Encyclopedia / Pharmaceutical Intermediates / Organic Intermediate

BOC-PHE-ONP

CAS：7535-56-0
MW:386.39848
MF：C20H22N2O6

BOC-PHE-ONP, with the chemical formula C23H27NO7 and CAS registry number 7535-56-0, is a compound known for its applications in peptide synthesis. This compound, also referred to as tert-butyloxycarbonyl-L-phenylalanyl-ortho-nitrophenyl ester, is characterized by its tert-butyloxycarbonyl (BOC) protecting group and ortho-nitrophenyl (ONP) leaving group. It is commonly used as a reagent in solid-phase peptide synthesis, offering a reliable method for the introduction of the BOC protecting group and subsequent cleavage using acid. BOC-PHE-ONP is widely utilized in the pharmaceutical industry for the synthesis of various peptides and peptidomimetics, playing a crucial role in drug discovery and development.

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Names and ldentifier
Properties
Use and Manufacturing
Msds
Other Information
Computational chemical data
Realated Product Infomation

1. Names and Identifiers

1.1 Name: BOC-PHE-ONP

1.2 Synonyms: (S)-4-Nitrophenyl2-((tert-butoxycarbonyl)amino)-3-phenylpropanoate; (Tert-Butoxy)Carbonyl Phe-ONp; 4-nitrophenyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoate; 4-NITROPHENYL N-TERT-BUTYLOXYCARBONYL-L-PHENYLALANINATE; Alanine, N-carboxy-3-phenyl-, N-tert-butyl p-nitrophenyl ester; Alanine, N-carboxy-3-phenyl-, N-tert-butyl p-nitrophenyl ester, L-; AmbotzBAA5870; Boc-L-phenylalanine 4-nitrophenyl ester; BOC-L-Phenylalanine p-nitrophenyl ester; BOC-PHENYLALANINE-ONP; Boc-Phe-ONP; EINECS 231-404-7; L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-, 4-nitrophenyl ester; MFCD00042811; N-(tert-Butoxycarbonyl)-L-phenylalanine p-nitrophenyl ester; N-(tert-Butoxycarbonyl)phenylalanine 4-nitrophenyl ester; N-(tert-Butoxycarbonyl)phenylalanine p-nitrophenyl ester; N-(tert-Butyloxycarbonyl)-L-phenylalanine 4-nitrophenyl ester; N-(tert-Butyloxycarbonyl)-L-phenylalanine p-nitrophenyl ester; N-[(1,1-Dimethylethoxy)Carbonyl]-L-Phenylalanine 4-Nitrophenyl Ester; N-t-butoxycarbonyl-L-phenylalanine 4-nitrophenyl ester; N-tert-butoxycarbonyl L-phenylalanine p-nitrophenyl ester; N-TERT-BUTOXYCARBONYL-L-PHENYLALANINE-P-NITROPHENYL ESTER; N-tert-butyloxycarbonyl-L-phenylalanine 4-nitrophenyl ester; N-tert-butyloxycarbonyl-L-phenylalanine p-nitrophenyl ester; tert-butoxycarbonyl-L-phenylalanine p-nitrophenyl ester;

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1.3 CAS No.: 7535-56-0

1.4 CID: 111308

1.5 EINECS: 231-404-7

1.6 Molecular Formula: C20H22N2O6

1.7 Inchi: InChI=1S/C20H22N2O6/c1-20(2,3)28-19(24)21-17(13-14-7-5-4-6-8-14)18(23)27-16-11-9-15(10-12-16)22(25)26/h4-12,17H,13H2,1-3H3,(H,21,24)/t17-/m0/s1

1.8 InChkey: QZIWWFMMLBBICG-KRWDZBQOSA-N

1.9 Canonical Smiles: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1)C(=O)OC2=CC=C(C=C2)[N+](=O)[O-]

1.10 Isomers Smiles: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1)C(=O)OC2=CC=C(C=C2)[N+](=O)[O-]

2. Properties

2.1 Solubility: Insuluble (3.3E-3 g/L) (25 oC),

2.2 Appearance: White Crystalline Powder

2.3 Storage: ?20°C

2.4 Color/Form: White

2.5 StorageTemp: −20°C

3. Use and Manufacturing

3.1 Description

BOC-PHE-ONP, with the chemical formula C27H27NO6P, has the CAS number 7535-56-0. It is a chemical compound that appears as a white to off-white powder. It does not have a distinct odor. The basic structure of BOC-PHE-ONP consists of a phenylalanine residue attached to a p-nitrophenyl ester group through a carbonyl linkage. This compound is sparingly soluble in water. BOC-PHE-ONP is considered to be relatively safe for handling and use, but as with any chemical, precautions should be taken to avoid ingestion, inhalation, and contact with skin or eyes. It is recommended to use appropriate protective equipment when working with BOC-PHE-ONP.

Applicable Fields

Chemical Synthesis: BOC-PHE-ONP is commonly used in chemical synthesis as a reagent or building block. Its purpose in this field involves its ability to react with other compounds to form new chemical entities. The mechanism of action in chemical synthesis depends on the specific reaction being carried out, but BOC-PHE-ONP is often used as a protecting group for amino acids or peptides, allowing selective modification of specific functional groups.

Enzyme Assays: BOC-PHE-ONP is also utilized in enzyme assays to measure enzymatic activity. Its purpose in this field involves its ability to be cleaved by specific enzymes, resulting in the release of p-nitrophenol, which can be quantified spectrophotometrically. The mechanism of action in enzyme assays relies on the specific enzyme-substrate interaction and the subsequent enzymatic cleavage of BOC-PHE-ONP.

Storage

Conditions: Store in a cool and dry place, away from direct sunlight.

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4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

no data available

2.2 GHS label elements, including precautionary statements

Pictogram(s)	no data available
Signal word	no data available
Hazard statement(s)	no data available
Precautionary statement(s)
Prevention	no data available
Response	no data available
Storage	no data available
Disposal	no data available

2.3 Other hazards which do not result in classification

no data available

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5. Synthesis Route

7535-56-0Total: 7 Synthesis Route

100-02-7

7535-56-0 29 Suppliers

1070-19-5 1 Suppliers

7535-56-0 29 Suppliers

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6. Precursor and Product

precursor:

13734-34-4

1070-19-5

75-65-0

2577-90-4

107960-06-5

13303-10-1

16214-37-2

16480-57-2

product:

59481-77-5

13734-34-4

98760-08-8

1238-09-1

165727-45-7

33014-68-5

51987-73-6

19901-50-9

58569-55-4

58822-25-6

61543-56-4

7. Computed Properties

Molecular Weight：386.39848g/mol
Molecular Formula：C₂₀H₂₂N₂O₆
Compound Is Canonicalized：True
Exact Mass：4.2
XLogP3-AA：386.14778643
Monoisotopic Mass：386.14778643
Complexity：540
Rotatable Bond Count：8
Hydrogen Bond Donor Count：1
Hydrogen Bond Acceptor Count：6
Topological Polar Surface Area：110
Heavy Atom Count：：28
Defined Atom Stereocenter Count：1
Undefined Atom Stereocenter Count：0
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceB7OAAAAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgAUAAAADGzBmAQyzoLQRACJAiTSWwCCCAAgIgAoiIGObIsOJjKEsbuPOiDk1hEY6Ae4yKCOAEAAAAAAAAAAgAAAAAAAAAAAAAAAAA==