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Home > Encyclopedia > 2-(Bromomethyl)-5-(trifluoromethyl)furan

2-(Bromomethyl)-5-(trifluoromethyl)furan

2-(Bromomethyl)-5-(trifluoromethyl)furan structure

2-(Bromomethyl)-5-(trifluoromethyl)furan 

structure
  • CAS No:

    17515-77-4

  • Formula:

    C6H4BrF3O

  • Chemical Name:

    2-(Bromomethyl)-5-(trifluoromethyl)furan

  • Synonyms:

    2-(BROMOMETHYL)-5-(TRIFLUOROMETHYL)FURAN;2-(Bromomethyl)-5-(trifluoromethyl)furane;2-(Bromomethyl)-5-(trifluoromethyl)furan 97%;2-(Bromomethyl)-5-(trifluoromethyl)furan97%;Furan,2-(broMoMethyl)-5-(trifluoroMethyl)-

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

2-(Bromomethyl)-5-(trifluoromethyl)furan Basic Attributes

228.99

227.939758

DTXSID70383251

2932190090

Characteristics

13.1

2.5

1.693±0.06 g/cm3(Predicted)

38 °C

59.2±25.9 °C

1.448

1.5E-08mmHg at 25°C

Safety Information

8

1760

34-36/37/38-43

26-36/37/39-45-36/37

C

Corrosive

P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P405, P501

H302

|Danger|H226 (25%): Flammable liquid and vapor [Warning Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P370+P378, P403+P235, P405, and P501|Aggregated GHS information provided by 4 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-(Bromomethyl)-5-(trifluoromethyl)furan Use and Manufacturing

To a solution of 2-methyl-5-(trifluoromethyl)furan (4 g, 26.6 mmol) in chloroform (60 ml) were added N-bromosuccinimide (5.2 g, 29.3 mmol) and 2, 2'-azobis(isobutyronitrile) (220 mg, 1.33 mmol). The reaction solution was heated under reflux for 15 min. The reaction solution was cooled, poured into water (200 ml) and was extracted with chloroform. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give 2-(bromomethyl)-5-(trifluoromethyl)furan (4.79 g, 78percent). Ir ν maxKBr cm-1: 1738, 1688, 1599, 1559.1H-NMR (CDCl3)δ: 4.46 (2H, s) , 6.45 (1H, d, J = 3.8 Hz), 6.75 (1H, d, J = 3.8 Hz).To a solution of compound P2a (724 mg. 2.19 mmol), 2-(bromomethyl)-5-(trifluoro- methyl)furan (499 mg, 2.19 mmol) and K2C03(604 mg, 4.37 mmol) in ACN (40 mL) was added Kl (363 mg, 2.19 mmol) at rt. The mixture was stirred at 80 'C overnight, cooled, filtered, concentrated and purified by FCC (PE:EA = 25: 1 ) to give compound P2 as a yellow oil.To a solution of mesitylmethanamine (5.13 g, 34.4 mmol) and TEA (19.2 mL, 138 mmol) in THF (150 mL) was added To a solution of tert-butyl (4-bromobenzyl)carbamate (8.6 g, 30 mmoi) in dry DMF (120 mL) was added NaH (1.26 g, 31.6 mmoi, 60% in mineral oil) at 0C under N2. The mixture was stirred at 0C for 30 min, then a solution of To a solution of compound P15c (2.2 g, 8.1 mmol) in dry DMF (25 mL) was added NaH (324 mg, 60%, 8.9 mmol) under ice-bath cooling. The mixture was stirred for 30 min at 0 C. To the solution was added 2-(bromomethyl)-5-(trifiuoromethyl)furan (2.0 g, 8.9 mmol) and the mixture was stirred for 3 h at rt, poured into ice water and extracted with EA (3 x 50 mL). The combined organic layer was washed with water (3 x 100 mL) and brine (100 mL), dried over Na2S04, filtered, concentrated and purified by FCC (PE:EA = 20: 1 to 5: 1 ) to give compound P15d as a yellow oil.

Computed Properties

Molecular Weight:228.99
XLogP3:2.5
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:227.93976
Monoisotopic Mass:227.93976
Topological Polar Surface Area:13.1
Heavy Atom Count:11
Complexity:136
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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