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Cas Database

100-54-9

100-54-9

Identification

  • Product Name:3-Cyanopyridine

  • CAS Number: 100-54-9

  • EINECS:202-863-0

  • Molecular Weight:104.111

  • Molecular Formula: C6H4N2

  • HS Code:2933.33

  • Mol File:100-54-9.mol

Synonyms:Nicotinonitrile(8CI);3-Azabenzonitrile;3-Pyridinenitrile;3-Pyridylcyanide;3-Pyridylcarbonitrile;NSC 17558;Nicotinic acid nitrile;b-Cyanopyridine;3-Pyridinecarbonitrile;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn

  • Hazard Codes:Xn

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH318 Causes serious eye damage

  • 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

Supplier and reference price view more

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  • Manufacture/Brand:Usbiological
  • Product Description:3-Pyridinecarbonitrile
  • Packaging:100g
  • Price:$ 302
  • Delivery:In stock
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  • Manufacture/Brand:TRC
  • Product Description:3-Cyanopyridine
  • Packaging:1g
  • Price:$ 55
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Cyanopyridine >98.0%(GC)
  • Packaging:500g
  • Price:$ 70
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  • Manufacture/Brand:TCI Chemical
  • Product Description:3-Cyanopyridine >98.0%(GC)
  • Packaging:25g
  • Price:$ 18
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:3-Cyanopyridine 98%
  • Packaging:500 g
  • Price:$ 136
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Nicotinamide Impurity B Pharmaceutical Secondary Standard; Certified Reference Material
  • Packaging:100mg
  • Price:$ 428
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Pyridinecarbonitrile 98%
  • Packaging:5g
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:3-Pyridinecarbonitrile 98%
  • Packaging:100g
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Pyridine-3-carbonitrile 95%+
  • Packaging:1g
  • Price:$ 101
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:Pyridine-3-carbonitrile 95%+
  • Packaging:5g
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Relevant articles and documentsAll total 297 Articles be found

Metalloporphyrin catalyzed oxidation of N-hydroxyguanidines: A biomimetic model for the H2O2-dependent activity of nitric oxide synthase

Keseru, Gyoergy M.,Balogh, Gyoergy T.,Karancsi, Tamas

, p. 1775 - 1777 (2000)

A chemical model for the H2O2 promoted oxidation by nitric oxide synthase (NOS) has been developed. Biomimetic oxidations were carried out using H2O2 and tetrakis(perfluorophenyl)porphyrinato-iron(III) chloride (FeTPPF20) as a catalyst. Similarly to NOS our model system produces N(δ)-cyanoornithine, citrulline and NO from NOHA and did not oxidize arginine itself. Based on these results we propose a peroxide shunt to be involved in the catalytic cycle of NOS. To the best of our knowledge this is the first chemical system that semiquantitatively mimics NOS activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

Rhenium(VII) oxo complexes as extremely active catalysts in the dehydration of primary amides and aldoximes to nitriles

Ishihara, Kazuaki,Furuya, Yoshiro,Yamamoto, Hisashi

, p. 2983 - 2986 (2002)

An economical and environmentally benign process for the preparation of nitriles by the dehydration of primary amides and aldoximes is catalyzed by rhenium(VII) oxo complexes such as perrhenic acid and trimethylsilylperrhenate (see scheme). The reaction proceeds at azeotropic reflux (with the removal of water) under essentially neutral conditions.

-

Aumann,Deady

, p. 32 (1973)

-

1-Cyanoimidazole as a mild and efficient electrophilic cyanating agent

Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Hamilton, Gregory S.

, p. 795 - 797 (2000)

formula presented A mild and high-yielding cyanating reaction of amine, sulfur, and carbanion nucleophiles is reported here using 1-cyanoimidazole as an electrophilic cyanating agent.

Dispersion and 3-Picoline Ammonoxidation Investigation of V2O5/α-Al2O3 Catalysts

Reddy, Benjaram Narasimha,Reddy, Benjaram Mahipai,Subrahmanyam, Machiraju

, p. 1649 - 1655 (1991)

The effect of changing the precursor on the dispersion and 3-picoline ammonoxidation activity of various α-Al2O3 supported V2O5 catalysts has been investigated by the techniques of X-ray fluorescence, AES, SEM, EPR, XRD, oxygen chemisorption at 195 K and

-

Woodward et al.

