652-40-4|4,7-Difluoroisobenzofuran-1,3-dione| Ambeed

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Quality Control of [ 652-40-4 ] Purity: 98% SDS Specification

COA

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Product Details of [ 652-40-4 ]

CAS No. :	652-40-4
Formula :	C₈H₂F₂O₃
M.W :	184.10
SMILES Code :	O=C1OC(C2=C1C(F)=CC=C2F)=O
MDL No. :	MFCD00134537
InChI Key :	AVLRPSLTCCWJKC-UHFFFAOYSA-N
Pubchem ID :	513918

Safety of [ 652-40-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 652-40-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 652-40-4 ]

[ 652-40-4 ] Synthesis Path-Downstream 1~35

1
[ 652-40-4 ]
[ 540-36-3 ]
[ 18959-29-0 ]

References: [1]Israel Journal of Chemistry,1973,vol. 11,p. 791 - 804.

2
[ 652-40-4 ]
[ 71-43-2 ]
[ 28736-41-6 ]

References: [1]Bulletin de la Societe Chimique de France,1970,p. 1550 - 1552.

3
[ 651-97-8 ]
[ 652-40-4 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.

4
[ 652-40-4 ]
[ 123-31-9 ]
[ 131401-54-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With aluminum (III) chloride; sodium chloride; at 220℃; for 3h;	Reference Example 17; 1, 4-Difluoro-5, 8-Dihydroxyanthraquinone (C) A mixture of ground AtCtg (2.955 g, 22.16 mmol), NaCI (432 mg, 7.39 mmol), 1,4-dihydroxybenzene (224 mg, 2.03 mmol) and 3, 6-difluorophthalic dry (340 mg, 1.85 mmol) were stirred vigorously in a round bottom flask and heated to 220 °C in an oil-bath for 3 h. The oil-bath was removed and the reaction quenched by addition of ice and concentrated hydrochloric acid (10 mL). The final aqueous solution was filtered under suction and the precipitated material was washed with water followed by freeze-drying. No further work-up was required, as the brown title-compound (470 mg, 92 percent) was pure as observed by TLC and confirmed by NMR and MS: (250 MHz; Ceci3) ; 7.3 (s, 2H), 7.55 (m, 2H), 12.9 (s, 2H) ; FAB MS, m/z (M+H) + 277.
77%	With aluminum (III) chloride; In sulfolane; at 165℃; for 16h;	A mixture of 4,7-difluoroisobenzofuran-1 ,3-dione (8.50 g, 46.2 mmol), hydroquinone (5.64 g, 51.3 mmol), aluminium trichloride (36.9 g, 277 mmol) and sulfolane (10 mL) was stirred together for 16 hours at 165°C. The reaction was effectively a melt as the mixture does not become a viscous red syrup until ~ 150°C. To minimise the risk of a sudden exotherm and evolution of HCI gas, the reaction was stirred in portions, cooled in an ice bath and stirred again until mixing was sufficient. Only then was the mixture heated. The mixture was poured carefully into ice and 2M HCI added (50 mL). The mixture was stirred, then filtered, washing the resultant slurry with further 2M HCI. The solid was re- slurried a further 3 times with 2M HCI to reduce the aluminium content of the product. A final slurry was washed with ether twice; drying in a round bottom flask at 60°C until constant weight afforded 1 ,4-difluoro-5,8-dihydroxyanthracene-9,10-dione (9.82 g, 35.6 mmol, 77 percent yield). 1 6 H NMR (DMSO-d ) was clean and consistent with the desired material.
~ 68%	aluminum (III) chloride; In sulfolane; at 155 - 180℃; for 12h;	0.3 kg (1.63 mol) of DFPA, 0.2 kg (1.82 mol) of p- hydroquinone, 1.1 kg (8.25 mol) of powdered anhydrous A1C13 and tetramethylene sulfone (1.8 L) were stirred for approximately 12 hours at a temperature of 155°C to 180°C. The reaction mixture was then quenched with ice cold water (1.0 L) and treated with aqueous 2M hydrochloric acid (1.0 L). The suspension was filtered and the resulting solid was dried at 45°C under vacuum. A fine red powder (crude DDA) was obtained after drying. This reaction was performed on several batches of the same scale and yields of around 68percent were obtained. The isolated DDA was contaminated with aluminium containing impurities, where the aluminium content in the isolated product ranged from 3290 ppm to 975 ppm, see Table 1. All batches used 300 g as one molar equivalent of DDA with the exception of batch 5A, which used 200 g. Batch Yield (g) Analytical data Number (percent yield) Al (ppm) 1A 302 (67percent) 975 2A 296 (66percent) 1150 3A 305 (68percent) 3290 4A 310 (69percent) 1165 5A 256 (85percent) 1640 Table 1 : Yield and purity of crude DDA The organic components of the product were determined to be pure by using HPLC. Purification of crude DDA The solid, crude DDA, obtained using the previous method, was treated with aqueous 2M hydrochloric acid (1.0 L) to form a slurry. Filtration of the suspension resulted in the isolation of a solid. The solid was slurried and filtered several times before drying the solid at 45°C under vacuum to leave a fine red powder. The mass recovery for this procedure was typically 90percent. This procedure resulted in a reduction of the aluminium content in the crude DDA for all the batches, see Table 2. Batch Yield (g) Analytical data Number (percent recovery) Al (ppm) 1A 283 (94percent) 714 2A 276 (93percent) 801 3A 268 (88percent) 875 4A 280 (90percent) 865 5A 229 (89percent) 526 Table 2: Yield and purity after slurrying crude DDA The organic components of the product were determined to be pure by using HPLC.

