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Cas Database

100-55-0

100-55-0

Identification

  • Product Name:3-Pyridinemethanol

  • CAS Number: 100-55-0

  • EINECS:202-864-6

  • Molecular Weight:109.128

  • Molecular Formula: C6H7NO

  • HS Code:29333999

  • Mol File:100-55-0.mol

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;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:3-Pyridinemethanol
  • Packaging:10g
  • Price:$ 130
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Pyridinemethanol >98.0%(GC)
  • Packaging:500mL
  • Price:$ 487
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Pyridinemethanol >98.0%(GC)
  • Packaging:25mL
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-(Hydroxymethyl)pyridine
  • Packaging:100 g
  • Price:$ 56
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Pyridinemethanol analytical standard
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Pyridinemethanol 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Pyridinemethanol 98%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Pyridinemethanol 98%
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  • Manufacture/Brand:Oakwood
  • Product Description:3-Pyridinemethanol 99%
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  • Manufacture/Brand:Oakwood
  • Product Description:3-Pyridinemethanol 99%
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Relevant articles and documentsAll total 132 Articles be found

Mild Selective Deoxygenation of Amine Oxides by Tin-Tin Bonded Derivatives

Jousseaume, Bernard,Chanson, Evelyne

, p. 55 - 56 (1987)

A new method of deoxygenation of amine oxides with tin reagent is proposed.It utilizes the reductive properties of the tin-tin bond in hexabutyldistannane or 1,2-dichlorotetrabutyldistannane.Oxides of tertiary amines are reduced into amines by hexabutyldistannane in high yields, whereas pyridine N-oxides react cleanly with 1,2-dichlorotetrabutyldistannane to give the corresponding pyridines.These reactions occur under mild conditions and are very selective.

Mild and selective reduction of aldehydes utilising sodium dithionite under flow conditions

Neyt, Nicole C.,Riley, Darren L.

, p. 1529 - 1536 (2018)

We recently reported a novel hybrid batch-flow synthesis of the antipsychotic drug clozapine in which the reduction of a nitroaryl group is described under flow conditions using sodium dithionite. We now report the expansion of this method to include the reduction of aldehydes. The method developed affords yields which are comparable to those under batch conditions, has a reduced reaction time and improved space-time productivity. Furthermore, the approach allows the selective reduction of aldehydes in the presence of ketones and has been demonstrated as a continuous process.

REDUCTION WITH POLYMER-BOUND NADH MODELS.

Dupas, G.,Bourguignon, J.,Ruffin, C.,Queguiner, G.

, p. 5141 - 5144 (1982)

We have performed numerous reductions with a NADH model grafted on a Merrifield resin.The yields are generally excellent and in all cases always superior to those obtained with "free" models.

Partial photocatalytic oxidations of 3-pyridinemethanol and 3-picoline by TiO2 prepared in HCl, HNO3 and H2SO4 at different temperatures

?etinkaya, S?d?ka,Yurdakal, Sedat

, p. 237 - 247 (2021)

Home prepared TiO2 photocatalysts were prepared from TiCl4 precursor in the absence and presence of HCl (1?6 M), HNO3 (1 M) or H2SO4 (1 M) at room temperature (RT), 60 or 100 °C. The TiO2 catalysts were characterised by XRD, BET, SEM and TGA techniques. TiO2 catalyst could not form at low temperature (up to 60 °C) in the presence of H2SO4. Just rutile phase was obtained for all TiO2 samples prepared at RT and 60 °C in HCl or HNO3. At 100 °C mainly both brookite and rutile phases were obtained in the presence of HCl or HNO3, whilst mainly anatase phase appeared in the presence of H2SO4. Nanorod structured TiO2 was formed in the presence of 1 M HCl or HNO3 at RT and 60 °C. The prepared TiO2 catalysts were used for partial oxidation of 3-pyridinemethanol to 3-pyridinemethanal and vitamin B3 in water under UVA irradiation. Moreover, photocatalytic oxidation of 3-picoline, precursor of 3-pyridinemethanol, was also performed, but much lower product selectivity values were obtained with respect to 3-pyridinemethanol oxidation. However, selective 3-picoline oxidation could be performed at pH 2 with low activity. Degussa P25 was used for comparison and almost all home prepared catalysts showed a higher selectivity, but they showed to be less active than Degussa P25. The high selectivity of the home prepared samples was not due to the type of TiO2 phase, but mainly to the hydrophilicity of the TiO2 surface which allowed desorption of valuable products instead of their over-oxidation.

