(S)-N-Boc-2-Bromophenylalanine

Base Information

• Chemical Name: (S)-N-Boc-2-Bromophenylalanine
• CAS No.: 261165-02-0
• Molecular Formula: C₁₄H₁₈BrNO₄
• Molecular Weight: 344.205
• Hs Code.: 29223900
• European Community (EC) Number: 863-147-7
• DSSTox Substance ID: DTXSID30370324
• Wikidata: Q72448760
• Mol file: 261165-02-0.mol

Synonyms:261165-02-0;Boc-L-2-Bromophenylalanine;Boc-2-bromo-L-phenylalanine;BOC-PHE(2-BR)-OH;(S)-N-Boc-2-Bromophenylalanine;(2S)-3-(2-bromophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic Acid;N-Boc-2-bromo-L-phenylalanine;(S)-3-(2-Bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid;Boc-D-2-Bromophenylalanine;L-Phenylalanine, 2-bromo-N-[(1,1-dimethylethoxy)carbonyl]-;MFCD01317709;N-TERT-BUTOXYCARBONYL-L-2-BROMO PHENYLALANINE;SCHEMBL3560344;DTXSID30370324;AKOS015836660;AKOS015890059;AC-9631;AM82702;CS-W009287;DS-16136;A5182;Boc-Phe(2-Br)-OH, >=98.0% (HPLC);EN300-311854;2-Bromo-N-(tert-butoxycarbonyl)-L-phenylalanine;(S)-3-(2-bromophenyl)-2-(tert-butoxycarbonyl)propanoic acid;(2S)-3-(2-bromophenyl)-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;(S)-3-(2-BROMOPHENYL)-2-(TERT-BUTOXYCARBONYLAMINO)PROPANOIC ACID

Chemical Property of (S)-N-Boc-2-Bromophenylalanine

Chemical Property:

• Appearance/Colour: pale yellow crystalline powder
• Vapor Pressure: 1.1E-09mmHg at 25°C
• Melting Point: 142.1 °C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 471.3 °C at 760 mmHg
• PKA: 3.83±0.11(Predicted)
• Flash Point: 238.8 °C
• PSA: 75.63000
• Density: 1.405 g/cm³
• LogP: 3.36040
• Storage Temp.: Store at 0°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 343.04192
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Boc-2-bromo-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=CC=C1Br)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=CC=C1Br)C(=O)O

Technology Process of (S)-N-Boc-2-Bromophenylalanine

There total 1 articles about (S)-N-Boc-2-Bromophenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile (58632-95-4) + 2-amino-3-(2-bromophenyl)propanoic acid (1991-79-3) → 3-(2-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid (261165-02-0)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; at 20 ℃; Inert atmosphere;

DOI:10.1002/cmdc.201600248

Reference yield:

(S)-2-((tert-butoxycarbonyl)amino)-3-(2-bromophenyl)propanoic acid (261165-02-0) → (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate + (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere

2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 3 h / 85 °C / Inert atmosphere

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; sodium hydrogencarbonate; In 1,4-dioxane; N,N-dimethyl-formamide; 2: Miyaura borylation;

DOI:10.1021/jo202105v

Reference yield:

3-(2-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoic acid (261165-02-0) → S-phenethyl 2-amino-3-(2-bromophenyl)propanethioate hydrochloride

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

2: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere

With hydrogenchloride; dmap; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1002/cmdc.201600248

upstream raw materials:

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

2-amino-3-(2-bromophenyl)propanoic acid

Downstream raw materials:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Refernces