Product Name

  • Name

    5-METHYLCYTIDINE

  • EINECS 218-390-8
  • CAS No. 2140-61-6
  • Article Data13
  • CAS DataBase
  • Density 1.79 g/cm3
  • Solubility
  • Melting Point 212-215 °C (dec.)(lit.)
  • Formula C10H15N3O5
  • Boiling Point 537.5 °C at 760 mmHg
  • Molecular Weight 257.246
  • Flash Point 278.9 °C
  • Transport Information
  • Appearance Light Yellow Crystals
  • Safety 26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2140-61-6 (5-METHYLCYTIDINE)
  • Hazard Symbols IrritantXi
  • Synonyms 3:PN: US20060035254 PAGE: 63 claimed sequence;5-Methylcytidine;NSC 363933;
  • PSA 130.83000
  • LogP -1.67340

Synthetic route

2',3',5'-tri-O-benzoyl-5-methylcytidine
59237-68-2

2',3',5'-tri-O-benzoyl-5-methylcytidine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
With sodium methylate In methanol for 14h; Ambient temperature;91%
With ammonia In methanol
N4,5-dimethylcytidine
117862-70-1

N4,5-dimethylcytidine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
With manganese(IV) oxide; C17H20N4O9P(1-)*Na(1+); oxygen In water; acetonitrile at 20℃; under 760.051 Torr; for 7h; Irradiation; chemoselective reaction;70%
4-methoxy-5-methyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrimidin-2-one
7323-83-3

4-methoxy-5-methyl-1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-pyrimidin-2-one

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
With ammonia In methanol at 100℃; for 21h;67%
O2',O3',O5'-tribenzoyl-5-methyl-4-thio-uridine
28585-48-0

O2',O3',O5'-tribenzoyl-5-methyl-4-thio-uridine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
With ethanol; ammonia
tert-butyl peroxyacetate
107-71-1

tert-butyl peroxyacetate

CYTIDINE
65-46-3

CYTIDINE

A

4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one
10578-79-7

4-methylamino-1-(β-D-ribofuranosyl)pyrimidin-2(1H)-one

B

N3-methylcytidine
2140-64-9

N3-methylcytidine

C

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
at 32℃; for 20h; Product distribution; Mechanism; Irradiation; solutions of pH 1.4 - 12.4;
...Expand
1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose
6974-32-9

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SnCl4
2: NaHCO3 / H2O
3: 98 percent / Et3N; POCl3 / acetonitrile
4: NH3 / dioxane / 24 h / 20 °C
5: NH3 / methanol
View Scheme
Multi-step reaction with 2 steps
1: 99 percent / stannic chloride / acetonitrile / Ambient temperature
2: 67 percent / ammonia / methanol / 21 h / 100 °C
View Scheme
2',3',5'-tri-O-benzoyluridine
3180-76-5

2',3',5'-tri-O-benzoyluridine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / Et3N; POCl3 / acetonitrile
2: NH3 / dioxane / 24 h / 20 °C
3: NH3 / methanol
View Scheme
Multi-step reaction with 2 steps
1: pyridine; P2S5
2: ethanol; NH3
View Scheme
C33H27N5O8
163496-05-7

C33H27N5O8

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3 / dioxane / 24 h / 20 °C
2: NH3 / methanol
View Scheme
C34H34N2O9Si

C34H34N2O9Si

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: NaHCO3 / H2O
2: 98 percent / Et3N; POCl3 / acetonitrile
3: NH3 / dioxane / 24 h / 20 °C
4: NH3 / methanol
View Scheme
2,4-bis(trimethylsiloxy)-5-methylpyrimidine
7288-28-0

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SnCl4
2: NaHCO3 / H2O
3: 98 percent / Et3N; POCl3 / acetonitrile
4: NH3 / dioxane / 24 h / 20 °C
5: NH3 / methanol
View Scheme
5-methylcytosin
554-01-8

5-methylcytosin

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 5 h / Heating
2: 60 percent / SnCl2 / CH2Cl2 / 5 h
3: 91 percent / NaOMe / methanol / 14 h / Ambient temperature
View Scheme
2'-O,N4-bis-trimethylsilyl-5-methylcytosine
32865-88-6

2'-O,N4-bis-trimethylsilyl-5-methylcytosine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 60 percent / SnCl2 / CH2Cl2 / 5 h
2: 91 percent / NaOMe / methanol / 14 h / Ambient temperature
View Scheme
2,4-Dimethoxy-5-methylpyrimidine
5151-34-8

2,4-Dimethoxy-5-methylpyrimidine

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / stannic chloride / acetonitrile / Ambient temperature
2: 67 percent / ammonia / methanol / 21 h / 100 °C
View Scheme
thymin
65-71-4

thymin

1-halogenepoxy propane

1-halogenepoxy propane

5-methylcytidine
2140-61-6

5-methylcytidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 86 percent
2: 99 percent / stannic chloride / acetonitrile / Ambient temperature
3: 67 percent / ammonia / methanol / 21 h / 100 °C
View Scheme
tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

