2-Amino-6-chloropurine supplier

Name
6-Chloroguanine
EINECS 233-686-7
CAS No. 10310-21-1
Article Data27
CAS DataBase
Density 1.77 g/cm³
Solubility 1.7 g/L (20 °C) in water

Melting Point 300 °C

Formula C₅H₄ClN₅

Boiling Point 623.9 °C at 760 mmHg

Molecular Weight 169.573

Flash Point 331.1 °C

Transport Information

Appearance white to light yellow crystal powder

Safety 22-24/25-36-26

Risk Codes 20/21/22-36/37/38

Molecular Structure

Hazard Symbols Xn,Xi

Synonyms 6-chloro-7H-purin-2-amine;6-chloro-5H-purin-2-amine;2-Amino-6-chlorpurine;1H-Purin-2-amine, 6-chloro-;6-Chloroguanine;1H-Purin-2-amine, 6-chloro- (9CI);Purine, 2-amino-6-chloro-;6-CHLORO-1H-PURIN-2-AMINE;6-Chloro-7H-purin-2-ylamine;6-Chloro-2-aminopurine;2-Amino-6-chloropurine(6-Chloroguanine);6-Chloro guanine 98%;2-Amino-6-chloropurine ( 6-Chloroguanine );2-Amino-6-chloro-9H-purine;6-chloro-9H-purin-2-amine;2-amino-6-chloro-purin;

PSA 80.48000

LogP 1.16970

Synthetic route

190962-00-6
6-chloro-2-formylaminopurine acetate

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

Conditions

Conditions Yield

With water; sodium hydroxide at 20℃; for 3h; 89%

3056-33-5
2,9-diacetylguanine

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

Conditions

Conditions Yield

With trichlorophosphate In 1,2-dichloro-ethane; PEG-2000 at 80℃; for 6.33333h; 84%

C5H2ClN5O2

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

Conditions

Conditions Yield

With methanol; hydrazine hydrate at 50℃; Reagent/catalyst; Solvent; Reflux; 81.6%

149948-30-1
N-(6-chloro-9H-purin-2-yl)formamide

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

Conditions

Conditions Yield

With sodium hydroxide at 20 - 80℃; for 3h; 80%

With water; sodium hydrogencarbonate at 25℃; for 3h; Reagent/catalyst; 73.3%

2-phenylmethylamino-6-chloropurine

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

Conditions

Conditions Yield

75%

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

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

Conditions

Conditions Yield

With trichlorophosphate In N,N-dimethyl-formamide at 0℃; for 6h; Reflux; 70%

With trichlorophosphate In ammonium hydroxide; water; N,N-dimethyl-formamide 55%

With tetraethylammonium chloride; trichlorophosphate In water; acetonitrile 42%

methyltriethylammonium chloride (TEMAC)

methyltriethylammonium chloride (TEMAC)

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

7440-44-0
pyrographite

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

Conditions

Conditions Yield

With trichlorophosphate In water; acetone; acetonitrile 54%

...Expand

ammonium sulfate

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

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

Conditions

Conditions Yield

With N-benzyl-N,N,N-triethylammonium chloride; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate In N,N-dimethyl acetamide; acetonitrile

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate In N,N-dimethyl acetamide; acetonitrile

N2,9-diacetylguanine

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

Conditions

Conditions Yield

Multi-step reaction with 2 steps
1: trichlorophosphate
2: water; sodium hydroxide
View Scheme

97965-44-1
2-acetamido-9-acetyl-6-chloropurine

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

Conditions

Conditions Yield

With water; sodium hydroxide

73-40-5
2-amino-6-hydroxypurine

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

Conditions

Conditions Yield

Multi-step reaction with 3 steps
1: acetic acid
2: trichlorophosphate
3: water; sodium hydroxide
View Scheme

Multi-step reaction with 3 steps
1: dihydrogen peroxide / water / 2 h / 20 °C
2: thionyl chloride / methanol / 0.33 h / 0 - 5 °C / Reflux
3: methanol; hydrazine hydrate / 50 °C / Reflux
View Scheme

