l-Penicillamine supplier | CasNO.1113-41-3

Name
L-Penicillamine
EINECS 214-203-9
CAS No. 1113-41-3
Article Data11
CAS DataBase
Density 1.204g/cm³
Solubility
Melting Point 206 ºC (dec.)
Formula C5H11 N O2 S
Boiling Point 251.8°Cat760mmHg
Molecular Weight 149.214
Flash Point 106.1°C
Transport Information
Appearance
Safety A poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic vapors of NO_x and SO_x.
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols
Synonyms Valine,3-mercapto-, L- (8CI); (+)-Penicillamine; (R)-Penicillamine; L-Penicillamine;NSC 241261
PSA 102.12000
LogP 0.80700

Synthetic route

: C5H11NO2S*C4H6O6

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
With triethylamine In ethanol at 20℃;	95.2%

: 884311-05-1
N-formyl-L-penicillamine

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
With hydrogenchloride

: 2510-38-5
N-acetyl-D-penicillamine

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
With hydrogenchloride

: 54536-38-8
S-benzyl-L-penicillamine

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
With ammonia; sodium

: 71-23-8
propan-1-ol

: 58167-41-2
Penicillamine thiyl radical

A: 1113-41-3
L-penicillamine

B: 5723-77-3
1-hydroxy-propyl

Conditions

Conditions	Yield
With perchloric acid In water Rate constant; Ambient temperature;

...Expand

: 64-17-5
ethanol

: 58167-41-2
Penicillamine thiyl radical

A: 2348-46-1
ethanol radical

B: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
With perchloric acid In water Rate constant; Ambient temperature;

...Expand

: 107-21-1
ethylene glycol

: 58167-41-2
Penicillamine thiyl radical

A: 1113-41-3
L-penicillamine

B: 3250-66-6
1,2-dihydroxy-ethyl

Conditions

Conditions	Yield
With perchloric acid In water Rate constant; Ambient temperature;

...Expand

: 67-63-0
isopropyl alcohol

: 58167-41-2
Penicillamine thiyl radical

A: 1113-41-3
L-penicillamine

B: 5131-95-3
2-hydroxy-2-propyl radical

Conditions

Conditions	Yield
With perchloric acid In water Rate constant; Ambient temperature;

...Expand

(-)(R)-2.2.5.5-tetramethyl-3-formyl-thiazolidine-carboxylic acid-(4): (-)(R)-2.2.5.5-tetramethyl-3-formyl-thiazolidine-carboxylic acid-(4)

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
With hydrogenchloride unter CO2;

: 107-10-8
propylamine

heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with l-penicillamine: heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with l-penicillamine

A: 1113-41-3
L-penicillamine

B heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with n-propylamine: heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, complex with n-propylamine

Conditions

Conditions	Yield
In methanol; water Kinetics;

...Expand

: 107-10-8
propylamine

permethylated maltoheptaose, complex with D-penicillamine: permethylated maltoheptaose, complex with D-penicillamine

A: 1113-41-3
L-penicillamine

B permethylated maltoheptaose, complex with n-propylamine: permethylated maltoheptaose, complex with n-propylamine

Conditions

Conditions	Yield
In methanol; water Kinetics;

...Expand

: 884311-31-3
S-benzyl-N-formyl-L-penicillamine

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium; liquid NH3 2: aqueous HCl View Scheme

: 52-67-5
3,3-dimethyl-D-cysteine

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 2 h / 55 °C 2.1: 5 h / 53 °C 3.1: acetic acid / toluene / 1 h / 98 °C 3.2: 1 h / 95 °C / Inert atmosphere 4.1: triethylamine / ethanol / 20 °C View Scheme

: 72744-87-7
(4S)-2,2,5,5-tetramethylthiazolidine-4-carboxylic acid

: 1113-41-3
L-penicillamine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 5 h / 53 °C 2.1: acetic acid / toluene / 1 h / 98 °C 2.2: 1 h / 95 °C / Inert atmosphere 3.1: triethylamine / ethanol / 20 °C View Scheme

: 99350-05-7
(μ-1,5-bis(diphenylphosphine)pentane)bis(chlorogold)

