Conditions | Yield |
---|---|
With manganese(IV) oxide; silica gel In hexane for 8h; Heating; | 100% |
With manganese(IV) oxide; silica gel In chlorobenzene for 5h; Heating; | 100% |
With water at 30℃; for 5.5h; Large scale reaction; Enzymatic reaction; | 99% |
(1H-benzo[d][1,2,3]triazol-1-yl)(pyridin-3-yl)methanone
nicotinamide
Conditions | Yield |
---|---|
With ammonium hydroxide In tetrahydrofuran; ethanol at 20℃; for 4h; | 100% |
Conditions | Yield |
---|---|
With manganese(IV) oxide at 130℃; under 4560.31 Torr; for 3h; | 98% |
With (carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II); potassium tert-butylate In tert-butyl alcohol at 70℃; for 12h; | 96% |
With oxygen; potassium carbonate; copper(I) bromide In water; dimethyl sulfoxide at 140℃; under 760.051 Torr; for 6h; | 90% |
Conditions | Yield |
---|---|
With C55H45ClN5P2Ru(1+)*Cl(1-); hydroxylamine hydrochloride; sodium carbonate In water at 110℃; for 12h; Sealed tube; | 95% |
With C17H17BrClN2RuSe(1+)*F6P(1-); hydroxylamine hydrochloride; sodium hydroxide In toluene at 100℃; for 12h; Reagent/catalyst; Solvent; Temperature; | 91% |
With hydroxylamine hydrochloride; methanesulfonyl chloride In neat (no solvent) at 70℃; for 3.5h; | 90% |
Conditions | Yield |
---|---|
With thionyl chloride; dihydrogen peroxide In ethanol at 25℃; for 0.0166667h; | 94% |
With chloro-trimethyl-silane; dihydrogen peroxide In ethanol; water at 25℃; for 0.133333h; regioselective reaction; | 92% |
With sodium hydroxide; copper(l) chloride In water; acetonitrile at 25℃; for 0.166667h; | 88% |
With nitrosonium tetrafluoroborate In dichloromethane for 8h; Ambient temperature; | 74% |
With potassium superoxide; 18-crown-6 ether for 1h; Ambient temperature; | 71% |
Conditions | Yield |
---|---|
With titanium tetrachloride; tin(ll) chloride In diethyl ether for 0.5h; Ambient temperature; | 93% |
With indium; ammonium chloride In methanol; water for 5h; Reduction; Heating; | 91% |
With molybdenum(V) chloride; sodium iodide In acetonitrile at 20℃; for 2h; | 91% |
Conditions | Yield |
---|---|
With Aplysia cyclase at 23℃; | A n/a B 92% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; N-methoxylamine hydrochloride; sodium iodide; palladium dichloride In acetonitrile at 90℃; under 3800.26 Torr; for 8h; Autoclave; Inert atmosphere; | 92% |
With 1,4-diaza-bicyclo[2.2.2]octane; palladium 10% on activated carbon; ammonium carbamate; potassium iodide In acetonitrile at 90℃; for 8h; Autoclave; Green chemistry; | 85% |
Conditions | Yield |
---|---|
With potassium phosphate; palladium diacetate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In water; dimethyl sulfoxide at 120℃; for 20h; Inert atmosphere; Sealed tube; | 92% |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ammonia; oxygen In water; N,N-dimethyl-formamide at 80℃; under 1520.1 Torr; for 5h; Green chemistry; | 91% |
With ammonium hydroxide; cryptomelane; oxygen In 1,4-dioxane at 130℃; under 2280.15 Torr; for 2h; Autoclave; Green chemistry; | 89% |
Stage #1: 3-hydroxymethylpyridin With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonia; oxygen; copper(II) nitrate In water; dimethyl sulfoxide at 80℃; under 760.051 Torr; for 5h; Stage #2: With Acetaldehyde oxime In water; dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With water; oxygen at 140℃; under 3800.26 Torr; for 24h; | A n/a B 90% |
With ammonia; oxygen; vanadia at 375℃; Product distribution; other catalysts, effect of the presence of O2; | |
With ammonia In 1,4-dioxane; water at 130℃; under 4560.31 Torr; for 3h; Autoclave; | A 7 %Chromat. B 84 %Chromat. |
Conditions | Yield |
---|---|
