6313-54-8

Basic information

• Product Name: 2-Chloro-4-pyridinecarboxylic acid
• Synonyms: 2-CHLORO-4-PYRIDINYL CARBOXYLIC ACID;2-CHLORO-4-PYRIDINECARBOXYLIC ACID;2-CHLOROISONICOTINIC ACID;2-CHLOROPYRIDINE-4-CARBOXYLIC ACID;2-Chloroisonicotinic;2-CHLOROPYRIDINE-4-CARBOXYLICACID(2-CHLOROISO-NICOTINICACID);2-CHLORO-4-PYRIDINECARBOXYLIC ACID / 2-CHLOROISONICOTINIC ACID;2-Chloroisonicotinic acid ,97%
• CAS NO: 6313-54-8
• Molecular Formula: C₆H₄ClNO₂
• Molecular Weight: 157.55
• EINECS: -0
• Product Categories: blocks;Carboxes;Pyridines;Pyridine;pyridine derivative;Acids and Derivatives;Heterocycles;Pyridines, Pyrimidines, Purines and Pteredines;pharmacetical;Carboxylic Acids;Organic acids;Chloropyridines;Halopyridines;Carboxylic Acids;Picolinic acid series;pyridine series
• Mol File: 6313-54-8.mol

Chemical Properties

• Melting Point: 246 °C (dec.)(lit.)
• Boiling Point: 417.7 °C at 760 mmHg
• Flash Point: 206.4 °C
• Appearance: White to beige/Crystalline Powder
• Density: 1.47 g/cm³
• Vapor Pressure: 1.01E-07mmHg at 25°C
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol
• PKA: 3.00±0.10(Predicted)
• BRN: 115861
• CAS DataBase Reference: 2-Chloro-4-pyridinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-4-pyridinecarboxylic acid(6313-54-8)
• EPA Substance Registry System: 2-Chloro-4-pyridinecarboxylic acid(6313-54-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-36/37/39
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 6313-54-8(Hazardous Substances Data)

Usage

Uses

Used in monocomposite films.

InChI:InChI=1/C6H4ClNO2/c7-5-3-4(6(9)10)1-2-8-5/h1-3H,(H,9,10)/p-1

Synthetic route

2-chloro-4-pyridinenitrile (33252-30-1) → 2-chloroisonicotinic acid, (6313-54-8)

Conditions	Yield
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 2.4h; Green chemistry;	92%
With hydrogenchloride

Isonicotinic acid N-oxide (13602-12-5) → 2-chloroisonicotinic acid, (6313-54-8)

Conditions	Yield
With trichlorophosphate for 7h; Heating;	73%

ethyl isonicotinate N-oxide (14906-37-7) → 2-chloroisonicotinic acid, (6313-54-8)

Conditions	Yield
With trichlorophosphate at 130 - 150℃; Erhitzen des Reaktionsprodukts mit wss. KOH;

2,6-dichloropyridine-4-carboxylic acid (5398-44-7) → 2-chloroisonicotinic acid, (6313-54-8)

Conditions	Yield
With hydrazine hydrate Erwaermen des Reaktionsprodukts mit wss. CuSO4;

2.6-dichloro-pyridine-carboxylic acid-(4) → 2-chloroisonicotinic acid, (6313-54-8)

Conditions	Yield
With hydrazine hydrate nachfolgend Kochen des Reaktionsprodukts mit Kupfersulfat-Loesung und mit Alkalilauge;

2-chloroisonicotinic acid, → 2-chloropyridine-4-carbonyl chloride (65287-34-5)

Conditions	Yield
With thionyl chloride at 80℃; for 3h;	100%
With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 2.5h; Product distribution / selectivity; Reflux;	91%
With thionyl chloride for 28h; Reflux;	91%

2-chloroisonicotinic acid, (6313-54-8) + methyl iodide (74-88-4) → methyl 2-chloroisonicotinate (58481-11-1)

Conditions	Yield
Stage #1: 2-chloroisonicotinic acid, With sodium hydride In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 50℃; for 2h;	100%
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 4h;	98%
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20℃; for 20h;	87%

2-chloroisonicotinic acid, (6313-54-8) + 1-(tert-butyloxycarbonyl)-6'-chloro-1',2'-dihydrospiro[piperidine-4,3'-pyrrolo[3,2-b]pyridine] → 6-chloro-4-aza-1-(2-chloropyridin-4-yl)-carbonyl-1'-carboxylic acid tert-butylester spiro-[indoline-3,4'-piperidine]