, p. 540,542 (1944)

-

Iodine/aqueous NH4OAc: An improved reaction system for direct oxidative conversion of aldehydes and alcohols into nitriles

Ren, Yi-Ming,Zhu, Yi-Zhong,Cai, Chun

, p. 18 - 19 (2008)

A convenient method for direct oxidative conversion of aldehydes and alcohols into nitriles has been developed by using the inexpensive and environmentally friendly reagent I2/aqueous NH4OAc. The aqueous NH4OAc as a non-toxic cyanide source is more eco-friendly than aqueous ammonia, because gaseous ammonia evaporates easily from aqueous ammonia but not from aqueous NH4OAc.

A Selective and Mild Oxidation of Primary Amines to Nitriles with Trichloroisocyanuric Acid

Chen, Fen-Er,Kuang, Yun-Yan,Dai, Hui-Fang,Lu, Liang,Huo, Ming

, p. 2629 - 2631 (2003)

An efficient and highly selective method for the oxidative conversion of primary amines to the corresponding nitriles using trichloroisocyanuric acid in the presence of catalytic TEMPO under mild reaction conditions is described. Other functional groups such as C,C-double bonds, benzyloxy etc. were found to be unaffected under the reaction conditions. This procedure provides a new entry to the synthesis of various aliphatic, aromatic and heterocyclic nitriles in excellent yield.

Hydrothermal synthesis of microporous W-V-O as an efficient catalyst for ammoxidation of 3-picoline

Goto, Yoshinori,Shimizu, Ken-Ichi,Murayama, Toru,Ueda, Wataru

, p. 118 - 122 (2016)

W-V complex metal oxide (W-V-O) was prepared by hydrothermal synthesis method. Characterization by XRD, XPS, ICP-AES, N2 adsorption, and STEM showed that W-V-O had a layered structure with micropore. W-V-O was tested for the vapor phase ammoxid

Potassium hexacyanoferrate(II) - A new cyanating agent for the palladium-catalyzed cyanation of aryl halides

Schareina, Thomas,Zapf, Alexander,Beller, Matthias

, p. 1388 - 1389 (2004)

A new advantageous cyanating agent, potassium hexacyanoferrate(II), is described for the palladium-catalyzed cyanation of aryl halides. All cyanide ions on the iron(II) center can be transferred to the aryl halide using palladium(II) acetate and dppf as the catalyst. Under optimized reaction conditions good yields of benzonitriles and unprecedented catalyst productivities are observed.

A simple method for the synthesis of nitriles from primary amides under neutral conditions

Bose, D. Subhas,Sunder, K. Sugnana

, p. 4235 - 4239 (1999)

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) is a very useful reagent for the preparation of nitriles in good yields under neutral conditions.

TrocCl mediated efficient synthesis of nitriles from primary amides

Bose, D. Subhas,Kumar, K. Kiran

, p. 3047 - 3052 (2000)

In order to establish a rapid conversion method of primary amides to nitriles, various types of carboxamides were treated with 2,2,2- trichloroethyl chloroformate and Et3N, as a dehydrating agent to obtain the desired nitriles in 82-95% yields.

A convenient procedure for the palladium-catalyzed cyanation of aryl halides

Sundermeier, Mark,Zapf, Alexander,Beller, Matthias

, p. 1661 - 1664 (2003)

A useful source of cyanide for the palladium-catalyzed cyanation of aryl halides is acetone cyanohydrin (see scheme; dpppe = 1,5-bis(diphenylphosphanyl) pentane, tmeda = N,N,N′,N′-tetramethylethylenediamine). The key to the success of the reaction is the slow dosage of the cyanation reagent to the reaction mixture to prevent the deactivation of the palladium catalyst caused by excess cyanide ions in solution.

Aryl chlorothionoformate: A new versatile reagent for the preparation of nitriles and isonitriles under mild conditions

Subhas Bose,Ravinder Goud

, p. 747 - 748 (1999)

Aryl chlorothionoformate is a very useful reagent for the preparation of nitriles and isonitriles in high yields under essentially neutral conditions.

Transformation of alkaloid anabasin into nicotinonitrile

Iskakova,Kagarlitskii

, p. 656 - 658 (1999)

The possibility of preparing nicotinonitrile from the natural alkaloid anabasin via oxidative ammonolysis using a vanadium - titanium catalyst (V2O5:TiO2 = 1.0:0.5) is examined.

Sulfate additives generate robust and highly active palladium catalysts for the cyanation of aryl chlorides

Shevlin, Michael

, p. 4833 - 4836 (2010)

The use of sulfate additives such as H2SO4 greatly increases the reactivity of palladium catalysts for the cyanation of aryl and heteroaryl chlorides and renders them more robust toward adventitious air. Using this method, a wide variety of aromatic and heteroaromatic nitriles were prepared in high yield.

Triphenylphosphine-iodine: An efficient reagent system for the synthesis of nitriles from aldoximes

Venkat Narsaiah,Sreenu,Nagaiah

, p. 137 - 140 (2006)

A wide range of aldoximes were smoothly converted to the corresponding nitriles with triphenylphosphine-iodine. Copyright Taylor & Francis LLC.

Development of Pd/C-catalyzed cyanation of Aryl halides

Yu, Hannah,Richey, Rachel N.,Miller, William D.,Xu, Jiansheng,May, Scott A.

, p. 665 - 668 (2011)

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale.

Rapid cyanation of aryl iodides in water using microwave promotion

Arvela, Riina K.,Leadbeater, Nicholas E.,Torenius, Hanna M.,Tye, Heather

, p. 1119 - 1121 (2003)

We show that using water in conjunction with microwave heating it is possible to prepare aryl nitriles from the corresponding aryl iodides rapidly and in high yield without the need for a palladium catalyst.

New method of obtaining nicotinic acid from 2-methyl-5-ethylpyridine

Suvorov,Yakovlev,Kagarlitskii,Guseinov,Kutzhanov,Kan,Lebedeva

, p. 495 - 497 (1977)

-

Studies on the ammoxidation of N heterocyclic compounds. I. Vapor phase ammoxidation of 3 picoline (Japanese)

Okada,Morita,Miwa

, p. 1443 - 1450 (1972)

-

A SIMPLE REDUCTION OF AROMATIC HETEROCYCLIC N-OXIDES WITH HEXAMETHYLDISILANE: REACTIONS WITH HEXAMETHYLDISILANE AND FLUORIDE ION I

Vorbrueggen, Helmut,Krolikiewicz, Konrad

, p. 5337 - 5338 (1983)

Aromatic heterocyclic N-Oxides are readily reduced at room temperature by hexamethyldisilane in the presence of fluoride ion in THF.

Preparation of nitriles from primary amides under Swern oxidation conditions

Nakajima, Noriyuki,Ubukata, Makoto

, p. 2099 - 2102 (1997)

In order to establish a mild conversion method of primary amides to nitriles, various types of carboxamides were heated under Swern oxidation conditions, (COCl)2-DMSO and Et3N, as a dehydrating agent to obtain desired nitriles in 75-96% yields.

The Semmler-Wolff Aromatization and Schmidt Reaction Applied to Some Pyridopyrazolobenzotriazines

Kocevar, Marijan,Stanovnik, Branko,Tisler, Miha

, p. 597 - 604 (1988)

Pyridopyrazolobenzotriazin-4(1H)ones were transformed via their oximes in a Semmler-Wolff aromatization process in the tetracyclic heteroaromatic amines 4 or by Schmidt reaction into a mixture of the same amine 4 and a ring enlarg

A facile microwave-assisted palladium-catalyzed cyanation of aryl chlorides

Chobanian, Harry R.,Fors, Brett P.,Lin, Linus S.

, p. 3303 - 3305 (2006)

We report an efficient method for the preparation of aryl nitriles from aryl chlorides under either microwave assisted or thermal conditions. A catalyst system comprising tris(dibenzylidene acetone)dipalladium (Pd2(dba)3) and 2-(2′,6′-dimethoxybiphenyl)dicyclohexylphosphine (S-Phos) is shown to effectively promote cyanation of various aryl chlorides with Zn(CN)2 as the cyanide source.

Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones

Ano, Yusuke,Chatani, Naoto,Higashino, Masaya,Yamada, Yuki

supporting information, p. 3799 - 3802 (2022/04/07)

The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles involving the cleavage of an N-N bond is reported. The use of N-heterocyclic carbene as a ligand is essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones are applicable to this transformation, which gives aryl or alkenyl nitriles, respectively.

Bis-morpholinophosphorylchloride, a novel reagent for the conversion of primary amides into nitriles

Rao, P. Purnachandra,Nowshuddin, Shaik,Jha, Anjali,Rao, B. Leela Maheswara,Divi, Murali K.,Rao

supporting information, (2021/01/21)

Bis-morpholinophosphorylchloride (Bmpc), in the presence of a base, is an efficient dehydrating agent for both aromatic and aliphatic primary amides, and gives corresponding nitriles under mild conditions in god yields and purity. During the reaction the enantiomeric integrity remains intact.

