[ CAS No. 57319-65-0 ]

Name: 6-Aminoisobenzofuran-1(3H)-one
Brand: Ambeed
SKU: A385893
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Quality Control of [ 57319-65-0 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 57319-65-0 ]

Product Details of [ 57319-65-0 ]

CAS No. :	57319-65-0	MDL No. :	MFCD00033530
Formula :	C₈H₇NO₂	Boiling Point :	420.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	149.15	Pubchem ID :	93631
Synonyms :

Computed Properties of [ 57319-65-0 ]

TPSA :Topological Polar Surface Area	52.3	H-Bond Acceptor Count :	3
XLogP3 :	-	H-Bond Donor Count :	1
SP3 :	0.13	Rotatable Bond Count :	0

Safety of [ 57319-65-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P280-P305+P351+P338-P304+P340-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 57319-65-0 ]

Upstream synthesis route of [ 57319-65-0 ]
Downstream synthetic route of [ 57319-65-0 ]

[ 57319-65-0 ] Synthesis Path-Upstream 1~5

1
[ 610-93-5 ]
[ 57319-65-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogen In tetrahydrofuran; methanol at 20℃; for 20.00 h;	Commercially available 6-nitro-1(3H)-isobenzofuranone (9.9 g, 55 mmol) was dissolved in a mixed solvent of tetrahydrofuran (20 ml)-methanol (60 ml), then 5percent palladium-charcoal catalyst (1.5 g) was added thereto, and the mixture was stirred at room temperature for 20 hours under an atmosphere of hydrogen gas. The reaction mixture was filtered, and the solid was washed successively with ethyl acetate and methanol. The filtrate and washings were combined, and the resulting solution was concentrated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (6.21 g) as a crystalline solid. The washings were concentrated, and the residue was crystallized from a mixed solvent of ethyl acetate-hexane to give an additional amount of the title compound (0.95 g, total yield 87percent). NMR spectrum (400 MHz, CD3OD) δ ppm: 5.225 (2H, s), 7.060 (1H, d-like, J=2 Hz), 7.071 (1H, dd-like, J=9, 2 Hz), 7.288 (1H, d, J=9 Hz) IR spectrum ν max KBr cm-1: 3473, 3372, 3278, 1735, 1631, 1504, 1330, 1059, 992.
86%	With palladium on carbon; hydrogen In methanol at 20℃; for 12.00 h;	6-Nitro-3H-isobenzofuran-1-one 1)> (2.00 g, 11.1 mmol) was dissolved in methanol (25 ml), and 20percent palladium/ carbon (200 mg) was added thereto, followed by stirring at room temperature for 12 hours in the presence of hydrogen gas (50 psi). The reaction solution was filtered and concentrated under reduced pressure to obtain the title compound (1.43 g, 86percent). [1326] 1H NMR (400 MHz, DMSO-d₆): δ 7.30 (d, J=8.0 Hz, 1H), 6.96 (dd, J=8.0, 2.0 Hz, 1H), 6.91 (d, J=4.0 Hz, 1H), 5.56 (s, 2H), 5.21 (s, 2H)
78%	With hydrogenchloride; tin(ll) chloride In water for 4.00 h; Heating / reflux	Step b: 6-Aminoisobenzofuran-1(3H)-one To a solution of 6-nitroisobenzofuran-1(3H)-one (15 g, 0.080 mol) in HCl/H₂O (375 mL/125 mL) was added SnCl₂.2H₂O (75 g, 0.33 mol). The reaction mixture was heated at reflux for 4 h before it was quenched with water and extracted with EtOAc (300 mL*3). The organics were dried over Na₂SO₄ and evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10 g, 78percent). ¹H NMR (300 MHz, CDCl₃) δ 7.23 (d, J=8.1, 1H), 7.13 (d, J=2.1, 1H), 6.98 (dd, J=8.1, 2.1, 1H), 5.21 (s, 2H), 3.99 (br s, 2H).

