Conditions | Yield |
---|---|
With water at 230℃; for 2h; | 99.9% |
With water at 205℃; | |
With water at 175 - 180℃; under 22065.2 Torr; |
Conditions | Yield |
---|---|
With oxygen; V2O5/Sb2O3-TiO2 In water at 260 - 280℃; Industry scale; Inert atmosphere; Gas phase; | 99.58% |
With oxygen; V2O5/Sb2O3-TiO2 In water at 260 - 280℃; Product distribution / selectivity; Inert atmosphere; Gas phase; Industry scale; | 99.58% |
With water; oxygen Product distribution / selectivity; | 97.3% |
Conditions | Yield |
---|---|
With hydrogenchloride; [RuCl2(CO)2(Ph2P-3-C6H4COOH)2] In methanol; water at 75℃; for 0.333333h; | A 99.1% B n/a C n/a |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water at 30℃; for 24h; Enzymatic reaction; | 99% |
With C4H11FeMo6NO24(3-)*3C16H36N(1+); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 8h; Green chemistry; | 99% |
With 4H3N*4H(1+)*CuMo6O18(OH)6(4-); water; oxygen; sodium carbonate at 50℃; under 760.051 Torr; for 12h; | 99% |
Conditions | Yield |
---|---|
With tert-butyldimethylsilyl chloride In methanol; water at 20℃; for 0.5h; Reagent/catalyst; Green chemistry; | 99% |
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 12h; pH=9.8 - 10.1; Electrolysis; | 96% |
With ferrous(II) sulfate heptahydrate; Oxone In water at 20℃; for 0.5h; Sonication; Green chemistry; | 94% |
Conditions | Yield |
---|---|
With PPA at 155℃; for 4.5h; | 98% |
With alkaline H2O In dimethyl sulfoxide at 30℃; Rate constant; other solvent (EtOH); variation of water concentrations; | |
esterase in WBN; IL-Ht rat abdominal skin homogenate at 37℃; Enzyme kinetics; |
methyl-3-oxo-3-(pyridin-3-yl)propanedithioate
nicotinic acid
Conditions | Yield |
---|---|
With sodium hydroxide In water at 100℃; for 10h; Reflux; chemoselective reaction; | 98% |
quinoline-5-sulfonic acid
nicotinic acid
Conditions | Yield |
---|---|
With sulfuric acid; selenium at 240 - 300℃; for 1h; Product distribution; reaction time; SeO2 as catal.; | 95% |
nicotinic acid
Conditions | Yield |
---|---|
With indium; ammonium chloride In tetrahydrofuran for 11h; Heating; | 95% |
Conditions | Yield |
---|---|
With potassium trimethylsilonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 0.333333h; | 95% |
Conditions | Yield |
---|---|
With water; oxygen at 310℃; Product distribution / selectivity; | A 93.13% B 5.56% |
With water; oxygen at 300℃; Product distribution / selectivity; | A 93.16% B 6.39% |
With water; oxygen at 285℃; Product distribution / selectivity; | A 92.22% B 7.11% |
Conditions | Yield |
---|---|
With tert.-butylnitrite; acetic acid at 75℃; for 2.5h; Inert atmosphere; | 92% |
With niobium(V) oxide; water In neat (no solvent) for 20h; Reflux; Inert atmosphere; | 83% |
With barium dihydroxide In water for 1h; Heating; | |
With recombinant Borrelia burgdorferi nicotinamidase at 25℃; pH=7.3; Kinetics; Reagent/catalyst; Concentration; aq. phosphate buffer; Enzymatic reaction; | |
With water In aq. phosphate buffer at 30℃; for 6h; pH=7; Time; Enzymatic reaction; | 41.66 mmol |
1-(4-methoxyphenyl)-2-(pyridin-3-yl)-ethanone
A
nicotinic acid
B
4-methoxybenzoic acid
Conditions | Yield |
---|---|
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction; | A 92% B 92% |
pyridine-3-ylglyoxal
nicotinic acid
Conditions | Yield |
---|---|
With iodine; dimethyl sulfoxide at 180℃; for 0.0833333h; Inert atmosphere; Microwave irradiation; | 91% |
Conditions | Yield |
---|---|
With sodium hypochlorite; C8H18NPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 90.1% B 3.4% |
With sodium hypochlorite; C13H26N2OPol; sodium hydrogencarbonate In water; toluene at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 87.7% B 3.5% |
With sodium hypochlorite; C16H28N2O5Pol; sodium hydrogencarbonate In water; 1,2-dichloro-ethane at 15 - 20℃; for 4.5h; Product distribution / selectivity; | A 85.3% B 5.3% |
Conditions | Yield |
---|---|
With sulfuric acid; selenium at 240 - 300℃; for 1h; Product distribution; reaction time; SeO2 as catal.; | 90% |
Conditions | Yield |
---|---|
With Oxone; trifluoroacetic acid In 1,4-dioxane for 10h; Reflux; Green chemistry; | 90% |
With copper(l) iodide; hydroxylamine hydrochloride; oxygen In dimethyl sulfoxide at 100℃; for 12h; | 68% |
Conditions | Yield |