With hydrogenchloride; dihydrogen peroxide In water at 40 - 50℃; for 3h; Reagent/catalyst; 95.6 g

149948-29-8
C8H9ClN6

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

Conditions

Conditions Yield

Multi-step reaction with 2 steps
1: water / 4.5 h / 70 °C
2: water; sodium hydroxide / 3 h / 20 °C
View Scheme

(E)-N'-(6-chloro-9H-purin-2-yl)-N,N-dimethylformimidamide

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

Conditions

Conditions Yield

Multi-step reaction with 2 steps
1: water / 4 h / 70 °C
2: sodium hydroxide / 3 h / 20 - 80 °C
View Scheme

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

75-50-3
trimethylamine

34798-95-3
2-amino-N,N,N-trimethyl-9H-purine-6-ylammonium chloride

Conditions

Conditions Yield

In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; 100%

In ethanol; dimethyl sulfoxide at 20℃; for 12h; 76%

In dimethyl sulfoxide for 12h; 72%

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

470483-92-2
9-acetyl-2-amino-6-chloro-9H-purine

Conditions

Conditions Yield

With acetic anhydride; triethylamine In isopropyl alcohol; toluene 100%

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

197644-83-0
1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside

897364-66-8
2-amino-6-chloro-9-[2'-O-acetyl-5'-O-benzyl-3'-O-(3'',4''-di-O-acetyl-2'',6''-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranosyl]purine

Conditions

Conditions Yield

With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 70℃; 100%

Stage #1: 2-Amino-6-chloropurin; 1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside In acetonitrile at 100℃; for 0.5h;
Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 70℃; Vorbrueggen condensation; Further stages.; 90%

1380167-26-9
1-N-Boc-7-N(3-bromopropyl)-4-N,7-N-di(2-nosyl)-4-azeheptane-1,7-diamine

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

C31H39ClN10O10S2

Conditions

Conditions Yield

With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 108h; Inert atmosphere; 100%

630-10-4
selenourea

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

5375-85-9
6‑selenoguanine

Conditions

Conditions Yield

In ethanol for 2h; Reflux; Inert atmosphere; Schlenk technique; 100%

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

3863-11-4
3,4-difluoroaniline

N6-(3,4-difluorophenyl)-9H-purine-2,6-diamine

Conditions

Conditions Yield

at 130℃; for 0.0833333h; Irradiation; 100%

141-52-6
sodium ethanolate

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

51866-19-4
NU2046

Conditions

Conditions Yield

In 1-methyl-pyrrolidin-2-one at 100℃; for 0.05h; microwave irradiation; 98%

24424-99-5
di-tert-butyl dicarbonate

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

309947-85-1
tert-butyl 2-[bis(tert-butoxycarbonyl)amino]-6-chloro-9H-purine-9-carboxylate

Conditions

Conditions Yield

With dmap In tetrahydrofuran at 20℃; for 18h; Acylation; 97%

With dmap

With dmap

124-40-3
dimethyl amine

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

5437-49-0
N6,N6-dimethyl-9H-purine-2,6-diamine

Conditions

Conditions Yield

In ethanol at 110℃; for 16h; 97%

In N,N-dimethyl-formamide at 180℃; Microwave irradiation; Inert atmosphere; 39%

at 95℃; for 2h;

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

56-40-6
glycine

2-[(2-amino-9H-purin-6-yl)amino]acetic acid

Conditions

Conditions Yield

With sodium carbonate In water for 8h; Reflux; 97%

280-57-9
1,4-diaza-bicyclo[2.2.2]octane

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

1-(2-amino-9H-purin-6-yl)-4-aza-1-azoniabicyclo[2.2.2]octane chloride

Conditions

Conditions Yield

In dimethyl sulfoxide at 25℃; for 24h; 96%

In dimethyl sulfoxide for 12h; Ambient temperature; 90%

In N,N-dimethyl-formamide 90%

With dimethyl sulfoxide In N,N-dimethyl-formamide 87%

In dimethyl sulfoxide for 3h;

