3,4-Difluorobenzoyl chloride supplier

Name
3,4-Difluorobenzoyl chloride
EINECS 278-570-7
CAS No. 76903-88-3
Article Data26
CAS DataBase
Density 1.42 g/cm³
Solubility
Melting Point 53-54 °C
Formula C₇H₃ClF₂O
Boiling Point 186.2 °C at 760 mmHg
Molecular Weight 176.55
Flash Point 78.3 °C
Transport Information UN 3265 8/PG 2
Appearance clear yellow liquid
Safety 26-36/37/39-45
Risk Codes 34
Molecular Structure
Hazard Symbols C
Synonyms 3,4-Difluorobenzoylchloride;
PSA 17.07000
LogP 2.34380

Synthetic route

: 455-86-7
3,4-Difluorobenzoic acid

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 70 - 80℃; Substitution;	96.3%
With thionyl chloride Heating;	88%
With thionyl chloride In benzene Heating;	81%

: 32137-19-2
1,2-difluoro-4-(trifluoromethyl)benzene

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / conc. sulfuric acid / 2 h / 80 °C 2: thionyl chloride / benzene / 2 h / Heating View Scheme

: 328-84-7
1,2-dichloro-4-(trifluoromethyl)benzene

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: KF / various solvent(s) / 24 h / 265 °C / other temperatures, other solvents 2: 86 percent / conc. sulfuric acid / 2 h / 80 °C 3: thionyl chloride / benzene / 2 h / Heating View Scheme

: 5216-25-1
4-chlorotrichloromethylbenzene

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: chlorosulfuric acid / 1) 120 deg C, 1 h 2) 150 deg C, 2 h 2: 94 percent / SOCl2 / benzene / 8 h / Heating 3: 71 percent / KF, Ph4PBr / acetonitrile / 16 h / Heating 4: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 5: 93 percent / 10percent NaOH / 1 h 6: 81 percent / SOCl2 / benzene / Heating View Scheme

: 2494-79-3
4-chloro-3-(chlorosulfonyl)benzoic acid

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 94 percent / SOCl2 / benzene / 8 h / Heating 2: 71 percent / KF, Ph4PBr / acetonitrile / 16 h / Heating 3: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 4: 93 percent / 10percent NaOH / 1 h 5: 81 percent / SOCl2 / benzene / Heating View Scheme

: 62574-66-7
3-chlorosulfonyl-4-chlorobenzoyl chloride

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / KF, Ph4PBr / acetonitrile / 16 h / Heating 2: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 3: 93 percent / 10percent NaOH / 1 h 4: 81 percent / SOCl2 / benzene / Heating View Scheme

: 127269-25-4
3,4-difluorobenzoyl fluoride

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / 10percent NaOH / 1 h 2: 81 percent / SOCl2 / benzene / Heating View Scheme

: 127986-80-5
4-fluoro-3-(fluorosulfonyl)benzoyl fluoride

: 76903-88-3
3,4-difluorobenzoyl chloride

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 45 percent / KF, PPh4Br / tetrahydrothiophene 1,1-dioxide; toluene / 210 °C / 270 Torr 2: 93 percent / 10percent NaOH / 1 h 3: 81 percent / SOCl2 / benzene / Heating View Scheme

: 1408075-34-2
1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]-piperidin-4-amine

: 76903-88-3
3,4-difluorobenzoyl chloride

: N-{1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)-9H-purin-6-yl]piperidin-4-yl}-3,4-difluorobenzamide

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 3h;	100%

: 41994-51-8
1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride

: 76903-88-3
3,4-difluorobenzoyl chloride

: 1147550-70-6
2-(3,4-difluorobenzoyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Conditions

Conditions	Yield
Stage #1: 1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride; 3,4-difluorobenzoyl chloride With sodium hydroxide In water; acetone for 1h; pH=> 10; Stage #2: Stage #3: With hydrogenchloride In water	98.8%
Stage #1: 1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid ; hydrochloride With sodium hydroxide In acetone at 20℃; Stage #2: 3,4-difluorobenzoyl chloride With sodium hydroxide In acetone at 20℃; pH=> 10; Stage #3: With hydrogenchloride In water pH=5 - 6;	95%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 75-05-8
acetonitrile

