Product Name

  • Name

    2,6-Dichloropurine

  • EINECS 226-681-6
  • CAS No. 5451-40-1
  • Article Data33
  • CAS DataBase
  • Density 1.792 g/cm3
  • Solubility soluble in water
  • Melting Point 184-186 °C
  • Formula C5H2Cl2N4
  • Boiling Point 405.4 °C at 760 mmHg
  • Molecular Weight 189.004
  • Flash Point 231.3 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 22-24/25-37/39-26-36
  • Risk Codes 36/37/38-22
  • Molecular Structure Molecular Structure of 5451-40-1 (2,6-Dichloropurine)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Purine, 2,6-dichloro-;2,6-Dichloro-1H-purine;2,6-Dichloro purine 98%;2,6-Dichloropurine 99%;Purine, 2,6-dichloro- (VAN) (8CI);2,6-dichloro-5H-purine;1H-Purine, 2,6-dichloro-;2,6-dichloro-9H-purine;9H-purine, 2,6-dichloro-;1H-Purine, 2,6-dichloro- (9CI);
  • PSA 54.46000
  • LogP 1.65970

Synthetic route

2,6-dihydroxypurine
69-89-6

2,6-dihydroxypurine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With pyridine; trichlorophosphate at 180℃; under 150.015 - 900.09 Torr; for 3h; Neat (no solvent);88%
xanthine
69-89-6

xanthine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate for 16h; Reflux;62%
With pyrophosphoryl chloride sealed tube, 1) 175 deg C, 7h 2) 150 deg C, 13h;42%
With pyrophosphoryl chloride 1) 175 deg C, 7 h, 2) 150 deg C, 13 h;42%
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With hydrogenchloride; zinc(II) chloride; sodium nitrite In water at -5 - 5℃; for 1h;54%
Stage #1: 2-Amino-6-chloropurin With hydrogenchloride; zinc(II) chloride at 10℃;
Stage #2: With sodium nitrite at -5 - 0℃; for 0.5h;		47%
With hydrogenchloride; copper(l) chloride; sodium nitrite In water at 0 - 5℃;16.4%
2,4-Dioxo-1,2,3,4-tetrahydropyrrolo<3,2-d>pyrimidine
65996-50-1

2,4-Dioxo-1,2,3,4-tetrahydropyrrolo<3,2-d>pyrimidine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; trichlorophosphate at 105℃; for 6h; Reagent/catalyst; Inert atmosphere; Reflux;47%
hypoxanthine 1-N-oxide
5167-14-6

hypoxanthine 1-N-oxide

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With triethylamine; trichlorophosphate for 3h; Heating;39.9%
2-amino-6-chloropurine
10310-21-1

2-amino-6-chloropurine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With hydrogenchloride; zinc(II) chloride; sodium nitrite In water at -5℃; for 0.5h;39%
adenine 1-oxide
700-02-7

adenine 1-oxide

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 66.2 percent / aq. NaNO2, aq. HOAc / H2O / 2 h / 70 - 80 °C
2: 39.9 percent / POCl3, NEt3 / 3 h / Heating
View Scheme
2-Amino-6-chloropurin
10310-21-1

2-Amino-6-chloropurin

isopentyl nitrite
110-46-3

isopentyl nitrite

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
With thionyl chloride; acetic anhydride; lithium chloride In N,N-dimethyl acetamide
N2,9-diacetylguanine

N2,9-diacetylguanine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trichlorophosphate
2: water; sodium hydroxide
3: hydrogenchloride; copper(l) chloride; sodium nitrite / water / 0 - 5 °C
View Scheme
2-acetamido-9-acetyl-6-chloropurine
97965-44-1

2-acetamido-9-acetyl-6-chloropurine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; sodium hydroxide
2: hydrogenchloride; copper(l) chloride; sodium nitrite / water / 0 - 5 °C
View Scheme
2-amino-6-hydroxypurine
73-40-5