: 1113-41-3
L-penicillamine

: 7732-18-5
water

: C39H50Au2N2O4P2S2*3H2O

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 2h;	97%

...Expand

: 50-00-0
formaldehyd

: 1113-41-3
L-penicillamine

: 72778-00-8
(R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
With pyridine In ethanol; water at 110℃; for 0.0833333h; Microwave irradiation;	95%
In water at 0℃; for 1h;	87%
Stage #1: formaldehyd; L-penicillamine In water at 8℃; for 14h; Stage #2: In methanol at 20℃; for 12h;	86%

: 15200-13-2
6-ethoxy-2,3,4,5-tetrahydro-pyridine

: 1113-41-3
L-penicillamine

: 122861-59-0
(R)-3-mercapto-3,3-dimethyl-2-(piperidine-2-ylideneamino)-propanoic acid

Conditions

Conditions	Yield
In methanol for 8h; Ambient temperature;	91%

: 63640-04-0
1,4-bis(diphenylphosphino)butane digold(I) dichloride

: 1113-41-3
L-penicillamine

: 7732-18-5
water

: C38H48Au2N2O4P2S2*2H2O

Conditions

Conditions	Yield
With potassium hydroxide In ethanol at 20℃; for 2h;	91%

...Expand

: 84152-18-1
[(ClAu)]3(1,1,1-tris(diphenylphosphinomethyl)ethane)

: 1113-41-3
L-penicillamine

: [Au3(1,1,1-tris(diphenylphosphinomethyl))(D-penicillamininate)3]*5H2O

Conditions

Conditions	Yield
In ethanol at 20℃; for 1h;	90%

: 1113-41-3
L-penicillamine

: 540-51-2
2-bromoethanol

: 286459-94-7
4-but-2-ynyloxybenzenesulfonyl chloride

: 287407-19-6
N-{[4-(2 butynyloxy)phenyl]-sulfonyl}-3-[(2-hydroxyethyl)sulfanyl]valine

Conditions

Conditions	Yield
Stage #1: L-penicillamine With sodium hydroxide In methanol at 0℃; Stage #2: 2-bromoethanol In acetonitrile at 0 - 20℃; for 2.5h; Stage #3: 4-but-2-ynyloxybenzenesulfonyl chloride With hydrogenchloride; sodium carbonate more than 3 stages;	89.6%

...Expand

: 1113-41-3
L-penicillamine

: 540-51-2
2-bromoethanol

: 286459-94-7
4-but-2-ynyloxybenzenesulfonyl chloride

: (2S)-2-({[4-(2-butynyloxy)-phenyl]sulfonyl}amino)-3-[(2-hydroxyethyl)thio]-3-methylbutanoic acid

Conditions

Conditions	Yield
Stage #1: L-penicillamine With sodium hydroxide In methanol at 0℃; Stage #2: 2-bromoethanol In methanol at 0 - 20℃; for 2.5h; Stage #3: 4-but-2-ynyloxybenzenesulfonyl chloride With hydrogenchloride more than 3 stages;	89.6%

...Expand

: 1113-41-3
L-penicillamine

: 24424-99-5
di-tert-butyl dicarbonate

: (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(pyridin-2-yldisulfaneyl)ethyl)-docosa-4,7,10,13,16,19-hexaenamide

: (R)-2-((tert-butoxycarbonyl)amino)-3-((2-((4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamido)ethyl)disulfanyl)-3-methylbutanoic acid

Conditions

Conditions	Yield
Stage #1: L-penicillamine; (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-(pyridin-2-yldisulfaneyl)ethyl)-docosa-4,7,10,13,16,19-hexaenamide In methanol at 20℃; for 18h; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In methanol; water at 20℃; for 4h;	88.2%

...Expand

: 1113-41-3
L-penicillamine

: 24424-99-5
di-tert-butyl dicarbonate

: 110763-40-1
(R)-2-((tert-butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 22h; Cooling with ice;	88%
In tetrahydrofuran at 20℃; for 16h; Acylation;
In sodium carbonate; tert-butyl alcohol
With triethylamine In N,N-dimethyl-formamide for 18h;

: 1113-41-3
L-penicillamine

: 34619-03-9
tert-butyldicarbonate

: 110763-40-1
(R)-2-((tert-butoxycarbonyl)amino)-3-mercapto-3-methylbutanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 20h; Cooling with ice; Inert atmosphere;	88%

: 1113-41-3
L-penicillamine

: 136911-96-1
Trifluoro-methanesulfonate2-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yldisulfanyl]-1-methyl-pyridinium;

: (R)-2-Amino-3-[(3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yldisulfanyl]-3-methyl-butyric acid

