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2-Amino-4-methoxyphenol

2-Amino-4-methoxyphenol structure

CAS No:
20734-76-3
Formula:
C7H9NO2
Chemical Name:
2-Amino-4-methoxyphenol
Synonyms:
Phenol,2-amino-4-methoxy-;2-Amino-4-methoxyphenol;1-Amino-2-hydroxy-5-methoxybenzene;4-Methoxy-2-aminophenol;2-Hydroxy-5-methoxyaniline
Categories:
Organic Chemistry > Alcohols, Phenols, Phenol Alcohols

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2-Amino-4-methoxyphenol Basic Attributes

Molecular Weight：

139.15

Exact Mass：

139.15

DSSTox ID：

DTXSID40362896

HScode：

2922509090

Characteristics

PSA：

55.5

XLogP3：

1.2

Density：

1.2±0.1 g/cm3

Melting Point：

124 °C

Boiling Point：

289.1°C at 760 mmHg

Flash Point：

128.7±23.2 °C

Refractive Index：

1.600

Storage Conditions：

2-8°C

Vapor Pressure：

0.00129mmHg at 25°C

Safety Information

Hazard category：

IRRITANT

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

22-52/53

safety instructions：

Marks：

T,Xi,Xn

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (95.12%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 41 companies from 4 notifications to the ECHA C&L Inventory.

2-Amino-4-methoxyphenol Use and Manufacturing

To a round bottom flask was added 4-methoxy-2-nitrophenol (10g, 59.17mmol) (4), methanol (500mL) and 10percent palladium on carbon (500mg) in methanol (5mL). A hydrogen atmosphere was then inserted via balloon and reaction mixture allowed to stir overnight at room temperature. Reaction mixture was then filtered through celite and the mother liquor concentrated in vacuo to yield 2-amino-4-methoxyphenol as brown oil (7.9 g, 96percentyield).To a solution of 4-methoxy-2-nitrophenol (5g, 0.029mo1) in methanol (250mL) was added palladium on charcoal (10percent, 0.5g). The mixture was submitted to a H2 balloon over weekend at room temperature. The catalyst was filtered through Celite and the solvent was removed under reduced pressure giving the title compound as a yellow solid (4.85g, 93percent).LRMS (mlz): 140 (M+1)+Compound 1 (60.0 g, 355.0 mmol) and Pd/C (8 g) were added to EA/MeOH (320 mL/480 mL). The reaction mixture was stirred at RT under HGeneral procedure: TAPEHA-Pd (0.015 g) was added to a solution of nitroarenes (1.0 mmol) in EtOH (20 mL). After N2H4 .H2O(4.0 mmol) was added the color of the catalyst was turned to black rapidly in the same way as reducing with NaBH4 . This color change means formation of palladium nanoparticles43 TAPEHA-PdNPs as mentioned above. After being stirred for 20 min at room temperature and atmospheric pressure, the catalyst was removedby ltering and EtOH was removed under a vacuum.General procedure: SAC (300mg) and NaBHA mixture of Example 14a (10 g, 59.1 mmol) and Pd/C (1 g 10percent) was stirred under the hydrogen balloon in MeOH (500 mL) at r.t for 16 hrs. After the reaction (detected by TLC and LCMS) was completed, the black suspension was filtered through celite, and then concentrated at 45°C under reduced pressure to give the desired product (Example 14b, 7g, yield 85percent) as brown solid. LCMS [M+1]General procedure: To a mixture of 1a (2.84 g, 17.40 mmol) in MeOH (35 ml) was addedPd/C (568.2 mg, 20percent w/w) under argon atmosphere, then the reaction mixture washydrogenated at RT for 2 h under HTo a mixture of 4-methoxy-2-nitrophenol (23, 5.0 g, 29.56 mmol) and NHReference

Computed Properties

Molecular Weight:139.15
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:139.063328530
Monoisotopic Mass:139.063328530
Topological Polar Surface Area:55.5
Heavy Atom Count:10
Complexity:108
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes