A
6-methoxy-2-(p-tolyl)quinoline
B
Cytosine
C
6-methoxy-4-methyl-2-(p-tolyl)quinoline
Conditions | Yield |
---|---|
In isopropyl alcohol Irradiation; 350 nm; | A n/a B 94% C n/a |
Conditions | Yield |
---|---|
With dihydrogen peroxide at 80℃; for 20h; Temperature; | 93% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxylacrylic nitrile With sodium t-butanolate In tert-butyl alcohol Stage #2: urea In tert-butyl alcohol at 50℃; for 8h; Solvent; Reagent/catalyst; Temperature; | 91.5% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxylacrylic nitrile With sodium methylate In methanol Stage #2: urea, monosodium salt In methanol at 40℃; for 6h; | 91.5% |
Conditions | Yield |
---|---|
Stage #1: 3-hydroxylacrylic nitrile With sodium methylate In methanol Stage #2: urea, monopotassium salt In methanol at 40℃; for 6h; | 91.5% |
Conditions | Yield |
---|---|
With hydrogenchloride; water at 100℃; for 1h; Temperature; | 91.2% |
With hydrogenchloride; water |
Conditions | Yield |
---|---|
With hydrogenchloride; water at 90℃; for 1h; | 90.9% |
2-benzylsulfanyl-pyrimidin-4-ylamine
Cytosine
Conditions | Yield |
---|---|
With hydrogenchloride; water at 90℃; for 1h; | 90.6% |
2-ethylsulfanyl-pyrimidin-4-ylamine
Cytosine
Conditions | Yield |
---|---|
With hydrogenchloride; water at 90℃; for 1h; | 89.7% |
With ethanol; water; dihydrogen peroxide |
Conditions | Yield |
---|---|
With sodium hydroxide In toluene for 12h; Reflux; | 89% |
Conditions | Yield |
---|---|
With ammonium chloride In 1-methyl-pyrrolidin-2-one at 180℃; for 8h; Reagent/catalyst; Temperature; Solvent; | 87% |
Conditions | Yield |
---|---|
In toluene for 5h; | 84% |
sodium cyanamide
N4-<(Dimethylamino)methylene>cytosine
A
Cytosine
B
<(Dimethylamino)methylene>cyanamide
Conditions | Yield |
---|---|
In isopropyl alcohol for 2h; Heating; | A n/a B 81% |
N4-<(Dimethylamino)methylene>cytosine
A
Cytosine
B
<(Dimethylamino)methylene>cyanamide
Conditions | Yield |
---|---|
With sodium cyanamide In isopropyl alcohol for 2h; Heating; | A n/a B 81% |
4-methylsulfanylpyrimidin-2(1H)-one
Cytosine
Conditions | Yield |
---|---|
With ferrous(II) sulfate heptahydrate; ammonium hydroxide at 80℃; for 72h; | 77% |
4-(benzoylamino)-1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-1H-pyrimidin-2-one
A
N-(1,3-propanediol-2-yl)acetamide
B
Cytosine
Conditions | Yield |
---|---|
With ammonium hydroxide; water In methanol at 70℃; for 24h; Sealed tube; | A 71% B 75% |
Cytosine
Conditions | Yield |
---|---|
With ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene at 120℃; under 11251.1 Torr; for 20h; Autoclave; | 74% |
N4-<(Dimethylamino)methylene>cytosine
A
Cytosine
B
N-[6-Oxo-6,7-dihydro-pyrimido[1,6-a][1,3,5]triazin-(4E)-ylidene]-guanidine; hydrochloride
Conditions | Yield |
---|---|
With guanidine hydrochloride In isopropyl alcohol for 17h; Heating; | A 67% B 8% |
Conditions | Yield |
---|---|
With purine nucleoside phosphorylase at 14 - 15℃; pH=7; aq. phosphate buffer; Enzymatic reaction; | 60% |
4 % Chromat. |
4-(benzoylamino)-1-[N-(1,3-dipivaloyloxyprop-2-yl)acetylaminomethyl]-1H-pyrimidin-2-one
A
N-(1,3-propanediol-2-yl)acetamide
D
Cytosine
Conditions | Yield |
---|---|
With ammonium hydroxide; water In methanol at 20℃; for 24h; | A 58% B 4% C 12% D 60% |
Conditions | Yield |
---|---|
With sodium persulfate In water at 75℃; for 4h; sodium phosphate buffer pH 7.0, other substrates; | A 53% B 6% |
Conditions | Yield |
---|---|
for 3h; Mechanism; Product distribution; Irradiation; other alcohol; | A 36% B 9% C 31% |