---|---|
With oxygen; potassium hydroxide at 20℃; Schlenk technique; chemoselective reaction; | 90% |
3-Methylpyridine
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
A
pyridine
B
3-pyridinecarboxaldehyde
C
nicotinic acid
D
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
at 140℃; for 14h; Product distribution; | A 5% B 18% C 60% D 88% |
at 140℃; for 14h; Further byproducts given; | A 5% B 18% C 60% D 88% |
2,2'-diphenyl-[3,3']biindolylidene 1,1'-dioxide
A
pyridine
B
3-pyridinecarboxaldehyde
C
nicotinic acid
D
2,2'-diphenyl-1H,1'H-3,3'-biindole
Conditions | Yield |
---|---|
With 3-Methylpyridine at 140℃; for 14h; Further byproducts given; | A 5% B 18% C 60% D 88% |
3-pyridinecarboxaldehyde
A
nicotinic acid
B
1,2-di(pyridine-3-yl)ethane-1,2-dione
Conditions | Yield |
---|---|
With 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy In aq. buffer at 20℃; for 8h; pH=11.5; Electrolysis; | A 86% B 6% |
Conditions | Yield |
---|---|
With pyridine for 30h; Heating; other temperature, other reactant ratio, sealed tube; | 85% |
With 2,3-dimethyl-2,3-butane diol; bis(N,N-dimethylformamide)dichloridodioxidomolybdenum(VI) In N,N-dimethyl acetamide at 130℃; Microwave irradiation; Sealed tube; Green chemistry; chemoselective reaction; | 84% |
With molybdenum(V) chloride; sodium iodide In acetonitrile at 20℃; for 2h; | 83% |
3-picolyl bromide
nicotinic acid
Conditions | Yield |
---|---|
With 5,10,15,20-tetra(4-nitrophenyl) porphyrinato iron chloride; [bis(acetoxy)iodo]benzene; water In methanol at 50℃; for 12h; | 85% |
Conditions | Yield |
---|---|
With D-glucose at 200℃; for 1h; pH=7.5; Temperature; pH-value; | 84% |
Conditions | Yield |
---|---|
With TEA; magnesium bromide In dichloromethane at 20℃; for 48h; Cannizzaro reaction; | A 82% B n/a |
With N,N,N',N'-tetramethylguanidine In water at 20℃; for 7h; Cannizzaro reaction; | A 44% B 41% |
With barium dihydroxide; formaldehyd at 100 - 110℃; for 0.0333333h; Irradiation; | A 97 % Chromat. B 3 % Chromat. |
With aluminum oxide; sodium hydroxide; water for 0.00416667h; Irradiation; Yield given; Yields of byproduct given; |
Conditions | Yield |
---|---|
With [PhCOPd(PtBu3)I]; dtbpf In 2-methyltetrahydrofuran at 80℃; for 18h; Inert atmosphere; | 82% |
Conditions | Yield |
---|---|
With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); water; N-ethyl-N,N-diisopropylamine at 130℃; for 0.333333h; Microwave irradiation; | 81% |
6-iodo-nicotinic acid
nicotinic acid
Conditions | Yield |
---|---|
With hydrogenchloride; indium In water for 2h; Reflux; | 80% |
With indium In water for 5h; Heating; | 57% |
Conditions | Yield |
---|---|
With N,N-bis[2-oxo-3-oxazolidinyl]phosphorodiamidic chloride In dichloromethane for 1h; Ambient temperature; | 100% |
With N,N'-dimethylaminopyridine; di-tert-butyl dicarbonate In nitromethane at 50℃; for 16h; | 81% |
With boric acid; glycerol Entfernen des entstehenden H2O; |
nicotinic acid
pyridine-3-carbonyl chloride hydrochloride
Conditions | Yield |
---|---|
With thionyl chloride for 4h; Heating; | 100% |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; Inert atmosphere; | 100% |
With thionyl chloride In toluene at 100℃; for 24h; | 100% |
nicotinic acid
1-hydroxy-pyrrolidine-2,5-dione
nicotinic acid succinimidyl ester
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In 1,4-dioxane | 100% |
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 48h; | 85% |
With dicyclohexyl-carbodiimide In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | 80% |
nicotinic acid
3-pyridinecarbonyl chloride
Conditions | Yield |
---|---|
With thionyl chloride for 5h; Reflux; | 100% |
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere; Cooling with ice; | 100% |
With oxalyl dichloride at 20℃; for 0.5h; | 100% |
nicotinic acid
Conditions | Yield |
---|---|
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane Ambient temperature; | 100% |
nicotinic acid
4-(5-nitro-1H-indol-1-yl)-1-butanol
nicotinic acid 4-(5-nitro-indol-1-yl)-butyl ester
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 100% |
nicotinic acid
Conditions | Yield |
---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In dichloromethane at 0 - 20℃; for 20h; | 100% |