Silver-catalyzed hydrogenation of aldehydes in water

Jia, Zhenhua,Zhou, Feng,Liu, Mingxin,Li, Xingshu,Chan, Albert S. C.,Li, Chao-Jun

, p. 11871 - 11874 (2013)

Silver bullet: The first silver-catalyzed hydrogenation in water was developed. A silver complex containing a bulky monodentate phosphine ligand was used to generate alcohols from a broad range of aldehydes, including aliphatic, aromatic, and heterocyclic aldehydes. This method provides a direct and efficient route to alcohols from aldehydes and opens a new avenue in silver catalysis. Copyright

-

Mosher,Tessieri

, p. 4925 (1951)

-

4-Aza-N-benzyl bicyclo[2,2,2]octyl ammonium borohydride a highly chemoselective reagent for the reduction of aldehydes in the presence of ketones

Firouzabadi,Afsharifar

, p. 497 - 507 (1992)

The title compound reduces aldehydes in the presence of ketones with high chemoselectivity in t-butanol under reflux condition in high yields.

BIOMIMETIC REDUCTION WITH NON WATER-SENSITIVE NADH MODELS

Cazin, J.,Dupas, G.,Bourguignon, J.,Queguiner, G.

, p. 2375 - 2378 (1986)

Two NADH models were synthesized which are considerably less water-sensitive than classical-1,4 dihydronicotinamide derivatives such as N-benzyl-1,4 dihydronicotinamide (BNAH): these two models are reactive and more stable in the presence of water than previously reported models.

High-throughput synthesis and analysis of acylated cyanohydrins

Hamberg, Anders,Lundgren, Stina,Wingstrand, Erica,Moberg, Christina,Hult, Karl

, p. 4334 - 4341 (2007)

The yields and optical purities of products obtained from chiral Lewis acid/Lewis base-catalysed additions of ct-ketonitriles to prochiral aldehydes could be accurately determined by an enzymatic method. The amount of remaining aldehyde was determined after its reduction to an alcohol, whilst the two product enantiomers were analysed after subsequent hydrolysis first by the (S)-selective Candida antarctica lipase B and then by the unselective pig liver esterase. The method could be used for analysis of products obtained from a number of aromatic aldehydes and aliphatic ketonitriles. Microreactor technology was successfully combined with high-throughput analysis for efficient catalyst optimization.

Purification and characterization of an NADH-dependent alcohol dehydrogenase from Candida maris for the synthesis of optically active 1-(pyridyl)ethanol derivatives

Kawano, Shigeru,Yano, Miho,Hasegawa, Junzo,Yasohara, Yoshihiko

, p. 1055 - 1060 (2011)

A novel (R)-specific alcohol dehydrogenase (AFPDH) produced by Candida maris IFO10003 was purified to homogeneity by ammonium sulfate fractionation, DEAE-Toyopearl, and Phenyl-Toyopearl, and characterized. The relative molecular mass of the native enzyme was found to be 59,900 by gel filtration, and that of the subunit was estimated to be 28,900 on SDS-polyacrylamide gel electrophoresis. These results suggest that the enzyme is a homodimer. It required NADH as a cofactor and reduced various kinds of carbonyl compounds, including ketones and aldehydes. AFPDH reduced acetylpyridine derivatives, β-keto esters, and some ketone compounds with high enantioselectivity. This is the first report of an NADH-dependent, highly enantioselective (R)-specific alcohol dehydrogenase isolated from a yeast. AFPDH is a very useful enzyme for the preparation of various kinds of chiral alcohols.

CALCIUM ALKOXYALANATES. III. REDUCTION OF ORGANIC FUNCTIONAL GROUPS BY CALCIUM TETRAKIS(ALKOXY)ALANATES

Cucinella, S.,Dozzi, G.,Bruzzone, M.

