2-BROMO-4-METHOXY-PHENYLAMINE
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2-BROMO-4-METHOXY-PHENYLAMINE
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CAS No:
32338-02-6
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Formula:
C7H8BrNO
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Chemical Name:
2-BROMO-4-METHOXY-PHENYLAMINE
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Synonyms:
2-BROMO-4-METHOXY-PHENYLAMINE;2-BROMO-4-METHOXYANILINE;2-Bromo-p-anisidine;2-N,4-N-diethyl-6-ethylsulfanyl-1,3,5-triazine-2,4-diamine;ethyl-[4-(ethylamino)-6-(ethylthio)-s-triazin-2-yl]amine;N2,N4-diethyl-6-ethylsulfanyl-1,3,5-triazine-2,4-diamine;2-Bromo-4-methoxyaniline 95%;4-Amino-3-bromoanisole, 2-Bromo-p-anisidine
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CAS No:
Safety Information
IRRITANT
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
H301+H311+H331
|Danger|H301+H311+H331 (50%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]|P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2-BROMO-4-METHOXY-PHENYLAMINE Use and Manufacturing
To a solution of Intermediate 103A (1.7g, 7.33 mmol) in MeOH (30 mL) was added ammonium chloride (7.84 g, 147 mmol) and zinc dust (4.79 g, 73.3 mmol). The mixture was stirred at room temperature for lh. LCMS indicated a clean reaction.MeOH was removed. The residue was diluted with EtOAc/saturated sodium bicarbonate and stirred at room temperature for 10 mm. The mixture was filtered to remove insoluble material. The filtrate was collected, organic layer was washed with brine, dried over sodium sulfate, concentrated. The cmde sample was purified with a 120g ISCO column eluted with 0-100percent EtOAc in hexanes for 40 mm. The desired fraction was collected andconcentrated to give Intermediate 103B (1.3 g, 6.43 mmol, 88 percent yield) as oil. ‘H NMR (400MHz, chloroform-d) 7.01 (d, J2.0 Hz, 1H), 6.76-6.70 (m, 2H), 3.79 (br. s., 2H), 3.74 (s, 3H). LC-MS: method C, RT = 0.80 mm, MS (ESI) m/z: 202 and 204 (M+H)To a solution of 4-methoxyaniline (10 g, 81 mmol) in DMF (150mL) cooled in ice-bath was added NBS (14.5 g, 81 mmol) portionwise under strictly exclusion of light, and the mixture was stirred for 30 min at the same temperature. Then the ice-bath was removed and the stirring was continued at rt overnight (18 h). The mixture was poured into water (300 mL) and extracted with CH2Cl2, the combined organic phase was over MgSO4 and filtered. The filtrate was evaporated to give a black-brown tar which was purified by column chromatography (PE : EtOAc = 20 : 1) to obtain a pale-yellow oil (10.1 g, 62 percent); Rf = 0.50 (PE : EtOAc = 5 : 1); 1H-NMR (CDCl3, 300 MHz) δ: 7.01 (d, J = 1.5 Hz, 1H), 6.73 (m, 2H), 3.72 (s, 5H).At -10 °C, to a solution of 4-methoxyaniline (100 g, 812 mmol) in THF (3 L) was added N-bromosuccinimide (152 g, 853 mmol) in three portions and the mixture was stirred at the same temperature for 30 min. The mixture was concentrated under reduced pressure. The residue was purified by column chromatography, (petroleum ether/ethyl acetate 15/1) to give 2-bromo-4-methoxyaniline as red oil (30.58 g, 18.6percent yield). MR (400 MHz, CDCh) δ = 7.01 (d, J=2.4 Hz, 1H), 6.74-6.70 (m, 2H), 3.85-3.74 (m, 2H), 3.73 (s, 3H).
Computed Properties
Molecular Weight:202.05
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:200.97893
Monoisotopic Mass:200.97893
Topological Polar Surface Area:35.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