With phosphate buffer; Aplysia cyclase at 23℃; for 5h; pH=7.0; | A n/a B 90% |
nicotinaldehyde oxime
nicotinamide
Conditions | Yield |
---|---|
With aluminum oxide; water; methanesulfonyl chloride at 100℃; for 0.25h; | 90% |
Conditions | Yield |
---|---|
With C55H45ClN5P2Ru(1+)*Cl(1-) In water at 110℃; for 12h; Sealed tube; | 90% |
With copper(II) acetate monohydrate In ethanol; acetonitrile for 5.5h; Time; Reflux; | 89.74% |
With cis,cis,trans-[RuCl2{κ2-(P,N)-2-Ph2PC6H4CH=NOH}2] In water at 100℃; for 6h; Sealed tube; Inert atmosphere; | 86% |
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; ammonium carbamate; sodium hydrogencarbonate In 1,4-dioxane at 100℃; for 20h; Inert atmosphere; | 89% |
With 2-(2'-pyridyl)(di(1-adamantyl)phosphino)benzene; ammonia; palladium diacetate In 1,4-dioxane at 120℃; under 1500.15 Torr; for 16h; Autoclave; | 76% |
With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 100℃; under 3000.3 Torr; for 16h; Autoclave; | 90 %Chromat. |
With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate In 1,4-dioxane at 100℃; under 1500.15 Torr; for 16h; | 94 %Chromat. |
With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 100℃; under 1500.15 Torr; for 16h; Autoclave; |
3-Bromopyridine
dicobalt octacarbonyl
nicotinamide
Conditions | Yield |
---|---|
With 1H-imidazole; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; ammonium chloride; N-ethyl-N,N-diisopropylamine In 1,4-dioxane at 90℃; for 3h; Sealed tube; | 89% |
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; urea for 0.025h; microwave irradiation; | 88% |
With ammonium chloride; triethylamine at 20℃; for 0.0166667h; | 87% |
Stage #1: nicotinic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5h; Stage #2: With ammonium chloride In tetrahydrofuran; water at 0℃; for 0.5h; | 84% |
Conditions | Yield |
---|---|
With ammonium nitrate; oxygen at 120℃; under 37503.8 Torr; for 24h; Autoclave; | 83% |
With tert.-butylhydroperoxide; cobalt ferrite; ammonium chloride; calcium carbonate In water; acetonitrile at 80℃; for 9h; Inert atmosphere; Green chemistry; | 53% |
With manganese(IV) oxide; carbon dioxide; ammonia at 155℃; under 22502.3 Torr; for 3.5h; Temperature; Pressure; |
Conditions | Yield |
---|---|
With phosphate buffer; Aplysia cyclase at 23℃; for 5h; pH=7.0; | A n/a B 81% |
Conditions | Yield |
---|---|
With water; potassium carbonate In dimethyl sulfoxide at 110℃; for 12h; | 81% |
Conditions | Yield |
---|---|
With thiamine diphosphate In methanol at 80℃; for 1h; | 80% |
Conditions | Yield |
---|---|
With (1,3-(dicyclohexylphosphino)propane )Pd(ethylene); ammonia; potassium carbonate In dimethyl sulfoxide at 110℃; under 450 Torr; for 24h; Schlenk technique; Inert atmosphere; | 77% |
With ammonia; palladium diacetate; catacxium A In 1,4-dioxane at 130℃; under 3000.3 Torr; for 20h; Autoclave; | 40 %Chromat. |
With 1,1'-bis-(diphenylphosphino)ferrocene; ammonia; palladium diacetate In 1,4-dioxane at 130℃; under 1500.15 Torr; for 20h; | 54 %Chromat. |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; ammonia; iodine In water at 100℃; for 3h; Sealed tube; Green chemistry; | 76% |
pyridine-3-carbonitrile
formaldehyd
A
N-hydroxymethylnicotinamide
B
nicotinamide
Conditions | Yield |
---|---|
With anion exchange resin AB-17-8 OH-form; ammonia; water at 60 - 90℃; for 1h; | A 75.7% B 23.2% |
Conditions | Yield |
---|---|
With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; magnesium chloride; zinc In N,N-dimethyl-formamide at 70℃; for 24h; | 75% |
Conditions | Yield |
---|---|
With formaldehyd; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In water; toluene at 90℃; | A 21% B 74% |