5-methylcytidine
2140-61-6

5-methylcytidine

4-amino-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one
329897-75-8

4-amino-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidin-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide94%
5-methylcytidine
2140-61-6

5-methylcytidine

5-methylcytidine-5'-monophosphate

5-methylcytidine-5'-monophosphate

Conditions
ConditionsYield
With triethyl phosphate; trichlorophosphate at -5 - 0℃; for 10h;75%
5-methylcytidine
2140-61-6

5-methylcytidine

5-formylcytidine

5-formylcytidine

Conditions
ConditionsYield
With sodium anthraquinone-2-sulfonate; oxygen In water; dimethyl sulfoxide at 37℃; under 760.051 Torr; for 11h; Mechanism; Reagent/catalyst; Solvent; Wavelength; UV-irradiation;67%
Multi-step reaction with 3 steps
1: 94 percent / imidazole / dimethylformamide
2: 20 percent / Na2S2O8 / 70 °C / pH 7
3: 71 percent / TBAF / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 94 percent / imidazole / dimethylformamide
2: 27 percent / Na2S2O8 / 70 °C / pH 7
3: CAN
4: 71 percent / TBAF / tetrahydrofuran / 20 °C
View Scheme
5-methylcytidine
2140-61-6

5-methylcytidine

5-methyl-N4-hydroxycytidine
7803-85-2

5-methyl-N4-hydroxycytidine

Conditions
ConditionsYield
With hydroxylamine In water at 55℃; for 5h; Sealed tube; Inert atmosphere;51%
With hydroxylamine In water at 55℃; for 5h; pH=6; Sealed tube; Inert atmosphere;51%
With hydroxylamine In water at 55℃; for 5h; pH=6; Sealed tube; Inert atmosphere;51%
5-methylcytidine
2140-61-6

5-methylcytidine

2',3',5'-tri-O-benzoyluridine
3180-76-5

2',3',5'-tri-O-benzoyluridine

Conditions
ConditionsYield
With tris hydrochloride; magnesium chloride; human cytidine deaminase at 37℃; assay of cytidine deaminase;50%
5-methylcytidine
2140-61-6

5-methylcytidine

A

5-methylcytosin
554-01-8

5-methylcytosin

B

5-hydroxymethylcytosine
1123-95-1

5-hydroxymethylcytosine

C

5-hydroxymethyl-1-(β-D-ribofuranosyl)cytosine
19235-17-7

5-hydroxymethyl-1-(β-D-ribofuranosyl)cytosine

Conditions
ConditionsYield
With sodium persulfate In water at 75℃; for 4h; sodium phosphate buffer pH 7.0;A 27%
B 2%
C 23%
...Expand
P,P'-methanediyl-bis-phosphonic acid tetrachloride
1499-29-2

P,P'-methanediyl-bis-phosphonic acid tetrachloride

triethylamine carbonate
15715-58-9

triethylamine carbonate

5-methylcytidine
2140-61-6

5-methylcytidine

5-methylcytidine-5'-O-[(phosphonomethyl)phosphonic acid] sesquitriethylamine salt

5-methylcytidine-5'-O-[(phosphonomethyl)phosphonic acid] sesquitriethylamine salt

Conditions
ConditionsYield
Stage #1: P,P'-methanediyl-bis-phosphonic acid tetrachloride; 5-methylcytidine at 0℃; for 0.5h;
Stage #2: triethylamine carbonate With water at 0 - 20℃; for 0.75h; pH=8.4 - 8.6;		22%
...Expand
5-methylcytidine
2140-61-6

5-methylcytidine

(3aS)-2t-hydroxymethyl-6-imino-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3c-ol

(3aS)-2t-hydroxymethyl-6-imino-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3c-ol

Conditions
ConditionsYield
With 2-acetoxy-2-methylpropanoyl chloride In acetonitrile
5-methylcytidine
2140-61-6

5-methylcytidine

5-Methyluridine
1463-10-1

5-Methyluridine

Conditions
ConditionsYield
With sodium hydroxide at 90.1℃; Rate constant; Mechanism; various reagent concentration, decomposition to nonchromophoric products;
benzoyl chloride
98-88-4

benzoyl chloride

5-methylcytidine
2140-61-6

5-methylcytidine

N-benzoyl-5-methylcytidine
160107-15-3

N-benzoyl-5-methylcytidine

Conditions
ConditionsYield
With pyridine; sodium hydroxide 1.) RT, 1.5 h, 2.) THF, MeOH, 0 deg C, 30 min; Yield given. Multistep reaction;
benzoic acid anhydride
93-97-0

benzoic acid anhydride

5-methylcytidine
2140-61-6

5-methylcytidine

N-benzoyl-5-methylcytidine
160107-15-3

N-benzoyl-5-methylcytidine

Conditions
ConditionsYield
In water; N,N-dimethyl-formamide
5-methylcytidine
2140-61-6