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

100-46-9
benzylamine

4014-90-8
2-amino-6-benzylaminopurine

Conditions

Conditions Yield

With triethylamine In butan-1-ol at 110℃; for 3h; 96%

at 110℃; for 0.25h; microwave irradiation; 93%

In butan-1-ol at 110℃; for 3h; 51%

With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 90℃;

139-02-6
sodium phenoxide

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

2-amino-6-(phenyloxy)purine

Conditions

Conditions Yield

In dimethyl sulfoxide at 150℃; for 0.166667h; microwave irradiation; 96%

62-53-3
aniline

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

14051-72-0
N6-phenyl-9H-purine-2,6-diamine

Conditions

Conditions Yield

at 130℃; for 0.0833333h; microwave irradiation; 96%

With triethylamine In N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere; 75%

With triethylamine In N,N-dimethyl-formamide at 90℃; for 0.3h; Inert atmosphere; Microwave irradiation;

109178-34-9
2-(2-Bromo-2-nitro-propoxy)-tetrahydro-pyran

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

911798-67-9
2-amino-6-chloro-9-<1-nitro-1-<(tetrahydropyran-2-yloxy)methyl>ethyl>-9H-purine

Conditions

Conditions Yield

With potassium carbonate In dimethyl sulfoxide; acetonitrile for 1.75h; Irradiation; 95%

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

169566-58-9
ethyl 2-(N-(2-((tert-butoxycarbonyl)amino)ethyl)-2-chloroacetamido)acetate

169566-61-4
[[2-(2-Amino-6-chloro-purin-9-yl)-acetyl]-(2-tert-butoxycarbonylamino-ethyl)-amino]-acetic acid ethyl ester

Conditions

Conditions Yield

With potassium carbonate In N,N-dimethyl-formamide for 4h; Ambient temperature; 95%

72581-32-9, 1679-51-2
cyclohex-3-enylmethanol

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

NU2073

Conditions

Conditions Yield

Stage #1: cyclohex-3-enylmethanol With sodium hydride In tetrahydrofuran for 0.5h; deprotonation;
Stage #2: 2-Amino-6-chloropurin In tetrahydrofuran Etherification; Heating; Further stages.; 95%

924633-25-0
2,6-di-(pyrazol-1-yl)-4-(bromomethyl)pyridine

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

924633-27-2
6-chloro-9-[2,6-di(pyrazol-1-yl)pyridin-4-yl]-methyl-9H-purin-2-ylamine

Conditions

Conditions Yield

With sodium hydride; potassium iodide In N,N-dimethyl-formamide at 50℃; for 5h; 95%

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

60-34-4
methylhydrazine

6-(1-methylhydrazino)-9H-purin-2-amine

Conditions

Conditions Yield

95%

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

365441-86-7
tert-butyl N-[cyclohexyl(p-tolylsulfonyl)methyl]carbamate

1389318-44-8
tert-butyl (2-amino-6-chloro-9H-purin-9-yl)(cyclohexyl)methylcarbamate

Conditions

Conditions Yield

With sodium carbonate In water at 20℃; for 12h; 95%

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

163226-45-7
(3aS,4S,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

1449328-92-0
6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine

Conditions

Conditions Yield

With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 50℃; for 18h; Mitsunobu Displacement; Inert atmosphere; 95%

2-Amino-6-chloropurine Specification

The IUPAC name of 2-Amino-6-chloropurine is 6-chloro-7H-purin-2-amine. With the CAS registry number 10310-21-1, it is also named as 6-Chloroguanine. The product's categories are Fine Chemical & Intermediates; Starting Raw Materials & Intermediates; Miscellaneous Biochemicals; Amines; Nucleotides and Nucleosides; Purines; Biochemistry; Nucleobases and Their Analogs; Nucleosides, Nucleotides & Related Reagents; Bases & Related Reagents; Fused Ring Systems. It is white to light yellow crystal powder which is used as intermediate of antivirotic Famciclovir and Acyclovir. What's more, this chemical can be obtained by 2,9-Diacetylguanine or 2,4,5-Triamino-6-chloropyrimidine. Additionally, it should be sealed in the container and stored in the cool and dry place.

