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Home > Encyclopedia > 3-Bromo-2-methylaniline

3-Bromo-2-methylaniline

3-Bromo-2-methylaniline structure

3-Bromo-2-methylaniline 

structure
  • CAS No:

    55289-36-6

  • Formula:

    C7H8BrN

  • Chemical Name:

    3-Bromo-2-methylaniline

  • Synonyms:

    Benzenamine,3-bromo-2-methyl-;3-Bromo-2-methylbenzenamine;2-Amino-6-bromotoluene;3-Bromo-2-methylaniline;(3-Bromo-2-methylphenyl)amine;2-Methyl-3-bromoaniline;1-Bromo-2-methyl-3-aminobenzene

  • Categories:

    Pharmaceutical Intermediates  >  Bulk Drug Intermediates

Description

Colorless to pale brown liquid

3-Bromo-2-methylaniline Basic Attributes

186.05

186.05

2354213

259-568-5

VM496N698A

DTXSID60203792

29214300

Characteristics

26

2.3

Clear colorless to yellow to pale brown Liquid

1.5±0.1 g/cm3

130 °C @ Press: 16 Torr

230 °F

1.609

Safety Information

III

6.1

2810

3

36/37/38

26-36

Xi

Harmful/Irritant

P261-P305 + P351 + P338

H315-H319-H335

|Danger|H301 (10.64%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 47 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

3-Bromo-2-methylaniline Use and Manufacturing

To ethanol Compound g (500mg, 2.32mmol) and tin dichloride hydrate (2.62g, 11.63mmol) was added andreaction was conducted for 3 hours at 80°C. Rotary evaporation was performed to remove ethanol, and then pH wasadjusted to about 8 with saturated aqueous sodium bicarbonate. The resultant was filtered with Celite and the filter cakewas washed with ethyl acetate, and the filtrate was collected and extracted with ethyl acetate three times. The filtratewas dried under rotation to obtain Compound h (410mg, 2.20mmol) at a yield of 95percent.To a mixture of compound 1-Bromo-2-methyl-3-nitro-benzene (2.0 g, 9.26 mmol) in EtOH (20 mL) and saturated NH3-Bromo-2-methyl-phenylamine To a mixture of compound l-Bromo-2-methyl-3-nitro-benzene (2.0 g, 9.26 mmol) in EtOH (20 mL) and saturated NH(233) Synthesis of lntermediate-62: To a stirred solution of Starting Material-14 (2.0 g, 8.6 mmol) in THF: MeOH (40 ml_, 1 :1), activated Zn powder (3.71 g, 69.5 mmol) was added, followed by saturated NH1 -Bromo-2-methyl-3-nitrobenzene (4 g) is dissolved in ethanol (30 mL) and acetic acid (6 mL) and heated to gentle reflux. Iron powder (4.1 g) is added in small portions and the mixture is heated for 2 hours. After addition of 3 N hydrochloric acid (0.5 mL) iron powder (1 g) is cautiously added and the mixture is heated for 8 hours to reflux. After cooling to room temperature 2 N aqueous sodium hydroxide (50 mL) is added, the mixture is filtered over celite and the filter cake is rinsed with ethyl acetate. The organic phase is separated, washed with brine and dried (MgSO10778] To a stirred solution of Starting Material-14 (2.0 g, 8.6 mmol) inTHF:MeOH (40 mE, 1:1), activated Zn powder (3.71 g, 69.5 mmol) was added, followedby saturatedNH4Cl solution and stirred at room temperature for 3 hours. After completion of the reaction, the reaction mixture it was concentrated and diluted with H20, extracted with EtOAc and concentrated to give Intermediate-62 (1.7 g) as pale yellow solid.

Computed Properties

Molecular Weight:186.05
XLogP3:2.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:184.98401
Monoisotopic Mass:184.98401
Topological Polar Surface Area:26
Heavy Atom Count:9
Complexity:94.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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