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6-CHLORO-L-TRYPTOPHAN

Product Name
6-CHLORO-L-TRYPTOPHAN
CAS No.
33468-35-8
Chemical Name
6-CHLORO-L-TRYPTOPHAN
Synonyms
H-6-Cl-Trp-OH;6-Chlo-L-Tryptophan;L-6-CHLOROTRYPTOPHAN;6-CHLORO-L-TRYPTOPHAN;Tryptophan Impurity 14;Tryptophan Impurity 30;6-Chloro-(s)-Tryptophan;6-Chloro-L-tryptophane ;L-Tryptophan, 6-chloro-;6-CHLORO-L-TRYPTOPHAN USP/EP/BP
CBNumber
CB0399395
Molecular Formula
C11H11ClN2O2
Formula Weight
238.67
MOL File
33468-35-8.mol
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6-CHLORO-L-TRYPTOPHAN Property

Melting point:
244-246°C
Boiling point:
476.9±45.0 °C(Predicted)
Density 
1.474±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
Aqueous Acid (Slightly), Methanol (Very Slightly, Heated)
form 
Solid
pka
2.22±0.10(Predicted)
color 
Off-White to Pale Beige
InChI
InChI=1S/C11H11ClN2O2/c12-7-1-2-8-6(3-9(13)11(15)16)5-14-10(8)4-7/h1-2,4-5,9,14H,3,13H2,(H,15,16)/t9-/m0/s1
InChIKey
FICLVQOYKYBXFN-VIFPVBQESA-N
SMILES
C(O)(=O)[C@H](CC1C2=C(C=C(Cl)C=C2)NC=1)N
CAS DataBase Reference
33468-35-8
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Safety

HS Code 
2933998090
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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.

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

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N-Bromosuccinimide Price

TRC
Product number
C423210
Product name
6-ChloroL-Tryptophan
Packaging
10mg
Price
$95
Updated
2021/12/16
Usbiological
Product number
C5034-42
Product name
6-Chloro-L-tryptophan
Packaging
10mg
Price
$355
Updated
2021/12/16
Usbiological
Product number
268109
Product name
6-Chloro L-tryptophan
Packaging
50mg
Price
$446
Updated
2021/12/16
TRC
Product number
C423210
Product name
6-ChloroL-Tryptophan
Packaging
500mg
Price
$755
Updated
2021/12/16
Biosynth Carbosynth
Product number
FC19949
Product name
6-Chloro L-tryptophan
Packaging
25mg
Price
$65
Updated
2021/12/16
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6-CHLORO-L-TRYPTOPHAN Chemical Properties,Usage,Production

Chemical Properties

Colourless Prisms

Uses

The natural enantiomer of Chlorotryptophan.

Definition

ChEBI: 6-chloro-L-tryptophan is a non-proteinogenic L-alpha-amino acid that is L-tryptophan in which the hydrogen at position 6 on the indole ring has been replaced by a chlorine. It is a non-proteinogenic L-alpha-amino acid, a L-tryptophan derivative and an organochlorine compound. It is a tautomer of a 6-chloro-L-tryptophan zwitterion.