References: [1]Patent: WO2005/61453,2005,A1 .Location in patent: Page/Page column 19.
[2]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.
[3]Patent: WO2014/23956,2014,A1 .Location in patent: Page/Page column 32.
[4]Patent: WO2005/80314,2005,A2 .Location in patent: Page/Page column 14-16; 22.
[5]Journal of Medicinal Chemistry,2010,vol. 53,p. 6851 - 6866.

5
[ 652-40-4 ]
[ 150-78-7 ]
[ 131401-54-2 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.

6
[ 652-40-4 ]
[ 100-63-0 ]
5,8-Difluoro-2-phenyl-2,3-dihydro-phthalazine-1,4-dione [ No CAS ]

References: [1]Tetrahedron Letters,1996,vol. 37,p. 4145 - 4148.

7
[ 652-40-4 ]
[ 130154-76-6 ]
2-(3,5-Diethoxy-pyridin-4-ylmethyl)-4,7-difluoro-isoindole-1,3-dione [ No CAS ]

References: [1]Chemical Communications,1998,p. 1515 - 1516.

8
[ 652-40-4 ]
[ 102908-42-9 ]
2-(3-Cyano-4-oxo-1,4-dihydro-quinolin-2-yl)-3,6-difluoro-benzoic acid [ No CAS ]

References: [1]Heterocycles,1998,vol. 48,p. 641 - 655.

9
[ 4466-59-5 ]
[ 652-40-4 ]
3-Chloro-6-fluorophthalic anhydride [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2755 - 2758.

11
[ 652-40-4 ]
[ 106-42-3 ]
[ 403509-28-4 ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

12
[ 652-40-4 ]
[ 222022-28-8 ]
4,7-difluoro-2-{2-[2-(toluene-4-sulfonyl)-1,2,3,4-tetrahydro-isoquinolin-1-yl]-ethyl}-isoindole-1,3-dione [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2001,vol. 9,p. 2609 - 2624.

13
[ 652-40-4 ]
[ 3685-23-2 ]
[ 473435-61-9 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11503 - 11513.

14
[ 652-40-4 ]
[ 4426-72-6 ]
5,8-difluoro-1,4-dioxo-3,4-dihydrophthalazine-2(1H)-carboxamide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 1011 - 1015.

15
[ 652-40-4 ]
[ 79-19-6 ]
5,8-difluoro-1,4-dioxo-3,4-dihydrophthalazine-2(1H)-carbothioamide [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 1011 - 1015.

16
[ 652-40-4 ]
methyl cis-4-(3,6-difluorophthaloylamino)cyclohexanecarboxylate [ No CAS ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11503 - 11513.

17
[ 652-40-4 ]
[ 473435-67-5 ]

References: [1]Journal of the American Chemical Society,2002,vol. 124,p. 11503 - 11513.

18
[ 652-40-4 ]
[ 389633-53-8 ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

19
[ 652-40-4 ]
1,4-dimethyl-5-pyrrolidino-8-fluoro-9,10-anthracenedione [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

20
[ 652-40-4 ]
1,4-dimethyl-5-morpholino-8-fluoro-9,10-anthracenedione [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

21
[ 652-40-4 ]
1,4-dimethyl-5-methylpiperazino-8-fluoro-9,10-anthracenedione [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

22
[ 652-40-4 ]
1,4-dimethyl-5,8-dipyrrolidino-9,10-anthracenedione [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

23
[ 652-40-4 ]
1,4-dimethyl-5,8-dimorpholino-9,10-anthracenedione [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

24
[ 652-40-4 ]
1,4-dimethyl-5,8-di(methylpiperazino)-9,10-anthracenedione [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 549 - 554.

