5-Azacytosine supplier | CasNO.931-86-2

Name
5-Azacytosine
EINECS 213-242-9
CAS No. 931-86-2
Article Data24
CAS DataBase
Density 1.86 g/cm³
Solubility
Melting Point >300 °C(lit.)
Formula C₃H₄N₄O
Boiling Point 503.1 °C at 760 mmHg
Molecular Weight 112.091
Flash Point 258.1 °C
Transport Information
Appearance crystalline solid
Safety 22-24/25-36-26
Risk Codes 20/21/22-36/37/38
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms 4-amino-3H-1,3,5-triazin-2-one;4-Amino-1,3,5-triazin-2(1H)-one;4-Amino-1,3,5-triazin-2-one;1,3,5-Triazin-2(1H)-one, 4-amino-;s-Triazin-2(1H)-one, 4-amino-;4040-10-2;s-Triazin-2-ol, 4-amino-;4-amino-[1,3,5]triazin-2-ol;
PSA 84.66000
LogP -0.67170

Synthetic route

: 10043-39-7
guanylurea formate

: 4637-24-5
N,N-dimethyl-formamide dimethyl acetal

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
With sodium methylate In methanol at 40 - 50℃; for 4h; Large scale;	90%
Stage #1: guanylurea formate With sodium methylate In methanol at 25 - 35℃; for 0.0833333h; Stage #2: N,N-dimethyl-formamide dimethyl acetal In methanol at 28 - 50℃;

: 64-18-6
formic acid

: 127099-85-8, 780722-26-1
N-Cyanoguanidine

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
Stage #1: formic acid; N-Cyanoguanidine With toluene-4-sulfonic acid at 110℃; Autoclave; Large scale; Stage #2: With hydrogenchloride In water for 0.5h; Temperature; Reagent/catalyst; Reflux; Large scale;	85%

: 110-74-7
propyl methanoate

: 56563-07-6
N-cyanoacetamidine

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
at 115℃; for 2h;	80%

: 56563-07-6
N-cyanoacetamidine

: 109-94-4
formic acid ethyl ester

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
at 115℃; for 2h;	75%

: 107-31-3
Methyl formate

: 56563-07-6
N-cyanoacetamidine

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
at 115℃; for 2h; Temperature;	73%

: 7709-13-9
4-amino-2-chloro-1,3,5-triazine

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
In hydrogenchloride; methanol for 0.5h; Heating;

: 2353-33-5, 22432-95-7
5-aza-2'-deoxycytidine

A: 931-86-2
5-azacytosine

B: 452-51-7, 13046-70-3, 29780-54-9, 36792-87-7, 36792-88-8, 113890-35-0, 113890-38-3
D-2-deoxyribose

Conditions

Conditions	Yield
With water at 20℃; Acidic aqueous solution;

: 141-83-3
carbamimidoylurea

: 122-51-0
orthoformic acid triethyl ester

: 931-86-2
5-azacytosine

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 155℃; for 1.5h;

: 931-86-2
5-azacytosine

: 999-97-3
1,1,1,3,3,3-hexamethyl-disilazane

: 52523-35-0
2-(trimethylsilylamino)-4-(trimethylsilyloxy)-s-triazine

Conditions

Conditions	Yield
With ammonium sulfate for 8h; Product distribution / selectivity; Reflux;	98%
at 145 - 150℃; for 20h; Concentration;	96%
With ammonium sulfate at 120 - 150℃;	95.7%

: 931-86-2
5-azacytosine

: 129940-50-7
(S)-tritylglycidol

: 933460-54-9
1-[(2S)-2-hydroxy-3-(triphenylmethoxy)propyl]-5-azacytosine

Conditions

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 120℃; for 10h;	83%
With sodium hydroxide In dimethyl sulfoxide at 120℃; for 10h;	83%

: 931-86-2
5-azacytosine

: 13035-61-5, 23094-61-3, 28708-32-9, 39727-26-9, 42927-46-8, 50730-26-2, 56272-01-6, 61248-15-5, 61826-42-4, 61849-90-9, 69855-18-1, 69855-19-2, 79120-80-2, 79120-81-3, 86782-36-7, 86782-94-7, 105453-36-9, 144490-03-9, 43225-70-3
1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose

: 4-amino-1-(2,3,5-tri-O-acetyl-α-D-arabinofuranosyl)-1,3,5-triazin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 60 - 85℃; for 2h; Stage #2: 1,2,3,5-tetra-O-acetyl-α-D-arabinofuranose With trifluorormethanesulfonic acid In acetonitrile at 85℃; for 1h;	75%

: 359-41-1
1,1,1-trifluoro-2,3-epoxypropane

: 931-86-2
5-azacytosine

: 4-amino-1-(3,3,3-trifluoro-2-hydroxypropyl)-1,3,5-triazin-2(1H)-one

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide at 105 - 120℃; for 18h;	73%

: 931-86-2
5-azacytosine

: 3080-30-6, 6974-32-9, 14215-97-5, 16162-35-9, 20822-87-1, 21138-42-1, 22249-15-6, 22249-17-8, 26287-72-9, 53403-35-3, 53403-36-4, 57236-69-8, 70832-64-3, 99395-04-7, 100101-51-7, 109668-83-9, 120019-54-7
1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

: 206269-45-6
1-(2,3,5-tri-O-benzoyl-β-L-ribofuranosyl)-5-azacytosine

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 18h; Heating; Stage #2: 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane at 20℃; for 5h;	70%

: 931-86-2
5-azacytosine

: 1160512-81-1
(R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate

A: 1-[(2S)-2-(diisopropoxyphosphoryl)methoxy-3-hydroxypropyl]-5-azacytosine

B: 1207842-50-9
diisopropyl {[(1R)-2-[(4-amino-1,3,5-triazin-2-yl)oxy]-1-(hydroxymethyl)ethoxy]methyl}-phosphonate

C: 1207842-49-6
3-[(2S)-2-(diisopropoxyphosphoryl)methoxy-3-hydroxypropyl]-5-azacytosine

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With sodium methylate In methanol for 14h; Reflux; Stage #2: (R)-2-[(diisopropoxyphosphoryl)methoxy]-3-hydroxypropyl p-toluenesulfonate With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 2h; regioselective reaction;	A 62% B 8% C 14%

...Expand

: 848644-37-1
1,2,3,5-tetra-O-acetyl-3-C-ethynyl-D-ribo-pentofuranose

: 931-86-2
5-azacytosine

: 848644-46-2
1-[2,3,5-tri-O-acetyl-3-C-ethynyl-β-D-ribo-pentofuranosyl]-5-azacytosine

Conditions

Conditions	Yield
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile at 50℃;	50%

: 931-86-2
5-azacytosine

: 4-methyl-1-phenyl-1H-pyrrol-2(3H)-one

: 61466-03-3
5-methyl-4-[(5-methyl-3-oxo-2-phenyl-2,4-dihydro-3H-pyrazol-4-yl)methylene]-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

Conditions

Conditions	Yield
In butan-1-ol for 4h; Condensation; Heating;	45%

: 931-86-2
5-azacytosine

: 134700-26-8
1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose

: 1161853-96-8
C22H24N4O3S

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 80℃; Reflux; Stage #2: 1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose With trifluorormethanesulfonic acid In acetonitrile at 80℃;	44%

: 931-86-2
5-azacytosine

: (6aR,9aS)-2,2,4,4-tetraisopropyl-8-((4-(octyloxy)benzyl)thio)tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocine

: 4-amino-1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1,3,5-triazin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 21h; Inert atmosphere; Reflux; Stage #2: (6aR,9aS)-2,2,4,4-tetraisopropyl-8-((4-(octyloxy)benzyl)thio)tetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocine With N-Bromosuccinimide In dichloromethane at 0℃; for 2h; Inert atmosphere;	41.7%

: 931-86-2
5-azacytosine

: 318239-79-1
2,3-O,O-dibenzyl-4-(5,6-epoxy)-L-ascorbic acid

: 1313583-60-6
4-amino-1-[2-(3,4-bis-benzyloxy-5-oxo-2,5-dihydro-furan-2-yl)-2-hydroxy-ethyl]-1H-[1,3,5]triazin-2-one

