3-Chloro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine

Basic Information

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CAS Number

80102-25-6

Molecular Formula

C14H18ClNO4

Molecular Weight

299.75 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

110 ºC

Boiling Point

452.5℃ at 760 mmHg

Density

1.245

Flash Point

227.5°C

Refractive Index

1.538

SMILES

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

InChI

InChI=1S/C14H18ClNO4/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-/m1/s1

InChIKey

RCZHBTHQISEPPP-LLVKDONJSA-N

LogP

2.860400000000001

Topological Polar Surface Area

75.63 Å²

Hydrogen Bond Donor/Acceptor

2 / 5

Complexity

354

Safety Information

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Hazard Class

Class IRRITANT Class IRRITANT

Synonyms & References

English

(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-chlorophenyl)propanoic acid
(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-phenyl)-propionic acid
Boc-L-phe(3-Cl)-OH
(R)-2-(tert-butoxycarbonylamino)-3-(3-chlorophenyl)propanoic acid
(2R)-3-(3-chlorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
AKOS015836554
DS-15341
Boc-D-3-Chlorophenylalanine
CS-W012137
MFCD00672516
Boc-D-Phe(3-Cl)-OH, >=98.0% (HPLC)
Boc-3-chloro-D-phenylalanine
80102-25-6
Boc-D-phe(3-Cl)-OH
AC-9876
N-(tert-butoxycarbonyl)-3-chloro-D-phenylalanine
N-Boc-3-chloro-D-phenylalanine
DTXSID40427297
M03178
SCHEMBL3553561
(R)-2-((tert-Butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid
AM82745
D-Phenylalanine, 3-chloro-N-[(1,1-dimethylethoxy)carbonyl]-
Boc-D-3-Chlorophe
J-300383
N-(tert-Butoxycarbonyl)-D-3-chlorophenylalanine
RCZHBTHQISEPPP-LLVKDONJSA-N
EN300-3367020
N10792
N-alpha-t-Butyloxycarbonyl-D-3-chlorophenylalanine (Boc-D-Phe(3-Cl)-OH)
N-TERT-BUTOXYCARBONYL-D-3-CHLORO PHENYLALANINE

MDL Number

MFCD00672516

Customs Code

2924299090

FAQ

What are the physical and chemical properties of 3-Chloro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine (CAS: 80102-25-6)?

The compound 3-Chloro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine is a white or off-white crystalline solid with a molecular weight of approximately 292.87 g/mol. It has poor water solubility but is soluble in organic solvents like ethanol and methanol. Chemically, it is relatively stable but can undergo hydrolysis under basic conditions. It may react with nucleophiles due to its carboxylic acid functionality.

How is 3-Chloro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine (CAS: 80102-25-6) typically synthesized?

This compound can be synthesized via a multi-step reaction involving the protection of D-phenylalanine, followed by the installation of a chloro group and subsequent acylation with a 2-methyl-2-propanol derivative. Commonly used catalysts include HOBt and DCC, and the reaction is typically carried out in anhydrous organic solvents like dichloromethane under nitrogen atmosphere. The yield is generally around 70-80%, and the selectivity is high.

What industries use 3-Chloro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine (CAS: 80102-25-6)?

This compound is primarily used in the pharmaceutical industry for its potential in drug synthesis and development. It is also explored for applications in polymer chemistry and as a building block for other synthetic intermediates. Additionally, it may have uses in the production of sensors and semiconductors due to its chemical structure.

What precautions should be taken when handling 3-Chloro-N-{[(2-methyl-2-propanyl)oxy]carbonyl}-D-phenylalanine (CAS: 80102-25-6)?

When handling this compound, it is important to wear appropriate personal protective equipment (PPE), including gloves, goggles, and a lab coat. The compound should be stored in a cool, dry place away from moisture and heat. Spills should be cleaned up using appropriate absorbent materials and disposed of according to local regulations. Always refer to the Safety Data Sheet (SDS) for specific handling and safety information.