, p. 21 - 28 (1982)

Calcium tetrakis(alkoxy)alanates obtained from different alcohols reduce aldehydes, ketones, acids, esters, acid chlorides and anhydrides to alcohols in high yields.Good results are achieved in the reduction of amides to amines.The reductions of nitrile and oxime groups and dehalogenation reactions are more difficult.Selectivity is possible in the reduction of organic epoxides.

Microwave-heated γ-Alumina Applied to the Reduction of Aldehydes to Alcohols

Dhokale, Bhausaheb,Susarrey-Arce, Arturo,Pekkari, Anna,Runemark, August,Moth-Poulsen, Kasper,Langhammer, Christoph,H?relind, Hanna,Busch, Michael,Vandichel, Matthias,Sundén, Henrik

, p. 6344 - 6355 (2020)

The development of cheap and robust heterogeneous catalysts for the Meerwein-Ponndorf-Verley (MPV) reduction is desirable due to the difficulties in product isolation and catalyst recovery associated with the traditional use of homogeneous catalysts for MPV. Herein, we show that microwave heated γ-Al2O3 can be used for the reduction of aldehydes to alcohols. The reaction is efficient and has a broad substrates scope (19 entries). The products can be isolated by simple filtration, and the catalyst can be regenerated. With the use of microwave heating, we can direct the heating to the catalyst rather than to the whole reaction medium. Furthermore, DFT was used to study the reaction mechanism, and we can conclude that a dual-site mechanism is operative where the aldehyde and 2-propoxide are situated on two adjacent Al sites during the reduction. Additionally, volcano plots were used to rationalize the reactivity of Al2O3 in comparison to other metal oxides.

Uncatalyzed Meerwein-Ponndorf-Oppenauer-Verley Reduction of Aldehydes and Ketones under Supercritical Conditions

Sominsky, Lena,Rozental, Esther,Gottlieb, Hugo,Gedanken, Aharon,Hoz, Shmaryahu

, p. 1492 - 1496 (2004)

When a solution of a carbonyl compound in alcohol (primary or secondary) is heated to ca. 300 °C, a disproportionation reaction, in which a carbonyl compound is reduced to the corresponding alcohol and the alcohol is oxidized to the corresponding ketone, takes place. This uncatalyzed variation of the Meerwein-Ponndorf-Oppenauer-Verley reaction gives, in certain cases, e.g., reduction of acetophenone or benzaldehyde by i-PrOH, almost quantitative yields. Yields are higher with secondary alcohols such as i-PrOH than with a primary alcohol such as EtOH. The reactions were also performed in a flow system by passing at a slow rate the same solutions through a glass or a metal coil heated to elevated temperatures. Ab initio calculations performed at the B3LYP/6-31G* level show that thermodynamically i-PrOH is a more potent reducing agent than EtOH by ca. 4 kcal/mol. The computations also show that in cases of aromatic carbonyl compounds, part of the deriving force is obtained from the entropy change of the reaction. The major contributor to the high yield, however, is the excess alcohol used, which shifts the equilibrium to the right. Calculated entropy of activation as well as isotopic H/D labeling suggest a cyclic transition state.

Disproportionation of aliphatic and aromatic aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions

Sharifi, Sina,Sharifi, Hannah,Koza, Darrell,Aminkhani, Ali

, p. 803 - 808 (2021/07/20)

Disproportionation of aldehydes through Cannizzaro, Tishchenko, and Meerwein–Ponndorf–Verley reactions often requires the application of high temperatures, equimolar or excess quantities of strong bases, and is mostly limited to the aldehydes with no CH2 or CH3 adjacent to the carbonyl group. Herein, we developed an efficient, mild, and multifunctional catalytic system consisting AlCl3/Et3N in CH2Cl2, that can selectively convert a wide range of not only aliphatic, but also aromatic aldehydes to the corresponding alcohols, acids, and dimerized esters at room temperature, and in high yields, without formation of the side products that are generally observed. We have also shown that higher AlCl3 content favors the reaction towards Cannizzaro reaction, yet lower content favors Tishchenko reaction. Moreover, the presence of hydride donor alcohols in the reaction mixture completely directs the reaction towards the Meerwein–Ponndorf–Verley reaction. Graphic abstract: [Figure not available: see fulltext.].

