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10009-20-8 Usage

Chemical Properties

Off-White Solid

Uses

A cysteine conjugate metabolite adduct formation with specific mitochondrial proteins using antibodies raised against halothane metabolite adducts.

Definition

ChEBI: An N6-acyl-L-lysine where the N6-acyl group is trifluoroacetyl.

Check Digit Verification of cas no

The CAS Registry Mumber 10009-20-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,0,0,0 and 9 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 10009-20:
(7*1)+(6*0)+(5*0)+(4*0)+(3*9)+(2*2)+(1*0)=38
38 % 10 = 8
So 10009-20-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H13F3N2O3/c9-8(10,11)7(16)13-4-2-1-3-5(12)6(14)15/h5H,1-4,12H2,(H,13,16)(H,14,15)/t5-/m0/s1

10009-20-8 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (T2815)  Nε-Trifluoroacetyl-L-lysine  >98.0%(T)

  • 10009-20-8

  • 5g

  • 210.00CNY

  • Detail
  • TCI America

  • (T2815)  Nε-Trifluoroacetyl-L-lysine  >98.0%(T)

  • 10009-20-8

  • 25g

  • 680.00CNY

  • Detail
  • Sigma

  • (53604)  Nε-Trifluoroacetyl-L-lysine  ≥96.0% (TLC)

  • 10009-20-8

  • 53604-5G-F

  • 499.59CNY

  • Detail
  • Sigma

  • (53604)  Nε-Trifluoroacetyl-L-lysine  ≥96.0% (TLC)

  • 10009-20-8

  • 53604-25G-F

  • 1,719.90CNY

  • Detail

10009-20-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name N6-trifluoroacetyl-L-lysine

1.2 Other means of identification

Product number -
Other names N6-Trifluoroacetyl-L-lysine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:10009-20-8 SDS

10009-20-8Synthetic route

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Conditions
ConditionsYield
With sodium In ethanol at 5 - 20℃;62%
Stage #1: L-Lysine hydrochloride With ethanol; sodium
Stage #2: ethyl trifluoroacetate, In ethanol at 20℃; Cooling with ice;
Stage #3: With acetic acid In ethanol
62%
Stage #1: L-Lysine hydrochloride With sodium In ethanol for 1h;
Stage #2: ethyl trifluoroacetate, at 5 - 20℃; for 3h;
Stage #3: With acetic acid for 0.166667h;
56%
ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

sodium salt of L-lysine
16079-52-0

sodium salt of L-lysine

A

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

B

Nα,Nε-bis(trifluoroacetyl)-L-lysine
329-53-3

Nα,Nε-bis(trifluoroacetyl)-L-lysine

Conditions
ConditionsYield
In ethanol at 5 - 20℃;A 25%
B 56%
S-ethyl trifluoroacetate
383-64-2

S-ethyl trifluoroacetate

L-Lysine hydrochloride
657-27-2, 10098-89-2

L-Lysine hydrochloride

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Conditions
ConditionsYield
With sodium hydroxide
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

(S)-6-trifluoroacetylamino-2-(tert-butoxycarbonylamino)-hexanoic acid
96561-04-5, 16965-06-3

(S)-6-trifluoroacetylamino-2-(tert-butoxycarbonylamino)-hexanoic acid

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; (S)-6-trifluoroacetylamino-2-aminohexanoic acid With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;
Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide pH=2;
92%
In N,N-dimethyl-formamide at 20℃; for 2h;92%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

N-phenyl-1H-benzo[d][1,2,3]triazole-1-carboxamide
86298-24-0

N-phenyl-1H-benzo[d][1,2,3]triazole-1-carboxamide

C15H18F3N3O4

C15H18F3N3O4

Conditions
ConditionsYield
With triethylamine In water; acetonitrile at 20℃; for 0.5h; chemoselective reaction;92%
phosgene
75-44-5

phosgene

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
In tetrahydrofuran at 20 - 30℃; for 4.33333h; Inert atmosphere;86.5%
In 1,4-dioxane at 45℃; for 2h;70%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

