BOC-DL-PHE-OH

BOC-DL-PHE-OH Property

Melting point:

106-108 °C

Boiling point:

426.6±38.0 °C(Predicted)

Density 

1.160±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

3.88±0.10(Predicted)

form 

Solid

color 

White to off-white

CAS DataBase Reference

4530-18-1(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Risk Statements 

43

Safety Statements 

36/37

HS Code 

29224999

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..…

BOC-DL-PHE-OH Chemical Properties,Usage,Production

Uses

2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid is a phenylalanine derivative[1].

Synthesis

General procedure for the synthesis of 2-((tert-butoxycarbonyl)amino)-3-phenylpropionic acid from DL-phenylalanine and di-tert-butyl dicarbonate: DL-phenylalanine (1 g, 6.05 mmol) was suspended in a mixture of dioxane (15 mL) and NaOH (2M aqueous solution; 3.63 mL, 7.26 mmol) at 0 °C. Subsequently, di-tert-butyl dicarbonate (1.546 mL, 6.66 mmol) was added slowly and dropwise to this suspension. The reaction mixture was stirred continuously for 5 hours at room temperature. Upon completion of the reaction, the mixture was concentrated under vacuum to remove the solvent. Water (30 mL) was added to the concentrate and the pH of the mixture was adjusted to 3 by dropwise addition of cold 1.5 N HCl solution.The aqueous layer was extracted with ethyl acetate (3 x 50 mL) and the organic layers were combined and washed with brine solution (2 x 50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to afford the target product 2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.3 g, 4.90 mmol, 81% yield) as a gelatinous liquid. The product was confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (ESI): 1H NMR δ 12.6 (br-s, 1H), 7.32-7.26 (m, 5H), 7.10-6.95 (br-s, 1H), 4.12-4.00 (m, 1H), 3.05-2.92 (m, 1H), 2.87- 2.75 (m, 1H), 1.31 (s, 9H); MS (ESI) m/z 266.2 [M+H]+.

References

[1] Luckose F, et al. Effects of amino acid derivatives on physical, mental, and physiological activities. Crit Rev Food Sci Nutr. 2015;55(13):1793-882. DOI:10.1080/10408398.2012.708368