25
[ 632-58-6 ]
[ 652-40-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2755 - 2758.

26
[ 117-08-8 ]
magnesium bromide-<1.1-dipentyl-hexylate> [ No CAS ]
[ 652-40-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2755 - 2758.

27
[ 16110-99-9 ]
[ 652-40-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2755 - 2758.

28
[ 62268-16-0 ]
[ 652-40-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1999,p. 2755 - 2758.

29
[ 652-40-4 ]
[ 69895-68-7 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.
[2]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.

30
[ 35730-09-7 ]
[ 652-40-4 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.
[2]Synlett,2012,vol. 23,p. 2501 - 2503,3.

31
[ 131401-55-3 ]
[ 652-40-4 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.
[2]Synlett,2012,vol. 23,p. 2501 - 2503,3.

32
[ 131401-56-4 ]
[ 652-40-4 ]

References: [1]Synthetic Communications,1990,vol. 20,p. 2139 - 2146.
[2]Synlett,2012,vol. 23,p. 2501 - 2503,3.

33
[ 652-40-4 ]
[ 28736-42-7 ]

References: [1]Bulletin de la Societe Chimique de France,1970,p. 1550 - 1552.

34
[ 652-40-4 ]
[ 28736-44-9 ]

References: [1]Bulletin de la Societe Chimique de France,1970,p. 1550 - 1552.

35
[ 652-40-4 ]
[ 28736-46-1 ]

References: [1]Bulletin de la Societe Chimique de France,1970,p. 1550 - 1552.

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bouveault-Blanc Reduction • Bucherer-Bergs Reaction • Catalytic Hydrogenation • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Ester Cleavage • Fischer Indole Synthesis • Grignard Reaction • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions with Organometallic Reagents • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Related Functional Groups of
[ 652-40-4 ]

Fluorinated Building Blocks

A190235 [652-39-1]

4-Fluoroisobenzofuran-1,3-dione

Similarity: 1.00

A147249 [708-25-8]

Ethyl 2,5-difluorobenzoate

Similarity: 0.96

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Ethyl 2,4-difluorobenzoate

Similarity: 0.95

A225680 [1640117-38-9]

Ethyl 3-fluoro-4-formylbenzoate

Similarity: 0.93

A252345 [114312-57-1]

Ethyl 3-fluoro-2-methylbenzoate

Similarity: 0.93

Anhydrides

A190235 [652-39-1]

4-Fluoroisobenzofuran-1,3-dione

Similarity: 1.00

A180871 [25569-77-1]

4-Fluorobenzoic anhydride

Similarity: 0.89

A231148 [18959-30-3]

4,5-Difluorophthalic Anhydride

Similarity: 0.86

A187318 [13222-85-0]

4-Methylbenzoic anhydride

Similarity: 0.71

A253041 [93-97-0]

Benzoic anhydride

Similarity: 0.71

Esters

A190235 [652-39-1]

4-Fluoroisobenzofuran-1,3-dione

Similarity: 1.00

A147249 [708-25-8]

Ethyl 2,5-difluorobenzoate

Similarity: 0.96

A253948 [108928-00-3]

Ethyl 2,4-difluorobenzoate

Similarity: 0.95

A225680 [1640117-38-9]

Ethyl 3-fluoro-4-formylbenzoate

Similarity: 0.93

A252345 [114312-57-1]

Ethyl 3-fluoro-2-methylbenzoate

Similarity: 0.93

Related Parent Nucleus of
[ 652-40-4 ]

Benzofurans

A190235 [652-39-1]

4-Fluoroisobenzofuran-1,3-dione

Similarity: 1.00

A231148 [18959-30-3]

4,5-Difluorophthalic Anhydride

Similarity: 0.86

A175091 [23932-84-5]

6-Fluoroisobenzofuran-1(3H)-one

Similarity: 0.82

A217215 [700-85-6]

5-Fluoroisobenzofuran-1(3H)-one

Similarity: 0.82

A169465 [1255208-34-4]

5-Bromo-7-fluoroisobenzofuran-1(3H)-one

Similarity: 0.81

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
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P311	Call a POISON CENTER or doctor/physician.
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P321
P322
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
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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.
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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.
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P401
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Disposal
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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
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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

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CAS No.: 652-40-4

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