5-Bromo-2,4-dichloropyrimidine

Iupac Name：5-bromo-2,4-dichloropyrimidine

Molecular Weight：227.87

Modify Date.: 2022-11-22 16:09

Introduction: Starting material for the synthesis of trisubstituted pyrimidines via a combination of nucleophilic substitution and palladium-catalyzed aryl cross-coupling.1 5-Bromo-2,4-dichloropyrimidine Preparation Products And Raw materials Preparation Products View more+

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1. Names and Identifiers

1.1 Name: 5-Bromo-2,4-dichloropyrimidine
1.2 Synonyms: 2,4-DICHLORO-5-BROMO PYRIMIDINE 2,4-Dichloro-5-bromopyrimidine 2,6-Dichloro-5-bromopyrimidine 5-Bromo-2,4-dichL 5-Bromo-2,4-Dichloropyridimidine 5-Bromo-2,6-dichloropyrimidine BUTTPARK 48\06-22 NSC 152517 Pyrimidine, 5-bromo-2,4-dichloro- TIMTEC-BB SBB003301

1.3 CAS No.: 36082-50-5

1.4 CID: 289973

1.5 EINECS(EC#): 000-000-0

1.6 Molecular Formula: C4HBrCl2N2 (isomer)

1.7 Inchi: InChI=1S/C4HBrCl2N2/c5-2-1-8-4(7)9-3(2)6/h1H

1.8 InChkey: SIKXIUWKPGWBBF-UHFFFAOYSA-N

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

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

2. Properties

2.1 Density: 1.781

2.1 Melting point: 29-30℃

2.1 Boiling point: 128℃ (15 mmHg)

2.1 Refractive index: n20/D 1.603(lit.)

2.1 Flash Point: 127.7 °C

2.1 Precise Quality: 225.87000

2.1 PSA: 25.78000

2.1 logP: 2.54590

2.1 Appearance: Clear colorless to light yellow Liquid or Low Melting Solid

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: Colourless Oil

2.4 Color/Form: Clear colorless to light yellow

2.5 pKa: -4.26±0.29(Predicted)

2.6 Water Solubility: Insoluble

2.7 StorageTemp: Keep Cold

3. Use and Manufacturing

3.1 Methods of Manufacturing: 5-bromouracil (6.0 g, 31.4 mmol) was mixed with PCl5 (16.4 g, 87.9 mmol) in a reaction flask.Add 1, 1, 2-trichloroethane (50 mL), The reaction mixture was heated to reflux.During the reaction, the mixture changed from a suspended state to a pale yellow clear solution.At this point TLC showed that the starting material was completely reacted.Drop to room temperature.Slowly pour the reaction mixture into stirred ice water.Stir for 1h, Add DCM (3 x 50 mL) for extraction.The organic layer was dried over anhydrous MgSO4.Evaporate the solvent, A pale yellow transparent liquid was obtained.Further purified on a silica gel column.Obtaining a colorless transparent liquid, That is, Compound 2 (yield 99.5percent, purity 97percent).5-bromo-uracil 19.1g (100mmol) was mixed with 60ml phosphorus oxy trichloride, and the reaction was stirred for five days at 125 deg.] C, was added 100ml of ice water quench the reaction.Extracted three times with 120ml of diethyl ether the reaction solution, and the combined organic phases were evaporated under reduced pressure to remove ether and excess phosphorus oxychloride to give 5-bromo-2, 4-dichloropyrimidine 19.4g (87percent).

3.2 Usage: Starting material for the synthesis of trisubstituted pyrimidines via a combination of nucleophilic substitution and palladium-catalyzed aryl cross-coupling.1 5-Bromo-2,4-dichloropyrimidine Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Hazard Codes: T

4.1 Risk Statements: R23/24/25;R34

4.1 Safety Statements: S26;S27;S36/37/39;S45

4.1 Packing Group: III

4.1 Hazard Class: 8

4.1 Hazard Declaration: H301 + H311 + H331-H314-H317

4.1 RIDADR: UN 3263

4.1 Caution Statement: P261-P280-P301 + P310-P305 + P351 + P338-P310

4.1 WGK Germany: 3

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 3

Skin corrosion, Category 1B

Skin sensitization, Category 1

Acute toxicity - Inhalation, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301+H311+H331 Toxic if swallowed, in contact with skin or if inhaled H314 Causes severe skin burns and eye damage H317 May cause an allergic skin reaction
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P311 Call a POISON CENTER/doctor/\u2026
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

36082-50-5Total: 3 Synthesis Route

51-20-7 186 Suppliers

36082-50-5 238 Suppliers

Literatures:
PCR, Incorporated Patent: US4299961 A1, 1981 ;
Yield: ~81%

113138-12-8

36082-50-5 238 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 23 p. 7169 - 7173,5
Yield: null

51-20-7 186 Suppliers

10026-13-8 65 Suppliers

10025-87-3

36082-50-5 238 Suppliers

Literatures:
American Chemical Journal, , vol. 33, p. 443
Yield: null

7. Precursor and Product

precursor:

51-20-7

113138-12-8

10026-13-8

product :

733039-20-8

870722-92-2

205672-19-1

871254-61-4

41244-53-5

280581-95-5

62880-67-5

59549-51-8

205672-24-8

205672-25-9

19752-61-5

57054-86-1

872604-19-8

63558-77-0

57054-92-9

View all

8. Other Information

8.0 Storage Conditions: 5-bromouracil (6.0 g, 31.4 mmol) was mixed with PCl5 (16.4 g, 87.9 mmol) in a reaction flask.Add 1, 1, 2-trichloroethane (50 mL), The reaction mixture was heated to reflux.During the reaction, the mixture changed from a suspended state to a pale yellow clear solution.At this point TLC showed that the starting material was completely reacted.Drop to room temperature.Slowly pour the reaction mixture into stirred ice water.Stir for 1h, Add DCM (3 x 50 mL) for extraction.The organic layer was dried over anhydrous MgSO4.Evaporate the solvent, A pale yellow transparent liquid was obtained.Further purified on a silica gel column.Obtaining a colorless transparent liquid, That is, Compound 2 (yield 99.5percent, purity 97percent).5-bromo-uracil 19.1g (100mmol) was mixed with 60ml phosphorus oxy trichloride, and the reaction was stirred for five days at 125 deg.] C, was added 100ml of ice water quench the reaction.Extracted three times with 120ml of diethyl ether the reaction solution, and the combined organic phases were evaporated under reduced pressure to remove ether and excess phosphorus oxychloride to give 5-bromo-2, 4-dichloropyrimidine 19.4g (87percent).

9. Computational chemical data

Molecular Weight: 227.87g/mol
Molecular Formula: C₄HBrCl₂N₂
Compound Is Canonicalized: True
XLogP3-AA: 2.8
Exact Mass: 225.87002
Monoisotopic Mass: 225.87002
Complexity: 103
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 25.8
Heavy Atom Count: 9
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: AAADcQBjAAAGEAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHAJAAAABqALBEiQtkJYIEACgABBnZACAgCkRBKABUCAoRhCACIBASEAEBAgIAAJAACAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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