3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine

Basic Information

View in Editor

CAS Number

82278-73-7

Molecular Formula

C14H18BrNO4

Molecular Weight

344.21 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Agricultural Chemicals Pesticides Herbicides

Basic Physical Properties

Melting Point

106.1°C

Boiling Point

475.3°C at 760 mmHg

Density

1.5311 (rough estimate)

Water Solubility

Slightly soluble in water.

Flash Point

241.2°C

Refractive Index

1.6500 (estimate)

SMILES

View in Editor

CC(C)(C)OC(=O)NC(CC1=CC(=CC=C1)Br)C(=O)O

InChI

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

InChIKey

FBUDYESOPLBQIR-NSHDSACASA-N

LogP

2.969500000000001

Topological Polar Surface Area

75.63 Å²

Hydrogen Bond Donor/Acceptor

2 / 5

Complexity

354

Safety Information

View Safety Information

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H315 Causes skin irritation
Skin corrosion/irritation

H319 Causes serious eye irritation
Serious eye damage/eye irritation

H332 Harmful if inhaled
Acute toxicity, inhalation

H335 May cause respiratory irritation
Specific target organ toxicity, single exposure; Respiratory tract irritation

Hazard Class

Class IRRITANT Class IRRITANT

Synonyms & References

English

MFCD01317710
AC-4516
(S)-3-(3-Bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
Q-101731
N-BOC-3-BROMO-L-PHENYLALANINE
BOC-L-3-BR-PHE-OH
(2S)-3-(3-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid
SCHEMBL1073538
(2S)-3-(3-BROMOPHENYL)-2-(TERT-BUTOXYCARBONYLAMINO)PROPIONIC ACID
Boc-L-3-Bromophenylalanine
L-Phenylalanine, 3-bromo-N-[(1,1-dimethylethoxy)carbonyl]-
CS-W022606
Boc-3-bromo-L-phenylalanine
BCP06282
(S)-2-(tert-Butoxycarbonylamino)-3-(3-bromophenyl)propanoic acid
DTXSID90370325
(S)-3-(3-Bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid
(2S)-2-[(tert-butoxy)carbonylamino]-3-(3-bromophenyl)propanoic acid
(S)-N-Boc-3-Bromophenylalanine
3-Bromo-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine
VYL82Z3H4B
(2S)-3-(3-bromophenyl)-2-[(tert-butoxycarbonyl)amino]propanoic acid
ZB0894
(S)-3-(3-bromophenyl)-2-(tert-butoxycarbonylamino)propanoic acid
GS-2601
(S)-3-(3-Bromophenyl)-2-[(tert-butoxycarbonyl)amino]propionic acid
N-tert-Butoxycarbonyl-L-3-Bromo Phenylalanine
AKOS015969354
(2S)-3-(3-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
BOC-L-3-BROMOPHE
FBUDYESOPLBQIR-NSHDSACASA-N

MDL Number

MFCD01317710

Customs Code

2924299090

FAQ

What are the physical and chemical properties of 3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine (CAS: 82278-73-7)?

3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine is a white to off-white crystalline powder with a molecular weight of approximately 349.1 g/mol. It is sparingly soluble in water and alcohol. Chemically, it is highly reactive towards nucleophiles, making it a useful intermediate in organic synthesis. Reactivity is enhanced by the bromine substituent, which can participate in electrophilic aromatic substitution reactions.

How is 3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine (CAS: 82278-73-7) typically synthesized?

3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine is synthesized by the bromination of N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine using N-bromosuccinimide (NBS) in the presence of a suitable organic solvent like dichloromethane. The reaction is carried out under UV light to enhance the bromination step. Yield and selectivity are key factors in the synthesis, with high purity achieved through recrystallization.

What industries use 3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine (CAS: 82278-73-7)?

3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine is used in the pharmaceutical industry as an intermediate in the synthesis of various drugs. It is also utilized in polymer chemistry for the development of functional polymers and in the production of sensors due to its unique reactivity and functional groups. Its use in semiconductors and electronic materials is less common but is explored for specific applications requiring specific chemical functionalities.

What precautions should be taken when handling 3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine (CAS: 82278-73-7)?

When handling 3-Bromo-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-phenylalanine, it is essential to use appropriate personal protective equipment (PPE) including gloves, goggles, and a lab coat. This compound should be stored in a cool, dry place away from direct sunlight. In case of spills, wash the area with water and dispose of the material according to local regulations. Always refer to the Safety Data Sheet (SDS) for detailed handling instructions and emergency procedures.