for 3h; Irradiation; | A 36% B 9% C 31% |
1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)cytosine hydrochloride
A
Cytosine
Conditions | Yield |
---|---|
With Tris-HCl buffer at 37℃; for 6h; Rate constant; Mechanism; var. salt concentration and pH of buffer; | A n/a B 28% C 33% |
Conditions | Yield |
---|---|
In water at 90℃; for 16h; pH=6.5; Irradiation; Inert atmosphere; | A 12% B 5% C 11% D 22% E 5% F 9% G 14% H 5% |
Conditions | Yield |
---|---|
With hydrogenchloride; water |
Conditions | Yield |
---|---|
With ethanol; ammonia at 120℃; |
(4-amino-pyrimidin-2-ylsulfanyl)-acetic acid
Cytosine
Conditions | Yield |
---|---|
With hydrogenchloride; water |
cytidinium sulphate
Cytosine
Conditions | Yield |
---|---|
With sulfuric acid at 125℃; im Rohr; |
Conditions | Yield |
---|---|
With sodium butanolate |
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 70℃; for 0.116667h; Microwave irradiation; Green chemistry; | 100% |
With dmap In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; | 91% |
With dmap In tetrahydrofuran |
Conditions | Yield |
---|---|
Stage #1: Cytosine With N,O-bis-(trimethylsilyl)-acetamide In 1,2-dichloro-ethane at 20℃; for 2h; Reflux; Stage #2: C26H33FO6Si With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 2h; Reflux; | 100% |
Conditions | Yield |
---|---|
With N-iodo-succinimide In N,N-dimethyl-formamide for 12.5h; Sonographic reaction; Inert atmosphere; | 99% |
With iodine; iodic acid In acetic acid at 40℃; | 96% |
With iodine; iodic acid; acetic acid In tetrachloromethane; water at 50℃; | 86% |
N,N-dimethylformamide dipropyl acetal
Cytosine
N4-<(Dimethylamino)methylene>-1-propylcytosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; Heating; | 99% |
Cytosine
N,N-dimethyl-formamide dimethyl acetal
N4-<(Dimethylamino)methylene>-1-methylcytosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; Heating; other N,N-dimethylformamide dialkyl(diaralkyl) acetales; | 99% |
In N,N-dimethyl-formamide for 24h; Heating; | 99% |
trifluoroacetic acid for 15h; Heating; | 98% |
With trifluoroacetic acid |
Cytosine
N,N-dimethylformamide diethyl diacetal
N4-<(Dimethylamino)methylene>-1-ethylcytosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; Heating; | 99% |
di-tert-butyl dicarbonate
Cytosine
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran at 20℃; Inert atmosphere; | 99% |
Cytosine
Conditions | Yield |
---|---|
With pyridine; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane at 20℃; for 24h; Inert atmosphere; enantioselective reaction; | 98.5% |
Conditions | Yield |
---|---|
With phosphoric acid at 100℃; for 8h; | 98% |
With pyridine for 2.5h; Heating; | 97.2% |
With pyridine at 20℃; for 24h; | 85% |
N,N-dimethylformamide dipropyl acetal
Cytosine
N4-<(Dimethylamino)methylene>cytosine
Conditions | Yield |
---|---|
With trifluoroacetic acid at 85 - 90℃; for 12h; | 98% |
N,N-dimethylformamide di-n-butyl acetal
Cytosine
1-Butyl-N4-<(dimethylamino)methylene>cytosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; Heating; | 98% |
Conditions | Yield |
---|---|
With pyridine for 2h; Heating; | 98% |
In N,N-dimethyl-formamide Heating; | 80% |
Cytosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 2h; Ambient temperature; | 98% |
Cytosine
2-Chloro-N-[2-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl]-acetamide
2-(4-amino-2-oxo-2H-pyrimidin-1-yl)-N-[2-(3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl]-acetamide
Conditions | Yield |
---|---|
