone
98-86-2

acetophenone

1-phenyl-3-(pyridin-3-yl)prop-2-en-1-one
4452-13-5

1-phenyl-3-(pyridin-3-yl)prop-2-en-1-one

Conditions
ConditionsYield
With titanium nitride; potassium hydroxide In toluene at 100℃; for 10h; Sealed tube; Irradiation;98%
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

benzamidine monohydrochloride
1670-14-0

benzamidine monohydrochloride

2,4-di-phenyl-6-(pyridin-3-yl)-1,3,5-triazine
1596320-79-4

2,4-di-phenyl-6-(pyridin-3-yl)-1,3,5-triazine

Conditions
ConditionsYield
With oxygen; copper(II) acetate monohydrate; sodium carbonate In toluene at 110℃; for 24h;97%
With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 20 - 110℃; for 20h; Reagent/catalyst; Solvent;81%
With [RhCl2(p-cymene)]2; caesium carbonate In dimethyl sulfoxide at 110℃; for 16h; Sealed tube;78%
Stage #1: 3-hydroxymethylpyridin; benzamidine monohydrochloride With caesium carbonate In dimethyl sulfoxide at 20℃; for 0.0833333h; Schlenk technique; Green chemistry;
Stage #2: With N-iodo-succinimide In dimethyl sulfoxide at 100℃; for 16h; Schlenk technique; Green chemistry;		72%

3-Pyridinemethanol Chemical Properties

Molecular Structure of Nicotinyl alcohol (CAS NO.100-55-0):

Molecular Formula: C6H7NO
Molecular Weight: 109.14 g/mol
Density: 1.131 g/cm3
Melting Point: -7.7 °C
Boiling Point: 266 °C at 760 mmHg 
Flash Point: 97.5 °C
Index of Refraction: 1.551
Molar Refractivity: 30.79 cm3
Molar Volume: 96.4 cm3 
Surface Tension: 48.7 dyne/cm
Enthalpy of Vaporization: 53.24 kJ/mol
Vapour Pressure: 0.00442 mmHg at 25 °C 
Storage Temp.: 2-8 °C
Water Solubility: soluble
Sensitive: hygroscopic
H-Bond Donor: 1
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 109.052764
MonoIsotopic Mass: 109.052764
Topological Polar Surface Area: 33.1
Heavy Atom Count: 8 
Canonical SMILES: C1=CC(=CN=C1)CO
InChI: InChI=1S/C6H7NO/c8-5-6-2-1-3-7-4-6/h1-4,8H,5H2
InChIKey: MVQVNTPHUGQQHK-UHFFFAOYSA-N
EINECS: 202-864-6
Product Categories: Alkohols

3-Pyridinemethanol Uses

 Nicotinyl alcohol (CAS NO.100-55-0) is used as the intermediates of rodenticides in organic synthesis. It has a direct effect on peripheral vascular wall, so it can expand blood vessels and reduce the cholesterol.

3-Pyridinemethanol Toxicity Data With Reference

1.    

ivn-mus LD50:1000 mg/kg

     PHARAT    Pharmazie. 11 (1956),242.

3-Pyridinemethanol Consensus Reports

Reported in EPA TSCA Inventory.

3-Pyridinemethanol Safety Profile

Moderately toxic by intravenous route. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes: Xi
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin 
Safety Statements: 26-36-24/25
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36: Wear suitable protective clothing 
24/25: Avoid contact with skin and eyes 
WGK Germany: 3
RTECS: UT4690000
F: 3-10-23
F3: Hygroscopic
F10: Keep under argon
F23: Sensitive to air
Hazard Note: Irritant
HS Code: 29333999

3-Pyridinemethanol Specification

 Nicotinyl alcohol (CAS NO.100-55-0) is also named as 3-(Hydroxymethyl)pyridine ; 3-Picolyl alcohol ; 3-Pyridinylmethanol ; 3-Pyridylcarbinol ; 3-Pyridylmethanol ; 5-21-02-00172 (Beilstein Handbook Reference) ; BRN 0107851 ; NSC 526046 ; NU-2121 ; Nicotinic alcohol ; Pyridine-3-carbinol ; Ro-1-5155 ; Roniacol ; UNII-9TF312056Y ; beta-Picolyl alcohol ; beta-Pyridinecarbinol . Nicotinyl alcohol (CAS NO.100-55-0) is clear light yellow to yellow liquid. It is easily soluble in water and ether.

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