2-amino-6-hydroxypurine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid
2: trichlorophosphate
3: water; sodium hydroxide
4: hydrogenchloride; copper(l) chloride; sodium nitrite / water / 0 - 5 °C
View Scheme
C8H9ClN6
149948-29-8

C8H9ClN6

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water / 4.5 h / 70 °C
2: water; sodium hydroxide / 3 h / 20 °C
3: hydrogenchloride; zinc(II) chloride; sodium nitrite / water / 1 h / -5 - 5 °C
View Scheme
6-chloro-2-formylaminopurine acetate
190962-00-6

6-chloro-2-formylaminopurine acetate

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; sodium hydroxide / 3 h / 20 °C
2: hydrogenchloride; zinc(II) chloride; sodium nitrite / water / 1 h / -5 - 5 °C
View Scheme
2-amino-1,9-dihydro-6H-purin-6-one
73-40-5

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

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: trichlorophosphate / 1,2-dichloro-ethane / 8 h / 80 °C
2: water / 4.5 h / 70 °C
3: water; sodium hydroxide / 3 h / 20 °C
4: hydrogenchloride; zinc(II) chloride; sodium nitrite / water / 1 h / -5 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate / 1,2-dichloro-ethane / 6 h / 80 °C
2.1: water / 4 h / 70 °C
3.1: sodium hydroxide / 3 h / 20 - 80 °C
4.1: zinc(II) chloride; hydrogenchloride / 10 °C
4.2: 0.5 h / -5 - 0 °C
View Scheme
Multi-step reaction with 2 steps
1.1: trichlorophosphate / N,N-dimethyl-formamide; 1,2-dichloro-ethane / 12 h / 80 - 90 °C
1.2: 4.5 h / 70 °C
1.3: 3 h / 20 °C
2.1: zinc(II) chloride; sodium nitrite; hydrogenchloride / water / 0.5 h / -5 °C
View Scheme
(E)-N'-(6-chloro-9H-purin-2-yl)-N,N-dimethylformimidamide

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

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water / 4 h / 70 °C
2.1: sodium hydroxide / 3 h / 20 - 80 °C
3.1: zinc(II) chloride; hydrogenchloride / 10 °C
3.2: 0.5 h / -5 - 0 °C
View Scheme
N-(6-chloro-9H-purin-2-yl)formamide
149948-30-1

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

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / 3 h / 20 - 80 °C
2.1: zinc(II) chloride; hydrogenchloride / 10 °C
2.2: 0.5 h / -5 - 0 °C
View Scheme
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine
20419-68-5

2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In ethyl acetate at 25 - 50℃; for 17h; Inert atmosphere;100%
With toluene-4-sulfonic acid In ethyl acetate at 25 - 50℃; for 17h; Inert atmosphere;100%
With toluene-4-sulfonic acid In ethyl acetate at 50℃; for 0.75h;99%
2,6 dichloropurine
5451-40-1

2,6 dichloropurine

2-chloroadenine
1839-18-5

2-chloroadenine

Conditions
ConditionsYield
With ammonia In methanol at 100℃; for 12h;100%
With ammonia In methanol at 100℃; for 16h;97%
With ammonia In methanol at 160℃; for 24h;95%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

C10H10Cl2N4O2
1038588-23-6

C10H10Cl2N4O2

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran at 20℃;100%
p-tolyl 2,3,5-tri-O-benzoyl-1-thio-β-D-ribofuranoside
918800-27-8

p-tolyl 2,3,5-tri-O-benzoyl-1-thio-β-D-ribofuranoside

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate
15373-23-6

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate

Conditions
ConditionsYield
Stage #1: p-tolyl 2,3,5-tri-O-benzoyl-1-thio-β-D-ribofuranoside With trifluoromethylsulfonic anhydride; di(p-tolyl) sulfoxide In dichloromethane at -50 - -40℃; for 0.833333h; Molecular sieve;
Stage #2: 2,6 dichloropurine In dichloromethane; acetonitrile at -50 - 20℃; stereoselective reaction;		100%
2,6 dichloropurine
5451-40-1