N-(4-(2,5-dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide

N-(4-(2,5-dioxo-4-oxazolidinyl)butyl)-2,2,2-trifluoroacetamide

Conditions
ConditionsYield
In tetrahydrofuran for 0.4h; Reflux; Large scale;81.9%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
With sodium hydroxide In tetrahydrofuran at 50℃; Inert atmosphere;75%
With Pinene In ethyl acetate at 105 - 110℃;
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

trichloromethyl chloroformate
503-38-8

trichloromethyl chloroformate

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Inert atmosphere; Reflux;75%
With sodium hydroxide In tetrahydrofuran for 2h; Inert atmosphere; Reflux;75%
In ethyl acetate at 70℃; for 4h;63%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

triethylamine
121-44-8

triethylamine

mono-4-methoxytrityl chloride
14470-28-1

mono-4-methoxytrityl chloride

C6H15N*C28H29F3N2O4

C6H15N*C28H29F3N2O4

Conditions
ConditionsYield
Stage #1: (S)-6-trifluoroacetylamino-2-aminohexanoic acid With chloro-trimethyl-silane; triethylamine In dichloromethane for 2h; Reflux; Inert atmosphere;
Stage #2: mono-4-methoxytrityl chloride In dichloromethane for 2h; Reflux; Inert atmosphere;
Stage #3: triethylamine In methanol; dichloromethane for 0.5h; Inert atmosphere;
74%
potassium cyanate
590-28-3

potassium cyanate

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-carbamoyl-Nε-trifluoroacetyl-L-lysine

Nα-carbamoyl-Nε-trifluoroacetyl-L-lysine

Conditions
ConditionsYield
In water at 50℃; for 3h; pH=7.5;73.8%
In water at 50℃; pH=8; Kinetics;
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

docosa-10,12-diynedioic acid mono-(2,5-dioxo-pyrrolidin-1-yl) ester
340701-06-6

docosa-10,12-diynedioic acid mono-(2,5-dioxo-pyrrolidin-1-yl) ester

21-[(S)-1-Carboxy-5-(2,2,2-trifluoro-acetylamino)-pentylcarbamoyl]-henicosa-10,12-diynoic acid

21-[(S)-1-Carboxy-5-(2,2,2-trifluoro-acetylamino)-pentylcarbamoyl]-henicosa-10,12-diynoic acid

Conditions
ConditionsYield
With potassium hydroxide In tetrahydrofuran at 20℃; for 24h; pH=9;62%
methanol
67-56-1

methanol

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

methyl 2-bromo-6-(2,2,2-trifluoroacetamido)hexanoate

methyl 2-bromo-6-(2,2,2-trifluoroacetamido)hexanoate

Conditions
ConditionsYield
Stage #1: (S)-6-trifluoroacetylamino-2-aminohexanoic acid With sulfuric acid; hydrogen bromide; sodium bromide; sodium nitrite In water at 3 - 20℃; Inert atmosphere;
Stage #2: methanol With toluene-4-sulfonic acid at 65℃; Inert atmosphere;
62%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

C16H22F6N4O4
366001-61-8

C16H22F6N4O4

Conditions
ConditionsYield
phosphorus pentoxide In 1-methyl-pyrrolidin-2-one at 170℃; Product distribution / selectivity;59%
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

(2S)-2-{[(benzyloxy)carbonyl]amino}-6-[(trifluoroacetyl)amino]hexanoic acid
14905-30-7

(2S)-2-{[(benzyloxy)carbonyl]amino}-6-[(trifluoroacetyl)amino]hexanoic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate
phosgene
75-44-5

phosgene

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

A

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

B

C9H11Cl2F3N2O3
112139-30-7

C9H11Cl2F3N2O3

Conditions
ConditionsYield
In tetrahydrofuran; N,N-dimethyl-formamide at 30℃; for 2.5h; Title compound not separated from byproducts;
phosgene
75-44-5

phosgene

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

C9H12ClF3N2O4
112139-31-8

C9H12ClF3N2O4

Conditions
ConditionsYield
In tetrahydrofuran at 30℃; for 2.5h;
chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

C11H21F3N2O3Si
110579-79-8

C11H21F3N2O3Si

Conditions
ConditionsYield
In chloroform; acetonitrile for 2h; Heating;
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

N,O-Bis(trimethylsilyl)acetamide
10416-59-8, 132255-83-5

N,O-Bis(trimethylsilyl)acetamide

C14H29F3N2O3Si2

C14H29F3N2O3Si2

Conditions
ConditionsYield
In 1,4-dioxane
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

2-nitrobenzenesulfenyl chloride
7669-54-7

2-nitrobenzenesulfenyl chloride

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)lysine
41918-63-2

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)lysine

Conditions
ConditionsYield
With sodium hydroxide In acetone
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

21-((S)-5-Amino-1-carboxy-pentylcarbamoyl)-henicosa-10,12-diynoic acid
736142-36-2

21-((S)-5-Amino-1-carboxy-pentylcarbamoyl)-henicosa-10,12-diynoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 62 percent / aq. KOH / tetrahydrofuran / 24 h / 20 °C / pH 9
2: 46 percent / aq. KOH / tetrahydrofuran; methanol / 12 h / 35 °C / pH 12 - 13
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Boc-Ser-Lys(TFA)-Pro-Met-Gly(OBzl)2

