Product Name

  • Name

    N,9-Diacetylguanine

  • EINECS 221-287-0
  • CAS No. 3056-33-5
  • Article Data20
  • CAS DataBase
  • Density 1.67 g/cm3
  • Solubility Insoluble in water
  • Melting Point 285 °C(lit.)
  • Formula C9H9N5O3
  • Boiling Point
  • Molecular Weight 235.202
  • Flash Point
  • Transport Information
  • Appearance white or brownish crystalline powder
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 3056-33-5 (N,9-Diacetylguanine)
  • Hazard Symbols IrritantXi
  • Synonyms Guanine,N,9-diacetyl- (7CI,8CI);2,9-Diacetylguanine;N2,9-Diacetylguanine;N-(9-acetyl-6-oxo-6,9-dihydro-3H-purin-2-yl)acetamide;acetamide, N-(9-acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)-;N-(9-Acetyl-6-hydroxy-9H-purin-2-yl)acetamide;N-(9-Acetyl-6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide;
  • PSA 109.74000
  • LogP -0.18890

Synthetic route

2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

acetic anhydride
108-24-7

acetic anhydride

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Conditions
ConditionsYield
In N,N-dimethyl acetamide at 160℃; for 18h;97%
In N,N-dimethyl-formamide at 160℃; for 2h; Acetylation;95%
for 16h; Heating;95%
acetic anhydride
108-24-7

acetic anhydride

G
118-00-3

G

A

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

B

1,2,3,5-tetraacetylribose
13035-61-5

1,2,3,5-tetraacetylribose

Conditions
ConditionsYield
Stage #1: acetic anhydride; G at 136℃; for 1h;
Stage #2: With trifluoroacetic acid at 60 - 100℃;		A 96%
B 86%
...Expand
guanine powder

guanine powder

acetic anhydride
108-24-7

acetic anhydride

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Conditions
ConditionsYield
With acetic acid at 135℃; for 7.5h;95%
2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

acetyl chloride
75-36-5

acetyl chloride

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Conditions
ConditionsYield
With pyridine; dmap at -5 - 20℃;91.7%
2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

acetic anhydride
108-24-7

acetic anhydride

A

N,N'-diacetylguanine
137226-08-5

N,N'-diacetylguanine

B

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Conditions
ConditionsYield
In acetic acid at 140℃; for 18h; Yield given. Title compound not separated from byproducts;
...Expand
2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Conditions
ConditionsYield
With acetic anhydride
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide
19962-37-9

N-(6-oxo-6,9-dihydro-1H-purin-2-yl)acetamide

Conditions
ConditionsYield
In ethanol; water for 2h; Reflux;98%
With ethanol In water Reflux;
In ethanol; water at 80℃;12 g
2-acetoxyethyl acetoxymethyl ether
59278-00-1

2-acetoxyethyl acetoxymethyl ether

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

Conditions
ConditionsYield
at 105℃; for 80h;95.1%
With toluene-4-sulfonic acid In toluene at 110℃; Temperature; Large scale;94.3%
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

2-amino-1,9-dihydro-6H-purin-6-one

Conditions
ConditionsYield
With sodium hydroxide In water for 1h; Heating;95%
diphenylcarbamic chloride
83-01-2

diphenylcarbamic chloride

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

N2-acetyl-O6-(diphenylcarbamoyl)guanine
112233-74-6

N2-acetyl-O6-(diphenylcarbamoyl)guanine

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In pyridine for 1h; Ambient temperature;92%
Stage #1: diphenylcarbamic chloride; 2,9-diacetylguanine With pyridine; N-ethyl-N,N-diisopropylamine for 4h;
Stage #2: In ethanol; water at 70℃; for 3.5h;		91%
With ethanol; N-ethyl-N,N-diisopropylamine 1.) pyridine, room temp., 1 h, 2.) heating; Yield given. Multistep reaction;
Stage #1: diphenylcarbamic chloride; 2,9-diacetylguanine With pyridine; N-ethyl-N,N-diisopropylamine at 20℃; for 2h;
Stage #2: With ethanol; water for 1.5h; Heating / reflux;
2-(acetoxymethoxy)-1,3-propanediyl diacetate
86357-13-3