2,6 dichloropurine

(2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
172847-85-7

(2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate

2’,3’,4’,6’-tetra-O-benzoyl-β-D-glucopyranosyl-2,6-dichloropurine
66782-02-3

2’,3’,4’,6’-tetra-O-benzoyl-β-D-glucopyranosyl-2,6-dichloropurine

Conditions
ConditionsYield
Stage #1: (2R,3R,4S,5R,6S)-2-((benzoyloxy)methyl)-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate With trifluoromethylsulfonic anhydride; di(p-tolyl) sulfoxide In dichloromethane at -50 - -40℃; for 0.833333h; Molecular sieve;
Stage #2: 2,6 dichloropurine In dichloromethane; acetonitrile at -50 - 20℃; stereoselective reaction;		100%
morpholine
110-91-8

morpholine

2,6 dichloropurine
5451-40-1

2,6 dichloropurine

4-(2-chloro-9H-purin-6-yl)morpholine
4010-81-5

4-(2-chloro-9H-purin-6-yl)morpholine

Conditions
ConditionsYield
In water at 100℃; for 0.25h; Heating / reflux;99%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;99%
In ethanol at 30℃; for 3h;97%

2,6-Dichloropurine Specification

The 2,6-Dichloropurine, with the CAS registry number 5451-40-1, is also known as 1H-Purine, 2,6-dichloro- (9CI). It belongs to the product categories of Fine Chemical & Intermediates; Starting Raw Materials & Intermediates; Heterocycles; Pyridines, Pyrimidines, Purines and Pteredines; Halides; Purine; Nucleotides and Nucleosides; Purines; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Nucleic acids; Bases & Related Reagents; Nucleotides; Fused Ring Systems; Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; PurinesHeterocyclic Building Blocks. Its EINECS registry number is 226-681-6. This chemical's molecular formula is C5H2Cl2N4 and molecular weight is 189.00218. Its IUPAC name is called 2,6-dichloro-7H-purine. What's more, this chemical can be used as anti-tumor, antiviral drug intermediates.

Physical properties of 2,6-Dichloropurine: (1)ACD/LogP: 1.10; (2)ACD/LogD (pH 5.5): 1.09; (3)ACD/LogD (pH 7.4): 0.62; (4)ACD/BCF (pH 5.5): 3.92; (5)ACD/BCF (pH 7.4): 1.35; (6)ACD/KOC (pH 5.5): 91.91; (7)ACD/KOC (pH 7.4): 31.62; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)Index of Refraction: 1.741; (11)Molar Refractivity: 42.59 cm3; (12)Molar Volume: 105.4 cm3; (13)Surface Tension: 90.1 dyne/cm; (14)Density: 1.792 g/cm3; (15)Flash Point: 231.3 °C; (16)Enthalpy of Vaporization: 63.14 kJ/mol; (17)Boiling Point: 405.4 °C at 760 mmHg; (18)Vapour Pressure: 2.07E-06 mmHg at 25°C.

Preparation of 2,6-Dichloropurine: this chemical can be prepared by 3,7(9)-dihydro-purine-2,6-dithione. This reaction will need reagents HCl gas, Cl2 and solvent methanol. The reaction need the temperature of 0 - 13 °C. The yield is about 64%.

2,6-Dichloropurine can be prepared by 3,7(9)-dihydro-purine-2,6-dithione

Uses of 2,6-Dichloropurine: it can be used to produce 2,6-dichloro-9-tetrahydrofuran-2-yl-9H-purine with 2,3-dihydro-furan. The yield is about 88%.

2,6-Dichloropurine can be used to produce 2,6-dichloro-9-tetrahydrofuran-2-yl-9H-purine with 2,3-dihydro-furan

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=NC2=C(N1)C(=NC(=N2)Cl)Cl
(2)InChI: InChI=1S/C5H2Cl2N4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11)
(3)InChIKey: RMFWVOLULURGJI-UHFFFAOYSA-N

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