Carbamic acid, (2,6-dichloro-4-pyridinyl)-, 1,1-dimethylethyl ester (9CI)

Carbamic acid, (2,6-dichloro-4-pyridinyl)-, 1,1-dimethylethyl ester (9CI) Property

Boiling point:

309.6±42.0 °C(Predicted)

Density 

1.345

storage temp. 

2-8°C

pka

11.30±0.70(Predicted)

Appearance

White to off-white Solid

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

Carbamic acid, (2,6-dichloro-4-pyridinyl)-, 1,1-dimethylethyl ester (9CI) Chemical Properties,Usage,Production

Synthesis

Step 1. 4-Amino-2,6-dichloropyridine (5.04 g, 30.3 mmol) was dissolved in dichloromethane (DCM, 100 mL) at room temperature, and 4-dimethylaminopyridine (DMAP, 0.61 g, 4.99 mmol) and di-tert-butyl dicarbonate (Boc2O, 13.71 g, 60.9 mmol) were added sequentially. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the organic phase was washed sequentially with saturated aqueous ammonium chloride solution (3 × 30 mL) and brine (40 mL), followed by drying and concentration with anhydrous sodium sulfate. The residue was dissolved in a solvent mixture of tetrahydrofuran (THF, 30 mL) and water (30 mL) and sodium hydroxide (4.5 g, 112 mmol) was added. The reaction mixture was heated at 65 °C for 4 h. After cooling to room temperature, it was extracted with ethyl acetate (EtOAc, 5 × 30 mL). The organic phases were combined and washed sequentially with 1N hydrochloric acid (2 × 30 mL) and water (40 mL), followed by drying and concentration with anhydrous sodium sulfate to give a solid product. The solid was collected by filtration, washed sequentially with 1N hydrochloric acid (4 × 10 mL) and water (20 mL), and finally dried in a vacuum oven at 50 °C to afford N-Boc-4-amino-2,6-dichloropyridine (7.44 g, 93% yield) as a white solid.

References

[1] Patent: WO2015/76800, 2015, A1. Location in patent: Page/Page column 292
[2] Tetrahedron Letters, 2006, vol. 47, # 50, p. 8917 - 8920
[3] Journal of Organic Chemistry, 2008, vol. 73, # 15, p. 6025 - 6028
[4] Patent: WO2016/6974, 2016, A2. Location in patent: Paragraph 516; 517; 518; 519; 520; 521; 522