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6-Bromo-2-hexanone

6-Bromo-2-hexanone structure

CAS No:
10226-29-6
Formula:
C6H11BrO
Chemical Name:
6-Bromo-2-hexanone
Synonyms:
2-Hexanone,6-bromo-;6-Bromo-2-hexanone;1-Bromo-5-hexanone;5-Oxohexyl bromide
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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Description

Colourless Oil

6-Bromo-2-hexanone Basic Attributes

Molecular Weight：

179.05494

Exact Mass：

179.05

EC Number：

233-544-4

DSSTox ID：

DTXSID90144846

HScode：

2914700090

Characteristics

PSA：

17.1

XLogP3：

1.4

Density：

1.33 g/cm³ @ Temp: 20 °C

Melting Point：

50-53 °C(lit.)

Boiling Point：

216 °C

Flash Point：

78.2±9.9 °C

Refractive Index：

1.4890 (estimate)

Water Solubility：

Practically insoluble in water

Vapor Pressure：

0.0784mmHg at 25°C

Safety Information

wgk germany：

safety instructions：

S22-S24/25-S182.26

RTECS Number：

DT4375000

Marks：

6-Bromo-2-hexanone Use and Manufacturing

Methods of Manufacturing

From 1, 3-bromochloropropane through cyclization, ring opening, elimination, bromination and other steps. (1) Cycling. 1, 3-Bromochloropropane reacts with ethyl acetoacetate to obtain 2-methyl-3-ethoxyhydroxy-5, 6-dihydropyran: Mix ethanol and anhydrous potassium carbonate, stir and cool to below 10°C, Add ethyl acetoacetate dropwise. Then add bromochloropropane, reflux for 5h at 78-80°C. Cool, filter, and wash the filter residue with ethanol. The filtrate was combined with the ethanol washing solution, and after the ethanol was recovered under reduced pressure, the 102-107°C (1.33-2kPa) fraction was collected to obtain 2-methyl-3-ethoxycarbonyl-5, 6-dihydropyran. The yield is over 80%. (2) Ring opening, elimination and bromination to obtain 6-bromo-2-hexanone: add 2-methyl-3-ethoxycarbonyl-5, 6-dihydropyran, hydrobromic acid and sodium bromide to the reaction Pot, stir, add sulfuric acid dropwise at 15°C, keep it for 1h, and reflux for 3h. Cool, add water-soluble salt. Extract with chloroform 3 times. The chloroform extract is distilled to recover chloroform and then distilled under reduced pressure to collect 98-104°C (1.33-2kPa) fractions to obtain 6-bromo-2-hexanone.

Uses

Pharmaceutical intermediates.

Computed Properties

Molecular Weight:179.05
XLogP3:1.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:177.99933
Monoisotopic Mass:177.99933
Topological Polar Surface Area:17.1
Heavy Atom Count:8
Complexity:70.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Potassium carbonate