(1-S)-{4-[(5-tert-butoxycarbonylamino-1-hydroxymethyl-pentyl)-isobutyl-sulfamoyl]-phenyl}-carbamic acid tert-butyl ester
nicotinic acid
(2S)-nicotinic acid 6-tert-butoxycarbonylamino-2-[(4-tert-butoxycarbonylamino-benzenesulfonyl)-isobutyl-amino]-hexyl ester
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; | 100% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethylformamide) at 20℃; | 100% |
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; | 100% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU; dmap In N,N-dimethyl-formamide at 0 - 20℃; for 2.16667h; | 100% |
nicotinic acid
nicotinic acid sulfate
Conditions | Yield |
---|---|
With sulfuric acid In dichloromethane at 20℃; Cooling with ice; | 100% |
With sulfuric acid In dichloromethane at 20℃; for 0.5h; | 100% |
nicotinic acid
methyl pyrrolidine-2-carboxylate
1-(pyridine-3-carbonyl)pyrrolidine-2-carboxylic acid methyl ester
Conditions | Yield |
---|---|
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap In dichloromethane at 0 - 25℃; | 100% |
nicotinic acid
C21H33N3O
N-(((1S,2S,3R,8aS)-2,5,5,8a-tetramethyl-3-(nicotinamido)decahydronaphthalen-1-yl)methyl)nicotinamide
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h; Inert atmosphere; | 100% |
nicotinic acid
1,1,1,3,3,3-hexamethyl-disilazane
trimethylsilyl 3-pyridinecarboxylate
Conditions | Yield |
---|---|
With ammonium bisulphate for 24h; Reflux; Inert atmosphere; | 100% |
With ammonium sulfate In toluene at 95 - 110℃; Inert atmosphere; | 92% |
With iodine In neat (no solvent) at 20℃; for 19h; Green chemistry; | 61% |
nicotinic acid
cholin hydroxide
2-hydroxy-N,N,N-trimethylethanaminium nicotinate
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 9; Cooling with ice; | 100% |
In water pH=7.66; |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 6 - 6.2; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 5.5 - 5.8; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice; Heating; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 2.8 - 3.3; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 2.3 - 3.3; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 3.3 - 3.9; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 7 - 7.2; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 2.8 - 3; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
In water for 0.166667h; pH=Ca. 2.8 - 3.3; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
at 120℃; under 0.450045 Torr; for 7h; Temperature; | 100% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; molybdic acid In water at 92 - 95℃; for 3h; Green chemistry; | 99.6% |
With dihydrogen peroxide In tetrahydrofuran; water for 5h; Reflux; | 91% |
With hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid In methanol; N,N-dimethyl-formamide at 25℃; for 3h; | 87% |
IUPAC Name: Pyridine-3-carboxylic acid
Molecular Formula: C6H5NO2
Molecular Weight: 123.11 g/mol
Canonical SMILES: C1=CC(=CN=C1)C(=O)O
InChI: InChI=1/C6H5NO2/c8-6(9)5-2-1-3-7-4-5/h1-4H,(H,8,9)
EINECS: 200-441-0
Classification Code: Antihyperlipidemic; Antilipemic Agents; Antimetabolites; Cardiovascular Agents; Drug / Therapeutic Agent; Growth Substances; Human Data; Micronutrients; Tumor data; Vasodilator Agents; Vitamin B Complex; Vitamin; Vitamins
H-Bond Donor: 1
H-Bond Acceptor: 3
Density: 1.293 g/cm3
Flash Point: 130.7 °C
Enthalpy of Vaporization: 56.18 kJ/mol
Boiling Point: 292.5 °C at 760 mmHg
Melting Point: 236-239 °C(lit.)
Storage temperature: 0-6°C
Water Solubility: 1.80E+04 mg/L at 25 °C
Henry's Law Constant: 5.11E-11 atm-m3/mole at 25 °C
Atmospheric OH Rate Constant: 1.72E-13 cm3/molecule-sec at 25 °C
Vapour Pressure of Niacin (CAS NO.59-67-6): 5.70E-06 mm Hg at 25 °C
In 1873, Niacin was first described by Hugo Weidel in his studies of nicotine.Niacin was extracted from livers by Conrad Elvehjem who later identified the active ingredient, then referred to as the "pellagra-preventing factor" and the "anti-blacktongue factor." When the biological significance of nicotinic acid was realized, it was thought appropriate to choose a name to dissociate it from nicotine, in order to avoid the perception that vitamins or niacin-rich food contains nicotine, or that cigarettes contain vitamins. The resulting name 'niacin' was derived from nicotinic acid + vitamin.
