(S)-N-Boc-3-Bromophenylalanine

Product Name: (S)-N-Boc-3-Bromophenylalanine
CAS No.: 82278-73-7
Chemical Name: (S)-N-Boc-3-Bromophenylalanine
Synonyms: (S)-3-(3-broMophenyl)-2-((tert-butoxycarbonyl)aMino)propanoic acid;BOC-L-3-BROMOPHE;BOC-PHE(3-BR)-OH;Boc-L-3-Br-Phe-OH;BOC-S-PHE(3-BR)-OH;RRSYY(Avadomide)-4;Lifitegrast Impurity 37;Lifitegrast Impurity 56;BOC-L-3-BROMOPHENYLALANINE;BOC-3-BROMO-L-PHENYLALANINE
CBNumber: CB5200735
Molecular Formula: C14H18BrNO4
Formula Weight: 344.2
MOL File: 82278-73-7.mol

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(S)-N-Boc-3-Bromophenylalanine Property

Melting point:: 106.1°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
pka: 3.81±0.10(Predicted)
form: Solid
color: White to off-white
optical activity: Consistent with structure
Water Solubility: Slightly soluble in water.
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
SMILES: C(O)(=O)[C@H](CC1=CC=CC(Br)=C1)NC(OC(C)(C)C)=O
CAS DataBase Reference: 82278-73-7(CAS DataBase Reference)

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Safety

HazardClass: IRRITANT
HS Code: 2922498590

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

TRC

Product number: B201038
Product name: (S)-N-Boc-3-Bromophenylalanine
Packaging: 50mg
Price: $60
Updated: 2021/12/16

Chem-Impex

Product number: 15104
Product name: Boc-3-bromo-L-phenylalanine
Purity: ≥ 98%
Packaging: 1G
Price: $40
Updated: 2021/12/16

AK Scientific

Product number: Q519
Product name: Boc-L-3-Bromophenylalanine
Packaging: 1g
Price: $44
Updated: 2021/12/16

Matrix Scientific

Product number: 041854
Product name: Boc-3-bromo-L-phenylalanine
Purity: 98%
Packaging: 1g
Price: $47
Updated: 2021/12/16

ChemScene

Product number: CS-W022606
Product name: Boc-Phe(3-Br)-OH
Packaging: 1g
Price: $50
Updated: 2021/12/16

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(S)-N-Boc-3-Bromophenylalanine Chemical Properties,Usage,Production

Chemical Properties

off-white powder

Uses

N-Boc-3-bromo-L-phenylalanine is used as pharmaceutical intermediate.

Synthesis

24424-99-5

82311-69-1

82278-73-7

The general procedure for the synthesis of (S)-3-(3-bromophenyl)-2-((tert-butoxycarbonyl)amino)propionic acid from di-tert-butyl dicarbonate and (S)-2-amino-3-(3-bromophenyl)propionic acid was as follows: first, the reaction was carried out using sodium bicarbonate (3 eq.) and di-tert-butyl dicarbonate (Boc2O, 1.1 eq.) on the (S)-2-amino-3-(3-bromophenyl)propionic acid in a mixed solvent of dioxane and water. -(3-bromophenyl)propionic acid by tert-butoxycarbonyl (Boc) protection reaction to afford the Boc-protected intermediate 7 in 98% yield.Subsequently, the reaction was carried out in dimethylsulfoxide (DMSO) with cuprous iodide (0.4 eq.), cesium carbonate (0.5 eq.), L-proline (0.8 eq.), and sodium salt of methanesulfinic acid (3.9 eq.) as catalysts at 95-100 °C for 9 hours, during which two additional additions of cuprous iodide (0.2 eq.) and L-proline (0.4 eq.) were made, converting the brominated intermediate 7 to the methylsulfoxide-functionalized product 8 in 96% yield. Next, the carboxylic acid group of compound 8 was esterified to a benzyl ester using benzyl alcohol (1.1 eq.), 4-dimethylaminopyridine (DMAP, 0.1 eq.) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC, 1.0 eq.) to give compound 9 in 99% yield. Finally, a Boc deprotection reaction of the amino group was carried out by adding a dioxane solution of 4N HCl to a dichloromethane solution of compound 9 at 0 °C to give the target product 10 in the form of the HCl salt of the free amino group in 94% yield.