nicotinamide
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In water at 20℃; for 2h; | 74% |
Conditions | Yield |
---|---|
With ammonia; water; iodine In tetrahydrofuran at 20℃; for 12h; Haller-Bauer reaction; | 69% |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In chloroform at 20℃; for 20h; Product distribution; | A 63% B n/a |
nicotinamide
benzyl bromide
3-(aminocarbonyl)-1-benzylpyridinium bromide
Conditions | Yield |
---|---|
In acetone for 12h; Reflux; | 100% |
In acetonitrile | 93% |
In acetonitrile at 140℃; for 1.5h; Sealed tube; Microwave irradiation; | 89% |
Conditions | Yield |
---|---|
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; mercury(II) diacetate In N,N-dimethyl-formamide for 12h; Ambient temperature; or AgOAc; | 100% |
With aluminum oxide; potassium fluoride; sodium hypochlorite In water for 0.5h; modified Hofmann rearrangement; Heating; | 90% |
Stage #1: nicotinamide With trichloroisocyanuric acid; 1,8-diazabicyclo[5.4.0]undec-7-ene at 20℃; Hofmann rearrangement; Inert atmosphere; Stage #2: methanol at 65℃; Hofmann rearrangement; Inert atmosphere; | 84% |
With potassium hydroxide; [bis(acetoxy)iodo]benzene 1) 5-10 deg C, 15 min, 2) to r. t., 45 min; | 82% |
Conditions | Yield |
---|---|
With 1,1,1,3,3,3-hexamethyl-disilazane at 150℃; for 12h; | 100% |
With 1,1,1,3,3,3-hexamethyl-disilazane at 120℃; for 5h; |
nicotinamide
3,5-di-O-benzoyl-D-ribofuranosyl chloride
3-Carbamoyl-1-(3,5-di-O-benzoyl-β-D-ribofuranosyl)-pyridiniumchlorid
Conditions | Yield |
---|---|
100% |
Conditions | Yield |
---|---|
In water pH=Ca. 3.3 - 3.9; Cooling with ice; | 100% |
In methanol | 33% |
trimethylsilyl trifluoromethanesulfonate
nicotinamide
1,2,3,5-tetraacetylribose
Conditions | Yield |
---|---|
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose In acetonitrile at 20℃; Stage #2: trimethylsilyl trifluoromethanesulfonate In acetonitrile for 0.333333h; | 100% |
Stage #1: nicotinamide; 1,2,3,5-tetraacetylribose With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile Stage #2: trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; Reagent/catalyst; | |
Stage #1: trimethylsilyl trifluoromethanesulfonate; nicotinamide In acetonitrile for 0.0833333h; Stage #2: 1,2,3,5-tetraacetylribose In acetonitrile at 20℃; for 0.5h; Inert atmosphere; | |
In acetonitrile at -5℃; for 8h; Inert atmosphere; | 19 g |
nicotinamide
4-chlorobenzotrifluoride
N-(4-(trifluoromethyl)phenyl)nicotinamide
Conditions | Yield |
---|---|
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 95℃; for 5h; Inert atmosphere; Sonication; | 99.4% |
With 5-(di-tert-butylphosphino)-1′, 3′, 5′-triphenyl-1′H-[1,4′]bipyrazole; bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; potassium carbonate In 1,4-dioxane at 90℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Glovebox; | 91% |
With C33H37N4P; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tert-butyl alcohol at 95℃; for 5h; Inert atmosphere; Sonication; |
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℃; under 0.001 Torr; for 0.666667h; Pyrolysis; | 98% |
With oxalyl dichloride; triethylamine; Triphenylphosphine oxide In acetonitrile at 20℃; for 0.166667h; | 96% |
Conditions | Yield |
---|---|
With 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl; potassium phosphate; water; palladium diacetate In tert-butyl alcohol at 110℃; for 3h; Inert atmosphere; | 99% |
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0) In tert-butyl alcohol at 110℃; for 24h; | 97% |
potassium tetrachloroplatinate(II)
nicotinamide
Conditions | Yield |
---|---|
In water | 99% |
Conditions | Yield |
---|---|
