Mecarbinate supplier | CasNO.15574-49-9

Name
Mecarbinate
EINECS 605-026-1
CAS No. 15574-49-9
Article Data23
CAS DataBase
Density 1.2 g/cm³
Solubility
Melting Point 208-212oC
Formula C₁₃H₁₅NO₃
Boiling Point 399.8 °C at 760 mmHg
Molecular Weight 233.267
Flash Point 195.6 °C
Transport Information
Appearance Off-white crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Indole-3-carboxylicacid, 5-hydroxy-1,2-dimethyl-, ethyl ester (6CI,7CI,8CI);1,2-Dimethyl-3-carbethoxy-5-hydroxyindole;3-(Ethoxycarbonyl)-5-hydroxy-1,2-dimethylindole;Ba 2676;Dimecarbin;Dimecarbine;Dimekarbin;Ethyl 5-hydroxy-1,2-dimethylindole-3-carboxylate;
PSA 51.46000
LogP 2.36900

Synthetic route

: 21759-71-7
ethyl N-methyl-β-aminocrotonate

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
With zinc(II) iodide In dichloromethane at -30℃; for 15h; Product distribution; Further Variations:; Solvents; Reagents; Nenitzescu reaction;	92%

: 21759-70-6
ethyl (Z)-3-(methylamino)-2-butenoate

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
In acetone at 30℃; for 2h; Nenitzescu Synthesis;	75.2%
In acetone at 30℃; for 2h;	75.2%
In 1,2-dichloro-ethane at 20 - 60℃; Heating / reflux;

: 870-85-9
ethyl 3-methylaminocrotonate

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
In 1,2-dichloro-ethane at 50℃; for 12h; Reflux;	74.9%
In acetone at 30℃; for 2h;	73.7%
In acetone at 30℃; for 2h;	73.7%

: 65578-36-1
ethyl N-methyl β-aminocrotonate

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
With zinc(II) chloride In dichloromethane at 10 - 20℃; for 4h; Reagent/catalyst;	73.3%
In nitromethane for 24h;	30.6%

: 21759-71-7
ethyl N-methyl-β-aminocrotonate

: 106-51-4
p-benzoquinone

A: 7287-40-3
ethyl 5-hydroxy-2-methyl-benzofuran-3-carboxylate

B: 15574-49-9
mecarbinate

C: 75785-33-0
α-(Hydrochinonyl)-β-(methylamino)-crotonsaeureethylester

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane Nenitzescu reaction;	A 14% B n/a C n/a

...Expand

: 870-85-9
ethyl 3-methylaminocrotonate

: 67-64-1
acetone

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

...Expand

: 141-97-9
ethyl acetoacetate

: 74-89-5
methylamine

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
Stage #1: ethyl acetoacetate; methylamine In methanol at 20℃; Stage #2: p-benzoquinone With acetic acid at 20℃; Nenitzescu reaction; Further stages.;

...Expand

: 141-97-9
ethyl acetoacetate

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 3 h / 20 °C 2: acetone / 2 h / 30 °C View Scheme
Multi-step reaction with 2 steps 1: water / 3 h / 20 °C 2: acetone / 2 h / 30 °C View Scheme
Multi-step reaction with 2 steps 1: silica gel / water 2: nitromethane / 24 h View Scheme

: 870-85-9
ethyl 3-methylaminocrotonate

: 637-88-7
1,4-Cyclohexanedione

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
In 1,2-dichloro-ethane for 8h; Reflux;

: C28H31NO3Si

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

: C29H33NO3Si

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;

: 7598-91-6
ethyl 5-hydroxy-2-methylindole-3-carboxylate

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1H-imidazole / dichloromethane / 16 h / 20 °C 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

: 106-51-4
p-benzoquinone

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid / 5 h / 20 - 45 °C 2: 1H-imidazole / dichloromethane / 16 h / 20 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

: 626-34-6, 7318-00-5, 41867-20-3
ethyl aminocrotonate

: 15574-49-9
mecarbinate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: acetic acid / 5 h / 20 - 45 °C 2: 1H-imidazole / dichloromethane / 16 h / 20 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 - 20 °C 4: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C View Scheme

