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4-Dibenzofuranamine

4-Dibenzofuranamine structure

CAS No:
50548-43-1
Formula:
C12H9NO
Chemical Name:
4-Dibenzofuranamine
Synonyms:
4-Dibenzofuranamine;4-Aminodibenzofuran
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

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4-Dibenzofuranamine Basic Attributes

Molecular Weight：

183.20596

Exact Mass：

183.21

DSSTox ID：

DTXSID80332639

HScode：

2932999099

Characteristics

PSA：

39.2

XLogP3：

3.4

Density：

1.3±0.1 g/cm3

Melting Point：

84.5-85.5 °C

Boiling Point：

369.1±15.0°C at 760 mmHg

Flash Point：

177.0±20.4 °C

Refractive Index：

1.755

Safety Information

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

4-Dibenzofuranamine Use and Manufacturing

Palladium hydroxide (20percent, 0.75 g, 1.068 mmol) was added to a Parr hydrogenation bottle, and the bottle was purged with nitrogen. Next, 4-azidodibenzo[b, d]furan (7.39 g, 35.3 mmol) and 150 mL ethanol were added, and the reaction mixture was hydrogenated on Parr hydrogenator overnight. The reaction mixture was filtered through a pad of CeliteN-(dibenzo[b, d]furan-4-yl)acetamide (90 g, 400 mmol) was suspended in the mixture of concentrated HCl (240 mL) and methanol (240 mL).Add toluene solvent to the reaction flask, Intermediate 2-3 (26.18 g, 80 mmol), Intermediate 1-1 (2 g, 2.75 mmol), Intermediate 1-2 (603 mg, 3.3 mmol) and NaOtBu (tert-butoxysodium) (396 mg, 4.12 mmol) were placed in a 250 ml round bottom flask. 100 ml of Toluene was added under nitrogen, and the temperature was raised to 100 C. Pd (P (tBu3)) 2 (70 mg, 0.14 mmol) was added to a round bottom flask, and the mixture was stirred for 8 hours after blocking light.After lowering the temperature, the material was extracted using DCM (Dichloromethane) and water, and stirred with MgSO 4 and acid clay. After passing through silica gel, the solvent was removed. The material was separated by column chromatography (methyl chloride / Hexane).Dibenzo [b, d] furan-4-amine (dibenzo [b, d] furan-4-amine) (13 g, 1 eq) 3-bromophenyl (3-bromobiphenyl) (25 g, 1.2 eq), Pd 2 (dba) 3 (2.4 g, 0.03 eq), t-BuONa (12.5 g, 1.5 eq), t-Bu 3P (1.05 g, 0.06 eq), Toluene 400 ml are placed in a single round bottom flask (1-neck-R.B.F.) and stirred. (3h) MC / Hx = 1/5 N - ([1, 1'-biphenyl] -3-yl) dibenzo [b, d] furan- (N - ([1, 1'-biphenyl] -3-yl) dibenzo [b, d] furan-4-amine. (16 g, step yield = 73%)In a 250 ml three-necked flask, 0.01 mol of raw material O1 was added under nitrogen protection.0.012 mol of raw material P1, 150 ml of toluene were stirred and mixed.Then add 5×10-5 mol Pd2(dba)3, 5×10-5 mol P(Ph)3, 0.03 mol of sodium tert-butoxide, heated to 105 C, refluxed for 24 hours, sampling plate, Show no bromine residue remaining, the reaction is complete; naturally cool to room temperature, filter, The filtrate is steamed to no fraction, and passed through a neutral silica gel column to obtain the target product intermediate B1;HPLC purity 99.03%, yield 74.8%;

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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