Conditions

Conditions	Yield
In N,N-dimethyl-formamide reaction of other N-alkylpyridyl disulfides; other substrates;	87%
In N,N-dimethyl-formamide Yield given;

: 1113-41-3
L-penicillamine

: 24424-99-5
di-tert-butyl dicarbonate

: 274900-91-3
3-(5-bromo-2-thienyl)-1-phenyl-1H-pyrazole-4-carboxaldehyde

: 612500-41-1
(2RS,4R)-2-[3-(5-bromo-2-thienyl)-1-phenyl-1H-pyrazol-4-yl]-3-(tert-butyloxycarbonyl)-5,5-dimethylthiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
Stage #1: L-penicillamine; 3-(5-bromo-2-thienyl)-1-phenyl-1H-pyrazole-4-carboxaldehyde In ethanol; water for 5h; Heating; Stage #2: di-tert-butyl dicarbonate With sodium hydroxide In 1,4-dioxane; ethanol at 20℃; for 5h;	81%

...Expand

: 10025-99-7
potassium tetrachloroplatinate(II)

: 1113-41-3
L-penicillamine

: 4Pt(2+)*2(CH3)2CSCHNH2COOH(1-)*2(CH3)2CSCHNH2COO(2-)*2Cl(1-)=Pt4[(CH3)2CSCHNH2COOH]2[(CH3)2CSCHNH2COO]2Cl2

Conditions

Conditions	Yield
In water heating (50-55°C, 30 min); washing (water); elem. anal.;	81%

: 50-00-0
formaldehyd

: 1113-41-3
L-penicillamine

: 72778-00-8
5,5-dimethylthiazolidine-4-carboxylic acid

Conditions

Conditions	Yield
With pyridine In water a) water (pH 5), several h, b) 0 deg C, 3 h, c) ethanol, 0 deg C, overnight;	80%

: 1113-41-3
L-penicillamine

: 123-11-5
4-methoxy-benzaldehyde

: (1L)-2-imino-3-p-methoxybenzyl-4-sulfanyl-5,5-dimethyl-1-carboxylic acid

Conditions

Conditions	Yield
With manganese(IV) oxide In ethanol at 70℃; for 1h;	80%

: 1113-41-3
L-penicillamine

: 67-64-1
acetone

: (R)-4-carboxy-2,2,5,5-tetramethylthiazolidin-3-ium chloride

Conditions

Conditions	Yield
With hydrogenchloride In water for 3.5h; Reflux;	76%

: 1113-41-3
L-penicillamine

: 74-88-4
methyl iodide

: 100217-05-8
S-methyl-L-penicillamine

Conditions

Conditions	Yield
Stage #1: L-penicillamine With sodium hydroxide In methanol at 0℃; Stage #2: methyl iodide In methanol at 0 - 20℃; for 1.66667h; Stage #3: With hydrogenchloride In water pH=3;	75.8%
With sodium methylate
Stage #1: L-penicillamine With sodium hydroxide In methanol at 0℃; Stage #2: methyl iodide In methanol at 0 - 20℃; for 1.66667h; Stage #3: With hydrogenchloride In water pH=3;
With sodium hydroxide In methanol; water at 0℃; for 16h;

: 67-56-1
methanol

: 1113-41-3
L-penicillamine

: 70361-44-3
(R)-penicillamine methyl ester hydrochloride

Conditions

Conditions	Yield
With thionyl chloride for 120h; in a sealed vessel;	75%
With thionyl chloride at 0℃; for 96h; Heating / reflux;	75%

: 1113-41-3
L-penicillamine

: 61040-78-6
2,4,6-trimethoxybenzyl alcohol

: 1200836-59-4
(R)-2-amino-3-methyl-3-(2,4,6-trimethoxybenzylthio)butyric acid trifluoroacetate

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 17h;	75%

: 1113-41-3
L-penicillamine

: 1286276-26-3
7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one

: 1327278-91-0
(R)-2-amino-3-methyl-3-[(7-methoxy-2-oxo-2H-chromene-3-carbonyl)thio]butanoic acid

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 12h;	75%

: 15200-13-2
6-ethoxy-2,3,4,5-tetrahydro-pyridine

: 1113-41-3
L-penicillamine

A: 2-isopropylidene-5,6,7,8-tetrahydro-2H-imidazo<1,2-a>pyridine-3-one

B: 122861-59-0
(R)-3-mercapto-3,3-dimethyl-2-(piperidine-2-ylideneamino)-propanoic acid

