[ CAS No. 18959-30-3 ] {[proInfo.proName]}

Name: 18959-30-3|4,5-Difluorophthalic Anhydride|98%
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3d Animation Molecule Structure of 18959-30-3

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Quality Control of [ 18959-30-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 18959-30-3 ]

SDS Specification

Alternatived Products of [ 18959-30-3 ]

Product Details of [ 18959-30-3 ]

CAS No. :	18959-30-3	MDL No. :	MFCD08695033
Formula :	C₈H₂F₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UATBWQQFLABWKR-UHFFFAOYSA-N
M.W :	184.10	Pubchem ID :	639745
Synonyms :

Calculated chemistry of [ 18959-30-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.1
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.08
Log Po/w (XLOGP3) :	1.49
Log Po/w (WLOGP) :	2.12
Log Po/w (MLOGP) :	2.51
Log Po/w (SILICOS-IT) :	2.66
Consensus Log Po/w :	1.97

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.26
Solubility :	1.01 mg/ml ; 0.00547 mol/l
Class :	Soluble
Log S (Ali) :	-2.01
Solubility :	1.81 mg/ml ; 0.00981 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.02
Solubility :	0.174 mg/ml ; 0.000944 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.73

Safety of [ 18959-30-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 18959-30-3 ]

* 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.

Upstream synthesis route of [ 18959-30-3 ]
Downstream synthetic route of [ 18959-30-3 ]

[ 18959-30-3 ] Synthesis Path-Upstream 1~6

1
[ 942-06-3 ]
[ 18959-30-3 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3045 - 3049[2] Angew. Chem., 2017, vol. 129, p. 3091 - 3095,5
[3] Synthetic Communications, 1992, vol. 22, # 21, p. 3067 - 3074

2
[ 56962-08-4 ]
[ 18959-30-3 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 11, p. 3045 - 3049[2] Angew. Chem., 2017, vol. 129, p. 3091 - 3095,5

3
[ 18959-30-3 ]
[ 64695-84-7 ]

Reference： [1] Synthetic Communications, 1992, vol. 22, # 21, p. 3067 - 3074
[2] Synthetic Communications, 1992, vol. 22, # 21, p. 3067 - 3074

4
[ 18959-30-3 ]
[ 455-86-7 ]

Reference： [1] Patent: US4937377, 1990, A,

5
[ 18959-30-3 ]
[ 83506-93-8 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide; hydroxylamine hydrochloride In water	(b) One step reactions: Sodium hydroxide (7.5 g, 0.19 mol) and hydroxylamine hydrochloride (5.4 g, 0.0781 mol) were combined in 100 mL of water. 4,5-difluorophthalic anhydride (11.5 g, 0.062 mol) was added, and the reaction was heated to 90°-100° C. for 0.5 hour. The reaction was cooled, and acidified with HCl to a pH between 4 and 5. The precipitate was collected and dried to yield 10.2 g (91percent) of 4,5-difluoroanthranilic acid.

Reference： [1] Synthetic Communications, 1992, vol. 22, # 21, p. 3067 - 3074
[2] Patent: US4954639, 1990, A,
[3] Patent: US4954639, 1990, A,

6
[ 18959-30-3 ]
[ 83506-93-8 ]

Reference： [1] Patent: US4343951, 1982, A,

[ 18959-30-3 ] Synthesis Path-Downstream 1~9

1
[ 18959-30-3 ]
[ 64695-84-7 ]

Reference： [1]Synthetic Communications,1992,vol. 22,p. 3067 - 3074
[2]Synthetic Communications,1992,vol. 22,p. 3067 - 3074

2
[ 18959-30-3 ]
[ 83506-93-8 ]

Yield	Reaction Conditions	Operation in experiment
10.2 g (91%)	With sodium hydroxide; hydroxylamine hydrochloride; In water;	(b) One step reactions: Sodium hydroxide (7.5 g, 0.19 mol) and hydroxylamine hydrochloride (5.4 g, 0.0781 mol) were combined in 100 mL of water. 4,5-difluorophthalic anhydride (11.5 g, 0.062 mol) was added, and the reaction was heated to 90-100 C. for 0.5 hour. The reaction was cooled, and acidified with HCl to a pH between 4 and 5. The precipitate was collected and dried to yield 10.2 g (91%) of 4,5-difluoroanthranilic acid.
	With sodium hydroxide; sulfuric acid; hydroxylamine hydrochloride; hydroxylamine sulfate; In water;	Sodium hydroxide (65 g, 1.63 mol) and hydroxylamine hydrochloride (47.2 g, 0.679 mol) were combined in 500 mL of water. 4,5-difluorophthalic anhydride (100 g., 0.543 mol) was added, and the reaction was heated to 90-100 C. for 0.5 hour. The reaction was cooled, and acidified with HCl to pH 7. Glacial acetic acid, which has a pH between 4 and 5, was added (70 mL) to fully precipitate the product. Isolation as usual led to 51.09 g (54%) of DFAA. Sodium hydroxide (6.5 g, 0.163 mol) and hydroxylamine sulfate (4.9 g, 0.029 mol) were combined in 40 mL of water. 4,5-difluorophthalic anhydride (10 g, 0.0543 mol) was added, and the reaction was heated to reflux for 0.5 hour. The reaction was cooled and acidified to a pH between 4 and 5 with a 50% sulfuric acid solution. Isolation led to 6.67 g (71%) of 4,5-difluoroanthranilic acid.

Reference： [1]Synthetic Communications,1992,vol. 22,p. 3067 - 3074
[2]Patent: US4954639,1990,A
[3]Patent: US4954639,1990,A

3
[ 18959-30-3 ]
[ 878207-28-4 ]

Reference： [1]Synthetic Communications,1992,vol. 22,p. 3067 - 3074

4
[ 18959-30-3 ]
[ 2751-90-8 ]
dioxydiphthalic anhydride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.7%	With potassium fluoride; In sulfolane; water; acetone;	EXAMPLE 2 Preparation of Dioxydiphthalic Anhydride 4,5-Difluorophthalic anhydride (18.4 grams, 0.1 mole) was dissolved in 40 grams of anhydrous sulfolane and heated to 165 c. with stirring. <strong>[2751-90-8]Tetraphenylphosphonium bromide</strong> (0.184 grams, 0.0004 mole) and 1.8 grams (0.10 mole) of water were added and the temperature increased to 200 C. Anhydrous potassium fluoride (23.3 grams, 0.4 mole) was added with stirring. The reaction mixture was held at about 200 C. with stirring for about 3 1/2 hours at which time another 0.2 grams of water was added and the reaction mixture was maintained at temperature for an additional hour. The reaction mixture was cooled to less than 150 C. and 35 grams of acetone added and the solids filtered off. The solids were washed with acetone followed by three 100 ml washes with distilled water. The solid material was dried at 150 C. for 16 hours to yield 15.5 grams (95.7% yield) of dioxydiphthalic anhydride.
95.7%	With potassium fluoride; In sulfolane; water; acetone;	EXAMPLE 2 Preparation of Dioxydiphthalic Anhydride 4,5-Difluorophthalic anhydride (18.4 grams, 0.1 mole) was dissolved in 40 grams of anhydrous sulfolane and heated to 165 C. with stirring. <strong>[2751-90-8]Tetraphenylphosphonium bromide</strong> (0.184 grams, 0.0004 mole) and 1.8 grams (0.10 mole) of water were added and the temperature increased to 200 C. Anhydrous potassium fluoride (23.3 grams, 0.4 mole) was added with stirring. The reaction mixture was held at about 200 C. with stirring for about 31/2 hours at which time another 0.2 grams of water was added and the reaction mixture was maintained at temperature for an additional hour. The reaction mixture was cooled to less than 150 C. and 35 grams of acetone added and the solids filtered off. The solids were washed with acetone followed by three 100 ml washes with distilled water. The solid material was dried at 150 C. for 16 hours to yield 15.5 grams (95.7% yield) of dioxydiphthalic anhydride.
95.7%	With potassium fluoride; In sulfolane; water; acetone;	EXAMPLE 7 Preparation of Dioxydiphthalic Anhydride 4,5-Difluorophthalic anhydride (18.4 grams, 0.1 mole) was dissolved in 40 grams of anhydrous sulfolane and heated to 165 C. with stirring. <strong>[2751-90-8]Tetraphenylphosphonium bromide</strong> (0.184 grams, 0.0004 mole) and 1.8 grams (0.10 mole) of water were added and the temperature increased to 200 C. Anhydrous potassium fluoride (23.3 grams, 0.4 mole) was added with stirring. The reaction mixture was held at about 200 C. with stirring for about 31/2 hours at which time another 0.2 grams of water was added and the reaction mixture was maintained at temperature for an additional hour. The reaction mixture was cooled to less than 150 C. and 35 grams of acetone added and the solids filtered off. The solids were washed with acetone followed by three 100 ml washes with distilled water. The solid material was dried at 150 C. for 16 hours to yield 15.5 grams (95.7% yield) of dioxydiphthalic anhydride.

Reference： [1]Patent: US5185451,1993,A
[2]Patent: US4943642,1990,A
[3]Patent: US5003031,1991,A

5
aqueous sodium hypochlorite [ No CAS ]
[ 18959-30-3 ]
[ 83506-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In sodium hydroxide; 1,2-dimethoxyethane;	(A) Dimethoxyethane (43 parts) was charged to a reactor and ammonia was bubbled in to form a saturated solution. The ammonia addition was maintained while a solution of 1.84 parts of 4,5-difluorophthalic anhydride in 13 parts of dimethoxyethane was added slowly over a period of 0.5 hours. The reaction mixture was stirred for an additional 5 minute period and the dimethoxyethane was removed by vacuum distillation. The remaining white solid (the ammonium salt of 4,5-difluorophthalamic acid) was dissolved in 20 parts of aqueous sodium hydroxide (40% NaOH) and the solution was de-gassed under moderately reduced pressure to remove any remaining ammonia; then heated at atmospheric pressure, to 50 C. and maintained at tha temperature while 14.1 parts of a 5.78% aqueous sodium hypochlorite solution was added. The solution was then heated to 60-65 C. and maintained at that temperature, with stirring for about 30 minutes; then cooled to about 20-25 C. and acidified to a pH of 4-6, by addition of concentrated hydrochloric acid. A precipitate formed and the mixture was extracted with chloroform. The acidification procedure was repeated until no additional precipitate formed. The combined extracts were dried over anhydrous sodium sulfate, filtered, and the chloroform removed by vacuum distillation to yield 1.34 parts of solid 4,5-difluoroanthranilic acid having a melting point of 180-181 C. The chemical structure of the product was confirmed by infra-red analysis.

