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

Medical Isotopes, Inc.

Product number: 8474
Product name: 6-Chloro-L-tryptophan
Purity: 98%
Packaging: 100mg
Price: $890
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

Canada 1 China 104 Germany 1 India 2 United Kingdom 1 United States 10 Global 119

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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