: 71682-97-8
3-(3,4-difluorophenyl)-3-oxopropanenitrile

Conditions

Conditions	Yield
Stage #1: acetonitrile With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 3,4-difluorobenzoyl chloride In tetrahydrofuran at 20℃; for 4h;	97%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 109-73-9
N-butylamine

: 387831-85-8
2-(3',4'-difluorophenyl)pyridine

Conditions

Conditions	Yield
With dmap; copper(II) ethylacetoacetate; C26H36NP; silver(I) acetate In propan-1-ol at 60℃; for 12h; Reagent/catalyst;	96.2%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 56-40-6
glycine

: 315707-69-8
2-(3,4-difluorobenzamido)acetic acid

Conditions

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 0 - 20℃;	96%
With hydrogenchloride; sodium hydroxide In water

: trans-4-(4-quinolyloxy)cyclohexylamine

: 76903-88-3
3,4-difluorobenzoyl chloride

: N-[trans-4-(4-quinolyloxy)cyclohexyl]-3,4-difluorobenzamide

Conditions

Conditions	Yield
With pyridine; triethylamine at 0 - 20℃;	96%

: 15401-69-1
berberrubine chloride

: 76903-88-3
3,4-difluorobenzoyl chloride

: 1297302-82-9
9-O-(3,4-diflourobenzoyl)berberrubine chloride

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	94%

: 5680-79-5
glycine ethyl ester hydrochloride

: 76903-88-3
3,4-difluorobenzoyl chloride

: methyl N-(3,4-difluorobenzoyl)glycinate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 18 - 25℃; for 2h; Cooling with ice;	94%

: 870-24-6
2-chloroethanamine hydrochloride

: 76903-88-3
3,4-difluorobenzoyl chloride

: 1082817-08-0
N-(2-chloroethyl)-2-(3,4-difluorophenyl)acid amide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;	93%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 126-81-8
dimedone

: 5,5-dimethyl-3-oxocyclohex-1-en-1-yl 3,4-difluorobenzoate

Conditions

Conditions	Yield
With pyridine In 1,2-dichloro-ethane at 20℃; for 12h; Inert atmosphere;	93%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 2450-71-7
Propargylamine

: 1250231-35-6
3,4-difluoro-N-(prop-2-ynyl)benzamide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	92%
With dmap; triethylamine In dichloromethane at 0 - 20℃;

: 1484-98-6
7-hydroxy-4,6-dimethylcoumarin

: 76903-88-3
3,4-difluorobenzoyl chloride

: 4,6-dimethyl-2-oxo-2H-chromen-7-yl-3,4-difluorobenzoate

Conditions

Conditions	Yield
With potassium carbonate for 0.25h;	92%

: 1121-89-7
piperidine-2,6-dione

: 76903-88-3
3,4-difluorobenzoyl chloride

: 1-(3,4-difluorobenzoyl)piperidine-2,6-dione

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	91.2%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	91%
With dmap; triethylamine In dichloromethane at 0 - 23℃; Inert atmosphere;
With dmap; triethylamine In dichloromethane at 0 - 23℃; Inert atmosphere; Schlenk technique;

: 76903-88-3
3,4-difluorobenzoyl chloride

: 3-chloro-6-hydroxy-4,7-dimethyl-2H-chromen-2-one

: 3-chloro-4,7-dimethyl-2-oxo-2H-chromen-6-yl 3,4-difluorobenzoate

Conditions

Conditions	Yield
With potassium carbonate In neat (no solvent) at 20℃; for 0.25h; Milling;	91%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 223444-29-9
N-(tert-butyl)-3,4-difluorobenzamide

Conditions

Conditions	Yield
	90%

: 109-86-4
2-methoxy-ethanol

: 333-20-0
potassium thioacyanate

: 76903-88-3
3,4-difluorobenzoyl chloride

: O-(2-methoxyethyl)(3,4-difluorobenzoyl)carbamothioate

Conditions

Conditions	Yield
Stage #1: potassium thioacyanate; 3,4-difluorobenzoyl chloride In acetone at 55℃; for 1h; Inert atmosphere; Stage #2: 2-methoxy-ethanol In acetone at 55℃; for 12h;	90%

