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

Name
2-Amino-3-[(4-methoxybenzyl)thio]propanoic acid
EINECS
CAS No. 2544-31-2
Article Data12
CAS DataBase
Density 1.257 g/cm³
Solubility
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
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
PSA 97.85000
LogP 2.04060

Synthetic route

: 23619-36-5
Z(OMe)-Cys(MBzl)-OH

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With trifluoroacetic acid

: 222404-25-3
(R)-2-(4-Methoxy-phenyl)-thiazolidine-4-carboxylic acid

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogen fluoride

: 73285-37-7
Z(OMe)-Cys(MBzl)(O)-OH

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide In ethanol; chloroform; water at 20℃;

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 52-90-4
L-Cysteine

Conditions

Conditions	Yield
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

Conditions	Yield
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;

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 56-89-3
L-cystine

Conditions

Conditions	Yield
With Methyltrichlorosilane; 1,1'-sulfinylbisbenzene at 4℃; for 0.166667h;	95%
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h;	86.7%
With methoxybenzene; thallium(III) trifluoroacetate In trifluoroacetic acid at 0℃; for 1h; Product distribution; cleavage various S-protecting groups of cystein;	86.7%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 73243-09-1
(R)-2-Amino-3-(4-methoxy-phenylmethanesulfinyl)-propionic acid

: 56-89-3
L-cystine

Conditions

Conditions	Yield
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h;	92.2%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 503-38-8
trichloromethyl chloroformate

: 4-methoxybenzylcysteine N-carboxy anhydride

Conditions

Conditions	Yield
In tetrahydrofuran at 55℃; for 0.5h; Temperature;	87%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 75893-05-9
H-Cys(Acm)(O)-OH

: 56-89-3
L-cystine

Conditions

Conditions	Yield
With dimethylsulfide In trifluoroacetic acid at 25℃; for 1h;	85.3%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 18942-46-6
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane; water for 3h;	83%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 790244-47-2
N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester

: 1041170-88-0
N-tert-butyloxycarbonyl-α-p-methoxybenzyl-δ-(L-α-aminoadipoyl)-S-p-methoxybenzyl-L-cysteine

Conditions

Conditions	Yield
Stage #1: N-tert-butyloxycarbonyl-L-α-aminoadipic acid α-p-methoxybenzyl ester With triethylamine; isobutyl chloroformate In tetrahydrofuran at -12℃; for 0.5h; Stage #2: S-(4-methoxybenzyl)-L-cysteine With triethylamine In tetrahydrofuran; water at 0 - 20℃; for 1.83333h;	82%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 77-76-9
2,2-dimethoxy-propane

: 71449-22-4
S-<(4-methoxyphenyl)methyl>-L-cysteine methyl ester hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride	79%

: 64-17-5
ethanol

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 156757-43-6
(R)-2-amino-3-(4-methoxy-benzylsulfanyl)propionic acid ethyl ester hydrochloride

Conditions

Conditions	Yield
With acetyl chloride at 50℃; for 12h;	69%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 23931-69-3
(S)-2-(4-Methoxy-benzyloxycarbonylamino)-succinamic acid 4-nitro-phenyl ester

: 96105-49-6
Z(OMe)-Asn-Cys(MBzl)-OH

Conditions

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide for 24h; Ambient temperature;	57%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: azido-Cys(4-MeO-Bzl)

Conditions

Conditions	Yield
With triflic azide; potassium carbonate; copper(II) sulfate In methanol; dichloromethane; water at 20℃;	41%

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: (R)-3-(Adamantane-1-sulfinyl)-2-amino-propionic acid

: 56-89-3
L-cystine

Conditions

Conditions	Yield
With dimethylsulfide; trifluorormethanesulfonic acid In trifluoroacetic acid at 0℃; for 1h;	15.5%

: 1070-19-5
N-(tert-butyloxycarbonyl) azide

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 18942-46-6
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 501-53-1
benzyl chloroformate

: 3081-32-1
Z-Cys(BzlOMe)-OH

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 58635-29-3
N-(4-methoxybenzyloxycarbonyl)-α-(4-methoxybenzylester)-δ-L-α-aminoadipic acid

: 111360-78-2, 131478-88-1
<(N-4-methoxybenzyloxycarbonyl)-(α-4-methoxybenzyl)-δ-(L-α-aminoadipoyl)>-S-(4-methoxybenzyl)-L-cysteine

Conditions

Conditions	Yield
With triethylamine; isobutyl chloroformate 1) THF, -15 deg C, 30 min, 2) H2O, RT, 50 min; Yield given. Multistep reaction;
With triethylamine; isobutyl chloroformate 1) THF; Multistep reaction;

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 58290-08-7
Boc-Lys(Z)-Thr-Phe-Thr-Ser-NHNH2

: 85641-07-2
Boc-Lys(Z)-Thr-Phe-Thr-Ser-Cys(MBzl)-OH

Conditions

Conditions	Yield
With hydrogenchloride; tert.-butylnitrite; triethylamine 1) THF, DMF, 15 min, -15 deg C 2) THF, DMF, 0 deg C, 24 h, room temp.,48 h; Yield given. Multistep reaction;

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 77-76-9
2,2-dimethoxy-propane

: 61314-87-2
S-p-methoxybenzyl-L-cysteine methyl ester

Conditions

Conditions	Yield
With hydrogenchloride; sodium carbonate Multistep reaction;

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 3481-31-0
Z(OMe)-Ser-NHNH2

: 56936-26-6
Z(OMe)-Ser-Cys(CH2PhOMe)-OH

Conditions

Conditions	Yield
(i) isopentyl nitrite, HCl, (ii) /BRN= 2055074/, aq. Et3N; Multistep reaction;

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 7669-54-7
2-nitrobenzenesulfenyl chloride

: (R)-3-(4-Methoxy-benzylsulfanyl)-2-(2-nitro-phenylsulfanylamino)-propionic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 96105-50-9
H-Asn-Cys(MBzl)-OH

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 57 percent / Et3N / dimethylformamide; H2O / 24 h / Ambient temperature 2: TFA-anisole View Scheme

: 2544-31-2
S-(4-methoxybenzyl)-L-cysteine

: 96105-54-3
H-Cys(MBzl)-Asn-Cys(MBzl)-OMe

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 57 percent / Et3N / dimethylformamide; H2O / 24 h / Ambient temperature 2: TFA-anisole 3: 82 percent / Et3N / dimethylformamide / 12 h / Ambient temperature 4: 88 percent / dimethylformamide; diethyl ether 5: TFA-anisole View Scheme

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

Product Name

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

Synthetic route

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

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