METHOD FOR PRODUCING NITRILE

-

Paragraph 0080; 0090, (2021/02/05)

The present invention provides a method of producing a nitrile from a primary amide, characterized in that the primary amide is subjected to a dehydration reaction in a supercritical fluid in the presence of an acid catalyst. The present invention achieves the object of reducing the corrosion of a reactor and the thermal decomposition of raw materials, as well as provides the effect of improving the reaction rate and nitrile selectivity.

Process route upstream and downstream products

Process route

3-pyridinealdoxime
1193-92-6

3-pyridinealdoxime

Conditions
Conditions Yield
With thionyl chloride; polyvinylpyrrolidone; In dichloromethane; at 20 ℃; for 0.25h;
95%
With 1,4-diaza-bicyclo[2.2.2]octane; trichlorophosphate; In dichloromethane; at 20 ℃; for 0.0833333h;
94%
With aluminium trichloride; sodium iodide; In acetonitrile; for 2.5h; Heating;
92%
With 8-bromocaffeine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; for 0.0166667h; chemoselective reaction; Microwave irradiation;
92%
With oxalyl dichloride; Tropone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 50 ℃; for 0.0833333h; Schlenk technique; Inert atmosphere;
92%
With trifluoromethylsulfonic anhydride; triethylamine; In tetrahydrofuran; at 0 ℃; for 1.5h;
91%
With acetonitrile; for 3h; Reflux; Green chemistry;
90%
With gallium(III) trichloride; In acetonitrile; at 80 ℃; for 6h; Reagent/catalyst; Inert atmosphere;
90%
With 1,8-diazabicyclo[5.4.0]undec-7-ene; N-tosylimidazole; In N,N-dimethyl-formamide; for 0.416667h; Reflux;
89%
With oxalyl dichloride; 2,3-bis(4-methoxyphenyl)cyclopropenone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h; Reflux;
88%
With triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;
87%
With polystyrene supported chloro diphenylphsophonium chloride; In chloroform; at 60 ℃; for 18h;
86%
With Nonafluorobutanesulfonyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.166667h;
86%
With pyrographite; methanesulfonyl chloride; at 100 ℃; for 0.25h;
85%
With eosin; carbon tetrabromide; N,N-dimethyl-formamide; In acetonitrile; at 25 ℃; for 16h; Irradiation; Inert atmosphere;
85%
With acetyl chloride; zinc(II) oxide; for 0.416667h; Heating;
84%
With iodine; triphenylphosphine; In dichloromethane; at 20 ℃; for 4h;
84%
With trifluoromethylsulfonic anhydride; triethylamine; triphenylphosphine; In dichloromethane; at 0 ℃; for 0.166667h;
84%
With oxalyl dichloride; Triphenylphosphine oxide; In ethyl acetate; at 20 ℃; for 1h;
77%
With S,S-dimethyl dithiocarbonate; triethylamine; In 1,4-dioxane; at 90 ℃;
76%
With aluminium trichloride; potassium iodide; In water; acetonitrile; at 80 ℃; for 8h;
69%
With bis(trichloromethyl) carbonate; In chloroform; at 20 ℃;
Multi-step reaction with 2 steps
1: triethylamine; silica gel / CHCl3 / 20 °C
2: 0 h / microwave irradiation
With silica gel; triethylamine; In chloroform;
With chloro-trimethyl-silane; at 90 ℃; for 3h;
73 %Chromat.
3-Chloropyridine
626-60-8

3-Chloropyridine

potassium ferrocyanide

potassium ferrocyanide

Conditions
Conditions Yield
With sodium carbonate; palladium diacetate; In 1-methyl-pyrrolidin-2-one; Hexadecane; at 160 ℃; for 16h;
95%
With sodium carbonate; cyclopalladated ferrocenylimine tricyclohexylphosphine; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 18h;
82%
With sodium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 16h;
57%
With tetra(adamantyl)biphosphine; palladium diacetate; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 16h; Inert atmosphere;
66 %Chromat.
3-pyridinecarboxaldehyde
500-22-1