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane for 3h; Inert atmosphere; Reflux; Stage #2: 2,3-O,O-dibenzyl-4-(5,6-epoxy)-L-ascorbic acid With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 55 - 70℃; for 12h; Inert atmosphere;	27.2%

: 931-86-2
5-azacytosine

: 98495-56-8
3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine

A: 1163302-11-1
α-5',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-5-azacytidine

B: 117399-71-0
β-5',3'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-5-azacytidine

Conditions

Conditions	Yield
Stage #1: 5-azacytosine; 3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-2'-deoxyuridine With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane for 3h; Reflux; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In dichloromethane for 6h; Reflux; Inert atmosphere;	A n/a B 25%

...Expand

: 931-86-2
5-azacytosine

: 457653-05-3
1-O-acetyl-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-D-erythro-pentofuranose

: 4-amino-1-((6aR,8R,9aS)-2,2,4,4-tetraisopropyltetrahydro-6H-thieno[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-1,3,5-triazin-2(1H)-one

Conditions

Conditions	Yield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile	25%

: 931-86-2
5-azacytosine

: 17039-17-7
2-deoxy–α-D-ribose 1-phosphate

: 2353-33-5, 22432-95-7
5-aza-2'-deoxycytidine

Conditions

Conditions	Yield
With Escherichia coli purine nucleoside phosphorylase In aq. buffer at 20℃; for 0.5h; pH=7; Enzymatic reaction;	15%

: 931-86-2
5-azacytosine

: 231619-90-2
5',6'-di-O-acetyl-2',3'-di-O-benzyl-L-ascorbic acid

: 1313583-54-8
(Z)-4-amino-1-(2-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidene)ethyl)-1,3,5-triazin-2(1H)-one

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With ammonium sulfate; 1,1,1,3,3,3-hexamethyl-disilazane Inert atmosphere; Reflux; Stage #2: 5',6'-di-O-acetyl-2',3'-di-O-benzyl-L-ascorbic acid With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 55 - 70℃; for 16h; Inert atmosphere;	3.06%

: 931-86-2
5-azacytosine

: 110874-22-1
2-(acetoxymethoxy)-1,3-propanediyl dibenzoate

: 82410-28-4
4-Amino-1-(2-hydroxy-1-hydroxymethyl-ethoxymethyl)-1H-[1,3,5]triazin-2-one

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 931-86-2
5-azacytosine

: 1-O-acetyl-2,3-di-O-benzoyl-4-thio-DL-erythrofuranoside

: 1-(2,3-di-O-benzoyl-4-thio-β-DL-erythrofuranosyl)-5-azacytosine

Conditions

Conditions	Yield
With ammonium sulfate; tin(IV) chloride; 1,1,1,3,3,3-hexamethyl-disilazane 1.) reflux, 3 h, 2.) CH2Cl2, r.t., 10 h; Yield given. Multistep reaction;

: 931-86-2
5-azacytosine

: 208173-53-9
1-O-acetyl-4-(carboethoxy)-2,3-dideoxy-L-ribofuranose

A: (2R,5S)-5-(4-Amino-2-oxo-2H-[1,3,5]triazin-1-yl)-tetrahydro-furan-2-carboxylic acid ethyl ester

B: (2R,5R)-5-(4-Amino-2-oxo-2H-[1,3,5]triazin-1-yl)-tetrahydro-furan-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; trimethylsilyl iodide; t-butyldimethylsiyl triflate 1.) CH2Cl2; 2.) r.t.; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 931-86-2
5-azacytosine

: 75-77-4
chloro-trimethyl-silane

: 108-24-7
acetic anhydride

: N-(4-Trimethylsilanyloxy-[1,3,5]triazin-2-yl)-acetamide

Conditions

Conditions	Yield
With triethylamine

...Expand

: 931-86-2
5-azacytosine

: 169736-17-8
1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose

A: 676487-18-6
1-(2-deoxy-3,5-di-O-p-toluoyl-4-thio-β-D-erythropentofuranosyl)-5-azacytosine

