[ CAS No. 27550-59-0 ]

Name: 5-Hydroxyisobenzofuran-1,3-dione
Brand: Ambeed
SKU: A114888
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Quality Control of [ 27550-59-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 27550-59-0 ]

SDS

Alternatived Products of [ 27550-59-0 ]

Product Details of [ 27550-59-0 ]

CAS No. :	27550-59-0	MDL No. :	MFCD00997252
Formula :	C₈H₄O₄	Boiling Point :	407.8±28.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	164.12	Pubchem ID :	639747
Synonyms :

Computed Properties of [ 27550-59-0 ]

TPSA :Topological Polar Surface Area	63.6	H-Bond Acceptor Count :	4
XLogP3 :	0.9	H-Bond Donor Count :	1
SP3 :	0.00	Rotatable Bond Count :	0

Safety of [ 27550-59-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 27550-59-0 ]

Upstream synthesis route of [ 27550-59-0 ]
Downstream synthetic route of [ 27550-59-0 ]

[ 27550-59-0 ] Synthesis Path-Upstream 1~7

1
[ 610-35-5 ]
[ 27550-59-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	at 210℃; Green chemistry	(3) 12.3 g (67.5 mmol) of 4-hydroxyphthalic acid was placed in a sublimation tube and sublimed at 210 ° C to give 10.8 g of 4-hydroxyphthalic anhydride as a pale yellow solid in 97percent yield.
74.9%	at 220℃;	4-Hydroxyphthalic acid (1 g, 5.49 mmol) was sublimated at 220° C. under vacuum (about 10 mbar). The obtained white solid 5-hydroxyisobenzofuran-1,3-dione (675 mg, 4.11 mmol, 74.9percent yield, MS/ESI⁺164.9 [MH]⁺) was collected, stored under vacuum and used as such in the next step.
74.9%	at 220℃;	Example 45 (S)-3,5-Dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy) phenyl)-2-(2-(1 ,3-dioxo-5-(pyridin-3-ylmethoxy)isoindolin-2-yl)acetoxy)ethyl) pyridine 1 -oxide 2,2,2-trifluoroacetic acid salt (Compound 248) Scheme 45 Step 1 : Preparation of 5-hydroxyisobenzofuran-1 ,3-dione (244): 4-Hydroxyphthalic acid (1 g, 5.49 mmol) was sublimated at 220°C under vacuum (about 10 mbar). The obtained white solid 5-hydroxyisobenzofuran-1 ,3- dione (675 mg, 4.1 1 mmol, 74.9percent yield, MS/ESI⁺ 164.9 [MH] ⁺) was collected, stored under vacuum and used as such in the next step.

74%	at 200℃; for 1.00 h;	2^nd Stage: 4-hydroxyphthalic anhydride 4-hydroxyphthalic acid (23.80 g, 0.131 mol) was heated for 1 h in an oil bath preheated to 200° C. After cooling the brownish solid was recrystallized from ethyl acetate/n-hexane (1:1). 15.82 g (96.4 mmol; 74percent yield) of a white solid was obtained. ¹H-NMR (DMSO-d₆, 400 MHz): δ=7.25 (d, 1H; J=2.0 Hz), 7.28 (dd, 1H; J=2.0 Hz, 8.5 Hz), 7.89 (d, 2H, J=8.0 Hz), 11.44 (br s, 1H). ¹³C-NMR (DMSO-d₆, 100 MHz): δ=111.0, 120.7, 123.0, 127.6, 133.9, 162.7, 163.2, 164.8.
74%	at 200℃; for 1.00 h;	2^nd Stage: 4-hydroxyphthalic anhydride 4-hydroxyphthalic acid (23.80 g, 0.131 mol) was heated for 1 h in an oil bath preheated to 200° C. After cooling the brownish solid was recrystallized from ethyl acetate/n-hexane (1:1). 15.82 g (96.4 mmol; 74percent yield) of a white solid was obtained. ¹H-NMR (DMSO-d₆, 400 MHz): δ=7.25 (d, 1H; J=2.0 Hz), 7.28 (dd, 1H; J=2.0 Hz, 8.5 Hz), 7.89 (d, 2H, J=8.0 Hz), 11.44 (br s, 1H). ¹³C-NMR (DMSO-d₆, 100 MHz): δ=111.0, 120.7, 123.0, 127.6, 133.9, 162.7, 163.2, 164.8.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4427 - 4431
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 1, p. 342 - 353
[3] Patent: CN104910113, 2017, B. Location in patent: Page/Page column 0041; 0044-0046
[4] European Journal of Medicinal Chemistry, 1987, vol. 22, p. 229 - 238
[5] Patent: US2013/102576, 2013, A1. Location in patent: Paragraph 0607
[6] Patent: WO2013/57013, 2013, A2. Location in patent: Page/Page column 193
[7] Patent: US2013/90404, 2013, A1. Location in patent: Paragraph 0075; 0076; 0077; 0078
[8] Patent: US9393181, 2016, B2. Location in patent: Page/Page column 9
[9] Monatshefte fuer Chemie, 1902, vol. 23, p. 401
[10] Journal of the Chemical Society, 1907, vol. 91, p. 103
[11] Chemische Berichte, 1877, vol. 10, p. 1079
[12] Journal of Medicinal Chemistry, 1987, vol. 30, # 10, p. 1798 - 1806
[13] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 5, p. 1249 - 1256
[14] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 1, p. 283 - 287
[15] Patent: EP1681283, 2006, A1. Location in patent: Page/Page column 4-5
[16] Synthesis, 2008, # 21, p. 3415 - 3422
[17] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 14, p. 5323 - 5338
[18] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
[19] Marine Drugs, 2016, vol. 14, # 6,