3-pyridinecarboxaldehyde

Conditions
Conditions Yield
With ammonium sulfate; sodium carbonate; sulfur; In dimethyl sulfoxide; at 120 ℃; for 10h; Sealed tube;
99%
With ammonia; oxygen; In ethanol; water; for 1.5h; Reflux;
94%
With hydroxylamine hydrochloride; pyrographite; methanesulfonyl chloride; at 100 ℃; for 1h;
92%
With hydroxylamine hydrochloride; methanesulfonyl chloride; In neat (no solvent); at 70 ℃; for 1h;
91%
With aluminum oxide; hydroxylamine; methanesulfonyl chloride; at 100 ℃; for 0.583333h;
90%
With ammonium hydroxide; at 25 ℃; for 5h;
90%
With hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 120 ℃; for 2h; Green chemistry;
90%
With S,S-Diphenylsulfilimine; In benzene;
87%
With ammonium acetate; iodine; at 70 ℃; for 0.333333h;
87%
With hydroxylamine hydrochloride; In glycerol; at 90 ℃; for 7h; Green chemistry;
86%
3-pyridinecarboxaldehyde; With ammonia; In water; at 20 ℃; for 0.166667h;
With tetra-N-butylammonium tribromide; In water; at 20 ℃; for 8h;
84%
With oxygen; copper; ammonium chloride; In pyridine; 1.) 20 deg C, 15 h, 2.) 60 deg C, 24 h;
83%
3-pyridinecarboxaldehyde; With ammonium hydroxide; potassium iodide; In tetrahydrofuran; at 20 ℃; for 0.166667h;
With chloroamine-T; In tetrahydrofuran; at 20 ℃; for 8h;
81%
With (2-hydroxyethyl)trimethylazanium urea chloride; hydroxylamine hydrochloride; In neat (no solvent); at 140 ℃; for 0.166667h; Microwave irradiation; Green chemistry;
81%
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In dichloromethane; at 20 ℃; for 22h;
80%
With carbon tetrabromide; hydroxylamine hydrochloride; triethylamine; 1-butyl-2,3-dimethylimidazolium diphenyl(3-sulfonatophenyl)phosphine; In acetonitrile; at 20 ℃;
80%
With [2,2]bipyridinyl; 4-sulfantooxy-2,2,6,6-tetramethylpiperidinyloxy; ammonia; copper(II) bis(trifluoromethanesulfonate); sodium hydroxide; In water; acetonitrile; at 40 ℃; for 16h;
78%
With ammonium acetate; phenyltrimethylammonium tribromide; In acetonitrile; at 20 ℃; for 17h;
78%
With manganese(IV) oxide; ammonia; magnesium sulfate; In tetrahydrofuran; isopropyl alcohol; at 20 ℃; for 17h;
76%
With tin(II) chloride dihdyrate; hydroxylamine hydrochloride; sodium hydrogencarbonate; In acetonitrile; at 80 ℃; for 48h;
76%
With Envirocat EPZGR; hydroxylamine hydrochloride; triethylamine; for 0.05h; Irradiation;
74%
With 1-methyl-pyrrolidin-2-one; hydroxylamine hydrochloride; at 100 ℃; for 0.25h; microwave irradiation;
70%
With hydroxylamine hydrochloride; In 1-methyl-pyrrolidin-2-one; for 0.0833333h; Heating;
70%
With O-(diphenylphosphinyl)hydroxylamine; trifluoroacetic acid; In toluene; at 20 - 95 ℃; for 15.75h; chemoselective reaction;
64%
3-pyridinecarboxaldehyde; With hydroxylamine hydrochloride; triethylamine; In acetonitrile; for 2h; Heating;
With oxalyl dichloride; In acetonitrile; for 0.333333h; Heating;
60%
With ammonia; oxygen; copper(II) nitrate; In water; dimethyl sulfoxide; at 80 ℃; for 5h; under 760.051 Torr;
11%
Multi-step reaction with 2 steps
1: NH2OH*HCl; ZnO / Heating
2: 84 percent / CH3COCl; ZnO / 0.42 h / Heating
With hydroxylamine hydrochloride; acetyl chloride; zinc(II) oxide;
Multi-step reaction with 2 steps
1: NH2OH*HCl; Et3N / CHCl3 / 0 - 20 °C
2: bis(trichloromethyl) carbonate / CHCl3 / 20 °C
With bis(trichloromethyl) carbonate; hydroxylamine hydrochloride; triethylamine; In chloroform;
Multi-step reaction with 2 steps
1: 100 percent / NH2OH*HCl; pyridine / ethanol
2: 88 percent / [RuCl2(p-cymene)]2; 4 Angstroem molecular sieves / acetonitrile / 1 h / 80 °C
With pyridine; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; 4 A molecular sieve; hydroxylamine hydrochloride; In ethanol; acetonitrile;
With ammonia; iodine; In tetrahydrofuran; water; at 20 ℃;
Multi-step reaction with 2 steps
1: triethylamine; hydroxylamine hydrochloride / dichloromethane / 16 h / 20 °C / Inert atmosphere
2: ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate; triethylamine / ethyl acetate / 1 h / 20 °C / Inert atmosphere
With hydroxylamine hydrochloride; triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In dichloromethane; ethyl acetate;
With ammonia; oxygen; In tert-Amyl alcohol; at 40 ℃; for 24h; under 750.075 Torr; Green chemistry;
95 %Chromat.
Multi-step reaction with 2 steps
1: sodium acetate; hydroxylamine hydrochloride / water; ethanol / Reflux
2: Tropone; oxalyl dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.08 h / 50 °C / Schlenk technique; Inert atmosphere
With oxalyl dichloride; Tropone; hydroxylamine hydrochloride; sodium acetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In ethanol; water; acetonitrile;
3-hydroxymethylpyridin
100-55-0

