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| CAS No.: | 98-92-0 |
|---|---|
| Name: | Nicotinamide |
| Article Data: | 222 |
| Molecular Structure: | |
|
|
|
| Formula: | C6H6N2O |
| Molecular Weight: | 122.126 |
| Synonyms: | Nikotinamid;Nicotylamide;beta-Pyridinecarboxamide;Vitamin B3； Niacin； Niacinmide；;nicotinamide,niacinamide;pyridine-3-carboxamide;Nicobion;Nicotamide;Nicota;Pyridine, 3-carbamoyl-;Amixicotyn;Amide PP;Nicomidol;Delonin Amide;3-Pyridinecarboxamide;NAM;Nicotine acid amide;PP-Faktor;Nicovitol;m-(Aminocarbonyl)pyridine;Nicotinic acid amide;Nicotililamido;Hansamid;Endobion;Vitamin B (VAN);Nicasir;3-Pyridinecarboxylic acid amide;Nicogen;Niacinamide (USP);Nicosan 2;Amnicotin;Pelmine;Nicotinic amide;Savacotyl;Nicofort;Niavit PP;Nicotinamida [INN-Spanish];DEA No. 1405;a-Alanine,N-[(2R)-2,4-dihydroxy-3,3- dimethyl-1-oxobutyl]- [79-83-4] 3-Pyridinecarboxamide;3-Carbamoylpyridine;Niacinamide [USAN];Papulex;Nicotinamide(Vitamin B3);Nikotinsaeureamid [German];Aminicotin;Nicosylamide;Nicovit; |
| EINECS: | 202-713-4 |
| Density: | 1.204 g/cm3 |
| Melting Point: | 128-131 °C |
| Boiling Point: | 334.4 °C at 760 mmHg |
| Flash Point: | 156 °C |
| Solubility: | Incompatible with strong oxidizing agents |
| Appearance: | White to off white powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36-37/39 |
| PSA: | 55.98000 |
| LogP: | 0.88080 |
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| 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% |
- 144223-30-3
(1H-benzo[d][1,2,3]triazol-1-yl)(pyridin-3-yl)methanone
- 98-92-0
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% |
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Chemistry
Molecular Structure of Nicotinamide (CAS NO.98-92-0):
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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
Uses
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.
Production
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.
Toxicity Data With Reference
| 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. |
Safety Profile
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.
Specification
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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