Stage #1: Cytosine With sodium hydride; triethylamine In N,N-dimethyl-formamide for 0.0833333h; Stage #2: 2-Chloro-N-[2-((1S,2R,6S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-ethyl]-acetamide In N,N-dimethyl-formamide at 20℃; Further stages.; | 98% |
Cytosine
Conditions | Yield |
---|---|
Stage #1: Cytosine With platinum(IV) oxide; sodium tetrahydroborate; palladium on activated charcoal; water-d2 at 160℃; for 1.33333h; Microwave irradiation; Stage #2: With hydrogen chloride at 0℃; | 98% |
Cytosine
[(1,5-cyclooctadiene)PtMe(cytosine)](SbF6)
Conditions | Yield |
---|---|
In acetone (Ar); Ag salt was added to stirred soln. of Pt in acetone; stirred for 30 min; filtered; suspn. of cytosine in acetone was added; stirred for 30min; solvent removed; washed (H2O); dried (vac.); elem. anal.; | 97.5% |
Cytosine
Conditions | Yield |
---|---|
Stage #1: Cytosine With molybdenum(IV) oxide; sodium tetrahydroborate; palladium 10% on activated carbon; water-d2 at 20 - 160℃; for 1.83333h; Microwave irradiation; Stage #2: With hydrogen chloride In water for 0.333333h; | 97.5% |
Cytosine
Conditions | Yield |
---|---|
With pyridine; sulfamate de pentachlorophenyle at 100℃; for 2h; regioselective transfer of the sulfamoyl group to the extracyclic NH2 group of amniopyrimidines and amonopurines; | 97% |
With pyridine; sulfamate de pentachlorophenyle at 100℃; for 2h; | 97% |
N,N-Dimethylformamide diallyl acetal
Cytosine
1-Allyl-N4-<(dimethylamino)methylene>cytosine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide for 24h; Heating; | 96% |
Conditions | Yield |
---|---|
Stage #1: Cytosine; water at 45℃; for 0.5h; Stage #2: barium(II) perchlorate at 20℃; | 96% |
Conditions | Yield |
---|---|
Stage #1: Cytosine With hydrogen fluoride at -15 - 0℃; Inert atmosphere; Stage #2: at -20℃; for 4h; Inert atmosphere; Further stages; | 95.7% |
With 1,1,1,3',3',3'-hexafluoro-propanol; fluorine at 20℃; under 1125.11 Torr; Temperature; Pressure; Reagent/catalyst; Inert atmosphere; | 87.4% |
With formic acid for 1.5h; Time; Flow reactor; Autoclave; | 63% |
With formic acid; fluorine at 9℃; for 0.0833333h; Temperature; Concentration; Inert atmosphere; |
Conditions | Yield |
---|---|
With N-Bromosuccinimide In N,N-dimethyl-formamide at 15℃; for 1h; Reagent/catalyst; Solvent; Sonication; | 95.6% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 10h; Large scale; | 93.6% |
With N-Bromosuccinimide In N,N-dimethyl-formamide at 25℃; for 10h; | 93.6% |
Conditions | Yield |
---|---|
With pyridine at 20℃; | 95% |
With pyridine at 80℃; for 2h; Acylation; | 93% |
With pyridine at 80℃; for 2h; | 81% |
With pyridine; dmap In dichloromethane at 20℃; Inert atmosphere; |
Cytosine
tert-butyl (2R,3S,5R)-2-(acetyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate
tert-butyl (2RS,3S,5R)-2-[4-amino-2-oxopyrimidin-1(2H)-yl]-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate
Conditions | Yield |
---|---|
Stage #1: Cytosine; tert-butyl (2R,3S,5R)-2-(acetyloxy)-5-[(tert-butyldimethylsilyloxy)methyl]-3-(trifluoromethyl)pyrrolidine-1-carboxylate With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 0.5h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 16h; | 95% |
Cytosine
η3-allylchloro(cytosine)palladium(II)
Conditions | Yield |
---|---|
In methanol soln. stirred for 3h, pptn (molar ratio complex : ligand = 1:2); filtered, washed (MeOH, ether), dried (vac.), elem. anal.; | 95% |
Conditions | Yield |
---|---|
With acetic acid at 70 - 77℃; for 4.3h; | 95% |
(3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-2,3-diyl diacetate