References

[1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 3, p. 203 - 206
[2] Patent: WO2014/18748, 2014, A1. Location in patent: Paragraph 00120; 00121; 00122; 00123; 00124; 00125
[3] Catalysis Science and Technology, 2016, vol. 6, # 12, p. 4086 - 4089
[4] Patent: WO2009/102876, 2009, A1. Location in patent: Page/Page column 56

(S)-N-Boc-3-Bromophenylalanine Preparation Products And Raw materials

Raw materials

Preparation Products

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(S)-N-Boc-3-Bromophenylalanine Suppliers

China 157 Europe 2 Germany 3 India 4 Japan 3 United Kingdom 5 United States 24 Global 198

Shanghai Jifeng Biotechnology Co., Ltd.

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View Lastest Price from (S)-N-Boc-3-Bromophenylalanine manufacturers

Career Henan Chemical Co

Product: (S)-N-Boc-3-Bromophenylalanine 82278-73-7
Price: US $100.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: Customized
Release date: 2018-07-30

Career Henan Chemical Co

Product: BOC-3,5-DIIODO-D-TYROSINE 82278-73-7
Price: US $20.00/KG
Min. Order: 10KG
Purity: 99%
Supply Ability: 100kg
Release date: 2018-07-31

82278-73-7, (S)-N-Boc-3-BromophenylalanineRelated Search:

L-Alanine DL-Phenylalanine 3-Bromofluorobenzene Phenprobamate 2-Bromobenzaldehyde Bromoxynil octanoate 1,4-Dibromobenzene 1,2-Dibromobenzene Bromoxynil 4-Bromobenzaldehyde N-(tert-Butoxycarbonyl)-L-phenylalanine D-Phenylalanine EC 2.6.1.2 D-Alanine L-Phenylalanine DI-TERT-BUTYL ETHER 1-Bromo-4-nitrobenzene Boc-(S)-4-Bromophenylalanine

BOC-L-3-BROMOPHE

BOC-L-3-BROMOPHENYLALANINE

BOC-3-BROMO-L-PHENYLALANINE

BOC-S-PHE(3-BR)-OH

BOC-PHE(3-BR)-OH

(S)-3-(3-BROMO-PHENYL)-2-TERT-BUTOXYCARBONYLAMINO-PROPIONIC ACID

(S)-N-BOC-3-BROMOPHENYLALANINE

(S)-N-ALPHA-T-BUTYLOXYCARBONYL-3-BROMO-PHENYLALANINE

N-ALPHA-T-BUTOXYCARBONYL-3-BROMO-L-PHENYLALANINE

N-TERT-BUTOXYCARBONYL-3-BROMOPHENYL-L-ALANINE

3-Bromo-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine

N-TERT-BUTOXYCARBONYL-L-3-BROMO PHENYLALANINE

BOC-L-3-BROMOPHENYLALANINE 98%

(S)-N-BOC-3-Bromophenylalanine, 98% ee, 95%

(S)-N-BOC-3-Bromophenylalanine,95%,98% ee

(S)-N-BOC-3-BromophenylalanineN-tert-Butoxycarbonyl-3-bromophenyl-L-alanine

Boc-L-3-Br-Phe-OH

L-Phenylalanine,3-broMo-N-[(1,1-diMethylethoxy)carbonyl]-

N-Boc-3-broMo-L-phenylalanine, 95%

Boc-L-3-Br-Phe-OH Boc-3-BroMo-L-Phenylalanine

(R)-3-(3-broMophenyl)-2-(tert-butoxycarbonylaMino)propanoic acid

(S)-3-(3-broMophenyl)-2-((tert-butoxycarbonyl)aMino)propanoic acid

(Tert-Butoxy)Carbonyl Phe(3-Br)-OH

(2S)-3-(3-Bromophenyl)-2-(tert-butoxycarbonylamino)propionic acid

N-Boc-3-bromo-L-phenylalanine,95%

(S)-N-Boc-3-Bromophenylalanine USP/EP/BP

N-α-(t-Butoxycarbonyl)-3-bromo-L-phenylalanine

Lifitegrast Impurity 37

RRSYY(Avadomide)-4

(S) -3- (3-bromophenyl) -2- ((Tert-Butyloxycarbonyl ) amino) propionic acid

Lifitegrast Impurity 56

N-Boc-3-bromo-L-phenylalanine

82278-73-7

C14H17BrNO4

Phenylalanine analogs and other aromatic alpha amino acids

Amino Acids