Synthesis

50517-10-7

33468-35-8

The general procedure for the synthesis of (S)-2-amino-3-(6-chloro-1H-indol-3-yl)propionic acid from AC-DL-6-chlorotryptophan was as follows: 1. 6-Chloroindole (500 mg, 3.31 mmol, 1 eq.) and L-serine (695 mg, 6.62 mmol, 2 eq.) were dissolved in acetic acid (10 mL) and acetic anhydride (3.1 mL, 33.1 mmol, 10 eq.) was added. The mixture was stirred at 73 °C for 4 hours under argon protection. Upon completion of the reaction, the mixture was concentrated to half the original volume, diluted with water and extracted with ethyl acetate (EtOAc). The organic layers were combined, dried over sodium sulfate and evaporated to give the crude product N-acetyl-6-chloro-D,L-tryptophan (686 mg, 74% yield). 2. N-Acetyl-6-chloro-D,L-tryptophan (686 mg, 1.45 mmol) was dissolved in pH 8.0 phosphate buffer (50 mL) containing 1 mM CoCl2-6H2O. Acylase I (500 mg) was added and stirred at 37 °C for 24 h, during which time the pH was adjusted with LiOH to 8.0. Upon completion of the reaction, the mixture was heated to 60 °C and kept at 60 °C for 5 min, cooled to room temperature and then filtered through diatomaceous earth. The filtrate was acidified with HCl to pH about 3 and extracted with EtOAc. The aqueous layer was lyophilized and used as crude product for the next reaction (estimated yield 43%, based on the theoretical yield of L-enantiomer, 125.4 mg). 3. 6-Chloro-L-tryptophan (125.4 mg, 0.527 mmol, 1 eq.) was dissolved in a water/acetone (1:1, v/v) solvent mixture and NaHCO3 (88.5 mg, 1.05 mmol, 2 eq.) was added. Fmoc-OSu (195.6 mg, 0.58 mmol, 1.1 eq.) was dissolved in acetone and added to the reaction mixture in batches over 3 hours. After completion of the reaction, the acetone was evaporated and the aqueous layer was acidified with acetic acid to pH about 3 and extracted with EtOAc. The organic layers were combined, dried over sodium sulfate and evaporated. The crude product was purified by fast column chromatography (eluent: hexane:EtOAc:AcOH = 10:9:1) to give pure Fmoc-6-chloro-L-tryptophan (237 mg, 98% yield).

References

[1] Patent: WO2015/153761, 2015, A2. Location in patent: Paragraph 00256

6-CHLORO-L-TRYPTOPHAN Preparation Products And Raw materials

Raw materials

Preparation Products

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6-CHLORO-L-TRYPTOPHAN Suppliers

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View Lastest Price from 6-CHLORO-L-TRYPTOPHAN manufacturers

Career Henan Chemical Co
Product
6-CHLORO-L-TRYPTOPHAN 33468-35-8
Price
US $1.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
100KG
Release date
2018-12-22

33468-35-8, 6-CHLORO-L-TRYPTOPHANRelated Search:

(S)-2-AMINO-3-(5-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID H-TRP-GLY-OH (2S)-2-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid 6-broMo-L-tryptophan H-TRP(BOC)-OH (S)-2-AMINO-3-(4-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID (S)-2-AMINO-3-(6-FLUORO-1H-INDOL-3-YL)-PROPIONIC ACID 7-FLUORO-L-TRYPTOPHAN H-TRP-GLY-GLY-OH (S)-2-AMINO-3-(7-METHYL-1H-INDOL-3-YL)-PROPIONIC ACID 5-METHOXY-L-TRYPTOPHAN 7-Methoxy-L-tryptophan 5-CHLORO-L-TRYPTOPHAN 4-CHLORO-L-TRYPTOPHAN 7-CHLORO-L-TRYPTOPHAN L-Tryptophanol 5-CHLORO-DL-TRYPTOPHAN 6-CHLORO-L-TRYPTOPHAN

  • 6-CHLORO-L-TRYPTOPHAN
  • L-6-CHLOROTRYPTOPHAN
  • 6-Chloro-(s)-Tryptophan
  • (2S)-2-amino-3-(6-chloro-1H-indol-3-yl)propanoic acid
  • 6-Chloro-L-tryptophane
  • (S)-2-AMino-3-(6-chloro-1H-indol-3-yl)propanoic acid
  • L-Tryptophan, 6-chloro-
  • -2-Amino-3-(6-chloro-1H-indol-3-yl)
  • H-6-Cl-Trp-OH
  • Tryptophan Impurity 30
  • Tryptophan Impurity 14
  • 6-CHLORO-L-TRYPTOPHAN USP/EP/BP
  • 6-Chlo-L-Tryptophan
  • 33468-35-8
  • Heterocycles
  • Amino Acids 13C, 2H, 15N
  • Amino Acids & Derivatives
  • Chiral Reagents