The other characteristics of 2-Amino-6-chloropurine can be summarized as: (1)ACD/LogP: 0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.27; (4)ACD/LogD (pH 7.4): 0.26; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 33.28; (8)ACD/KOC (pH 7.4): 32.65; (9)#H bond acceptors: 5; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.826; (13)Molar Refractivity: 41.93 cm³; (14)Molar Volume: 95.7 cm³; (15)Polarizability: 16.62×10^-24 cm³; (16)Surface Tension: 116.8 dyne/cm; (17)Enthalpy of Vaporization: 92.39 kJ/mol; (18)Vapour Pressure: 1.75E-15 mmHg at 25°C; (19)Tautomer Count: 9; (20)Exact Mass: 169.015523; (21)MonoIsotopic Mass: 169.015523; (22)Topological Polar Surface Area: 80.5; (23)Heavy Atom Count: 11; (24)Complexity: 154.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should not breathe dust and avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES:Clc1nc(nc2ncnc12)N
2. InChI:InChI=1/C5H4ClN5/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H3,7,8,9,10,11)
3. InChIKey:RYYIULNRIVUMTQ-UHFFFAOYAP

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Conditions	Yield
With sodium hydroxide at 20 - 80℃; for 3h;	80%
With water; sodium hydrogencarbonate at 25℃; for 3h; Reagent/catalyst;	73.3%

Conditions	Yield
With trichlorophosphate In N,N-dimethyl-formamide at 0℃; for 6h; Reflux;	70%
With trichlorophosphate In ammonium hydroxide; water; N,N-dimethyl-formamide	55%
With tetraethylammonium chloride; trichlorophosphate In water; acetonitrile	42%

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate In N,N-dimethyl acetamide; acetonitrile
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate In N,N-dimethyl acetamide; acetonitrile

Conditions	Yield
Multi-step reaction with 3 steps 1: acetic acid 2: trichlorophosphate 3: water; sodium hydroxide View Scheme
Multi-step reaction with 3 steps 1: dihydrogen peroxide / water / 2 h / 20 °C 2: thionyl chloride / methanol / 0.33 h / 0 - 5 °C / Reflux 3: methanol; hydrazine hydrate / 50 °C / Reflux View Scheme
With hydrogenchloride; dihydrogen peroxide In water at 40 - 50℃; for 3h; Reagent/catalyst;	95.6 g

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	100%
In ethanol; dimethyl sulfoxide at 20℃; for 12h;	76%
In dimethyl sulfoxide for 12h;	72%

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 70℃;	100%
Stage #1: 2-Amino-6-chloropurin; 1,2-di-O-acetyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-5-O-benzyl-α/β-D-ribofuranoside In acetonitrile at 100℃; for 0.5h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 70℃; Vorbrueggen condensation; Further stages.;	90%

Conditions	Yield
With dmap In tetrahydrofuran at 20℃; for 18h; Acylation;	97%
With dmap
With dmap

Conditions	Yield
In ethanol at 110℃; for 16h;	97%
In N,N-dimethyl-formamide at 180℃; Microwave irradiation; Inert atmosphere;	39%
at 95℃; for 2h;

Conditions	Yield
In dimethyl sulfoxide at 25℃; for 24h;	96%
In dimethyl sulfoxide for 12h; Ambient temperature;	90%
In N,N-dimethyl-formamide	90%
With dimethyl sulfoxide In N,N-dimethyl-formamide	87%
In dimethyl sulfoxide for 3h;

Conditions	Yield
With triethylamine In butan-1-ol at 110℃; for 3h;	96%
at 110℃; for 0.25h; microwave irradiation;	93%
In butan-1-ol at 110℃; for 3h;	51%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 90℃;

Conditions	Yield
at 130℃; for 0.0833333h; microwave irradiation;	96%
With triethylamine In N,N-dimethyl-formamide at 130℃; for 6h; Inert atmosphere;	75%
With triethylamine In N,N-dimethyl-formamide at 90℃; for 0.3h; Inert atmosphere; Microwave irradiation;

Product Name

6-Chloroguanine

Synthetic route

2-Amino-6-chloropurine Specification

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