| Identification | More | [Name]
2-Chloroisonicotinaldehyde | [CAS]
101066-61-9 | [Synonyms]
2-CHLORO-3-FORMYLPYRIDINE
2-CHLORO-3-PYRIDINECARBOXALDEHYDE
2-CHLORO-4-FORMYLPYRIDINE
2-CHLOROISONICOTINALDEHYDE
2-CHLORONICOTINALDEHYDE
2-CHLORO-PYRIDIN-3-CARBALDEHYDE
2-CHLORO-PYRIDINE-3-CARBALDEHYDE
2-CHLOROPYRIDINE-3-CARBOXALDEHYDE
2-CHLOROPYRIDINE-4-CARBALDEHYDE
2-CHLOROPYRIDINE-4-CARBOXALDEHYDE
BUTTPARK 154\50-03
CHLORO-2-FORMYL-3-PYRIDINE
TIMTEC-BB SBB004156
2-CHLORO-4-PYRIDINECARBOXALDEHYDE
2-Chloronicotinealdehyde
4-Pyridinecarboxaldehyde, 2-chloro-(9CI)
2-Chloropyridine-4-carboxaldehyde 97% | [Molecular Formula]
C6H4ClNO | [MDL Number]
MFCD01315308 | [Molecular Weight]
141.56 | [MOL File]
101066-61-9.mol |
| Chemical Properties | Back Directory | [Appearance]
white to yellow solid | [Melting point ]
46-50 °C | [Boiling point ]
243.4±20.0 °C(Predicted) | [density ]
1.332±0.06 g/cm3(Predicted) | [Fp ]
>230 °C
| [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [form ]
powder to crystal | [pka]
-1.23±0.10(Predicted) | [color ]
White to Almost white | [Sensitive ]
Air Sensitive | [BRN ]
7986625 | [InChI]
InChI=1S/C6H4ClNO/c7-6-3-5(4-9)1-2-8-6/h1-4H | [InChIKey]
UFPOSTQMFOYHJI-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=CC(C=O)=C1 | [CAS DataBase Reference]
101066-61-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36:Irritating to the eyes.
R43:May cause sensitization by skin contact.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37:Wear suitable protective clothing and gloves .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [WGK Germany ]
3
| [Hazard Note ]
Harmful | [HazardClass ]
IRRITANT | [HS Code ]
2933399990 |
| Hazard Information | Back Directory | [Chemical Properties]
white to yellow solid | [Uses]
2-Chloropyridine-4-carboxaldehyde is a reagent used in the chemoenzymic synthesis of α-fluoro β-hydroxy carboxylic esters. It is also a reagent in the combinatorial synthesis of methylene sulfonamides and related compounds as potential kinase inhibitors. | [Synthesis]
The general procedure for the synthesis of 2-chloropyridine-4-carboxaldehyde from 2-chloro-4-hydroxymethylpyridine was as follows: in a 250 mL three-necked flask equipped with a cryogenic thermometer and two constant-pressure dropping funnels, a dichloromethane (15 mL) solution of oxalyl dichloride (1.24 g, 9.81 mmol) was added. The reaction system was cooled to -78 °C under nitrogen protection and stirred. The first constant pressure dropping funnel was connected to the nitrogen line and a dichloromethane (15 mL) solution of 2-chloro-4-hydroxymethylpyridine (0.94 g, 6.54 mmol) was added. A solution of anhydrous dimethyl sulfoxide (1.7 mL, 19.63 mmol) in dichloromethane (2 mL) was added to the other dropping funnel, and the solution was slowly added dropwise (25 min), keeping the reaction temperature between -60°C and -70°C. After the dropwise addition, the reaction system was slowly warmed up to -60 °C over 20 min, and then a dichloromethane solution of 2-chloro-4-hydroxymethylpyridine was added dropwise (50 min), maintaining the temperature between -50 °C and -60 °C. Subsequently, the reaction mixture was warmed to -45 °C over 30 min. The dropping funnel was washed with dichloromethane (2 x 5 mL) and a solution of triethylamine (480 μL, 6.51 mmol) in dichloromethane (4 mL) was added to the reaction mixture (10 min), and finally the mixture in the reaction flask was warmed up to 0 °C within 10 min. The reaction solution was transferred to a 500 mL dispensing funnel and 130 mL of 5% NH4Cl aqueous solution was added. The two phases were separated and the aqueous phase was extracted with dichloromethane (3 x 50 mL). The organic phases were combined, washed with 1 M phosphate buffer (pH=7; 4×100 mL), dried over MgSO4, filtered and concentrated. 2-Chloropyridine-4-carbaldehyde was obtained as an orange solid (0.740 g, 76% yield). Product characterization: mw: 141.57; yield: 76%; orange solid. rf: 0.35 (EtOAc:cyclohexane=30:70). 1H-NMR (CDCl3, δ): 7.65 (dd, 1H, J=5.0 Hz, J=1.3 Hz, ArH), 7.75 (d, 1H, J=1.3 Hz, ArH), 8.66 (d. 1H, J=5.0 Hz, ArH), 10.05 (s, 1H, CHO). | [References]
[1] Patent: WO2008/11478, 2008, A2. Location in patent: Page/Page column 77-78
[2] Patent: US6218537, 2001, B1 |
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