2-(acetoxymethoxy)-1,3-propanediyl diacetate

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine
86357-14-4

9-(1,3-diacetoxy-2-propoxymethyl)-N2-acetylguanine

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 100℃; for 10h; Solvent; Temperature; Microwave irradiation;85.3%
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

2-amino-6-chloropurine
10310-21-1

2-amino-6-chloropurine

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane at 80℃;84%
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

Conditions
ConditionsYield
With trichlorophosphate In 1,2-dichloro-ethane; PEG-2000 at 80℃; for 6.33333h;84%
2-(4-nitrophenyl)ethanol
100-27-6

2-(4-nitrophenyl)ethanol

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

N2,N9-diacetyl-O6-2-(4-nitrophenyl)ethylguanine
917376-69-3

N2,N9-diacetyl-O6-2-(4-nitrophenyl)ethylguanine

Conditions
ConditionsYield
With ethyl azodicarboxylate; triphenylphosphine In 1,4-dioxane for 24h;80%
With triphenylphosphine; diethylazodicarboxylate In 1,4-dioxane at 20℃; Condensation; Mitsunobu reaction;
2-acetoxyethyl acetoxymethyl ether
59278-00-1

2-acetoxyethyl acetoxymethyl ether

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
91702-60-2

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions
ConditionsYield
With titanium tetrachloride In acetic acid at 10 - 15℃; for 6h;65.4%
2-(4-nitrophenyl)ethanol
100-27-6

2-(4-nitrophenyl)ethanol

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

N2-acetyl-O6-(2-(p-nitrophenyl)ethyl)guanine
218152-30-8

N2-acetyl-O6-(2-(p-nitrophenyl)ethyl)guanine

Conditions
ConditionsYield
With triphenylphosphine; diethylazodicarboxylate at 20℃;64%
trans-2,3-Dichlorotetrahydrofuran
3511-19-1, 13129-90-3, 29120-50-1, 106445-14-1

trans-2,3-Dichlorotetrahydrofuran

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

trans-9-(3-chlorotetrahydrofuran-2-yl)guanine
106445-17-4

trans-9-(3-chlorotetrahydrofuran-2-yl)guanine

Conditions
ConditionsYield
With Bis(p-nitrophenyl) phosphate In sulfolane at 100℃; for 16h;59.7%
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

1,3-dipivaloyloxy-2-((methylsulfinyl)methoxy)propane
100675-34-1

1,3-dipivaloyloxy-2-((methylsulfinyl)methoxy)propane

A

2,2-Dimethyl-propionic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-ylmethoxy)-3-(2,2-dimethyl-propionyloxy)-propyl ester
119824-58-7

2,2-Dimethyl-propionic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-ylmethoxy)-3-(2,2-dimethyl-propionyloxy)-propyl ester

B

N2-acetyl-9-((1,3-pivaloyloxy-2-propoxy)methyl)guanine
100675-29-4

N2-acetyl-9-((1,3-pivaloyloxy-2-propoxy)methyl)guanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide; N,N-dimethyl-formamide at 105℃; for 42h;A 17%
B 44.5%
...Expand
1-benzyloxy-3-benzyloxy-2acetyloxymethoxypropane
84245-11-4

1-benzyloxy-3-benzyloxy-2acetyloxymethoxypropane

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

N2-acetyl-7-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine
84222-48-0

N2-acetyl-7-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine

B

N2-acetyl-9-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine
82410-30-8

N2-acetyl-9-<<1,3-bis(benzyloxy)-2-propoxy>methyl>guanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In sulfolane at 95℃; for 72h; Yield given;A n/a
B 31%
With toluene-4-sulfonic acid In sulfolane at 95℃; for 72h; Yields of byproduct given;A n/a
B 31%
With toluene-4-sulfonic acid In sulfolane at 95℃; for 85h;A n/a
B 31%
...Expand
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Acetic acid 5-(diethoxy-phosphoryl)-pentyloxymethyl ester
174538-08-0

Acetic acid 5-(diethoxy-phosphoryl)-pentyloxymethyl ester

[5-(2-Acetylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-pentyl]-phosphonic acid diethyl ester
174538-32-0