B: 676487-25-5
1-(2-deoxy-3,5-di-O-p-toluoyl-4-thio-α-D-erythropentofuranosyl)-5-azacytosine

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate Substitution;
Stage #1: 5-azacytosine; 1-O-acetyl-2-deoxy-4-thio-3,5-di-O-p-toluoyl-4-thio-D-erythro-pentofuranose With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -78℃; for 2.5h;	A 100 mg B 200 mg

...Expand

: 931-86-2
5-azacytosine

: 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose

A: 676487-27-7
1-(2-deoxy-3,5-di-O-acetyl-4-thio-α-L-threopentofuranosyl)-5-azacytosine

B: 676487-22-2
1-(2-deoxy-3,5-di-O-acetyl-4-thio-β-L-threopentofuranosyl)-5-azacytosine

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate Substitution;
Stage #1: 5-azacytosine; 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -78℃; for 2h;	A 75 mg B 160 mg

...Expand

: 931-86-2
5-azacytosine

: 307002-00-2
(2R)-2-benzyloxymethyl-4-acetoxy-1,3-dioxolane

A: 4-Amino-1-((2R,4S)-2-benzyloxymethyl-[1,3]dioxolan-4-yl)-1H-[1,3,5]triazin-2-one

B: 4-Amino-1-((2R,4R)-2-benzyloxymethyl-[1,3]dioxolan-4-yl)-1H-[1,3,5]triazin-2-one

Conditions

Conditions	Yield
Stage #1: 5-azacytosine With 1,1,1,3,3,3-hexamethyl-disilazane for 4h; silylation; Heating; Stage #2: (2R)-2-benzyloxymethyl-4-acetoxy-1,3-dioxolane With trimethylsilyl trifluoromethanesulfonate In 1,2-dichloro-ethane for 18h; Condensation;

...Expand

5-Azacytosine Chemical Properties

Molecular Structure of 5-Azacytosine (CAS NO. 931-86-2):

IUPAC Name: 6-Amino-1H-1,3,5-triazin-2-one
Molecular Formula: C₃H₄N₄O
Molecular Weight: 112.090060 g/mol
Index of Refraction: 1.801
Molar Refractivity: 25.74 cm³
Molar Volume: 60.1 cm³
Surface Tension: 94.3 dyne/cm
Density: 1.86 g/cm³
Flash Point: 258.1 °C
Enthalpy of Vaporization: 80.15 kJ/mol
Boiling Point: 503.1 °C at 760 mmHg
Vapour Pressure: 9.61E-11 mmHg at 25 °C
Melting Point: >300 °C(lit.)
BRN: 116378
EINECS: 213-242-9
Product Categories: Amino Acids;Heterocyclic Compounds;All Inhibitors;Pyrimidines;Bases & Related Reagents;Inhibitors;Nucleotides

5-Azacytosine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
quail	LD50	oral	> 316mg/kg (316mg/kg)		Ecotoxicology and Environmental Safety. Vol. 6, Pg. 149, 1982.

5-Azacytosine Safety Profile

Safety Information of 5-Azacytosine (CAS NO. 931-86-2):
Hazard Codes: Xi,Xn Harmful
Risk Statements: 20/21/22-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed
R36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements: 22-24/25-36-26
S22:Do not breathe dust
S24/25:Avoid contact with skin and eyes
S36:Wear suitable protective clothing
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 3
RTECS: XZ2854300

5-Azacytosine Specification

5-Azacytosine with cas registry number of 931-86-2 is crystalline solid, also called 4-Amino-1,3,5-triazin-2(1H)-one ; s-Triazin-2(1H)-one, 4-amino- ; s-Triazin-2-ol, 4-amino- ; 1,3,5-Triazin-2(1H)-one, 4-amino- ; 4-Amino-1,3,5-triazin-2-one . It can be used to inhibit the growth of Escherichia coli.

Product Name

5-Azacytosine

Synthetic route

5-Azacytosine Chemical Properties

5-Azacytosine Toxicity Data With Reference

5-Azacytosine Safety Profile

5-Azacytosine Specification

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