CAS 6548-09-0 5-Bromo-DL-tryptophan (HCID 96735)

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Basic information

CAS: 6548-09-0
Standard SMILES: NC(Cc1c[nH]c2ccc(Br)cc12)C(=O)O
InChIKey: KZDNJQUJBMDHJW-UHFFFAOYSA-N
Molecular formula: C11H11BrN2O2
Average molar mass: 283.12 g/mol
Monoisotopic mass: 282.00038969

Overview

5-bromotryptophan is a non-proteinogenic alpha-amino acid that is tryptophan in which the hydrogen at position 5 on the indole ring is replaced by a bromo group. It is a bromoamino acid, a tryptophan derivative, a bromoindole and a non-proteinogenic alpha-amino acid. It is a tautomer of a 5-bromotryptophan zwitterion.

Names & identifiers

Preferred name: 5-Bromo-DL-tryptophan
IUPAC: 2-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid
English name: 5-Bromo-DL-tryptophan
Molecular formula: C11H11BrN2O2
Molecular weight: 283.12

Names & synonyms

5-Bromo-DL-tryptophan6548-09-02-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid5-BromotryptophanCHEBI:133686DTXSID908639042-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate5-BrTrpRefChem:534143DTXCID30812476229-464-4MFCD00005648

Show more names

H-5-BROMO-DL-TRP-OHTIMTEC-BB SBB003013DL-5-BROMOTRYPTOPHANTryptophan, 5-bromo-5-BROMO-DL-TRYPTOPHAN 99%5-Bromo-DL-tryptophan,99%

5-bromo-tryptophanH-Trp(5-Br)-OH2-amino-3-(5-bromoindol-3-yl)propanoic acidEINECS 229-464-4H-DL-Trp(5-Br)-OHSCHEMBL3077765-Bromo-DL-tryptophan, 99%CHEMBL513050

Database identifiers

CAS: 6548-09-0
PubChem CID: 96735
DTXSID: DTXSID90863904
ChEMBL: CHEMBL513050
ChEBI: CHEBI:133686

Properties

Computed structural properties

XLogP: -0.1
Topological polar surface area: 79.1 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 16
Formal charge: 0
Complexity: 275

Physicochemical properties

Melting point: 264 °C · 264 °C (dec.) (lit.)
Boiling point: 495.8 · 495.8±45.0 °C(Predicted)
Density: 1.704 · 1.704
refractive index: 1.541 · 1.5410 (estimate)
storage temp.: 2 · 2-8°C
pka: 2.21 · 2.21±0.10(Predicted)
form: Fine Crystalline Powder
color: Off-white to light beige
InChI: 1S/C11H11BrN2O2/c12-7-1-2-10-8(4-7)6(5-14-10)3-9(13)11(15)16/h1-2,4-5,9,14H,3,13H2,(H,15,16)
InChIKey: KZDNJQUJBMDHJW-UHFFFAOYSA-N
SMILES: NC(Cc1c[nH]c2ccc(Br)cc12)C(O)=O
CAS DataBase Reference: 6548 · 6548-09-0(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29339980
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H335-H319-H315
Precautionary statements: P264-P280-P302+P352-P321-P332+P313-P362-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Applications

Uses5-Bromo-DL-tryptophan can be useful in the study of genomic determinants in relation to the reactivity and regioselectivity of flavin-dependent halogenases in bacterial genomes and metagenomes.