[5-(2-Acetylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-pentyl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile for 96h; Heating;31%
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

(+/-)-1-(acetoxymethoxy)-2,3-diacetoxypropane
96429-67-3

(+/-)-1-(acetoxymethoxy)-2,3-diacetoxypropane

A

(+/-)-N2-acetyl-7-<(2,3-diacetoxy-1-propoxy)methyl>guanine
96429-69-5

(+/-)-N2-acetyl-7-<(2,3-diacetoxy-1-propoxy)methyl>guanine

B

(+/-)-N2-acetyl-9-<(2,3-diacetoxy-1-propoxy)methyl>guanine
96429-68-4

(+/-)-N2-acetyl-9-<(2,3-diacetoxy-1-propoxy)methyl>guanine

Conditions
ConditionsYield
With ethanesulfonic acid at 155 - 160℃; for 1.25h;A n/a
B 29%
...Expand
1,3-DIOXOLANE
646-06-0

1,3-DIOXOLANE

acetic anhydride
108-24-7

acetic anhydride

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

B

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
91702-60-2

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid; acetic acid In toluene at 120℃; for 2.5h;A 29%
B 29%
...Expand
Acetic acid 2-(2-oxo-propoxy)-ethyl ester
102728-65-4

Acetic acid 2-(2-oxo-propoxy)-ethyl ester

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

B

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
91702-60-2

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid 1.) 120-125 deg C, 2.) 150 deg C, 45 min;A 27%
B 22%
...Expand
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Acetic acid 2-acetoxymethoxy-3,3,3-trifluoro-propyl ester
181183-09-5

Acetic acid 2-acetoxymethoxy-3,3,3-trifluoro-propyl ester

A

Acetic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-ylmethoxy)-3,3,3-trifluoro-propyl ester

Acetic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-7-ylmethoxy)-3,3,3-trifluoro-propyl ester

B

Acetic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3,3,3-trifluoro-propyl ester

Acetic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-3,3,3-trifluoro-propyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 145℃; for 16h;A 14%
B 22%
...Expand
1,3-DIOXOLANE
646-06-0

1,3-DIOXOLANE

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

B

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
91702-60-2

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions
ConditionsYield
With acetic anhydride; toluene-4-sulfonic acid In acetic acid for 1h; Heating;A 18%
B 2.3%
...Expand
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

Acetic acid 6-(diethoxy-phosphoryl)-hexyloxymethyl ester
174538-09-1

Acetic acid 6-(diethoxy-phosphoryl)-hexyloxymethyl ester

[6-(2-Acetylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-hexyl]-phosphonic acid diethyl ester
174538-33-1

[6-(2-Acetylamino-6-oxo-1,6-dihydro-purin-9-ylmethoxy)-hexyl]-phosphonic acid diethyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile for 96h; Heating;14%
2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

diethyl <4-(acetoxymethoxy)butyl>phosphonate
174538-07-9

diethyl <4-(acetoxymethoxy)butyl>phosphonate

diethyl <4-<(2-acetamido-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy>butyl>phosphonate
174538-31-9

diethyl <4-<(2-acetamido-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy>butyl>phosphonate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile for 96h; Heating;12%
trans-2,3-Dichlorotetrahydrofuran
3511-19-1, 13129-90-3, 29120-50-1, 106445-14-1

trans-2,3-Dichlorotetrahydrofuran

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

trans-N2-acetyl-9-(3-chlorotetrahydrofuran-2-yl)guanine
106445-16-3

trans-N2-acetyl-9-(3-chlorotetrahydrofuran-2-yl)guanine

trans-N2-acetyl-7-(3-chlorotetrahydrofuran-2-yl)guanine
106445-15-2

trans-N2-acetyl-7-(3-chlorotetrahydrofuran-2-yl)guanine

Conditions
ConditionsYield
With Bis(p-nitrophenyl) phosphate In N,N-dimethyl-formamide 1) 90 to 95 deg C, 1 h, 2) RT, 16 h;A 11%
B 10.9%
...Expand
allyloxymethyl acetate
98485-52-0