Iron-catalyzed chemoselective hydride transfer reactions

Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc

supporting information, (2021/06/07)

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Process route upstream and downstream products

Process route

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
With hydrogenchloride; palladium on activated charcoal; Hydrogenation;
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
With sodium hydroxide; In methanol; water; at 240 ℃; for 2h; Autoclave; Inert atmosphere;
94%
With acetic acid; sodium nitrite; Diazotization;
methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 50 ℃; for 5h; under 7500.75 Torr; 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 ℃; for 16h; under 37503.8 Torr; Reagent/catalyst; Autoclave;
95%
With 2-(Aminomethyl)pyridine; RuCl2(norbornadiene)(pyridine); 1,3-bis-(diphenylphosphino)propane; potassium tert-butylate; hydrogen; In 2-methyltetrahydrofuran; at 100 ℃; for 16h; under 37503.8 Torr; Reagent/catalyst; Autoclave;
95%
With C18H28Br2N4Ru; potassium tert-butylate; hydrogen; In 1,4-dioxane; at 105 ℃; for 8h; under 22502.3 Torr;
95%
With methanol; sodium tetrahydroborate; sodium methylate; at 60 ℃; for 0.333333h;
93%
With C13H34BFeNOP2; hydrogen; In tetrahydrofuran; at 100 ℃; for 18h; under 22502.3 Torr; Autoclave; Inert atmosphere;
92%
With C32H36ClNO2P2Ru; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 120 ℃; for 12h; under 38002.6 Torr; Autoclave; Green chemistry;
92%
With lithium aluminium tetrahydride; In diethyl ether; for 4h; Ambient temperature;
85%
methyl 3-pyridinecarboxylate; With phenylsilane; potassium hydroxide; at 20 ℃; for 1.5h;
With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 1h;
85%
With C33H29FeMnN2O3P; hydrogen; potassium carbonate; at 90 ℃; for 16h; under 37503.8 Torr; Autoclave;
85%
With ethanol; potassium tert-butylate; C39H41FeMnN2O5P(1+)*Br(1-); In tert-butyl alcohol; at 100 ℃; for 22h; enantioselective reaction; Inert atmosphere; Schlenk technique;
84%
methyl 3-pyridinecarboxylate; With diethylzinc; lithium chloride; In tetrahydrofuran; hexane; at 20 ℃; for 6h; Inert atmosphere;
With sodium hydroxide; In tetrahydrofuran; hexane; water; at 20 ℃; for 8h; chemoselective reaction; Inert atmosphere;
80%
With sodium tetrahydroborate; In methanol; tert-butyl alcohol; for 2h; Heating;
78%
With sodium tetrahydroborate; In methanol; tert-butyl alcohol; Heating;
78%
With hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine]; tris(2,4-pentanedionato)ruthenium(III); In isopropyl alcohol; at 150 ℃; for 24h; under 112511 Torr; Product distribution / selectivity;
60.5%
With lithium aluminium tetrahydride; diethyl ether; at 0 ℃;
With hydrogen; C40H39BN2P2Ru; In tetrahydrofuran; Product distribution / selectivity;
methyl 3-pyridinecarboxylate; With iron (II) stearate; ethylenediamine; In toluene; at 20 ℃; for 0.0833333h; Inert atmosphere; Schlenk technique;
In toluene; at 100 ℃; for 40h; Inert atmosphere; Schlenk technique;
35 %Chromat.
With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); hydrogen; In tetrahydrofuran; at 120 ℃; for 19h; under 37503.8 Torr; Autoclave;
81 %Chromat.
With C23H29Cl2N2OPRuS; potassium tert-butylate; hydrogen; at 100 ℃; for 16h; under 37503.8 Torr; Inert atmosphere; Schlenk technique;
With C15H29MnNO3P2(1+)*Br(1-); potassium tert-butylate; hydrogen; In 1,4-dioxane; at 110 ℃; for 24h; under 22502.3 Torr; Inert atmosphere; Autoclave;
78 %Chromat.
With [RuCl2(N-heterocyclic carbene)(bis[2-(diphenylphosphino)ethyl]amine)]; potassium tert-butylate; hydrogen; In tetrahydrofuran; at 50 ℃; for 6h; Concentration; Schlenk technique;
99 %Chromat.
With dichlorido-bis[(2-diphenylphosphino)ethyl]amine-cobalt(II); hydrogen; sodium methylate; In 1,4-dioxane; at 120 ℃; for 24h; under 37503.8 Torr; Autoclave;
88 %Chromat.
With C43H42NOP3Ru; hydrogen; In 1,4-dioxane; methanol; at 130 ℃; for 17h; under 45004.5 Torr; Glovebox; Autoclave;
With aluminum (III) chloride; sodium tetrahydroborate; In tetrahydrofuran; toluene; at 0 - 5 ℃;
With HN(CH2CH2C3H3N2Mes)2Cl2; potassium tert-butylate; hydrogen; cobalt(II) chloride; In tetrahydrofuran; at 100 ℃; for 16h; under 22502.3 Torr; Autoclave; Glovebox;
94 %Chromat.
With aluminum (III) chloride; sodium tetrahydroborate; In tetrahydrofuran; toluene; at 0 - 5 ℃;
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
With C30H34Cl2N2P2Ru; potassium methanolate; hydrogen; In tetrahydrofuran; at 100 ℃; for 10h; under 38002.6 - 76005.1 Torr; 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 ℃; for 16h; under 37503.8 Torr;
80%
With Ca2; In toluene; at 80 ℃; for 0.5h;
73%
With ethanol; ruthenium(bis[2‐(ethylsulfanyl)ethyl]amine)(dichloro)(triphenylphosphine); potassium tert-butylate; In toluene; at 80 ℃; for 16h;
72%
With lithium aluminium tetrahydride; diethyl ether;
With n-butyllithium; [(1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene)FeCl2]; In hexane; toluene; at 100 ℃; for 20h; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;
7 %Chromat.
3-bromomethyl-pyridine; picrate

