7-Bromo-6-chloro-4-quinazolinone

Iupac Name：7-bromo-6-chloro-3H-quinazolin-4-one

Molecular Weight：259.49

Modify Date.: 2022-11-23 21:54

Introduction: 7-Bromo-6-chloro-4(3H)-quinazolinone is an important intermediate in the manufacturing of the anticoccidial drug (coccidiostat) halofuginone (Tempostatin). 7-Bromo-6-chloro-4-quinazolinone Preparation Products And Raw materials Preparation Products View more+

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1. Names and Identifiers

1.1 Name: 7-Bromo-6-chloro-4-quinazolinone
1.2 Synonyms: 4(3H)-Quinazolinone, 7-broMo-6-chloro- 7-broMo-6-chloro-3,4-dihydroquinazolin-4-one 7-Bromo-6-chloro-4(1H)-quinazolinone 7-Bromo-6-Chloro-4(3H)-Quinazo 7-Bromo-6-chloro-4(3H)-quinazolinone 7-BroMo-6-chloro-4-quinaz... 7-Bromo-6-chloro-4-quinazolinone 7-BROMO-6-CHLORO-QUINAZOLINE-4(3H)-ONE

1.3 CAS No.: 17518-98-8

1.4 CID: 135711216

1.5 EINECS(EC#): 634-004-4

1.6 Molecular Formula: C8H4BrClN2O (isomer)

1.7 Inchi: InChI=1S/C8H4BrClN2O/c9-5-2-7-4(1-6(5)10)8(13)12-3-11-7/h1-3H,(H,11,12,13)

1.8 InChkey: RFCXXKWROOFQSI-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=C2C(=CC(=C1Cl)Br)N=CNC2=O

1.10 Isomers Smiles: C1=C2C(=CC(=C1Cl)Br)N=CNC2=O

2. Properties

2.1 Density: 1.95

2.1 Melting point: >300 °C

2.1 Boiling point: 481.8 °C at 760 mmHg

2.1 Refractive index: 1.737

2.1 Flash Point: 481.8 °C at 760 mmHg

2.1 Precise Quality: 257.92000

2.1 PSA: 45.75000

2.1 logP: 2.33900

2.1 Appearance: yellow-brown solid

2.2 Chemical Properties: Yellow-Brown Solid

2.3 pKa: -0.55±0.20(Predicted)

2.4 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 Methods of Manufacturing: To a mixture of 3-chlorotoluene (200 g, 1.58 mol), FeCl3 (9.4 g, 0.06 mol) and CH2Cl2 (1000 mL)stirred at 0~10 °C, Br2 (500 g, 3.12 mol) was added slowly, during which the produced gas wasabsorbed by 15percent NaOH aqueous solution (2000 mL). After 1 h of continued vigorous stirring, water(100 mL) was added and the mixture was adjusted to pH 8.0~10.0 with 10percent aqueous NaOH (200 mL).The organic layer was separated and concentrated to dryness under vacuum to give a solid (95.7percent, m.p.95~96 °C), 426 g of which was added to a mixture of water (2000 mL), pyridine (200 mL) and KOH(112 g, 2.0 mol) and heated. When the interior temperature reached 80 °C, KMnO4 (800 g, 5.0 mol) wasadded in portions, and the mixture was refluxed until complete consumption of the KMnO4. Then thesolution was filtered, the precipitate was washed with 10percent KOH a.q. (1000 mL). The filtrates werecombined, and then vacuum evaporated to remove the pyridine and form a turbid solution, whichneeded to be filtered again. The fresh filtrate was acidified with concentrated HCl (360 mL) to pH 3~4.Then the precipitate was filtered, dried and crushed (80percent, m.p. 170~171 °C). A portion (340 g) wasdissolved in 25percent NH3-H2O (1700 mL). To the solution, Cu2O was added in batches at 30~40 °C. Afterabout 5 h of stirring, the solution without NH3 gas was diluted and acidified. Then the solid was filtered, washed, dried (yield 96percent, m.p. 248~249 °C) and 250 g was dissolved in 1500 mL of formamide, maintained at 150~170 °C for 5 h. The solution was allowed to cool to R.T., and the precipitate wasfiltered and washed to give a white solid (92percent, m.p. 306~307 °C). Thus, 2 was succesfully obtained inan overall yield of 67percent. IR (KBr), (cm1): 3188.6, 1643.4 (NH), 1680.3 (C=O); ESI-MS (m/z): 256.9[M - H]-, 258.9 [M + 2 - H]; 1H-NMR (300 MHz, DMSO-d6), δ (ppm): 12.50 (br, 1H), 8.15 (s, 1H), 8.14 (s, 1H), 8.05 (s, 1H).