3-hydroxymethylpyridin

Conditions
Conditions Yield
3-hydroxymethylpyridin; With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tert-butylhypochlorite; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
With ammonia; iodine; In dichloromethane; water; at 20 ℃; for 2h; Inert atmosphere;
99%
With ammonia; oxygen; In tert-Amyl alcohol; water; at 100 ℃; for 4h; under 3750.38 Torr; Autoclave; High pressure;
99%
With potassium phosphate; ammonium formate; In acetonitrile; at 115 ℃; for 16h; Sealed tube; Green chemistry;
91%
With ammonium hydroxide; oxygen; at 90 ℃; for 6h;
90%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; oxygen; copper(II) nitrate; In water; dimethyl sulfoxide; at 80 ℃; for 5h; under 760.051 Torr;
89%
With ammonia; oxygen; In 1,4-dioxane; for 3h; Reflux;
89%
With ammonia; oxygen; In ethanol; water; for 3h; Reflux;
89%
With ammonium hydroxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [{(MeOH)Cu(OAc)}(μ-k2:k1-2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)acetic acid(-H))]2*0.5H2O; tetraethylammonium iodide; oxygen; potassium carbonate; In water; at 60 ℃; for 24h; under 760.051 Torr;
85%
With ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In water; for 24h; Reflux; Green chemistry;
85%
With ammonium hydroxide; manganese sesquioxide; oxygen; at 130 ℃; for 48h; under 11251.1 Torr; Autoclave;
85.8%
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; ammonium acetate; In water; acetonitrile; at 20 ℃; for 0.75h;
80%
With 1,4-diaza-bicyclo[2.2.2]octane; TEMPOL; ammonia; copper(l) chloride; In water; acetonitrile; at 20 ℃; for 24h;
78%
With ammonium hydroxide; iodine; at 60 ℃; for 3h;
77%
With ammonium hydroxide; iodine; at 60 ℃; for 3h;
77%
With 2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; In ethanol; at 20 ℃; for 24h;
75%
With ammonium bicarbonate; In 1,3,5-trimethyl-benzene; at 140 ℃; for 4h; under 4560.31 Torr;
72%
With ammonium hydroxide; sodium periodate; potassium iodide; at 60 ℃; for 3h;
64%
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 130 ℃; for 48h; under 3750.38 Torr;
58%
3-hydroxymethylpyridin; With sodium bromate; ammonia; acetic acid; In water; at 95 ℃; for 2h;
With sodium hydrogencarbonate; In water; ethyl acetate;
43.3%
With ammonium hydroxide; oxygen; at 50 ℃; for 12h; under 750.075 Torr; Sealed tube; Green chemistry;
> 99 %Chromat.
With ammonium hydroxide; periodic acid; potassium iodide; at 60 ℃; for 131490h; Sealed tube; Green chemistry;
45 %Chromat.
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 120 ℃; for 20h; under 3750.38 Torr;
98 %Chromat.
Conditions
Conditions Yield
With N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; copper(l) chloride; In toluene; at 100 ℃; for 24h;
99%
With 3 A molecular sieve; at 150 - 500 ℃; for 0.666667h; under 0.001 Torr; Pyrolysis;
98%
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide; In acetonitrile; at 20 ℃; for 0.166667h;
96%
With triethylamine; 2,2,2-Trichloroethyl chloroformate; In dichloromethane; at 0 - 20 ℃;
95%
With trifluoromethylsulfonic anhydride; triethylamine; In dichloromethane; for 0.316667h; Ambient temperature;
93%
With uranyl nirate hexahydrate; N-methyl-N-trimethylsilyl-2,2,2-trifluoroacetamide; In 1,2-dimethoxyethane; at 100 ℃; for 24h;