Reference： [1]Patent: US4343951,1982,A

6
[ 18959-30-3 ]
[ 83684-73-5 ]

Yield	Reaction Conditions	Operation in experiment
74.8%	With formamide at 130℃; for 2h;	291A At 130° C., 1.0 g (5.4 mmol) of 4,5-difluorophthalic anhydride was stirred in 6 ml of formamide for 2 h. After cooling, the reaction mixture was then added to ice-cold water. The precipitated yellow solid was filtered off with suction, washed thoroughly with cold water and dried under high vacuum. This gave 744 mg of a white solid (74.8% of theory).LC-MS (method 10): Rt=1.10 min; m/z=182 (M-H)-.1H-NMR (400 MHz, DMSO-d6): δ=11.58 (s, 1H), 8.01 (t, 2H).
	With formamide at 130℃; for 2.5h;	48 5,6-Difluoroisoindoline-1,3-dione: A solution of 5,6-difluoroisobenzofuran-1,3-dione (7.5 g, 41 mmol) in formamide (40 mL) was stirred at 130 °C for 2h. The mixture was poured into ice water and stirred for 30 min. The white precipitate was filtered and dried to give 5,6-difluoroisoindoline-1,3-dione as an off-white solid (7.5 g, 94% yield, m/z: 203 [M+ H+H2O]+ observed). 1H NMR (300 MHz, DMSO-d6) d 1.55 (s, 1H), 8.02-7.95 (m, 2H).

Reference： [1]Current Patent Assignee: BAYER AG - US2011/34450, 2011, A1 Location in patent: Page/Page column 113
[2]Current Patent Assignee: ARBUTUS BIOPHARMA CORP - WO2019/222238, 2019, A2 Location in patent: Page/Page column 96

7
[ 18959-30-3 ]
[ 1192040-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: formamide / 2 h / 130 °C 2: ethanol; sodium tetrahydroborate / 0 - 20 °C 3: trifluoroacetic acid; triethylsilane / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: BAYER AG - US2011/34450, 2011, A1

8
[ 18959-30-3 ]
[ 16882-08-9 ]
tetramethyl 6,7-difluoronaphthalene-1,2,3,4-tetracarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With palladium diacetate; triphenylphosphine; silver carbonate In 1-methyl-pyrrolidin-2-one at 160℃; for 24h;

Reference： [1]Jafarpour, Farnaz; Hazrati, Hamideh; Nouraldinmousa, Sorour [Organic Letters, 2013, vol. 15, # 15, p. 3816 - 3819]

9
[ 18959-30-3 ]
[ 21436-03-3 ]
C₂₂H₁₄F₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With acetic acid; at 120℃; for 4h;	In a 2000-mL round-bottomed flask, 200 g (1.1 mol) of A, 57 g (0.5 mol) of (1S,2S)-1,2-cyclohexanediamine and 1000 mL of glacial acetic acid were successively added and the mixture was heated (heated at 120 C.) for 4 hours under reflux. ,After the reaction system was cooled to room temperature, 500 mL of glacial acetic acid was distilled off, and the remaining reaction system was recrystallized at a low temperature in a 4 C. environment, and the crude product was filtered and recrystallized with a small amount of glacial acetic acid to obtain 167 g of white needle crystals. The white crystals were compound B1 with a yield of 75%.

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 2889 - 2893
Angew. Chem.,2018,vol. 130,p. 2939 - 2943,5
[2]Patent: CN108117506,2018,A .Location in patent: Paragraph 0054; 0056; 0058

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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. 18959-30-3 ] {[proInfo.proName]}

Quality Control of [ 18959-30-3 ]

Related Doc. of [ 18959-30-3 ]

Product Details of [ 18959-30-3 ]

Calculated chemistry of [ 18959-30-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 18959-30-3 ]

Application In Synthesis of [ 18959-30-3 ]

[ 18959-30-3 ] Synthesis Path-Upstream 1~6

[ 18959-30-3 ] Synthesis Path-Downstream 1~9

Related Functional Groups of [ 18959-30-3 ]

Fluorinated Building Blocks

Acid Anhydrides

Esters

Related Parent Nucleus of [ 18959-30-3 ]

Benzofurans

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 18959-30-3 ]

Related Parent Nucleus of
[ 18959-30-3 ]