3D Mol Similar

2,6-Dichloropurine

: Iupac Name：2,6-dichloro-7H-purine; CAS No.: 5451-40-1; Molecular Weight：189.00218; Modify Date.: 2022-11-29 03:42; Introduction: Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1 View more+

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1. Names and Identifiers

: 1.1 Name; 2,6-Dichloropurine; 1.2 Synonyms; 1H-purine, 2,6-dichloro- 2, 6-Dichloropurine 2,6-Dichloro-1H-purine 2,6-Dichloro-5H-purine 2,6-dichloro-7H-purine 5H-Purine, 2,6-dichloro- 7H-Purine, 2,6-dichloro- EINECS 226-681-6 MFCD00077725 Purine, 2,6-dichloro-; View all

1.3 CAS No.: 5451-40-1

1.4 CID: 5324412

1.5 EINECS(EC#): 226-681-6

1.6 Molecular Formula: C5H2Cl2N4 (isomer)

1.7 Inchi: InChI=1S/C5H2Cl2N4/c6-3-2-4(9-1-8-2)11-5(7)10-3/h1H,(H,8,9,10,11)

1.8 InChIkey: RMFWVOLULURGJI-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=NC2=C(N1)C(=NC(=N2)Cl)Cl

1.10 Isomers Smiles: C1=NC2=C(N1)C(=NC(=N2)Cl)Cl

2. Properties

2.1 Density: 1.792

2.1 Melting point: 184-186℃

2.1 Refractive index: 1.741

2.1 Flash Point: 231.3 °C

2.1 Precise Quality: 187.96600

2.1 PSA: 54.46000

2.1 logP: 1.65970

2.1 Solubility: soluble

2.2 Appearance: White to yellow Crystalline Powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: white to light yellow crystal powder

2.5 Color/Form: White to Yellow Solid

2.6 pKa: 5.22±0.20(Predicted)

2.7 Water Solubility: soluble

2.8 Stability: Stable under normal temperatures and pressures.

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Methods of Manufacturing: To a solution of ZnCl2 (7.0 g, 110 mmol) in conc. hydrochloric acid(9.2 mL) at 10 °C was added finely powdered compound 4 (2.3 g, 13.6 mmol) with stirring. The resulting stirred mixture was cooledto 5 °C and added NaNO2 (1.27 g, 18.4 mmol) over a period of30 min keeping the temperature below 5 °C. The mixture wasstirred for additional 30 min and was diluted with 12 mL of water.The product was extracted with ethyl acetate (4 x 15 mL). Theorganic phase was washed with water (2 x 7 mL), dried overNa2SO4, and evaporated to dryness to yield 2.37 g (47percent) of finalcompound.

3.2 Purification Methods: It can be recrystallised from 150 parts of boiling H2O and dried at 100o to constant weight. It is soluble in EtOAc. The HgCl2 salt separates from EtOH solution. UV: max 275nm ( 8.9K) at pH 1; and 280nm ( 8.5K) at pH 11 [Elion & Hitchings J Am Chem Soc 78 3508 1956, Schaeffer & Thomas J Am Chem Soc 80 3738 1958, Beaman & Robins J Appl Chem (London) 12 432 1962, Montgomery J Am Chem Soc 78 1928 1956]. [Beilstein 26 III/IV 1747.] 2,6-Dichloropurine Preparation Products And Raw materials Preparation Products

3.3 Usage: Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1

4. Safety and Handling

4.1 Hazard Codes: Xn; Xi

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S22;S24/25

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H301

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P264, P270, P301+P310, P321, P330, P405, P501

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes:Xn,Xi
Risk Statements:36/37/38-22
36/37/38:Irritating to eyes, respiratory system and skin
22:Harmful if swallowed
Safety Statements:22-24/25-37/39-26-36
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany:3
HazardClass:IRRITANT
Hazard Note:Irritant

4.2 Specification: white to light yellow crystal powder
usageEng:Suzuki-Miyaura cross-coupling between halopurines and arylboronic acids in water-acetonitrile.1
Safety Statements:22-24/25-37/39-26-36
22:Do not breathe dust
24/25:Avoid contact with skin and eyes
37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : parameter in CDCl3

7. Other Information

7.0 Storage Conditions: To a solution of ZnCl2 (7.0 g, 110 mmol) in conc. hydrochloric acid(9.2 mL) at 10 °C was added finely powdered compound 4 (2.3 g, 13.6 mmol) with stirring. The resulting stirred mixture was cooledto 5 °C and added NaNO2 (1.27 g, 18.4 mmol) over a period of30 min keeping the temperature below 5 °C. The mixture wasstirred for additional 30 min and was diluted with 12 mL of water.The product was extracted with ethyl acetate (4 x 15 mL). Theorganic phase was washed with water (2 x 7 mL), dried overNa2SO4, and evaporated to dryness to yield 2.37 g (47percent) of finalcompound.

8. Computational chemical data

Molecular Weight: 189.00218g/mol
Molecular Formula: C₅H₂Cl₂N₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 187.9656515
Monoisotopic Mass: 187.9656515
Complexity: 155
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 54.5
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcQBjgAAGAAAAAAAAAAAAAAAAAWAAAAAsAAAAAAAAAFgB+AAAHAIQAAAACAoBFyQF8L7JkACgAQZhZACAgC2RFKABUaAoVhCASABASEBUBAgIAAJAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==