Conditions

Conditions	Yield
In methanol at 80℃; for 2h;	A 15% B 74%

...Expand

: 826-41-5
N-Methyl-2,2-diethoxypyrrolidine

: 1113-41-3
L-penicillamine

: (R)-3-mercapto-3,3-dimethyl-2-(1-methyl-pyrrolidine-2-ylideneamino)-propanoic acid

Conditions

Conditions	Yield
In ethanol at 80℃; for 6h;	73%

: 1113-41-3
L-penicillamine

: [Au(ppy)Cl2]

: [Au(ppy)(D-pen)]*2H2O

Conditions

Conditions	Yield
With sodium hydroxide In ethanol; water at 50℃; for 1h;	73%

: 15200-13-2
6-ethoxy-2,3,4,5-tetrahydro-pyridine

: 1113-41-3
L-penicillamine

A: 2-isopropylidene-5,6,7,8-tetrahydro-2H-imidazo<1,2-a>pyridine-3-one

B: (R)-5,5-dimethyl-2-<3-(piperidine-2-ylideneamino)-butyl>-4,5-dihydro-1,3-thiazole-4-carboxylic acid

Conditions

Conditions	Yield
In methanol at 80℃; for 8h;	A 15% B 72%

...Expand

: 1113-41-3
L-penicillamine

: 312929-01-4
3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one

: 1327278-85-2
(R)-2-amino-3-methyl-3-[(2-oxo-2H-chromene-3-carbonyl)thio]butanoic acid

Conditions

Conditions	Yield
In water; acetonitrile at 20℃; for 12h;	72%

: 1113-41-3
L-penicillamine

: 159000-76-7
(3R)-3-formamido-4,4-dimethylthietan-2-one

: 158945-06-3
N-(N-formyl-D-penicillaminyl)-L-penicillamine

Conditions

Conditions	Yield
With sodium hydroxide In chloroform for 1h;	71%

l-Penicillamine Chemical Properties

Molecular Structure of l-Penicillamine (CAS NO.1113-41-3):

IUPAC Name: (2R)-2-amino-3-methyl-3-sulfanylbutanoic acid
Empirical Formula: C₅H₁₁NO₂S
Molecular Weight: 149.2113
Index of Refraction: 1.527
Surface Tension: 48.1 dyne/cm
Density: 1.204 g/cm³
Flash Point: 106.1 °C
Enthalpy of Vaporization: 53.85 kJ/mol
Boiling Point: 251.8 °C at 760 mmHg
Vapour Pressure: 0.00631 mmHg at 25°C
Product Categories:Amino Acids ; Biochemistry ; non-Proteinorganic Amino Acids
Synonyms of l-Penicillamine (CAS NO.1113-41-3): 2-Amino-3-mercapto-3-methylbutanoic acid ; alpha-Amino-beta-methyl-beta-mercaptobutyric acid ; valine, 3-mercapto- ; (+-)-penicillamine ; 3-Mercapto-l-valine ; 3-Thiol-valine ; 3,3-Dimethyl-l-cysteine;L-beta,beta-dimethylcysteine ; L-beta-mercaptovaline ; L-(+)-penicillamine ; L-penicillamine ; L(+)-2-amino-3-mercapto-3-methylbutanoic acid

l-Penicillamine Toxicity Data With Reference

1.	mic-sat 5 µmol/plate	MUREAV Mutation Research. 224 (1989),89.
2.	mic-sat 4 µmol/plate	BCPCA6 Biochemical Pharmacology. 34 (1985),3725.
3.	mic-esc 250 µLg/plate	MUREAV Mutation Research. 467 (2000),41.
4.	ipr-rat LD50:350 mg/kg	PBPSDY Pharmacological and Biochemical Properties of Drug Substances. 2 (1979),465.

l-Penicillamine Safety Profile

A poison by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic vapors of NO_x and SO_x.
Hazard Codes: Irritant Xi, Harmful Xn
Risk Statements :36/37/38-40-20/21/22
R36/37/38:Irritating to eyes, respiratory system and skin.
R40:Limited evidence of a carcinogenic effect.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements :26-36-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S22:Do not breathe dust.

Product Name

L-Penicillamine

Synthetic route

l-Penicillamine Chemical Properties

l-Penicillamine Toxicity Data With Reference

l-Penicillamine Safety Profile

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