Conditions	Yield
Stage #1: 2-chloroisonicotinic acid, With thionyl chloride; N,N-dimethyl-formamide In toluene for 2h; Heating / reflux; Stage #2: 1-(tert-butyloxycarbonyl)-6'-chloro-1',2'-dihydrospiro[piperidine-4,3'-pyrrolo[3,2-b]pyridine] With triethylamine In dichloromethane at 0 - 20℃; for 1h; Stage #3: With sodium carbonate In dichloromethane; water	100%

2-chloroisonicotinic acid, (6313-54-8) → (2-chloropyridin-4-yl)methanol (100704-10-7)

Conditions	Yield
Stage #1: 2-chloroisonicotinic acid, With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; Stage #2: With sodium tetrahydroborate In tetrahydrofuran; water at 0℃; for 0.166667h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	99%
Stage #1: 2-chloroisonicotinic acid, With dimethylsulfide borane complex In tetrahydrofuran at 0 - 50℃; for 61h; Stage #2: With water; ammonium chloride In tetrahydrofuran; ethyl acetate at 20℃;	93%
Stage #1: 2-chloroisonicotinic acid, With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at -10 - 20℃; Stage #2: With water In tetrahydrofuran	85.8%

2-chloroisonicotinic acid, (6313-54-8) + 2-furan-2-yl-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (374790-93-9) → 2-(furan-2-yl)isonicotinic acid (1086379-95-4)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; lithium hydroxide In 1,4-dioxane; water at 80℃; for 0.5h; Suzuki-Miyaura cross-coupling; Inert atmosphere;	99%

2-chloroisonicotinic acid, (6313-54-8) → 2-oxo-1,2-dihydropyridine-4-carboxylic acid (22282-72-0)

Conditions	Yield
With water; potassium hydroxide at 0℃; for 36h; Reflux;	99%

Upstream product

• 33252-30-1 2-chloro-4-pyridinenitrile 
• 14906-37-7 ethyl isonicotinate N-oxide 
• 5398-44-7 2,6-dichloropyridine-4-carboxylic acid 
• 13602-12-5 Isonicotinic acid N-oxide 
• 7803-57-8 hydrazine hydrate 
• 2402-95-1 2-chloropyridine-N-oxide 
• 14432-12-3 4-Amino-2-chloropyridine 
• 14432-16-7 2-chloro-4-nitropyridine-N-oxide 
• 58481-11-1 methyl 2-chloroisonicotinate 
• 75-05-8 acetonitrile 

Downstream Products

• 54453-93-9 ethyl 2-chloroisonicotinate 
• 91940-86-2 2-ethoxyisonicotinic acid 
• 100727-33-1 2-benzylmercapto-isonicotinic acid 
• 65287-34-5 2-chloropyridine-4-carbonyl chloride 
• 18616-05-2 mercapto-2 pyridinecarboxylique-4 
• 58481-11-1 methyl 2-chloroisonicotinate 
• 13362-28-2 2-aminoisonicotinic acid 
• 85827-90-3 2-(4-Chloro-phenylamino)-isonicotinic acid 
• 85726-29-0 2-(4-Methoxy-phenylamino)-isonicotinic acid 
• 85726-28-9 2-(3,4-dichlorophenyl)amine-4-pyridinecarboxylic acid 
• 792965-89-0 5-(4'-methoxyphenyl)-2-(2-chloro-4-pyridyl)oxazole 
• 439931-33-6 2-chloro-N-isopropylisonicotinamide 
• 295349-62-1 tert-butyl 2-chloropyridine-4-carboxylate 
• 792965-90-3 {4-[5-(4'-methoxyphenyl)-2-oxazolyl]-2-pyridyl}hydrazine 

Relevant articles and documents

Method for preparing aldehyde and acid by electrochemical dehydrochlorination of polychloromethylpyridine derivatives

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Environmentally benign ionic liquid [bmim]HSO4 was found suitable for conversion of nitriles into carboxylic acids under mild conditions with excellent purity.