78%	With hydrogenchloride; tin(II) chloride dihdyrate In water for 4.00 h; Reflux	To a solution of 6-nitroisobenzofuran-1(3H)-one (15 g, 0.080 mol) in HCl/H2O (375 mL/125 mL) was added SnCl2.2H2O (75 g, 0.33 mol). The reaction mixture was heated at reflux for 4 h before it was quenched with water and extracted with EtOAc (300 mL*3). The organics were dried over Na2SO4 and evaporated in vacuo to give 6-aminoisobenzofuran-1(3H)-one (10 g, 78percent). 1H NMR (300 MHz, CDCl3) δ 7.23 (d, J=8.1, 1H), 7.13 (d, J=2.1, 1H), 6.98 (dd, J=8.1, 2.1, 1H), 5.21 (s, 2H), 3.99 (br s, 2H).
75%	With indium (III) iodide; 1,1,3,3-Tetramethyldisiloxane In toluene at 60℃; for 4.00 h; Inert atmosphere; Sealed tube	General procedure: To a screw top vial (5 mL) under N2 containing freshly distilled toluene (0.6 mL) were successively added an aromatic nitro compound (0.60 mmol), InI3 (14.9 mg, 0.030 mmol), and TMDS (318 μL, 1.80 mmol). After the vial was sealed with a cap that contained a PTFE septum, the mixture was stirred at 60 °C (bath temperature), and monitored via TLC analysis. Sat. aq NaHCO3 solution (5 mL) was added to the resultant mixture, which was then extracted with EtOAc (3 × 6 mL). The combined organic phases were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (n-hexane–EtOAc, 9:1 to 4:1) to afford the corresponding aniline derivative.

Reference： [1] Physical Chemistry Chemical Physics, 2005, vol. 7, # 24, p. 4070 - 4081
[2] Chemistry - A European Journal, 2016, vol. 22, # 13, p. 4600 - 4607
[3] ACS Catalysis, 2014, vol. 4, # 10, p. 3504 - 3511
[4] Patent: EP1362856, 2003, A1. Location in patent: Page/Page column 159
[5] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[6] Catalysis Letters, 2014, vol. 144, # 7, p. 1258 - 1267
[7] Patent: US2015/51395, 2015, A1. Location in patent: Paragraph 1325-1326
[8] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 6, p. 1519 - 1523
[9] Patent: US2008/9524, 2008, A1. Location in patent: Page/Page column 409; 409-410
[10] Journal of Organic Chemistry, 2009, vol. 74, # 18, p. 6960 - 6964
[11] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 1264
[12] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[13] Chemistry of Heterocyclic Compounds, 2010, vol. 46, # 2, p. 140 - 145
[14] Synthesis (Germany), 2015, vol. 47, # 20, p. 3179 - 3185
[15] Journal of the American Chemical Society, 1937, vol. 59, p. 864
[16] Patent: US2130480, 1935,
[17] Chemische Berichte, 1934, vol. 67, p. 675,681
[18] Tetrahedron, 1988, vol. 44, # 14, p. 4591 - 4604
[19] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3417 - 3423
[20] Patent: US4409017, 1983, A
[21] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 8, p. 3177 - 3188
[22] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33
[23] Organic Letters, 2012, vol. 14, # 14, p. 3748 - 3751
[24] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1063 - 1069
[25] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 5, p. 1269 - 1273
[26] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
[27] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 22, p. 5929 - 5940
[28] European Journal of Organic Chemistry, 2018, vol. 2018, # 2, p. 209 - 214
[29] Applied Catalysis A: General, 2018, vol. 559, p. 127 - 137
[30] Research on Chemical Intermediates, 2018, vol. 44, # 9, p. 5107 - 5122

2
[ 610-93-5 ]
[ 10025-69-1 ]
[ 57319-65-0 ]

Reference： [1] Patent: US2011/98311, 2011, A1

3
[ 87-41-2 ]
[ 57319-65-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 5, p. 1195 - 1204
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 22, p. 3417 - 3423
[3] Chemische Berichte, 1934, vol. 67, p. 675,681
[4] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33
[5] Patent: US2011/98311, 2011, A1
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 4, p. 1063 - 1069
[7] Patent: US2015/51395, 2015, A1
[8] Journal of Medicinal Chemistry, 2015, vol. 58, # 9, p. 3997 - 4015
[9] Patent: US2015/231142, 2015, A1

4
[ 5466-84-2 ]
[ 57319-65-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238

5
[ 85-44-9 ]
[ 57319-65-0 ]