3-bromomethyl-pyridine; picrate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
With water; Zerlegen des entstandenen 3-Oxymethyl-pyridin-pikrats mit Natronlauge;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

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

1-Benzyl-1,4-dihydronicotinamide

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

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

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

Conditions
Conditions Yield
With magnesium(II) perchlorate; In acetonitrile; at 65 ℃;
70%
With magnesium(II) perchlorate; In acetonitrile; at 65 ℃; Product distribution;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

methyl methoxyacetate
6290-49-9

methyl methoxyacetate

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

methyl 3-pyridinecarboxylate
93-60-7

methyl 3-pyridinecarboxylate

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

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

Conditions
Conditions Yield
With sodium methylate; In toluene; for 2h; Heating;
10%
31%
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

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

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
Conditions Yield
With magnesium(II) perchlorate; water; In acetonitrile; at 65 ℃;
80%
With magnesium(II) perchlorate; water; In acetonitrile; at 65 ℃;
80%
With magnesium(II) perchlorate; water; In acetonitrile; at 65 ℃; Product distribution; water-sensitivity;
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
With LaCu0.67Si1.33; hydrogen; In methanol; at 120 ℃; for 9h; under 22502.3 Torr; Autoclave;
99%
With isopropyl alcohol; at 300 ℃; for 3h;
98%
With triethylamine; isopropyl alcohol; lithium bromide; at 20 ℃; for 48h;
97%
3-pyridinecarboxaldehyde; With tetrabutylammonium tricarbonylnitrosylferrate; tricyclohexylphosphine; In 1,4-dioxane; at 50 ℃; Inert atmosphere;
With water; sodium hydroxide; In 1,4-dioxane; methanol; at 20 ℃; for 1.5h; chemoselective reaction; Inert atmosphere;
97%
With alumina; isopropyl alcohol; at 180 ℃; for 0.666667h; under 11251.1 Torr; Microwave irradiation; Sealed tube;
95%
With magnesium(II) perchlorate; polymer-bound NADH (2a); In acetonitrile; benzene; at 80 ℃; for 120h; Further byproducts given;
94%
3-pyridinecarboxaldehyde; With polymethylhydrosiloxane; iron(II) acetate; tricyclohexylphosphine; In tetrahydrofuran; at 65 ℃; for 16h;
With sodium hydrogencarbonate; In tetrahydrofuran; methanol; at 0 - 20 ℃; Further stages.;
92%
With sodium dithionite; sodium hydrogencarbonate; In water; isopropyl alcohol; for 12h; Inert atmosphere; Reflux;
92%
With indium isopropoxide; isopropyl alcohol; for 1h; Inert atmosphere;
90%
With formic acid; In ethanol; at 80 ℃; for 12h; Catalytic behavior;
89%
With aluminum (III) chloride; triethylamine; isopropyl alcohol; In dichloromethane; at 20 ℃; for 24h;
88%
With sodiumsulfide nonahydrate; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;
88%
With methanol; sodium tetrahydroborate; at 0 - 20 ℃; for 8h;
86.3%
With bis(triphenylphosphine)copper(I) nitrate; hydrogen; 1,4-di(diphenylphosphino)-butane; sodium hydroxide; In ethanol; at 50 ℃; for 16h; under 37503.8 Torr; chemoselective reaction; Autoclave; Inert atmosphere;
85%
With silver(I) hexafluorophosphate; hydrogen; N-ethyl-N,N-diisopropylamine; XPhos; In water; at 100 ℃; for 24h; under 30003 Torr; Autoclave;
83%
With 1-benzyl-1-azonia-4-azabicyclo[2.2.2]octane tetrahydroborate; In tert-butyl alcohol; for 0.4h; Heating;
80%
With C36H42Cu6N12S6; isopropyl alcohol; sodium hydroxide; In isopropyl alcohol; at 100 ℃; for 36h; chemoselective reaction; Sealed tube; Inert atmosphere;
80%
With trimethylamine-N-oxide; sodium formate; C34H44FeN4O4(2+)*2I(1-); In water; at 80 ℃; for 24h; Inert atmosphere; Schlenk technique;
75%
With [Ir(2,2':6',2'’-terpyridine)(1,10-phenanthroline)Cl](PF6)2; sodium formate; In ethanol; water; at 100 ℃; for 0.25h; chemoselective reaction; Microwave irradiation;
73%
With trimethylamine-N-oxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; potassium formate; In ethanol; at 45 - 60 ℃; for 24h; Inert atmosphere; Schlenk technique;
73%
With samarium; copper(l) iodide; methacrylic acid methyl ester; potassium iodide; In tetrahydrofuran; at 20 ℃;
71%
With magnesium(II) perchlorate; 1-Benzyl-1,4-dihydronicotinamide; In acetonitrile; at 80 ℃;
70%
With 1,1'-bis-(diphenylphosphino)ferrocene; silver(I) hexafluorophosphate; tripropylsilane; N-ethyl-N,N-diisopropylamine; In water; at 100 ℃; for 24h;
69%
With hydrogen; triphenylphosphine; sodium hydroxide; bis(triphenylphosphino)copper(I) nitrate; In ethanol; at 50 ℃; for 16h; under 37503.8 Torr; Inert atmosphere;
60%
With hydrogen; sodium hydroxide; bis(triphenylphosphane)copper(I) nitrate; triphenylphosphine; In ethanol; at 50 ℃; for 16h; under 37503.8 Torr; Autoclave;
60%
With Grubbs catalyst first generation; potassium hydroxide; In 1,4-dioxane; at 80 ℃; for 20h;
51%
With sodium tetrahydroborate; In methanol; 1) 0 deg C, 0.5 h, 2) reflux, 1 h;
41%
With sodium hydroxide; thiourea dioxide; at 90 ℃; for 3h;
40%
3-pyridinecarboxaldehyde; With phenylsilane; (Ph2PPrPDI)Mn; at 25 ℃; for 0.0333333h; Glovebox; Inert atmosphere;
With sodium hydroxide; In water; at 25 ℃; for 2h; Glovebox;
27%
With sodium tetrahydroborate; In methanol; at 0 ℃;
25%
3-pyridinecarboxaldehyde; With phenylsilane; C74H74Mn2N6P4; at 25 ℃; for 0.0333333h; Glovebox; Inert atmosphere;
With sodium hydroxide; In water; at 25 ℃; for 2h; Glovebox; Inert atmosphere;
21%
With 4-aza-N-benzyl-bicyclo<2,2,2>octyl ammonium borohydride; In tert-butyl alcohol; for 0.4h; Yield given;
With sodium methylate; In methanol; for 3h; Yield given; Ambient temperature;
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate; In tetrahydrofuran; for 0.25h; Ambient temperature;
100 % Chromat.
