(S)-N-BOC-4-Bromophenylalanine

(S)-N-BOC-4-Bromophenylalanine Property

Melting point:

118 °C

Boiling point:

475.3±40.0 °C(Predicted)

Density 

1.5311 (rough estimate)

refractive index 

1.6500 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

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

form 

Powder

pka

3.83±0.10(Predicted)

color 

Off-white to light brown

optical activity

14.001°(C=0.0025g/mL, MEOH, 20°C, 589nm)

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1

InChIKey

ULNOXUAEIPUJMK-NSHDSACASA-N

SMILES

C(O)(=O)[C@H](CC1=CC=C(Br)C=C1)NC(OC(C)(C)C)=O

CAS DataBase Reference

62129-39-9(CAS DataBase Reference)

Safety

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29223900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P405Store locked up.

P501Dispose of contents/container to..…

(S)-N-BOC-4-Bromophenylalanine Chemical Properties,Usage,Production

Chemical Properties

off-white powder

Uses

N-Boc-4-bromo-L-phenylalanine is used as pharmaceutical intermediate.

reaction suitability

reaction type: Boc solid-phase peptide synthesis

Synthesis

General procedure for the synthesis of (S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid from di-tert-butyl dicarbonate and L-4-bromophenylalanine: To a mixed solution of (S)-2-amino-3-(4-bromophenyl)propionic acid (7.3 g, 30.0 mmol) in methanol (50 mL) and water (50 mL) was slowly added di-tert-butyl dicarbonate ( 6.9 g, 31.5 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the solvent was removed by rotary evaporator. The residue was adjusted to pH=5 with dilute hydrochloric acid and then extracted with ethyl acetate (10 mL x 3). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated to afford (S)-3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid in white solid form (10.0 g, 96.9% yield), which could be used in the subsequent reaction without further purification.

References

[1] Patent: WO2015/32943, 2015, A1. Location in patent: Page/Page column 26
[2] Patent: WO2012/119941, 2012, A1. Location in patent: Page/Page column 112
[3] ACS Catalysis, 2015, vol. 5, # 9, p. 5410 - 5413