Cytosine
Conditions | Yield |
---|---|
Stage #1: Cytosine In acetonitrile at 20℃; for 3h; Vorbrueggen Nucleoside Synthesis; Stage #2: (3R,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-vinyltetrahydrofuran-2,3-diyl diacetate With tin(IV) chloride In acetonitrile at 65℃; for 1h; | 95% |
Cytosine
α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate
Conditions | Yield |
---|---|
Stage #1: Cytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Reflux; Industrial scale; Stage #2: α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate With hydrogenchloride; phosphomolybdic acid In pentan-1-ol at 128 - 137℃; for 5h; Temperature; Solvent; Industrial scale; | 95% |
Stage #1: Cytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 3h; Reflux; Stage #2: α-D-erythropentafuranose-2'-deoxy-2',2'-difluoro-3,5-dibenzoate-1-methanesulfonate With phosphotungstic acid In i-Amyl alcohol at 64℃; Reagent/catalyst; Temperature; Solvent; Time; Further stages; |
[ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2
Cytosine
Conditions | Yield |
---|---|
In methanol for 4h; Inert atmosphere; | 95% |
(fluorenylmethoxy)carbonyl chloride
Cytosine
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 100℃; for 2h; | 95% |
Molecule structure of Cytosine (CAS NO.71-30-7):
IUPAC Name: 6-Amino-1H-pyrimidin-2-one
Molecular Weight: 111.102 g/mol
Molecular Formula: C4H5N3O
Density: 1.55 g/cm3
Melting Point: >300 °C(lit.)
Boiling Point: 445.8 °C at 760 mmHg
Flash Point: 223.4 °C
Index of Refraction: 1.688
Molar Refractivity: 27.3 cm3
Molar Volume: 71.5 cm3
Surface Tension: 69.2 dyne/cm
Enthalpy of Vaporization: 73.1 kJ/mol
Vapour Pressure: 1.46E-08 mmHg at 25 °C
Storage Temp.: store at RT.
Water Solubility: soluble
XLogP3: -1.7
H-Bond Donor: 2
H-Bond Acceptor: 2
Tautomer Count: 9
Exact Mass: 111.043262
MonoIsotopic Mass: 111.043262
Topological Polar Surface Area: 67.5
Heavy Atom Count: 8
Canonical SMILES: C1=C(NC(=O)N=C1)N
InChI: InChI=1S/C4H5N3O/c5-3-1-2-6-4(8)7-3/h1-2H,(H3,5,6,7,8)
InChIKey: OPTASPLRGRRNAP-UHFFFAOYSA-N
EINECS: 200-749-5
Product Categories: Pharmaceutical Intermediates; PYRIMIDINE; FINE Chemical & INTERMEDIATES; Pyridines, Pyrimidines, Purines and Pteredines; Pyrimidine series; Nucleotides and Nucleosides; Cidofovir; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids; Bases & Related Reagents; Nucleotides
In 1894, Cytosine was discovered by Albrecht Kossel when it was hydrolysed from calf thymus tissues. A structure was proposed in 1903, and was synthesized in the laboratory in the same year. The first time any quantum mechanical properties were harnessed to process information took place on August 1st in 1998 when researchers at Oxford implemented David Deutsch's algorithm on a two qubit NMRQC based on the cytosine molecule.
Cytosine (CAS NO.71-30-7) is used as pharmaceutical intermediates.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | > 2222mg/kg (2222mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) | Journal of Pharmacology and Experimental Therapeutics. Vol. 207, Pg. 504, 1978. |
Hazard Codes: Xi, Xn
Risk Statements: 36/37/38-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 1
RTECS: UW7350150
Hazard Note: Irritant
Cytosine (CAS NO.71-30-7) is also named as 4-Amino-2(1H)-pyrimidinone ; 4-Amino-2-hydroxypyrimidine ; AI3-52281 ; Cyt ; Cytosinimine ; NSC 27787 ; 2(1H)-Pyrimidinone, 4-amino- . Cytosine (CAS NO.71-30-7) is white solid.
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