6-Chloropyridazine-3-carboxylic acid

Iupac Name：6-chloropyridazine-3-carboxylic acid

Molecular Weight：158.541

Modify Date.: 2022-11-29 07:49

Introduction: 6-Chloropyridazine-3-carboxylic acid is a pyradazine derivative used in the preparation of stearoyl-CoA desaturase inhibitors. 6-Chloropyridazine-3-carboxylic acid Preparation Products And Raw materials Raw materials View more+

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1. Names and Identifiers

1.1 Name: 6-Chloropyridazine-3-carboxylic acid
1.2 Synonyms: 3-Carboxy-6-chloropyridazine 3-Chloropyridazine-6-carb... 3-chloropyridazine-6-carboxylic acid 3-pyridazinecarboxylic acid, 6-chloro- 6-CHLORO-3-CARBOXY-PYRIDAZINE 6-Chloro-3-pyridazinecarboxylic acid 6-Chloropyridazine-3-caSNoxylic acid 6-Chloropyridazine-3-formic acid CML-036 REF DUPL: 3-Chloropyridazine-6-carboxylic acid

1.3 CAS No.: 5096-73-1

1.4 CID: 6415762

1.5 Molecular Formula: C5H3ClN2O2 (isomer)

1.6 Inchi: InChI=1S/C5H3ClN2O2/c6-4-2-1-3(5(9)10)7-8-4/h1-2H,(H,9,10)

1.7 InChkey: HHGZQZULOHYEOH-UHFFFAOYSA-N

1.8 Canonical Smiles: C1=CC(=NN=C1C(=O)O)Cl

1.9 Isomers Smiles: C1=CC(=NN=C1C(=O)O)Cl

2. Properties

2.1 Density: 1.58

2.1 Melting point: 140-150°C

2.1 Boiling point: 429 °C at 760 mmHg

2.1 Refractive index: 1.598

2.1 Flash Point: 213.2 °C

2.1 Precise Quality: 157.98800

2.1 PSA: 63.08000

2.1 logP: 0.82820

2.1 Appearance: White to cream Crystalline Powder

2.2 Chemical Properties: 6-Chloropyridazine-3-carboxylic acid is Brown green powder

2.3 Color/Form: Yellow to Brown Solid

2.4 pKa: 2.68±0.10(Predicted)

3. Use and Manufacturing

3.1 Methods of Manufacturing: Procedure for synthesis of 6-chloropyridazine-3-carboxylic acid (Step-1) To a mixture of ethyl 6-chloropyridazine-3-carboxylate (commercially available) (1.00 g, 5.36 mmol) in THF (10 mL) was added LiOH (0.655 g, 26.8 mmol, 5 equiv.) in water (10 mL). The resulting reaction mixture was stirred at ambient temperature for 45mins. The reaction mixture was poured into 2M hydrochloric acid and extracted with DCM. The organics were combined and evaporated to give product as a white solid (770 mg, 91 percent). LC-MS: (positive ES MH+ 159/161 ).A. A. PREPARATION 2 Potassium dichromate (3.3 g, 11.2 mmol) was added in portions to a solution of 3-Chloro-6-methyl-pyridazine (1.2 g, 9.3 mmol) in [H2SO4] (10 ml). After addition the mixture is stirred at 50 [°C] on. The reaction was pored on ice and the mixture was extracted three times with diethyl ether. The combined organic phases were dried and concentrated to give the title compound (840 mg, 57percent). [LC-MS] [(M++1)] : 159 and 161 (3: 1).To a stirred solution of 3-chloro-6-methylpyridazine (5.0 g, 39.0 mmol) in concentrated H3-Chloro-6-methylpyridazine (3.00 g, 23.3 mmol) was dissolved in concentrated sulfuric acid (23 mL), and potassium dichromate (8.24 g, 28.0 mmol) was added little by little under ice cooling. The mixture was stirred at room temperature for 1.5 hours, and the mixture was further stirred at 50°C for 60 hours. The reaction mixture was slowly poured into ice water, and the mixture was extracted with diethyl ether (x 3). The organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to give the title compound (1.27 g; yield, 34percent) as a white solid. 6-Chloro-pyridazine-3-carboxylic Acid β-Chloro-pyridazine-S-carboxylic acidA mixture of 3-chloro-6-methyl-pyridazine (10.0 g, 77.8 mmol) and KTo an aqueous solution (2 ml) of disodium hydrogen phosphate dodecahydrate (50 mg), were added acetnitrile (3 ml), 6-chloro-3-pyridazinecarboxyaldehyde (0.10 g, 0.70 mmol), 31percent aqueous hydrogen peroxide (0.12 g, 1.1 mmol) and sodium chlorite (0.10 g, 1.1 mmol), and stirred for 3 hours. A suspension of (1) (2.0g, 12.7mmol) and 4-(dimethylamino)pyridine (776mg, 6.3mmol) in THF (50ml_) was treated with di-fe/f-butyl dicarbonate (3.6g, 16.5mmol). It was heated up to 50C for 1 h, then stirred at rt overnight. The reaction mixture was concentrated in vacuo, re-dissolved in EtOAc (20ml_), poured into HCI solution (1 M, 20ml_) and extracted with EtOAc (2 x 20ml_). The combined organics were washed with NaHC03 solution (50ml_) and brine (50ml_), dried over MgS04, filtered and concentrated in vacuo. Purification by silica gel column chromatography with hexane/EtOAc (1 :0-3: 1 ) yielded (2) as a white solid (2.2g, 81 %). (0878) LCMS (ES): Found 237.0 [M+Naf. (0879) 1H NMR (300 MHz, Chloroform-cf), d: 8.08 (d, J= 8.7 Hz, 1 H), 7.63 (d, J=8.9 Hz, 1 H), 1.67 (s, 9H).