93%
With methoxycarbonylsulfamoyl-triethylammmonium hydroxide; In tetrahydrofuran;
92%
With pyridine; aryl chlorothionoformate; In dichloromethane; for 6h; Ambient temperature;
92%
With di(n-butyl)tin oxide; In toluene; Heating;
92%
With pyridine; phenyl chloroformate; In dichloromethane; at 0 - 20 ℃;
92%
With ethyl phosphodichloridite; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;
90%
With oxalyl dichloride; triethylamine; In dimethyl sulfoxide; acetonitrile; at 20 ℃; for 0.666667h;
90%
With di-morpholin-4-yl-phosphinic acid chloride; triethylamine; In dichloromethane; at 20 ℃; for 3.5h;
90%
With oxalyl dichloride; 2,3-bis(4-methoxyphenyl)cyclopropenone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4.5h; Reflux;
89%
at 325 ℃; for 1h; Temperature;
85%
With di(n-butyl)tin oxide; In toluene; Heating;
84%
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;
82%
With pyridine; <(chlorosulfinyloxy)methylene>dimethylammonium chloride; In dichloromethane; for 4h; Ambient temperature;
80%
With triethylamine; trifluoroacetyl chloride; In dichloromethane; for 1h; Ambient temperature;
77%
at 600 - 650 ℃;
77%
With C20H25Cl2CoN3; sodium triethylborohydride; In toluene; at 60 ℃; for 6h; Inert atmosphere;
77%
nicotinamide; With N-methylbenzamide; phenylsilane; C28H18ClMnN2O2; potassium tert-butylate; In tetrahydrofuran; at 50 ℃; Inert atmosphere; Glovebox; Sealed tube;
With sodium hydroxide; In tetrahydrofuran; for 2h; Inert atmosphere; Glovebox; Sealed tube;
Glovebox; Inert atmosphere;
72%
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine; In dichloromethane; at 20 ℃; for 18h;
65%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;
64%
nicotinamide; With C39H45N2; In acetonitrile; at 20 ℃; Schlenk technique; Glovebox; Inert atmosphere;
With phenylsilane; In acetonitrile; at 20 ℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;
52%
With trimethylsilylphosphate; for 0.0833333h; Heating;
49%
With triethylamine; ethanaminium,N-(difluoro-λ4-sulfanylidene)-N-ethyl-,tetrafluoroborate; In ethyl acetate; at 20 ℃; for 1h; Inert atmosphere;
45%
With phosphorus pentaoxide; In toluene; for 2h; Heating;
23%
With thionyl chloride; at 100 ℃;
With phosphorus pentaoxide; durch Destillation;
With phosphorus pentoxide; Destillation unter vermindertem Druck;
With pyridine; trichlorophosphate;
With pyridine; benzenesulfonyl chloride;
With ammonium sulfamate salt; at 200 ℃;
at 375 ℃; Erhitzen unter vermindertem Druck;
With phosphorus pentaoxide; under 25 Torr; bei der Destillation;
With phosphorus pentoxide;
With ammonium sulfamate; at 150 - 200 ℃; for 11h;
With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1) CH2Cl2, -78 deg C, 15 min, 2) CH2Cl2, -78 deg C to RT;
Multi-step reaction with 2 steps
1: triethylamine
2: 100 percent Spectr. / triethylamine / FeCl3 / 0.5 h / 80 °C
With triethylamine; iron(III) chloride;
With iron(III) oxide; ammonia; In tert-butyl alcohol; at 235 ℃; for 1h; under 38253.8 Torr; Autoclave; Inert atmosphere;
With phenylsilane-d3; C36H48F6N6NiO5S2; In acetonitrile; at 80 ℃; for 12h; Inert atmosphere; Schlenk technique;
97 %Chromat.
3-Aminomethylpyridine
3731-52-0