allyloxymethyl acetate

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

7-allyloxymethylguanine

7-allyloxymethylguanine

B

9-allyloxymethylguanine

9-allyloxymethylguanine

Conditions
ConditionsYield
With ammonia; toluene-4-sulfonic acid 1.) DMSO, from 95 deg C to 100 deg C, 40 h, 2.) MeOH, RT, 24 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With ammonia; toluene-4-sulfonic acid 1.) DMSO, from 95 deg C to 100 deg C, 40 h, 2.) MeOH, RT, 24 h; Yield given. Multistep reaction. Yields of byproduct given;
...Expand
allyloxymethyl acetate
98485-52-0

allyloxymethyl acetate

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

7-allyloxymethyl-N-acetylguanine

7-allyloxymethyl-N-acetylguanine

B

9-allyloxymethyl-N-acetylguanine

9-allyloxymethyl-N-acetylguanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dimethyl sulfoxide at 95 - 100℃; for 40h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With toluene-4-sulfonic acid In dimethyl sulfoxide at 95 - 100℃; for 40h; Yield given. Yields of byproduct given;
...Expand
2-methoxy-ethanol
109-86-4

2-methoxy-ethanol

acetic anhydride
108-24-7

acetic anhydride

2,9-diacetylguanine
3056-33-5

2,9-diacetylguanine

A

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one
75128-73-3

2-acetylamino-9-(2-acetoxyethoxymethyl)purine-6-one

B

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine
91702-60-2

7-<(2-acetoxyethoxy)methyl>-N2-acetylguanine

Conditions
ConditionsYield
With toluene-4-sulfonic acid 1.) AcOH, 2.) toluene, reflux, 16 h; Yield given. Multistep reaction. Yields of byproduct given;
...Expand

N,9-Diacetylguanine Specification

The Acetamide,N-(9-acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)-, with the CAS registry number 3056-33-5 and EINECS registry number 221-287-0, has the systematic name of N-(9-acetyl-6-oxo-6,9-dihydro-3H-purin-2-yl)acetamide. It is a kind of white or brownish crystalline powder, and belongs to the following product categories: Pyridines, Pyrimidines, Purines and Pteredines; Purine; Nucleotides and Nucleosides; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Nucleotides; Building Blocks; Heterocyclic Building Blocks; Purines. The molecular formula of the chemical is C9H9N5O3. It is always used in biochemical research. 

The physical properties of Acetamide,N-(9-acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)- are as followings: (1)ACD/LogP: -2.41; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.41; (4)ACD/LogD (pH 7.4): -2.43; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.17; (8)ACD/KOC (pH 7.4): 1.11; (9)#H bond acceptors: 8; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 87.87 Å2; (13)Index of Refraction: 1.752; (14)Molar Refractivity: 57.27 cm3; (15)Molar Volume: 140.2 cm3; (16)Polarizability: 22.7×10-24cm3; (17)Surface Tension: 71.1 dyne/cm; (18)Density: 1.67 g/cm3.  

Preparation: This chemical can be prepared by 2-amino-1,7(9)-dihydro-purin-6-one and acetic acid anhydride. The reaction will need reagent DMAP, and the menstruum acetic acid. The reaction time is 8 hours with temperature of 160°C, and the yield is about 88%. 

Uses of Acetamide,N-(9-acetyl-6,9-dihydro-6-oxo-1H-purin-2-yl)-: It can react with 2,3-dichlorotetrahydrofuran to produce trans-9-(3-chlorotetrahydrofuran-2-yl)guanine. This reaction will need reagent bis(p-nitrophenyl)phosphate, and the menstruum tetrahydrothiophene 1,1-dioxide. The reaction time is 16 hours with temperature of 100°C, and the yield is about 59.7%. 

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable gloves and eye/face protection, and in case of contacting 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=C(NC/1=N/C(=O)c2ncn(c2N\1)C(=O)C)C
(2)InChI: InChI=1/C9H9N5O3/c1-4(15)11-9-12-7-6(8(17)13-9)10-3-14(7)5(2)16/h3H,1-2H3,(H2,11,12,13,15,17)
(3)InChIKey: GILZZWCROUGLIS-UHFFFAOYAM

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