Reference： [1] Chemical Biology and Drug Design, 2010, vol. 76, # 1, p. 25 - 33

[ 57319-65-0 ] Synthesis Path-Downstream 1~10

1
[ 57319-65-0 ]
3-<i>m</i>-tolyl-2-trifluoromethanesulfonyloxy-propionic acid ethyl ester [ No CAS ]
2-(3-oxo-1,3-dihydro-isobenzofuran-5-ylamino)-3-<i>m</i>-tolyl-propionic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 4121 - 4124

2
[ 57319-65-0 ]
[ 64-17-5 ]
[ 7803-57-8 ]
5-amino-2-hydroxymethyl-benzoic acid hydrazide [ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1923,vol. 42,p. 37

5
[ 57319-65-0 ]
N-(2-(2-((bis-(tert-butoxycarbonyl)amino)oxy)acetamido)ethyl)-3-azido-2,4-dibromo-6-(hydroxymethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2020/43747,2020,A1

6
[ 57319-65-0 ]
N-(2-aminoethyl)-3-azido-2,4-dibromo-6-(hydroxymethyl)benzamide [ No CAS ]

Reference： [1]Patent: WO2020/43747,2020,A1

7
[ 57319-65-0 ]
5,7-dibromo-6-azidophthalide [ No CAS ]

Reference： [1]Patent: WO2020/43747,2020,A1

8
[ 57319-65-0 ]
5,7-dibromo-6-aminophthalide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrahydrofuran; acetonitrile; at 0 - 20℃; for 2h;	<strong>[57319-65-0]6-Aminophthalide</strong> (20.00 g, 132.75 mmol) was provided in a 1 L round bottom flask with a stirring bar and 550 ml. THF and 30 ml. MeCN was added at 0C. To the solution N- bromosuccinimide was added slowly as a solid through a powder funnel after witch the solution turned brownish. The ice-bath was removed then after some time the solution turned yellow. After 2h stirring at room-temperature UPLC-MS and TLC indicated complete conversion to the dibromide. The solvent was removed under reduced pressure at a rotational evaporator. The remaining solid was dissolved in 600 ml Ethyl acetate and washed 3 times with water. The organic phase was dried with MgS04 and after evaporation 39.86 g (129.86 mmol, 98%) of the desired product was gained as a pale yellow solid. Rf = 0.6 (cyclohexanes/Ethyl acetate 2:1 ), UPLC-MS: tR = 2.36 min (10-90% MeCN in 3 min), UPLC- purity (254 nm) = 87.0%, ESI-MS: (calculated MH+: 307.95 g/mol, found: 307.76 m/z).

Reference： [1]Patent: WO2020/43747,2020,A1.Location in patent: Page/Page column 63

9
[ 57319-65-0 ]
6-azido-7-bromophthalide [ No CAS ]

Reference： [1]Patent: WO2020/43747,2020,A1

10
[ 57319-65-0 ]
6-amino-7-bromophthalide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrahydrofuran; at 0℃; for 1h;	To a cooled solution (0 C) of <strong>[57319-65-0]6-aminophthalide</strong> (5.13 g, 34.05 mmol) in THF (80 ml.) was added /V-bromosuccinimide (6.12 g, 34.05 mmol, 1 eq). The cooling bath was removed and the solution stirred for 1 h, then the solvent was removed under reduced pressure. The yellow residue was taken up in ethyl acetate (400 ml) and washed three times with water (200 ml. each). The organic phase was dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to give 6-amino-7-bromophthalide as a brown solid (6.53 g, 28.63 mmol, 84%). Rf = 0.2 (cyclohexane/ethyl acetate 2:1 ); UPLC-MS: tR = 1.45 min (gradient 10-90% B in 5 min); UPLC-purity (210 nm) = 83.1%; ESI-MS: (calculated MH+: 227.97, 229.96, found: 228.01 , 230.01 )

Reference： [1]Patent: WO2020/43747,2020,A1.Location in patent: Page/Page column 60-61

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 57319-65-0 ]

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[ 57319-65-0 ] Synthesis Path-Upstream 1~5

[ 57319-65-0 ] Synthesis Path-Downstream 1~10

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Amines

Esters

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Benzofurans

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