...Expand

: 247570-24-7
tert-butyl N-[(1s,4s)-4-aminocyclohexyl]carbamate

: 76903-88-3
3,4-difluorobenzoyl chloride

: 771553-05-0
(cis-4-{[1-(3,4-difluoro-phenyl)-methanoyl]-amino}-cyclohexyl)-carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1h;	89%

: 887938-43-4
4-[2-(2-Methyl-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenylamine

: 76903-88-3
3,4-difluorobenzoyl chloride

: 3,4-difluoro-N-[4-[2-(2-methyl-piperidin-1-yl)-ethoxy]-3-(2-methyl-2H-pyrazol-3-yl)-phenyl]-benzamide

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	88.2%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 145782-15-6, 145782-16-7
cis-<2-(1,1'-biphenyl-4-yl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl>methanol

: 3,4-Difluoro-benzoic acid (2R,4R)-2-biphenyl-4-yl-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester

Conditions

Conditions	Yield
With pyridine at 0℃; for 2.5h;	88%

: 1877-77-6
3-aminobenzenemethanol

: 76903-88-3
3,4-difluorobenzoyl chloride

: 879871-58-6
3,4-difluoro-N-(3-hydroxymethyl-phenyl)-benzamide

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane	88%

: 548769-49-9
methyl-phenyl-carbamic acid 5-amino-pyridin-2-yl ester

: 76903-88-3
3,4-difluorobenzoyl chloride

: 812639-58-0
methyl-phenyl-carbamic acid 5-(3,4-difluoro-benzoylamino)-pyridin-2-yl ester

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 20℃; for 1h;	88%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 565460-55-1
methyl {(2R)-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl}acetate

: methyl [(2R)-1-(3,4-difluorobenzoyl)-3-oxo-1,2,3,4-tetrahydroquinoxalin-2-yl]-acetate

Conditions

Conditions	Yield
With 4-pyrrolidin-1-ylpyridine In tetrahydrofuran	88%
With 4-pyrrolidin-1-ylpyridine In tetrahydrofuran	88%

: C19H23N5O3

: 76903-88-3
3,4-difluorobenzoyl chloride

: C26H25F2N5O4

Conditions

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 3h;	88%

: 504-24-5
4-aminopyridine

: 76903-88-3
3,4-difluorobenzoyl chloride

: 3,4-difluoro-N-(pyridin-4-yl)benzamide

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; Inert atmosphere;	88%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 101337-92-2
2-amino-5-chloro-6-fluro[2,1-b][1,3]benzothiazole

: N-(5-chloro-6-fluoro-benzothiazol-2-yl)-3,4-difluoro-benzamide

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane at 50 - 60℃; for 2h;	87.2%

: 1139705-32-0
4-oxazol-2-yl-benzoic acid ethyl ester

: 76903-88-3
3,4-difluorobenzoyl chloride

: 1492786-00-1
ethyl 4-(5-(3,4-difluorobenzoyl)oxazol-2-yl)benzoate

Conditions

Conditions	Yield
Stage #1: 4-oxazol-2-yl-benzoic acid ethyl ester With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: 3,4-difluorobenzoyl chloride With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃; for 1h; Negishi Coupling; Inert atmosphere; Schlenk technique; regioselective reaction;	87%

Yield

Stage #1: 4-oxazol-2-yl-benzoic acid ethyl ester With zinc chloride-2,2,6,6-tetramethylpiperidin-1-ide lithium chloride complex In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; Schlenk technique;
Stage #2: 3,4-difluorobenzoyl chloride With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 25℃; for 1h; Negishi Coupling; Inert atmosphere; Schlenk technique; regioselective reaction;

87%

: 76903-88-3
3,4-difluorobenzoyl chloride

: 238743-29-8
3,4-difluoro-benzaldehyde oxime

: (E)-3,4-di-fluorobenzaldehyde O-3,4-difluorobenzoyloxime

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃;	85%
Stage #1: 3,4-difluorobenzoyl chloride; 3,4-difluoro-benzaldehyde oxime Stage #2: With triethylamine hydrochloride	85%

