(S)-N-BOC-4-Bromophenylalanine Chemical Properties

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 Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29223900

MSDS

• Language:English Provider:ACROS

(S)-N-BOC-4-Bromophenylalanine Usage And Synthesis

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

(S)-N-BOC-4-Bromophenylalanine(62129-39-9)Related Product Information

• L-Alanine
• D-Phenylalanine
• Phenprobamate
• 4-Bromobenzaldehyde
• N-Carbobenzyloxyglycine
• 3-Bromoanisole
• 4'-Bromopropiophenone
• 2-Bromobenzonitrile
• Bromoxynil octanoate
• 2-Bromofluorobenzene
• DL-Phenylalanine
• tert-Butanol
• N-(tert-Butoxycarbonyl)-L-phenylalanine
• L-Phenylalanine
• (R)-N-BOC-2-Bromophenylalanine
• (S)-N-BOC-2-Bromophenylalanine
• (S)-N-BOC-3-Bromophenylalanine, 98% ee, 95%,(S)-N-BOC-3-BROMOPHENYLALANINE
• BOC-(R)-ALPHA-(4-BROMOBENZYL)-PROLINE