3.2 Usage: 7-Bromo-6-chloro-4(3H)-quinazolinone is an important intermediate in the manufacturing of the anticoccidial drug (coccidiostat) halofuginone (Tempostatin). 7-Bromo-6-chloro-4-quinazolinone Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Hazard Declaration: H301

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 Specification

7-Bromo-6-chloro-4-quinazolinone , with cas registry number of 17518-98-8, is also called 7-Bromo-6-chloro-4(3H)-quinazolinone . Its systematic name is called 7-bromo-6-chloroquinazolin-4(3H)-one with SMILES of Clc1cc2c(cc1Br)/N=C\NC2=O based on its molecular structure. Other structure descriptions also include (1) InChI: InChI=1/C8H4BrClN2O/c9-5-2-7-4(1-6(5)10)8(13)12-3-11-7/h1-3H,(H,11,12,13); (2) InChIKey: RFCXXKWROOFQSI-UHFFFAOYAJ. According to its molecular structure, this compound can be classified to the product categories of Heterocycles; Aromatics Compounds; Aromatics.

The physical properties about 7-Bromo-6-chloro-4-quinazolinone include: (1) H bond acceptors: 3; (2) H bond donors: 1; (3) Freely Rotating Bonds: 0; (4) Index of Refraction: 1.737; (5) Molar Refractivity: 53.42 cm³; (6) Molar Volume: 132.8 cm³; (7) Surface Tension: 60.9 dyne/cm; (8) Enthalpy of Vaporization: 74.65 kJ/mol; (9) Vapour Pressure: 1.94E-09 mmHg at 25°C.

7-Bromo-6-chloro-4-quinazolinone can be obtained in the market from the suppliers such as Qingdao Vochem Co., Ltd., and Nanjing Trihedron Chemical Technology Co., Ltd.. The content is usually 98%.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H301 Toxic if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
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. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 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/... P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
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. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

7. Synthesis Route

17518-98-8Total: 1 Synthesis Route

150812-32-1 37 Suppliers

122-51-0 216 Suppliers

17518-98-8 61 Suppliers

Literatures:
Chen, Shao Peng; Sun, Yue; Wan, Sheng Biao; Jiang, Tao Chinese Chemical Letters, 2011 , vol. 22, # 9 p. 1033 - 1035
Yield: ~92%

8. Precursor and Product

precursor:

150812-32-1

122-51-0

product :

1260847-61-7

9. Other Information

9.0 Chemical Properties: Yellow-Brown Solid

9.1 Uses: 7-Bromo-6-chloro-4(3H)-quinazolinone is an important intermediate in the manufacturing of the anticoccidial drug (coccidiostat) halofuginone (Tempostatin).

9.2 Storage Conditions: To a mixture of 3-chlorotoluene (200 g, 1.58 mol), FeCl3 (9.4 g, 0.06 mol) and CH2Cl2 (1000 mL)stirred at 0~10 °C, Br2 (500 g, 3.12 mol) was added slowly, during which the produced gas wasabsorbed by 15percent NaOH aqueous solution (2000 mL). After 1 h of continued vigorous stirring, water(100 mL) was added and the mixture was adjusted to pH 8.0~10.0 with 10percent aqueous NaOH (200 mL).The organic layer was separated and concentrated to dryness under vacuum to give a solid (95.7percent, m.p.95~96 °C), 426 g of which was added to a mixture of water (2000 mL), pyridine (200 mL) and KOH(112 g, 2.0 mol) and heated. When the interior temperature reached 80 °C, KMnO4 (800 g, 5.0 mol) wasadded in portions, and the mixture was refluxed until complete consumption of the KMnO4. Then thesolution was filtered, the precipitate was washed with 10percent KOH a.q. (1000 mL). The filtrates werecombined, and then vacuum evaporated to remove the pyridine and form a turbid solution, whichneeded to be filtered again. The fresh filtrate was acidified with concentrated HCl (360 mL) to pH 3~4.Then the precipitate was filtered, dried and crushed (80percent, m.p. 170~171 °C). A portion (340 g) wasdissolved in 25percent NH3-H2O (1700 mL). To the solution, Cu2O was added in batches at 30~40 °C. Afterabout 5 h of stirring, the solution without NH3 gas was diluted and acidified. Then the solid was filtered, washed, dried (yield 96percent, m.p. 248~249 °C) and 250 g was dissolved in 1500 mL of formamide, maintained at 150~170 °C for 5 h. The solution was allowed to cool to R.T., and the precipitate wasfiltered and washed to give a white solid (92percent, m.p. 306~307 °C). Thus, 2 was succesfully obtained inan overall yield of 67percent. IR (KBr), (cm1): 3188.6, 1643.4 (NH), 1680.3 (C=O); ESI-MS (m/z): 256.9[M - H]-, 258.9 [M + 2 - H]; 1H-NMR (300 MHz, DMSO-d6), δ (ppm): 12.50 (br, 1H), 8.15 (s, 1H), 8.14 (s, 1H), 8.05 (s, 1H).

10. Computational chemical data

Molecular Weight: 259.49g/mol
Molecular Formula: C₈H₄BrClN₂O
Compound Is Canonicalized: True
XLogP3-AA: 2
Exact Mass: 257.91955
Monoisotopic Mass: 257.91955
Complexity: 259
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 41.5
Heavy Atom Count: 13
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: AAADcYBzIAAEEAAAAAAAAAAAAAAAAAAAAAAwQAAAAAAAAACBAAAAHgJQAAABrAqBmCQxwILAAACoAiVTdACCAAEkBwQBiIEIZugIIDqB3pGEIYhgggAIy9cYiACOAgBAIAECAAIEAIBAAgQABAAAAAAAAA==

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