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2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid

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Name

2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid

EINECS N/A
CAS No. 2544-31-2 Density 1.257 g/cm3
PSA 97.85000 LogP 2.04060
Solubility N/A Melting Point 198-199 °C(Solv: water (7732-18-5))
Formula C11H15NO3S Boiling Point 417.6 °C at 760 mmHg
Molecular Weight 241.311 Flash Point 206.4 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 2544-31-2 (2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid) Hazard Symbols N/A
Synonyms

Alanine,3-[(p-methoxybenzyl)thio]- (7CI);Alanine, 3-[(p-methoxybenzyl)thio]-, L-(8CI);(R)-2-Amino-3-[(4-methoxybenzyl)sulfanyl]propionic acid;S-(4-Methoxybenzyl)-L-cysteine;S-(p-Methoxybenzyl)-L-cysteine;H-Cys(pMeOBzl)-OH;

Article Data 12

2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid Synthetic route

23619-36-5

Z(OMe)-Cys(MBzl)-OH

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
With methanesulfonic acid; 3-methyl-phenol In dichloromethane at 25℃; for 0.5h;100%
Multi-step reaction with 3 steps
1: aq. sodium perborate / ethyl acetate
2: CF3CO2H / diethyl ether
3: HF
View Scheme
52-90-4

L-Cysteine

824-94-2

p-methoxybenzyl chloride

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane 1.) 0 deg C, 1 h; 2.) RT, 30 min;81%
Stage #1: p-methoxybenzyl chloride With hydrogenchloride In diethyl ether; water for 3h;
Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; water at 20℃; for 2h;
64%
With ammonia
52-90-4

L-Cysteine

105-13-5

4-Methoxybenzyl alcohol

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether; water for 3h;
Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; pH=7;
64%
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether
Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water at 0℃; pH=7;
64%
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In diethyl ether; water for 3h;
Stage #2: L-Cysteine With sodium hydroxide In diethyl ether; ethanol; water at 20℃; for 2h;
Stage #3: With hydrogenchloride In diethyl ether; ethanol; water pH=7;
64%
With trifluoroacetic acid In dichloromethane
52-90-4

L-Cysteine

18912-37-3

4-methoxybenzyl hydrazinecarboxylate

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
With trifluoroacetic acid
222404-25-3

(R)-2-(4-Methoxy-phenyl)-thiazolidine-4-carboxylic acid

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
With triethylsilane; trifluoroacetic acid In dichloromethane Ambient temperature;
73243-09-1

(R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
With hydrogen fluoride
73285-37-7

Z(OMe)-Cys(MBzl)(O)-OH

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CF3CO2H / diethyl ether
2: HF
View Scheme
52-89-1

l-cysteine hydrochloride

p-OCH3-C6H4-CH2-X, X=Cl or Br

p-OCH3-C6H4-CH2-X, X=Cl or Br

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

Conditions
ConditionsYield
With sodium hydroxide In ethanol; chloroform; water at 20℃;
2544-31-2

S-(4-methoxybenzyl)-L-cysteine

52-90-4

L-Cysteine

Conditions
ConditionsYield
With trimethylsilyl trifluoromethanesulfonate; methyl-phenyl-thioether In trifluoroacetic acid at 0℃; for 0.5h; Product distribution; New peptide deprotection procedure: hard-soft acid-base concept; the role of soft bases (thioanisole, dimethylsulfide, diphenylsulfide) employed.;100%
With trifluoroacetic acid In dichloromethane at 20℃; Rate constant;
24424-99-5

di-tert-butyl dicarbonate

2544-31-2

S-(4-methoxybenzyl)-L-cysteine

18942-46-6

N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; S-(4-methoxybenzyl)-L-cysteine With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;
Stage #2: With hydrogenchloride In water at 0℃; pH=3;
99%
Stage #1: di-tert-butyl dicarbonate; S-(4-methoxybenzyl)-L-cysteine With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;
Stage #2: With hydrogenchloride In water at 0℃; pH=3;
99%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;99%
With potassium carbonate In tetrahydrofuran; water at 20℃; for 2h;99%
In tetrahydrofuran; water Ambient temperature; pH=8; Yield given;

2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid Specification

The L-Cysteine,S-[(4-methoxyphenyl)methyl]-, with the CAS registry number 2544-31-2, is also known as S-(4-Methoxybenzyl)-L-cysteine and H-Cys(pMeOBzl)-OH. It belongs to the product categories of Pharmaceutical Intermediates; Amino Acids Derivatives; Amino Acids; Cysteine [Cys, C]; Amino Acids and Derivatives. This chemical's molecular formula is C11H15NO3S and molecular weight is 241.31. What's more, its systematic name is called (2R)-2-Ammonio-3-[(4-methoxybenzyl)sulfanyl]propanoate.

Physical properties about L-Cysteine,S-[(4-methoxyphenyl)methyl]- are: (1) ACD/LogP: 2.01; (2) # of Rule of 5 Violations: 0; (3) ACD/LogD (pH 5.5): -0.49; (4) ACD/LogD (pH 7.4): -0.52; (5) ACD/BCF (pH 5.5): 1; (6) ACD/BCF (pH 7.4): 1; (7) ACD/KOC (pH 5.5): 1; (8) ACD/KOC (pH 7.4): 1; (9) #H bond acceptors: 4; (10) #H bond donors: 3; (11) #Freely Rotating Bonds: 7; (12) Polar Surface Area: 71.83 Å2; (13) Index of Refraction: 1.59; (14) Molar Refractivity: 64.8 cm3; (15) Molar Volume: 191.9 cm3; (16) Surface Tension: 53.4 dyne/cm; (17) Density: 1.257 g/cm3; (18) Flash Point: 206.4 °C; (19) Enthalpy of Vaporization: 70.74 kJ/mol; (20) Boiling Point: 417.6 °C at 760 mmHg; (21) Vapour Pressure: 1.01E-07 mmHg at 25 °C.

Preparation of L-Cysteine,S-[(4-methoxyphenyl)methyl]-: this chemical can be prepared by 1-Chloromethyl-4-methoxy-benzene with L-cysteine.



This reaction needs reagent TFA and solvent CH2Cl2 at temperature of 0 °C. The reaction time is 30 min. The yield is 81 %.

Uses of L-Cysteine,S-[(4-methoxyphenyl)methyl]-: it can react with S-(4-Methoxybenzyl)-L-cysteine to give L-Cysteine.



The reaction occurs with reagent CF3CO2H and solvent CH2Cl2 at temperature of 20 °C.

You can still convert the following datas into molecular structure:
(1) SMILES:[O-]C(=O)[C@@H]([NH3+])CSCc1ccc(OC)cc1
(2) InChI: InChI=1/C11H15NO3S/c1-15-9-4-2-8(3-5-9)6-16-7-10(12)11(13)14/h2-5,10H,6-7,12H2,1H3,(H,13,14)/t10-/m0/s1
(3) InChIKey:PQPZSPJVMUCVAQ-JTQLQIEIBO

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