3-Aminomethylpyridine

Conditions
Conditions Yield
With aluminum oxide; In N,N-dimethyl-formamide; at 120 ℃; for 12h; Inert atmosphere;
93%
With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide; In dimethyl sulfoxide; at 100 ℃; for 24h;
92%
With potassium hydroxide; nickel copper formate; (Bu4N)2S2O8; In dichloromethane; at 20 ℃; for 12h;
90%
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; free radical; trichloroisocyanuric acid; In dichloromethane; at 10 ℃; for 2h;
89%
With tris(2,2’-bipyridine)dichlororuthenium(II) hexahydrate; oxygen; copper(I) bromide; lithium tert-butoxide; In dimethyl sulfoxide; at 20 ℃; for 18h; Schlenk technique; Irradiation;
63%
With oxygen; RuHAP; In monoethylene glycol diethyl ether; at 120 ℃; for 16h;
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 110 ℃; for 15h; under 2250.23 Torr; Autoclave; Green chemistry;
94 %Chromat.
With ammonium hydroxide; oxygen; In tert-Amyl alcohol; at 110 ℃; for 15h; under 1500.15 Torr; Autoclave; Green chemistry;
92 %Chromat.
3-Bromopyridine
626-55-1,163928-56-1

3-Bromopyridine

potassium ferrocyanide

potassium ferrocyanide

Conditions
Conditions Yield
With dichloro[bis{1-(dicyclohexylphosphanyl)piperidine}]palladium; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 18h; Inert atmosphere;
91%
With caesium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 8h; Inert atmosphere; Sealed tube;
91%
With 5,5’-(1,2-phenylene)bis(1H-tetrazole); copper(I) iodide; caesium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 130 ℃; for 10h; Inert atmosphere;
90%
With copper(II) acetate monohydrate; sodium carbonate; 1,3-phenylene-bis-(1H)-tetrazole; potassium iodide; In N,N-dimethyl-formamide; at 130 ℃; for 8h; Inert atmosphere;
89%
With 1-methyl-pyrrolidin-2-one; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; sodium carbonate; at 120 ℃; for 12h; Schlenk technique; Inert atmosphere;
83%
With sodium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 7h;
79%
With copper(l) iodide; per-6-amino-β-cyclodextrin; sodium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 130 ℃; for 36h; Microwave irradiation;
69%
1-Butylimidazole; copper(l) iodide; In toluene; at 160 ℃; for 16h;
82 % Chromat.
With 1-Butylimidazole; copper(l) iodide; In toluene; at 160 ℃; for 16h; Inert atmosphere;
82 %Chromat.
With hydrogen tetrachloropalladate; sodium phosphate; In N,N-dimethyl-formamide; at 120 ℃; for 16h; Inert atmosphere;
61 %Spectr.
With sodium carbonate; In N,N-dimethyl-formamide; at 120 ℃; for 1h; Inert atmosphere; Green chemistry;
With tetra(adamantyl)biphosphine; palladium diacetate; sodium carbonate; In 1-methyl-pyrrolidin-2-one; at 120 ℃; for 16h; Inert atmosphere;
40 %Chromat.
With sodium carbonate; In N,N-dimethyl-formamide; at 120 ℃;
2-chloro-3-pyridinecarbonitrile
6602-54-6

2-chloro-3-pyridinecarbonitrile

Conditions
Conditions Yield
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In methanol; at 20 ℃; for 2h; under 760.051 Torr; chemoselective reaction; Sealed tube;
80%
6-chloronicotinonitrile
33252-28-7

6-chloronicotinonitrile

Conditions
Conditions Yield
With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In methanol; at 20 ℃; for 2h; under 760.051 Torr; chemoselective reaction; Sealed tube;
80%
3-pyridinecarboxylic acid ethyl ester
614-18-6

3-pyridinecarboxylic acid ethyl ester

Conditions
Conditions Yield
3-pyridinecarboxylic acid ethyl ester; With sodium diisobutyl-tert-butoxyaluminium hydride; In tetrahydrofuran; at 0 ℃; for 4h; Inert atmosphere;
With ammonia; iodine; In tetrahydrofuran; water; at 0 - 20 ℃; for 3h;
75%
Multi-step reaction with 2 steps
1: ammonia
2: phosphorus pentoxide / durch Destillation
With phosphorus pentaoxide; ammonia;
Multi-step reaction with 2 steps
1: aqueous ammonia
2: phosphorus pentoxide / 25 Torr / bei der Destillation
With phosphorus pentaoxide; ammonium hydroxide;

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