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764-52-3

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764-52-3 Usage

Definition

ChEBI: An L-alpha-amino acid, methionine, with the S-methyl group trifluoro-substituted.

Check Digit Verification of cas no

The CAS Registry Mumber 764-52-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,6 and 4 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 764-52:
(5*7)+(4*6)+(3*4)+(2*5)+(1*2)=83
83 % 10 = 3
So 764-52-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H8F3NO2S/c6-5(7,8)12-2-1-3(9)4(10)11/h3H,1-2,9H2,(H,10,11)/t3-/m0/s1

764-52-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (2S)-2-amino-4-(trifluoromethylsulfanyl)butanoic acid

1.2 Other means of identification

Product number -
Other names Trifluoromethionine

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:764-52-3 SDS

764-52-3Synthetic route

iodotrifluoromethane
2314-97-8

iodotrifluoromethane

(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

Conditions
ConditionsYield
Stage #1: L-homocystine With ammonia; sodium at -78 - 35℃; Birch Reduction; Inert atmosphere;
Stage #2: iodotrifluoromethane at -78℃; for 0.333333h;
93%
Stage #1: L-homocystine With sodium In ammonia at -78℃; liquid NH3;
Stage #2: iodotrifluoromethane In ammonia at -78℃; for 0.333333h; liquid NH3;
93%
N-acetyltrifluoromethylhomocysteine

N-acetyltrifluoromethylhomocysteine

(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

Conditions
ConditionsYield
With pig liver acylase pH=7.2;26%
(S)-2-amino-N-phenyl-4-(trifluoromethylthio)butanamide hydrochloride
943925-89-1

(S)-2-amino-N-phenyl-4-(trifluoromethylthio)butanamide hydrochloride

A

aniline
62-53-3

aniline

B

(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

Conditions
ConditionsYield
With pyridoxal 5'-phosphate; water at 37℃; for 2h; Enzymatic reaction;
N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide
82911-69-1

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

Fmoc-S-trifluoromethionine

Fmoc-S-trifluoromethionine

Conditions
ConditionsYield
With sodium hydrogencarbonate In water; acetone94%
C25H26N2O2
1445869-56-6

C25H26N2O2

nickel(II) acetate tetrahydrate
6018-89-9

nickel(II) acetate tetrahydrate

(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

C30H30F3N3NiO3S

C30H30F3N3NiO3S

Conditions
ConditionsYield
With potassium carbonate In ethanol at 60 - 70℃;90%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

N-Boc-S-trifluoromethyl-L-homocysteine
201870-90-8

N-Boc-S-trifluoromethyl-L-homocysteine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; water at 0℃;85%
With sodium hydroxide In 1,4-dioxane at 20℃; for 27h; Cooling with ice;39%
(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

For-homoCys(S-CF3)-Leu-Phe-OH
143673-81-8

For-homoCys(S-CF3)-Leu-Phe-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 85 percent / NEt3 / tetrahydrofuran; H2O / 0 °C
2: 55 percent / HOBt, DCC / CH2Cl2; dimethylformamide / 0 deg C, 1 h, 23 deg C, 12 h
3: 2.) N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / 1.) 23 deg C, 3 h, 2.) CHCl3, 23 deg C, 3 h
4: 95 percent / aq. NaOH / dioxane / 0 - 23 °C
View Scheme
(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

(S)-2-[(S)-2-((S)-2-Formylamino-4-trifluoromethylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester
201870-94-2

(S)-2-[(S)-2-((S)-2-Formylamino-4-trifluoromethylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / NEt3 / tetrahydrofuran; H2O / 0 °C
2: 55 percent / HOBt, DCC / CH2Cl2; dimethylformamide / 0 deg C, 1 h, 23 deg C, 12 h
3: 2.) N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline / 1.) 23 deg C, 3 h, 2.) CHCl3, 23 deg C, 3 h
View Scheme
(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-trifluoromethylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester
201870-92-0

(S)-2-[(S)-2-((S)-2-tert-Butoxycarbonylamino-4-trifluoromethylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 85 percent / NEt3 / tetrahydrofuran; H2O / 0 °C
2: 55 percent / HOBt, DCC / CH2Cl2; dimethylformamide / 0 deg C, 1 h, 23 deg C, 12 h
View Scheme
(S)-2-amino-4-(trifluoromethylthio)butanoic
764-52-3

(S)-2-amino-4-(trifluoromethylthio)butanoic

A

2-Oxobutyric acid
600-18-0

2-Oxobutyric acid

B

trifluoromethylsulfide
1493-15-8

trifluoromethylsulfide

Conditions
ConditionsYield
With 5,5'-dithiobis-(2-nitrobenzoic acid); recombinant Entamoeba histolytica L-methionine γ-lyase 2; pyridoxal 5'-phosphate; water at 37℃; pH=7.2; Kinetics; Reagent/catalyst; Time; aq. phosphate buffer; Enzymatic reaction;

764-52-3Relevant articles and documents

Robust synthesis of trifluoromethionine and its derivatives by reductive trifluoromethylation of amino acid disulfides by CF3I/Na/Liq.NH 3 system

Yasui, Hiroyuki,Yamamoto, Takeshi,Tokunaga, Etsuko,Shibata, Norio

, p. 186 - 189 (2011)

We disclose the reductive trifluoromethylation of chemically stable homocystine and cystine to provide corresponding trifluoromethyl ethers by the CF3I/Na/Liq.NH3 system. Both non-protected and protected homocystines can be nicely converted into trifluoromethylated methionines under the same condition. The method described offers a robust synthesis of pharmaceutically important trifluoromethionine, suitable for multigram synthesis. Pentafluoroethylation of homocystine was also achieved by the CF 3CF2I/Na/Liq.NH3 system.

Simple preparation of trifluoromethionine and derivatives thereof

-

Page/Page column 4, (2011/02/18)

Disclosed is a process for the simple preparation of trifluoromethionine, its analogs trifluoromethylcysteine, fluoroalkylhomocysteines, and fluoroalkylcysteines, and derivatives of them. These compounds are drug-candidate compounds or raw materials of drug-candidate compounds. Specifically, trifluoromethionine, trifluoromethylcysteine, a fluoroalkylhomocysteine, or a fluoroalkylcysteine is simply and conveniently prepared directly without passing through homocysteine or cysteine by adding metallic sodium to an optically active or racemic homocystine or cystine in liquid ammonia and further adding a fluoroalkyl iodide thereto under Birch reduction conditions.

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