With isopropyl alcohol; aluminum oxide; Ru(OH)x; at 89.85 ℃; for 24h; under 760 Torr;
50 % Chromat.
With ammonium hydroxide; titanium(III) chloride; In methanol; at 20 - 25 ℃; for 0.0833333h; pH=10 - 11;
100 % Spectr.
With isopropyl alcohol; at 89.84 ℃; for 24h; under 760.051 Torr; Inert atmosphere;
64 %Chromat.
With potassium phosphate; recombinant rat brain aldo-keto reductase R1B10; NADP; In methanol; Kinetics; Enzymatic reaction;
With glucose dehydrogenase; D-glucose; (R)-specific alcohol dehydrogenase from Candida maris IFO10003; NADH; In dimethyl sulfoxide; at 30 ℃; for 17h; pH=6.5; aq. phosphate buffer; Enzymatic reaction;
Multi-step reaction with 2 steps
1.1: [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu] / benzene-d6 / 4.3 h / 20 °C / Inert atmosphere; Sealed tube
2.1: hydrogenchloride; water / methanol; toluene / 1 h / Reflux; Inert atmosphere
2.2: Inert atmosphere
With hydrogenchloride; [HC{(Me)CN(2,6-iPr2C6H3)}2MgnBu]; water; In methanol; benzene-d6; toluene;
With sodium tetrahydroborate; In methanol; at 0 - 20 ℃; for 3h;
With rabbit 3-hydroxyhexobarbital dehydrogenase (AKR1C29); NADPH; In aq. phosphate buffer; ethyl acetate; at 37 ℃; for 0.5h; pH=7.4; Catalytic behavior; Kinetics; Enzymatic reaction;
With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 0.666667h; chemoselective reaction; Inert atmosphere; Schlenk technique; Glovebox;
With hydrogen; In hexane; at 60 ℃; for 18h; under 30003 Torr; chemoselective reaction; Autoclave;
With C36H103AlO4Si14; isopropyl alcohol; In neat (no solvent); at 50 ℃; for 24h; Glovebox; Schlenk technique;
> 99 %Spectr.
With potassium tert-butylate; In isopropyl alcohol; at 90 ℃; for 0.533333h; Flow reactor; Inert atmosphere;
With formaldehyd; tricarbonyl(η4-1,3-bis(trimethylsilyl)-4,5,6,7-tetrahydro-2H-inden-2-one)iron; water; sodium carbonate; In dimethyl sulfoxide; at 120 ℃; for 24h; Inert atmosphere; Sealed tube;
57 %Chromat.
With recombinant male golden hamster liver aldo-keto reductase AKR1C35; NADH; In aq. phosphate buffer; at 25 ℃; pH=7.4; Reagent/catalyst; Enzymatic reaction;
With Au0998Ag0002; hydrogen; triethylamine; at 90 ℃; for 24h; under 6080.41 Torr; chemoselective reaction;
99 %Spectr.
With sodium tetrahydroborate; In methanol;
With methanol; sodium tetrahydroborate; for 1h; Cooling with ice;
With methanol; sodium t-butanolate; In 1,4-dioxane; at 100 ℃; for 5h;
92 mg
Multi-step reaction with 2 steps
1: C19H44FeOP4Se / tetrahydrofuran / 2 h / 50 °C
2: sodium hydroxide; methanol / 50 °C
With methanol; C19H44FeOP4Se; sodium hydroxide; In tetrahydrofuran;
With sodium tetrahydroborate; In methanol;
With borane-ammonia complex; In methanol; water; at 20 ℃; for 0.0333333h;
> 99 %Chromat.
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

3-Methylpyridine
108-99-6

3-Methylpyridine

Conditions
Conditions Yield
With tin(IV) oxide; In isopropyl alcohol; at 300 ℃; for 0.5h;
5 % Chromat.
35 % Chromat.

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