CHROMAN-4-YLAMINE

CHROMAN-4-YLAMINE Property

Boiling point:

237.4±39.0 °C(Predicted)

Density 

1.106±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

8.87±0.20(Predicted)

form 

liquid

color 

Brown

Safety

Hazard Codes 

Xn

Risk Statements 

22

HS Code 

2932990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P271Use only outdoors or in a well-ventilated area.

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.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

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

P312Call a POISON CENTER or doctor/physician if you feel unwell.

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..…

CHROMAN-4-YLAMINE Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of benzodihydropyran-4-ylamine from 2,3-dihydrochromen-4-one: 2,3-dihydrochromen-4-one (3 g, 20.1 mmol), titanium(IV) isopropoxide (12.0 mL, 40.2 mmol), and an ethanol solution of 2 M ammonia (60.6 mL, 121.2 mmol) were mixed and stirred at room temperature for 6 hours. Subsequently, the reaction mixture was cooled to 0 °C and sodium borohydride (1.14 g, 30.2 mmol) was added in batches over 10 min. The resulting mixture was continued to be stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction was quenched by pouring the mixture into 2 M ammonium hydroxide solution (60 mL), the precipitate formed was filtered out and washed with ethyl acetate (15 mL x 3). The organic layer was separated and the remaining aqueous layer was further extracted with ethyl acetate (15 mL x 2). The organic extracts were combined and washed with 1 M HCl (25 mL). The acidic aqueous layer was washed with ethyl acetate (50 mL), adjusted to pH 10-12 with 2M aqueous sodium hydroxide and extracted with ethyl acetate (40 mL × 3). The organic extracts were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuum to give benzodihydropyran-4-ylamine as an oil (2.61 g, 87% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.31 (d, 1H), 7.23 (m, 1H), 6.94 (m, 1H), 6.82 (d, 1H), 4.38 (m, 2H), 4.12 (m, 1H), 2.19 (m, 2H), 1.82 (m, 2H).

References

[1] Patent: WO2006/81332, 2006, A1. Location in patent: Page/Page column 98
[2] Science, 2017, vol. 358, # 6361, p. 326 - 332
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1981, vol. 20, # 12, p. 1063 - 1067
[4] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5265 - 5270
[5] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1338 - 1341