6-BROMO-TETRAL-1-ON Chemical Properties

Melting point:

40-42℃

Boiling point:

116°C/0.05mmHg(lit.)

Density 

1.511±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Toluene

form 

powder to lump

color 

White to Orange to Green

Sensitive 

Light Sensitive

InChI

InChI=1S/C10H9BrO/c11-8-4-5-9-7(6-8)2-1-3-10(9)12/h4-6H,1-3H2

InChIKey

OSDHOOBPMBLALZ-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=C(Br)C=C2)CCC1

Safety Information

HS Code 

2914790090

6-BROMO-TETRAL-1-ON Usage And Synthesis

Uses

6-bromo-1-tetralone used in Wittig-Horner reaction.

Synthesis

The general procedure for the synthesis of 6-bromo-3,4-dihydronaphthalen-1(2H)-one from 6-amino-1,2,3,4-tetrahydro-1-naphthalenone was as follows: an aqueous solution (10 mL) of NaNO2 (2.35 g, 34 mmol) was added slowly and dropwise at 0°C to a 6-amino-1,2,3,4-tetrahydronaphthalen-1-one (5.0 g, 31 mmol) in a 25% HBr (16 mL) solution. Subsequently, the resulting suspension was transferred to a stirred mixture of 48% HBr (30 mL) of CuBr (8.9 g, 62 mmol) at 0 °C. The reaction mixture was gradually warmed to room temperature and stirred continuously for 1 hour. After completion of the reaction, the mixture was extracted with EtOAc and the organic phase was dried and concentrated with Na2SO4. The residue was purified by silica gel column chromatography (elution gradient: 0%-60% EtOAc/Hex) to afford 5.6 g (80% yield) of 6-bromo-3,4-dihydronaphthalen-1(2H)-one as a light yellow oil.1H NMR (400 MHz, CDCl3) δ: 2.10-2.16 (2H, m), 2.64 (2H, t, J = 6.4 Hz), 2.94 (2H, t, J = 6.0 Hz), 7.42 (1H, s), 7.44 (1H, s), 7.87 (1H, d, J = 8.9 Hz). Mass spectral analysis: [M + H]+ calculated value C10H9BrO: 225,227; measured value: 225,227.

References

[1] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 4, p. 391 - 396
[2] Chemistry - A European Journal, 2018, vol. 24, # 50, p. 13150 - 13157
[3] Patent: WO2018/183370, 2018, A2. Location in patent: Paragraph 00136
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1284 - 1304
[5] Chemical and Pharmaceutical Bulletin, 1984, vol. 32, # 1, p. 130 - 151

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