5-methylcytidine

4-Amino-1-[(2R,3R,4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidine-5-carbaldehyde
329897-77-0

4-Amino-1-[(2R,3R,4S,5R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidine-5-carbaldehyde

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / imidazole / dimethylformamide
2: 20 percent / Na2S2O8 / 70 °C / pH 7
View Scheme
Multi-step reaction with 3 steps
1: 94 percent / imidazole / dimethylformamide
2: 27 percent / Na2S2O8 / 70 °C / pH 7
3: CAN
View Scheme
5-methylcytidine
2140-61-6

5-methylcytidine

4-amino-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-hydroxymethyl-1H-pyrimidin-2-one
329897-76-9

4-amino-1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-5-hydroxymethyl-1H-pyrimidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / imidazole / dimethylformamide
2: 27 percent / Na2S2O8 / 70 °C / pH 7
View Scheme
5-methylcytidine
2140-61-6

5-methylcytidine

N-(1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide
160107-17-5

N-(1-{(2R,3R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3,4-dihydroxy-tetrahydro-furan-2-yl}-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl)-benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) pyridine, 2.) aq. NaOH / 1.) RT, 1.5 h, 2.) THF, MeOH, 0 deg C, 30 min
2: 62 percent / pyridine / 0 °C
View Scheme
5-methylcytidine
2140-61-6

5-methylcytidine

N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide
160107-13-1

N-{1-[(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-2-oxo-1,2-dihydro-pyrimidin-4-yl}-benzamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) pyridine, 2.) aq. NaOH / 1.) RT, 1.5 h, 2.) THF, MeOH, 0 deg C, 30 min
2: 62 percent / pyridine / 0 °C
3: 71 percent / pyridine, AgNO3 / tetrahydrofuran / 5 h
View Scheme
5-methylcytidine
2140-61-6

5-methylcytidine

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-benzoylamino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Diisopropyl-phosphoramidous acid (2R,3R,4R,5R)-5-(4-benzoylamino-5-methyl-2-oxo-2H-pyrimidin-1-yl)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-3-yl ester 2-cyano-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) pyridine, 2.) aq. NaOH / 1.) RT, 1.5 h, 2.) THF, MeOH, 0 deg C, 30 min
2: 62 percent / pyridine / 0 °C
3: 71 percent / pyridine, AgNO3 / tetrahydrofuran / 5 h
4: 82 percent / collidine, N-methylimidazole / tetrahydrofuran / 1 h
View Scheme

Cytidine,5-methyl- Specification

The Cytidine,5-methyl-, with CAS registry number 2140-61-6, belongs to the following product categories: (1)Biochemistry; (2)Nucleosides and their analogs; (3)Nucleosides, Nucleotides & Related Reagents; (4)Biochemicals and Reagents; (5)Nucleoside Analogs; (6)Nucleosides, Nucleotides, Oligonucleotides. It has the systematic name of 5-methylcytidine. And the chemical formula of this chemical is C10H15N3O5.

Physical properties of Cytidine,5-methyl-: (1)ACD/LogP: -1.35; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -1.35; (4)ACD/LogD (pH 7.4): -1.34; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 4.36; (8)ACD/KOC (pH 7.4): 4.42; (9)#H bond acceptors: 8; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 72.83 Å2; (13)Index of Refraction: 1.725; (14)Molar Refractivity: 57.06 cm3; (15)Molar Volume: 143.6 cm3; (16)Polarizability: 22.62×10-24cm3; (17)Surface Tension: 77.4 dyne/cm; (18)Density: 1.79 g/cm3; (19)Flash Point: 278.9 °C; (20)Enthalpy of Vaporization: 93.67 kJ/mol; (21)Boiling Point: 537.5 °C at 760 mmHg; (22)Vapour Pressure: 8.5E-14 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
The Cytidine,5-methyl- irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1/N=C(/N)\C(=C/N1[C@@H]2O[C@@H]([C@@H](O)[C@H]2O)CO)C
(2)InChI: InChI=1/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1
(3)InChIKey: ZAYHVCMSTBRABG-JXOAFFINBK
(4)Std. InChI: InChI=1S/C10H15N3O5/c1-4-2-13(10(17)12-8(4)11)9-7(16)6(15)5(3-14)18-9/h2,5-7,9,14-16H,3H2,1H3,(H2,11,12,17)/t5-,6-,7-,9-/m1/s1
(5)Std. InChIKey: ZAYHVCMSTBRABG-JXOAFFINSA-N

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