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2-Bromo-3-methylthiophene

2-Bromo-3-methylthiophene structure

CAS No:
14282-76-9
Formula:
C5H5BrS
Chemical Name:
2-Bromo-3-methylthiophene
Synonyms:
Thiophene,2-bromo-3-methyl-;2-Bromo-3-methylthiophene;5-Bromo-4-methylthiophene
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

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Description

clear colorless to light yellow liquid

2-Bromo-3-methylthiophene Basic Attributes

Molecular Weight：

177.06

Exact Mass：

177.06

BRN：

105719

EC Number：

238-175-2

DSSTox ID：

DTXSID20162194

HScode：

29349990

Characteristics

PSA：

28.2

XLogP3：

Density：

1.571 g/cm³ @ Temp: 20 °C

Melting Point：

<25 °C

Boiling Point：

176 °C

Flash Point：

155 °F

Refractive Index：

n20/D 1.572(lit.)

Storage Conditions：

Keep Cold

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

UN 2810

wgk germany：

hazard class code：

25-41-43-36/37/38-20/21/22

safety instructions：

26-36/37/39-45

Marks：

T,Xi,Xn

Hazard note：

Harmful

Precautionary statement(s)：

P280-P305 + P351 + P338

Hazard Statements：

H302-H318

GHS Classification：

|Danger|H302 (97.78%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

2-Bromo-3-methylthiophene Use and Manufacturing

Methods of Manufacturing

NBS (8.90 g, 50.0 mmol) was added portion wise to a stirred solution of 3-mehylthiophene (4.90 g, 50.0 mmol) in acetic acid (20 mL) at rt. After complete addition, the reaction was stirred at rt until it was complete. The reaction mixture was poured into ice- water, and then extracted with a 3:1 mixture solvent of hexane and ether. The organic layer was washed with IN aq. NaOH and brine. After dried over anhydrous sodium sulphate, the organic phase was concentrated on vacuum to afford 2-bromo-3-methylthiphene (8.20 g, 92.7 percent), which was used directly in the next step without further purification.Compound 4 (5.00g, 51.01mmol) was dissolved in 30mL of anhydrous DMF. The mixture of N-bromosuccinimide (NBS) (9.08g, 51.01mmol) and anhydrous DMF (40mL) was added dropwise to the solution and stirred for 24h in the dark. The mixture was then poured into water and extracted with petroleum ether. The organic phase was dried over anhydrous MgSOIn a 1 L two-necked flask, 24.5 g of 3-methylthiophene (98 g mol-1, 24.5 g, 250 mmol) was added and 400 mL of chloroform / glacial acetic acid (V: V = 1: / L, Favoring the inhibition of the bis-brominated product), 44.5 g of NBS (178 g mol-1, 44.5 g, 250 mmol) were added in portions in an ice-water bath.After the addition of NBS to continue stirring for 2-3 hours, TLC monitoring.After treatment: deionized water to quench the reaction, liquid separation, the organic phase was NaOH solution, washed with water, dried, concentrated vacuum pump with fractional distillation.

Uses

New pharmaceutical intermediates.

Computed Properties

Molecular Weight:177.06
XLogP3:3
Hydrogen Bond Acceptor Count:1
Exact Mass:175.92953
Monoisotopic Mass:175.92953
Topological Polar Surface Area:28.2
Heavy Atom Count:7
Complexity:65.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of 2-Bromo-3-methylthiophene

Description
Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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2-Bromo-3-methylthiophene

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