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2-Dibenzofuranamine

2-Dibenzofuranamine structure

CAS No:
3693-22-9
Formula:
C12H9NO
Chemical Name:
2-Dibenzofuranamine
Synonyms:
2-Dibenzofuranamine;2-Aminodibenzofuran;NSC 402280
Categories:
Organic Chemistry > Coordination Complexes

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2-Dibenzofuranamine Basic Attributes

Molecular Weight：

183.21

Exact Mass：

183.21

UNII：

008JZJ6NVX

NSC Number：

402280

DSSTox ID：

DTXSID4039239

HScode：

2932999099

Characteristics

PSA：

39.2

XLogP3：

3.4

Density：

1.283g/cm3

Melting Point：

125 °C

Flash Point：

177ºC

Refractive Index：

1.755

Safety Information

Stability/Shelf Life：

Stability

GHS Classification：

|Warning|H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, 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-Dibenzofuranamine Use and Manufacturing

Methods of Manufacturing

General procedure: To a flame-dried reaction vial was added a solution of aryl bromide (1.0 mmol, 1.0 eq.) in 2 mL anhydrous THF. A solution of n-BuLi in hexanes (1.1 mmol, 1.1 eq.) was slowly added at −78° C. and the temperature was maintained at −78° C. After 30 min, this aryl lithium solution was transferred to a suspension of MgBrUnder a nitrogen atmosphere, 25 g (0.12 mol) of the intermediate A-2, 6.25 g of Raney nickel, 50 g (0.16 mol) of hydrazine monohydrate, and 150 ml of THF were loaded, and the mixture was stirred at 80 °C. 50 g (0.16 mol) of hydrazine monohydrate were added to the mixture, and then the whole was stirred at 80°C for 13 hr. The reaction solution was cooled to room temperature and then the inorganic salt was separated by filtration. After that, the solvent was distilled off under reduced pressure. The resultant residue was purified by column chromatography to provide 14.3 g (0.078 mol, 65percent yield) of an intermediate A-3.General procedure: In a sealed tube were added successively ArCl and aniline derivative in dioxane (2mL). One drop of HClconc. was added and the mixture was stirred at 100C for 12h. EtOAc was added to the cooled mixture which was neutralized with NaOHaq. (5N). After extraction, organic layer was dried on Na2SO4, filtered and concentrated. The crude mixture was added to a solution of Cs2CO3 (1.2 equiv.) in DMF (5mL) at 0C. CH3I (1.2 equiv.) was added dropwise at 0C and the mixture was stirred at room temperature for 12h. The crude mixture was concentrated and purified by silica gel column chromatography.

Uses

2-Aminodibenzofuran is a polycyclic aromatic hydrocarbon (PAH) used in the preparation of mono and bisazo dyes. 2-Aminodibenzofuran is a carcinogen.

Computed Properties

Molecular Weight:183.21
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:183.068413911
Monoisotopic Mass:183.068413911
Topological Polar Surface Area:39.2
Heavy Atom Count:14
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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