434-76-4

Basic information

• Product Name: 2-Amino-6-fluorobenzoic acid
• Synonyms: BUTTPARK 44\01-59;2-AMINO-6-FLUOROBENZOIC ACID;6-FLUOROANTHRANILIC ACID;RARECHEM AL BO 0279;TIMTEC-BB SBB006549;2-fluoro-6-aminobenzoic acid;TRIPHENYLBORANE, 0.25M SOLUTION IN TETRA;2-AMINO-6-FLUOROBENZOIC ACID (6-FLUOROANTHRANILIC ACID)
• CAS NO: 434-76-4
• Molecular Formula: C₇H₆FNO₂
• Molecular Weight: 155.13
• EINECS: -0
• Product Categories: Fluorin-contained Benzoic acid series;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid
• Mol File: 434-76-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 167-169 °C(lit.)
• Boiling Point: 223.67°C (rough estimate)
• Flash Point: 140.5 °C
• Appearance: Yellow to brown/Crystalline Powder
• Density: 1.3021 (estimate)
• Vapor Pressure: 9.12E-05mmHg at 25°C
• Refractive Index: 1.606
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 4.01±0.10(Predicted)
• BRN: 3540926
• CAS DataBase Reference: 2-Amino-6-fluorobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-fluorobenzoic acid(434-76-4)
• EPA Substance Registry System: 2-Amino-6-fluorobenzoic acid(434-76-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 434-76-4(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

Used in the synthesis of a novel benzamide with potent neuroleptic activity. 5- fluoro-2-methyl-3,l-benzoxazin-4-one was obtained from 2-amino-6-fluorobenzoic acid. The condensation of 2-amino-6-fluorobenzoic acid methyl ester and (4-fluorophenyl) acetyl chloride with N,N-dimethylamino-4-pyridine in CH 2 Cl 2 to give 2-fluoro-6-[2-(4-fluoro-phenyl)-acetylamino]-benzoic acid methyl ester in 61% yield. 2 Amino 6 fluorobenzoic acid is another easily ac cessible synthon for construction of monofluorinated heterocycles. Reactions of 2,3,4,6-tetra-O-acetyl-n-D_glucopyranosyl bromide (2) with p-hydroxybenzaldehyde, trifluoromethyl and fluoro substi- tuted aniline and 2-amino-6-fluorobenzoic acid gave lO-(Pformyl- pheny1)-2,3,4,6-tetra-O-acetyl-(3-D-glucopyranoside. 2-Fluoro-6-iodobenzoic acid,a loose white crystal,was synthesized by using 2-amino-6-fluorobenzoic acid as the starting material.

storage

Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.

Synthesis

The synthesis of 2-Amino-6-fluorobenzoic acid is as follows:A 50 ml three-necked flask was charged with 1.85 g (10 mmol) of 6-fluoro-2-nitrobenzoic acid, 25.6 mg (0.2 mmol) of molybdenum dioxide, and 76.8 mg of activated carbon. 30 ml of absolute ethanol was added dropwise 1.25 g (20 mmol) of hydrazine hydrate (80%) at room temperature. After the reaction was completed at room temperature for 7 h, TLC monitoring showed that the reaction was completed, filtered, and the filtrate was concentrated, then ethyl acetate (20 mL) and water (10 ml) were added and extracted. The organic phase was washed with water and concentrated to give 1.5g desired product as a pale yellow solid, yield 96.8%, HPLC purity 99.6%.

InChI:InChI=1/C7H6FNO2/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3H,9H2,(H,10,11)

Upstream product

• 385-02-4 6-fluoro-2-nitrobenzoic acid 
• 1897-52-5 2,6 difluorobenzonitrile 
• 1194-65-6 2,6-dichloro-benzonitrile 
• 77326-36-4 2-amino-6-fluorobenzonitrile 
• 652-39-1 3-fluorophthalic anhydride 

Downstream Products

• 70413-94-4 5-fluoro-2-methyl-4H-benzo[d][1,3]oxazin-4-one 
• 78755-94-9 5-fluoro-2H-benzo[d][1,3]-oxazine-2,4(1H)-dione 
• 888952-61-2 2-amino-6-fluoro-benzoic acid N'-(2-fluoro-phenyl)-hydrazide 
• 371243-68-4 2-Amino-N-(2-chlorophenyl)-6-fluorobenzamide 
• 1379359-98-4 2-amino-6-fluorobenzoyl N-methoxy-methylamide 
• 372-19-0 meta-fluoroaniline 
• 2252-37-1 2-bromo-6-fluorobenzoic acid 
• 870281-85-9 (S)-(1-(5-fluoro-4-carbonyl-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamic acid tert-butyl ester 
• 1116235-99-4 2-({2-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)-6-fluorobenzoic acid 
• 1098336-85-6 5-fluoro-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinazoline-2-thione 
• 192570-51-7 1-[2-deoxy-5-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-5-fluoro-quinazoline-2,4(3H)-dione 
• 192570-56-2 1-[2-deoxy-5-(4,4'-dimethoxytrityl)-α-D-erythro-pentofuranosyl]-5-fluoro-quinazoline-2,4(3H)-dione 

Relevant articles and documents

METHOD AND CATALYST FOR PREPARING ANILINE COMPOUNDS AND USE THEREOF

The present invention provides a method for preparing aniline compounds, and also provides a kind of catalyst and use thereof. This method for synthesizing an aniline compound in the invention includes following steps: use molybdenum oxide and activated carbon as catalyst, hydrazine hydrate as reducing agent, then reduce aromatic nitro compounds to aniline compounds. This method is green and high efficiency, and easy to be applied in industry.

Changes in the activity and selectivity of herbicides by selective fluorine substitution, taking bentranil and classic analogues as examples

The introduction of fluorine atoms into 2-phenyl-4H-3,1-benzoxazin-4-one (bentranil) led to sweeping changes in its herbicidal properties in some cases, and 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one ('fluorobentranil') was found to be the most active compound. It can be prepared from 2-amino-6-fluoro-benzoic acid or by direct halogen exchange of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one. The latter reaction was investigated on a pilot scale, including a high-temperature (350°C) potassium fluoride halogen exchange without solvent. When sulfolane was used as a solvent, a side reaction at 220°C - partial decomposition to a diphenylether - could be prevented by addition of a small amount of a radical scavenger. Other intermediates with a pseudohalogen substitution were obtained by side-chain chlorination of suitable methylsulfanyl benzoic acid precursors and halogen exchange. 'Fluorobentranil' shows good broad-leaf activity and selectivity on rice, cereals and maize. In a second case study, the fluoro-substituted anthranilic acids mentioned above were also found to be appropriate for synthesizing herbicidal sulfonylurea (SU) compounds via Meerwein reaction of their aniline function. Methyl 2-[({[(4-chloro-6-methoxy-2- pyrimidinyl)-amino]carbonyl}amino)sulfonyl]-6-fluorobenzoate is an example of a SU that is compatible with maize, whereas the unsubstituted Classic analogue is not selective.

AN IMPROVED PROCEDURE FOR THE SYNTHESIS OF 3-FLUOROANTHRANILIC ACID

3-Ffluoroanthranilic acid is derived in four steps from 3-nitrophthalic acid in 53percent overall yield.