2
[ 31643-49-9 ]
[ 27550-59-0 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215
[2] Patent: CN104910113, 2017, B

3
[ 30757-50-7 ]
[ 27550-59-0 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 96, p. 79207 - 79215

4
[ 89-08-7 ]
[ 27550-59-0 ]

Reference： [1] Patent: US2013/90404, 2013, A1

5
[ 64139-21-5 ]
[ 27550-59-0 ]

Reference： [1] Chemische Berichte, 1877, vol. 10, p. 1079

6
[ 22572-84-5 ]
[ 27550-59-0 ]

Reference： [1] Chemische Berichte, 1877, vol. 10, p. 1079

7
[ 4707-32-8 ]
[ 27550-59-0 ]
[ 1337915-27-1 ]
[ 53266-48-1 ]
[ 88-99-3 ]

Reference： [1] Journal of Pharmacy and Pharmacology, 2011, vol. 63, # 9, p. 1156 - 1160

[ 27550-59-0 ] Synthesis Path-Downstream 1~10

1
[ 27550-59-0 ]
[ 60-32-2 ]
[ 362672-06-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 283 - 287

2
[ 27550-59-0 ]
[ 101-80-4 ]
N,N'-(4,4'-oxydiphenylene)-bis-(5-hydroxy-2-phenyl-isoindole-1,3-dione) [ No CAS ]

Reference： [1]Journal of Molecular Structure,2002,vol. 602-603,p. 405 - 416

3
[ 27550-59-0 ]
[ 611-98-3 ]
4,4'-bis(4-hydroxyphthalimide)benzophenone [ No CAS ]

Reference： [1]Journal of Molecular Structure,2002,vol. 602-603,p. 405 - 416

4
[ 27550-59-0 ]
[ 139-65-1 ]
N,N'-(4,4'-sulfanyldiphenylene)-bis-(5-hydroxy-2-phenyl-isoindole-1,3-dione) [ No CAS ]

Reference： [1]Journal of Molecular Structure,2002,vol. 602-603,p. 417 - 428

5
[ 27550-59-0 ]
5-but-3-ynoxy-2-(2,6-dioxo-3-piperidyl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: US2019/192668,2019,A1

6
[ 27550-59-0 ]
2-(2,6-dioxopiperidin-3-yl)-5-(prop-2-yn-1-yloxy)isoindoline-1,3-dione [ No CAS ]

Reference： [1]Patent: US2019/192668,2019,A1

7
[ 27550-59-0 ]
[ 24666-56-6 ]
[ 64567-60-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium acetate; acetic acid; at 90℃; for 6h;	To a solution of <strong>[27550-59-0]5-hydroxyisobenzofuran-1,3-dione</strong> (1.00 g, 6.09 mmol, CAS27550-59-0) and 3-aminopiperidine-2,6-dione (1.05 g, 6.40 mmol, HCl) in HOAc (20 mL) was added KOAc (1.79 g, 18.3 mmol). The mixture was stirred at 90 C. for 6 hrs. On completion, the mixture was poured into ice water (100 mL), and solid was obtained and then filtered. The residue was washed with H2O (3×50 mL), dried in vacuo to give the title compound (1.40 g, 83% yield) as a light white solid. 1H NMR (400 MHz, DMSO-d6) delta 11.29-10.90 (m, 2H), 7.75 (d, J=8.2 Hz, 1H), 7.39-6.87 (m, 2H), 5.09 (dd, J=5.4, 12.8 Hz, 1H), 3.34 (s, 1H), 2.96-2.82 (m, 1H), 2.69-2.58 (m, 1H), 2.08-1.99 (m, 1H).

Reference： [1]Patent: US2019/192668,2019,A1.Location in patent: Paragraph 3346; 3347

8
[ 27550-59-0 ]
[ 2450-71-7 ]
5-hydroxy-2-(prop-2-yn-1-yl)isoindoline-1,3-dione [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 9152 - 9161

9
[ 27550-59-0 ]
C₂₆H₂₇N₅O₇S [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 9152 - 9161

10
[ 27550-59-0 ]
C₁₈H₁₀N₂O₃S [ No CAS ]

Reference： [1]New Journal of Chemistry,2019,vol. 43,p. 9152 - 9161

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P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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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. 27550-59-0 ]

Quality Control of [ 27550-59-0 ]

Related Doc. of [ 27550-59-0 ]

Product Details of [ 27550-59-0 ]

Computed Properties of [ 27550-59-0 ]

Safety of [ 27550-59-0 ]

Application In Synthesis of [ 27550-59-0 ]

[ 27550-59-0 ] Synthesis Path-Upstream 1~7

[ 27550-59-0 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 27550-59-0 ]

Esters

Anhydrides

Alcohols

Related Parent Nucleus of [ 27550-59-0 ]

Benzofurans

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Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 27550-59-0 ]

Related Parent Nucleus of
[ 27550-59-0 ]