Niacin is referred to as Vitamin B3 because it was the third of the B vitamins to be discovered. It has historically been referred to as "vitamin PP."
Niacin (CAS NO.59-67-6) feed grade is used as vitamin for poultry, swines, ruminants, fish, dogs and cats, etc. It is also used as intermediate for nicotinic acid derivatives and technical applications. Niacin USP is used for food fortification, as dietary supplement and as an intermediate of pharmaceuticals,as dietary supplement and as an intermediate of pharmaceuticals. It is a brand name for a sustained release Niacin tablet, which is used to reduce cholesterol.
Niacin (CAS NO.59-67-6) 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 |
---|---|---|---|---|---|
guinea pig | LDLo | intravenous | 3500mg/kg (3500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Proceedings of the Society for Experimental Biology and Medicine. Vol. 38, Pg. 241, 1938. |
man | TDLo | intravenous | 357ug/kg (0.357mg/kg) | CARDIAC: CARDIAC OUTPUT LUNGS, THORAX, OR RESPIRATION: CYANOSIS LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Annals of Internal Medicine. Vol. 29, Pg. 558, 1948. |
man | TDLo | oral | 2571mg/kg/90D (2571mg/kg) | BLOOD: CHANGE IN CLOTTING FACTORS BLOOD: CHANGES IN PLATELET COUNT | Archives of Internal Medicine. Vol. 152, Pg. 861, 1992. |
man | TDLo | oral | 9713mg/kg/58W (9713mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING SKIN AND APPENDAGES (SKIN): SWEATING: OTHER | Southern Medical Journal. Vol. 84, Pg. 496, 1991. |
man | TDLo | oral | 31200mg/kg/78 (31200mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | JAMA, Journal of the American Medical Association. Vol. 279, Pg. 1702, 1998. |
mouse | LD50 | intraperitoneal | 358mg/kg (358mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977. | |
mouse | LD50 | intravenous | 5gm/kg (5000mg/kg) | Therapie. Vol. 26, Pg. 831, 1971. | |
mouse | LD50 | oral | 3720mg/kg (3720mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES | Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 149, 1973. |
mouse | LD50 | subcutaneous | 3500mg/kg (3500mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977. | |
mouse | LD50 | unreported | 4gm/kg (4000mg/kg) | British UK Patent Application. Vol. #2041937, | |
rabbit | LD50 | oral | 4550mg/kg (4550mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977. | |
rat | LD50 | intraperitoneal | 730mg/kg (730mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 14, Pg. 741, 1977. | |
rat | LD50 | oral | 7gm/kg (7000mg/kg) | Drugs in Japan Vol. 6, Pg. 544, 1982. | |
rat | LD50 | subcutaneous | 5gm/kg (5000mg/kg) | Drugs in Japan Vol. 6, Pg. 544, 1982. | |
rat | LD50 | unreported | 4gm/kg (4000mg/kg) | United States Patent Document. Vol. #4412998, | |
rat | LDLo | intravenous | 3500mg/kg (3500mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Proceedings of the Society for Experimental Biology and Medicine. Vol. 38, Pg. 241, 1938. |
Reported in EPA TSCA Inventory.
Poison by intraperitoneal route. Moderately toxic by ingestion, intravenous, and subcutaneous routes. Human systemic effects: change in clotting factors, changes in platelet count. Questionable carcinogen with experimental carcinogenic data. When heated to decomposition it emits toxic fumes of NOx.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36: Wear suitable protective clothing.
S24/25: Avoid contact with skin and eyes.
WGK Germany of Niacin (CAS NO.59-67-6): 1
Niacin (CAS NO.59-67-6), its Synonyms are Nicotinic acid ; 3-Pyridinecarboxylic acid ; 3-Carboxypyridine ; Acide nicotinique ; Acido nicotinico ; Acidum nicotinicum ; Akotin ; Apelagrin ; Kyselina nikotinova ; Enduracin ; Daskil ; Davitamon PP ; Diacin ; Direktan ; Niaspan Titration Starter Pack ; Nicacid ; Nicagin ; Nicamin ; Nicangin ; Pyridine-3-carboxylic acid ; Pyridine-beta-carboxylic acid ; Pyridine-carboxylique-3 ; Pyridinecarboxylic acid, 3- . It is odorless white crystalline powder with a feebly acid taste.
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