Boc-Ser-Lys(TFA)-Pro-Met-Gly(OBzl)2

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CHCl3; acetonitrile / 2 h / Heating
2: 48 percent / pyridine, triethylamine, pivaloyl chloride / CHCl3; acetonitrile / 1 h / Ambient temperature
3: 53 percent / diphenylphosphorazide, triethylamine / dioxane; dimethylformamide / 7 h, 0 deg C; 40 h, 20 deg C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-tert-butyloxycarbonyl-L-seryl-Nε-trifluoroacetyl-L-lysine
107994-57-0

Nα-tert-butyloxycarbonyl-L-seryl-Nε-trifluoroacetyl-L-lysine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3; acetonitrile / 2 h / Heating
2: 48 percent / pyridine, triethylamine, pivaloyl chloride / CHCl3; acetonitrile / 1 h / Ambient temperature
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysine N-hydroxysuccinimide ester
64851-79-2

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysine N-hydroxysuccinimide ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

N-tert-butoxycarbonyl-L-leucyl-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester
82175-93-7

N-tert-butoxycarbonyl-L-leucyl-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 1.) triethylamine / 1.) dioxane, methylene chloride, 15 min, 2.) 0 - 20 deg C, 7 h
4: HCl / ethyl acetate; diethyl ether / 0.33 h / 20 °C
5: 69.5 percent / triethylamine / dioxane; CH2Cl2 / 16 h / 0 - 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester
82175-92-6

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 1.) triethylamine / 1.) dioxane, methylene chloride, 15 min, 2.) 0 - 20 deg C, 7 h
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester hydrochloride

Nε-(trifluoroacetyl)-L-lysyl-L-leucine methyl ester hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 1.) triethylamine / 1.) dioxane, methylene chloride, 15 min, 2.) 0 - 20 deg C, 7 h
4: HCl / ethyl acetate; diethyl ether / 0.33 h / 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-alanyl-L-alanine methyl ester
82175-94-8

Nα-(o-nitrophenylsulfenyl)-Nε-(trifluoroacetyl)-L-lysyl-L-alanyl-L-alanine methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2N NaOH / acetone
2: dicyclohexylcarbodiimide / dioxane; CH2Cl2 / 7 h / 0 - 20 °C
3: 50.9 percent / triethylamine / dioxane; CH2Cl2 / 16 h / 0 - 20 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride
42267-27-6

Nε-trifluoroacetyl-L-lysine Nα-carboxanhydride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran / 2.5 h / 30 °C
2: 88 percent / tetrahydrofuran / 4 h / 25 °C
View Scheme
(S)-6-trifluoroacetylamino-2-aminohexanoic acid
10009-20-8

(S)-6-trifluoroacetylamino-2-aminohexanoic acid

Nε-(trifluoroacetyl)-L-lysyl-L-proline
103300-89-6

Nε-(trifluoroacetyl)-L-lysyl-L-proline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran; dimethylformamide / 2.5 h / 30 °C
2: 94 percent Chromat. / tetrahydrofuran; H2O / 0.03 h / 0 - 12 °C
View Scheme
Multi-step reaction with 3 steps
1: tetrahydrofuran / 2.5 h / 30 °C
2: 88 percent / tetrahydrofuran / 4 h / 25 °C
3: 94 percent Chromat. / tetrahydrofuran; H2O / 0.03 h / 0 - 12 °C
View Scheme

10009-20-8Relevant articles and documents

N-trifluoroacyl lysine derivatives in the synthesis of L-lysyl-L-glutamic acid

Cherevin,Gulevich,Popova,Zubreichuk,Knizhnikov

, p. 1427 - 1431 (2007)

Conditions were developed for simultaneous preparation of N a-trifluoroacetyl-L-lysine and N α,N a-bis(trifluoroacetyl)-L-lysine at overall conversion of initial lysine monohydrochloride up to 82%. By reaction of dimethyl L-glutamate with N α,N a-bis(trifluoroacetyl)-L-lysyl chloride in the presence of triethylamine or with N α- carboxyanhydride of N a-trifluoroacetyl-L-lysine with subsequent removing protecting groups in the formed dipeptides by treating with water-ethanol solution of sodium hydroxide we obtained L-lysyl-L-glutamic acid. Physicochemical characteristics of samples obtained coincided with characteristics of L-lysyl-L-glutamic acid described in the literature thus suggesting that no racemization occurred either at the stage of peptide bond formation or at deprotection.

THERAPIES FOR CANCER USING ISOTOPICALLY SUBSTITUTED LYSINE

-

Page/Page column 7, (2009/10/22)

Methods of treatment and substances for treatment of cancer may use or cause the creation of isotopically modified lysine at levels that do not occur naturally.

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