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A benzene derivative of the formula (I): STR1 wherein R 1 is hydrogen, C 1-6 -alkyl, C 1-6 -haloalkyl, --NH 2, --NHR 21 ; R 2 is hydroxyl, --OR 22, three- to seven-membered saturated cycloaliphatic amino optionally interrupted by one or more nitrogen, oxygen or sulfur atoms, --NHR 23, --N(R 24) 2, --NH 2 ; R 4 is hydrogen, C 1-6 -alkyl, or --C( O)R 25 ; R 7 is --CO--, --SO 2 --; R 8 is --CO--, single bond; R 12 is --R 11 --R 5 ; R 11 is --N(R 5)--, --NH--, --O--, --N(R 26)--, --N(C( O)R 27)--, --N(C( O)NH 2)--, --N(C( O)NHR 28)--; R 13 is hydrogen, C 1-6 -alkyl, C 1-6 -haloalkyl, --NHC( O)(CH 2) m C 6 H 5, --NHC( O)R 29, --NHC( O)CH(C 6 H 5) 2, --NH 2, --NHR 30, --(CH 2) n C 6 H 5 ; Z is C, CH, N; A is CH, N; R 5 is hydrogen, --CH 2 C 6 H 4 COOH, --CH 2 C 6 H 4 COOR 31, --CH 2 C 6 H 4 OH, --CH 2 C 6 H 4 OR 32, --CH 2 C 6 H 4 NH 2, --CH 2 C 6 H 4 N(R 33) 2, --CH 2 C 6 H 4 -azole, --CH 2 C 6 H 4 NHR 34, --CH 2 C 6 H 4 C 6 H 4 R 14 ; R 14 is azole, --COOH; R 21 to R 34 are independently C 1-6 -alkyl or C 1-6 -haloalkyl; m is 0 to 6; n is 0 to 6; t is 0 or 1, with the proviso that when Z is N, R 5 is hydrogen, --CH 2 C 6 H 4 COOH, --CH 2 C 6 H 4 COOR 31, --CH 2 C 6 H 4 OH, --CH 2 C 6 H 4 OR 32, --CH 2 C 6 H 4 NH 2, --CH 2 C 6 H 4 N(R 33) 2, --CH 2 C 6 H 4 -azole, or --CH 2 C 6 H 4 NHR 34, or a salt thereof, and a pharmaceutical composition comprising said benzene derivative or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier are disclosed.

Synthesis, Chemistry, and Antineoplastic Activity of α-Halopyridinium Salts: Potential Pyridone Prodrugs of Acylated Vinylogous Carbinolamine Tumor Inhibitors

A series of 4- and 5-methyl>-1H-pyrrolizin-5-yl>-2-halopyridinium iodides were synthesized.The rates of hydrolysis of the α-halopyridinium salts to the corresponding pyridones, and the reactivities of the carbamate moieties were studied as a function of pH, buffer composition, and ionic strength.The 4- and 5-pyrrolizinyl-2-halopyridinium iodides and the corresponding pyridones were evaluated against P388 lymphocytic leukemia in vivo.The α-fluoropyridinium compounds were active but the α-chloro compounds were not.This activity was correlated with the rates of hydrolysis of the α-halopyridinium compounds to the active pyridone.Compounds that were active in the P388 screen were evaluated in L1210 leukemia, M5076 carcinoma, and MX-1 mammary xenograft assays in mice.

4-aminomethyl-pyridyl-2-oxy derivatives having anti-ulcer activity

A compound represented by the following formula or a salt thereof STR1 wherein each of R1 and R2 represents a lower alkyl group, or R1 and R2, together with the nitrogen atom to which they are bonded, may form a substituted or unsubstituted, saturated or partially unsaturated 4- to 8-membered heterocyclic group which may contain a hetero atom selected from N, O and S, Y represents a group of the formula --CH2 --CH2 -- or --CH=CH--, and n is 0, 1 or 2. This compound is useful as anti-peptic ulcer agent.

2-halo-pyridines

2-Halo-pyridines of the general formula I STR1 wherein X is Cl or Br; A is =0 or STR2 Ar is phenyl or substituted phenyl of the general formula STR3 in which n is 0, 1, 2 or 3; R is alkyl C1-4, alkoxy C1-4, phenoxy, alkylthio C1-4, halogen especially F and Cl, OH or C6 H5 ; and their salts, addition compounds and precursors (prodrugs). Furthermore the invention is directed to the production of these compounds and pharmaceuticals containing them.