3.2 Usage: 6-Chloropyridazine-3-carboxylic acid is a pyradazine derivative used in the preparation of stearoyl-CoA desaturase inhibitors. 6-Chloropyridazine-3-carboxylic acid Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H302

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501

4.1 Safety: Hazard Codes of 6-Chloropyridazine-3-carboxylic acid (CAS NO.5096-73-1): Xi
Hazard Note: Irritant

4.2 Specification: 6-Chloropyridazine-3-carboxylic acid , its cas register number is 5096-73-1. It also can be called 3-Pyridazinecarboxylic acid, 6-chloro- ; 6-Chloro-3-pyridazinecarboxylic acid ; and Acide 6-chloropyridazine-3-carboxylique .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Dermal, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 4

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H312 Harmful in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H332 Harmful if inhaled H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P321 Specific treatment (see ... on this label). P362+P364 Take off contaminated clothing and wash it before reuse. P332+P313 If skin irritation occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

5096-73-1Total: 3 Synthesis Route

1121-79-5 150 Suppliers

5096-73-1 104 Suppliers

Literatures:
XENON PHARMACEUTICALS INC. Patent: US2008/207587 A1, 2008 ; Location in patent: Page/Page column 14 ; US 20080207587 A1
Yield: ~68%

13327-27-0 90 Suppliers

5096-73-1 104 Suppliers

Literatures:
Homer et al. Journal of the Chemical Society, 1948 , p. 2191,2194
Yield: null

37972-69-3 57 Suppliers

5096-73-1 104 Suppliers

Literatures:
XENON PHARMACEUTICALS INC. Patent: US2008/207587 A1, 2008 ; Location in patent: Page/Page column 15 ; US 20080207587 A1
Yield: null

7. Precursor and Product

precursor:

37972-69-3

1121-79-5

13327-27-0

product :

840488-85-9

2164-61-6

146233-32-1

146233-35-4

59772-58-6

146233-34-3

300391-03-1

65202-50-8

8. Computational chemical data

Molecular Weight: 158.541g/mol
Molecular Formula: C₅H₃ClN₂O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 157.9883050
Monoisotopic Mass: 157.9883050
Complexity: 142
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 63.1
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcQBjMAAEAAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHgIICAAACAqBliAwiJAAAgCqASTySASSBAAmBwAYmCGwbtgKJrKBlpGA0QBkyAEI2YaYEQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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