4,5-Difluoro-1,2-phenylenediamine
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4,5-Difluoro-1,2-phenylenediamine
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CAS No:
76179-40-3
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Formula:
C6H6F2N2
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Chemical Name:
4,5-Difluoro-1,2-phenylenediamine
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Synonyms:
1,2-Benzenediamine,4,5-difluoro-;4,5-Difluoro-1,2-benzenediamine;4,5-Difluoro-o-phenylenediamine;4,5-Difluoro-1,2-phenylenediamine;2-Amino-4,5-difluoroaniline;1,2-Diamino-4,5-difluorobenzene;1,2-Diamine-4,5-difluorobenzene;4,5-Difluoro-1,2-diaminobenzene
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CAS No:
4,5-Difluoro-1,2-phenylenediamine Basic Attributes
144.12
144.12
1592732-453-0
DTXSID10371576
2921590090
Safety Information
36/37/39
24-36/37
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
4,5-Difluoro-1,2-phenylenediamine Use and Manufacturing
4, 5-Difluoro-2-nitro-aniline (10 g, 57 mmol) and 10percent palladium on carbon (2.0 g, 1.9 mmol) were placed in methanol (150 mL). The mixture was hydrogenated at 50 psi in a hydrogenator. After 3 hours the reaction mixture was filtered through diatomaceous earth and concentrated to a solid which was dried overnight (8.05 g, 98percent).Step 1: A mixture of 4, 5-difluoro-2-nitroaniline (1.73 g, 10 mmol), palladium on activated charcoal (200 mg), and MeOH (50 mL) was stirred under hydrogen (1 atm) at rt for 12 h. The mixture was filtered to remove the catalystand the filtrate was concentrated under reduced pressure to afford 4, 5-difluorobenzene-1, 2-diamine (1.42 g, 97percent) as abrown solid, which was not purified further. 1H NMR (300 MHz, CDCl3) δ 6.50 (m, 2H), 2.75 - 3.48 (br s, 4H).A mixture of 4, 5-difluoro-2- nitro-phenylamine (10.00 g, 57.46 mmol) and tin(II) chloride dihydrate (64.83 g, 287.32 mmol) in ethanol (100 mL) was heated to reflux under nitrogen atmosphere for 30 min. After mixture was cooled down to room temperature, the pH of the solution was made basic (10 to 12) by addition of 5percent of sodium hydroxide solution. The solution was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate. Solvent was removed under reduced pressure and the residue was crystallized in hexane to give a white solid (6.05 g, 62percent). 4, 5-Difluoro-1, 2-phenylenediamine (10)
Computed Properties
Molecular Weight:144.12
XLogP3:0.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Exact Mass:144.04990452
Monoisotopic Mass:144.04990452
Topological Polar Surface Area:52
Heavy Atom Count:10
Complexity:106
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4,5-Difluoro-1,2-phenylenediamine
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