In methanol; water for 0.333333h; | 99% |
nicotinamide
1-(pyridin-3-yl)urea
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; ammonia In methanol at 0 - 20℃; for 2h; Hofmann Rearrangement; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
In methanol at 50℃; | 98.62% |
(1R,2S,5R)-1-(chloromethoxy)-2-isopropyl-5-methylcyclohexane
nicotinamide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 20℃; Menschutkin quaternization; | 98.5% |
Conditions | Yield |
---|---|
With hydrogen; palladium 10% on activated carbon In isopropyl alcohol at 75℃; under 3750.38 Torr; for 4h; | 98.4% |
With hydrogen; Rh on carbon In water at 80℃; under 3800 Torr; for 1.5h; | 97% |
With 10% Rh/C; hydrogen In water at 80℃; under 3800.26 Torr; for 1.5h; | 97% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; VxSi4xO6.4x In acetonitrile at 80℃; for 3h; | 98% |
With 2,2,2-Trifluoroacetophenone; dihydrogen peroxide; acetonitrile In tert-butyl alcohol at 20℃; for 18h; Green chemistry; chemoselective reaction; | 95% |
With 1,2-diphenyl-1,1,2,2-tetrahydroperoxyethane In acetonitrile at 20℃; for 0.233333h; | 87% |
S-Ethenyl-S-(4-methylphenyl)-N-tolylsulfilimine
nicotinamide
2-(pyridin-3-yl)-4,5-dihydrooxazole
Conditions | Yield |
---|---|
With sodium hydride In 1,2-dimethoxyethane at 20 - 40℃; for 29h; | 98% |
1-chloromethoxy-heptane
nicotinamide
Conditions | Yield |
---|---|
at 20℃; for 1h; | 98% |
1-chloromethoxy-nonane
nicotinamide
Conditions | Yield |
---|---|
at 20℃; for 1h; | 98% |
1-trifluoromethanesulfonyloxy-4-t-butylcyclohexene
nicotinamide
Conditions | Yield |
---|---|
With potassium carbonate; tert-butyl XPhos; tris(dibenzylideneacetone)dipalladium (0) In tert-butyl alcohol at 80℃; for 24h; | 98% |
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 24h; | 98% |
nicotinamide
1-(2-bromomethylbenzyl)-4-hydroxyiminomethylpyridinium bromide
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 70℃; for 3.5h; | 98% |
In N,N-dimethyl-formamide at 80℃; for 5h; | 56% |
Conditions | Yield |
---|---|
at 125℃; for 2.5h; | 98% |
In methanol at 50℃; for 2h; |
Conditions | Yield |
---|---|
With niobium(V) oxide In neat (no solvent) at 160℃; Sealed tube; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With benzoic acid In para-xylene at 130℃; for 8h; Inert atmosphere; Schlenk technique; | 98% |
1-Bromotetradecane
nicotinamide
3-carbamoyl-1-tetradecylpyridinium bromide
Conditions | Yield |
---|---|
In acetonitrile for 48h; Reflux; | 98% |
Molecular Structure of Nicotinamide (CAS NO.98-92-0):
IUPAC Name: pyridine-3-carboxamide
Empirical Formula: C6H6N2O
Molecular Weight: 122.1246
EINECS: 202-713-4
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 33.2Å2
Index of Refraction: 1.57
Molar Refractivity: 33.27 cm3
Molar Volume: 101.3 cm3
Surface Tension: 54.8 dyne/cm
Density: 1.204 g/cm3
Flash Point: 156 °C
Enthalpy of Vaporization: 57.74 kJ/mol
Boiling Point: 334.4 °C at 760 mmHg
Vapour Pressure: 0.000128 mmHg at 25°C
Storage temp: 0-6°C
Form: powder
Color: white
Water Solubility: 1000 g/L (20 ºC)
Merck: 14,6523
BRN: 383619
Stability: Stable. Incompatible with strong oxidizing agents
Melting point: 128-131 °C
Product Categories: Biochemistry; Vitamins; Nutritional Supplements; Vitamins and derivatives; Vitamin Ingredients; Miscellaneous Compounds
Niacinamide (CAS NO.98-92-0) is used as food additive, for multivitamin preparations and as intermediate for pharmaceuticals and cosmetics, it is also an inhibitor of sirtuins and has been reported to restore cognition in Alzheimer's Disease transgenic mice, also has been reported to be an effective skin whitener in topical application.
For production of niacinamide (CAS NO.98-92-0) in the past, methylethylpyridine was oxidized with nitric acid to yield niacin, and β-picoline was treated with air and ammonia to produce the nitrile that was then hydrolyzed to niacin-amide. A more modem process can produce both niacin and niacinamide (CAS NO.98-92-0) from a single feedstock, either β-picoline or 2-methyl-5-ethylpyridine by oxidative ammonolysis, a combination of oxidation and amination.
Either niacin or niacinamide (CAS NO.98-92-0) can be selectively isolated from the hydrolysis by varying the hydrolysis time and nitrite concentration. A higher hydrolysis temperature favors production of niacin.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LD50 | unreported | 2500mg/kg (2500mg/kg) | Pharmaceutical Chemistry Journal Vol. 20, Pg. 29, 1986. | |
mouse | LD50 | intraperitoneal | 2050mg/kg (2050mg/kg) | Radiation Research. Vol. 109, Pg. 479, 1987. | |
mouse | LD50 | oral | 2500mg/kg (2500mg/kg) | Drugs in Japan Vol. 6, Pg. 545, 1982. | |
mouse | LD50 | subcutaneous | 2gm/kg (2000mg/kg) | Quarterly Journal of Pharmacy & Pharmacology. Vol. 19, Pg. 48, 1946. | |
rat | LD50 | oral | 3500mg/kg (3500mg/kg) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 1390, 1986. | |
rat | LD50 | subcutaneous | 1680mg/kg (1680mg/kg) | LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Proceedings of the Society for Experimental Biology and Medicine. Vol. 62, Pg. 19, 1946. |
Hazard Codes: Xi
Risk Statements: 36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 26-36-37/39
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37/39: Wear suitable gloves and eye/face protection.
Nicotinamide rarely causes side effects, and is considered generally safe as a food additive, and as a component in cosmetics and medication.
Nicotinamide , with CAS number of 98-92-0, can be called Niamide ; Niacinamide/Nicotinamide ; Austrovit PP ; beta.-Pyridinecarboxamide ; Nikotinsaeureamid ; Amid kyseliny nikotinove ; Nicotinamidum ; Pyridine-3-carboxylic acid amide ; Nikotinsaeureamid ; Nicotinamide(Vitamin B3) ; a-Alanine,N-[(2R)-2,4-dihydroxy-3,3- dimethyl-1-oxobutyl]- ; 3-Pyridinecarboxamide ; Nicotinamida ; Niacinamide ; 3-Pyridinecarboxylic acid amide ; Nicotine acid amide . Nicotinamide, also known as niacinamide and Nicotinic acid amide, is the amide of Nicotinic acid (vitamin B3). It is a water-soluble vitamin and is part of the vitamin B group.Nicotinic acid(also known as niacin)can be converte to niacinamide in vivo. It is a white to off white powder.
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