: 5356-71-8
1,3-diphenyl-1H-pyrazol-5-amine

: 76903-88-3
3,4-difluorobenzoyl chloride

: N-(1,3-diphenyl-1H-pyrazol-5-yl)-3,4-difluorobenzamide

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane	84%
Stage #1: 1,3-diphenyl-1H-pyrazol-5-amine With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Stage #2: 3,4-difluorobenzoyl chloride In dichloromethane at 20℃;

: 76903-88-3
3,4-difluorobenzoyl chloride

: 2,3-difluoro-N-[4-(2-trifluoromethyl-imidazo[1,2-a]pyrid-3-yl)-phenyl]-benzamide

Conditions

Conditions	Yield
Stage #1: 3-(4-nitrophenyl)-2-(trifluoromethyl)imidazo[1,2-a]pyridine With water; tin(ll) chloride In ethanol; dichloromethane Heating / reflux; Stage #2: 3,4-difluorobenzoyl chloride With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h;	84%

3,4-Difluorobenzoyl chloride Chemical Properties

IUPAC Name: 3,4-Difluorobenzoyl chloride
The MF of 3,4-Difluorobenzoyl chloride (76903-88-3) is C₇H₃ClF₂O.

The MW of 3,4-Difluorobenzoyl chloride (76903-88-3) is 176.55.
Synonyms of 3,4-Difluorobenzoyl chloride (76903-88-3): 3,4-Difluorobenzoyl chloride ; Benzoyl chloride, 3,4-difluoro- ; 3,4-Difluorobenzoylchloride
Product Categories: ACIDHALIDE;Miscellaneous;Acid Halides;Carbonyl Compounds
Form: Clear yellow liquid
Index of Refraction: 1.498
EINECS: 278-570-7
Density: 1.42 g/ml
Flash Point: 78.3 °C
Boiling Point: 186.2 °C
Sensitive: Moisture Sensitive
BRN: 4177619

3,4-Difluorobenzoyl chloride Uses

3,4-Difluorobenzoyl chloride (76903-88-3) is used as pharmaceutical intermediates.

3,4-Difluorobenzoyl chloride Production

The condensation of gamma-butyrolactone (I) with phenethyl amine (II) at high temperatures afforded phenethylpyrrolidinone (III). This was alkylated with isobutyl iodide (IV) in the presence of lithium diisopropylamide in cold THF yielding the 3-isobutyl pyrrolidinone (V), and further alkylated with tert-butyl bromoacetate (VI) to give (VII). Subsequent alkylation of (VII) at the alpha-position of carboxylate group with allyl bromide provided (VIII). Ozonolysis of the double bond of (VIII), followed by reductive treatment with NaBH4 produced alcohol (IX), which was coupled with dibenzyl iminodicarboxylate (X) under Mitsunobu conditions giving (XI). The biscarbamate (XI) was deprotected by hydrogenolysis over Pd/C, and the resulting primary amine (XII) was condensed with 3,4-difluorobenzoyl chloride (XIII) to furnish amide (XIV). Then, trifluoroacetic acid-promoted cleavage of the tert-butyl ester of (XIV) provided the corresponding carboxylic acid, which was finally coupled with hydroxylamine by means of EDC and HOBt to afford the target hydroxamic acid.

3,4-Difluorobenzoyl chloride Safety Profile

Safety information of 3,4-Difluorobenzoyl chloride (76903-88-3):
Hazard Codes C
Risk Statements
34 Causes burns
Safety Statements
26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37/39 Wear suitable protective clothing, gloves and eye/face protection
45 In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
RIDADR UN 3265 8/PG 2
WGK Germany 3
Hazard Note Corrosive
HazardClass 8
PackingGroup II

Product Name

3,4-Difluorobenzoyl chloride

Synthetic route

3,4-Difluorobenzoyl chloride Chemical Properties

3,4-Difluorobenzoyl chloride Uses

3,4-Difluorobenzoyl chloride Production

3,4-Difluorobenzoyl chloride Safety Profile

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