: 101151-96-6
1-hydroxygermatrane monohydrate

: 15574-49-9
mecarbinate

: 133517-08-5
1,2-dimethyl-3-carboethoxy-5-germatranoxyindole

Conditions

Conditions	Yield
In m-xylene=m-xylol byproducts: H2O; mixt. of the germatrane with the hydroxy compd. in m-xylene refluxed with azeotropic distn. of H2O; residue filtered off, washed with n-pentane, recrystn. from CH3CN; elem. anal.;	99%

: 15574-49-9
mecarbinate

: 75-36-5
acetyl chloride

: C14H15NO4

Conditions

Conditions	Yield
With triethylamine In acetone at 20℃; for 6h;	94.1%

: 15574-49-9
mecarbinate

: N-[2-(bromomethyl)-3-fluoro-allyl]carbamic acid tert-butyl ester

: 5-[(E)-2-[(tert-butoxycarbonylamino)methyl]-3-fluoroallyloxy]-1,2-dimethylindole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 40℃; for 4.5h;	94%

: 15574-49-9
mecarbinate

: 108-24-7
acetic anhydride

: 40945-79-7
1,2-dimethyl-5-acetoxy-1H-indole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With sodium acetate In dichloromethane for 3h; Reagent/catalyst; Reflux;	91.5%
for 4h; Reflux;	65%
With pyridine
With triethylamine

: 15574-49-9
mecarbinate

: 1067-21-6
triethylmethoxystannane

: 133642-00-9
1,2-dimethyl-3-carboethoxy-5-triethylstannoxyindole

Conditions

Conditions	Yield
In neat (no solvent) byproducts: MeOH; mixt. of the hydroxy deriv. and triethylmethoxystannane heated (formed MeOH removed continuously during react.); residue washed with n-pentane, dried in vac.; elem. anal.;	91%

: 15574-49-9
mecarbinate

: 98-59-9
p-toluenesulfonyl chloride

: 88461-72-7
1,2-Dimethyl-3-ethoxycarbonyl-5-tosyloxyindole

Conditions

Conditions	Yield
With potassium carbonate In acetone for 5h; Heating;	88.5%

: 15574-49-9
mecarbinate

: 74-88-4
methyl iodide

: 40963-98-2
ethyl 5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
With potassium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 4h;	81%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	81%
Stage #1: mecarbinate With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: methyl iodide	75.5%

: 15574-49-9
mecarbinate

: 25888-01-1
1,2-dimethyl-5-hydroxy-1H-indole-3-carboxylic acid

Conditions

Conditions	Yield
With water; sodium hydroxide In ethanol for 12h; Reflux;	77%
With water; sodium hydroxide In ethanol for 12h; Reflux;	77%
With water; sodium hydroxide In ethanol for 12h; Reflux;	76.98%
With sodium hydroxide In ethanol; water for 12h; Reflux;	76.98%

: 625-38-7
but-3-enoic acid

: 15574-49-9
mecarbinate

: C17H19NO4

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	70%

: 15574-49-9
mecarbinate

: 105-39-5
chloroacetic acid ethyl ester

: 64199-44-6
1-methyl-3-ethoxycarbonyl-5-ethoxycarbonylmethoxy-2-methylindole

Conditions

Conditions	Yield
With potassium carbonate; potassium iodide In acetone for 30h; Alkylation; Heating;	65%

: 4227-95-6
[13C]methyl iodide

: 15574-49-9
mecarbinate

: 1271786-83-4
C13(13)CH17NO3

Conditions

Conditions	Yield
With sodium hydride	64%

: 15574-49-9
mecarbinate

: 106-96-7
propargyl bromide

: ethyl 5-[(prop-2-yn-1-yl)oxy]-1,2-dimethyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
With sodium hydroxide In water for 0.0333333h; Heating;	63%

: 50-00-0
formaldehyd

: 42923-77-3
6-methoxy-1,2,3,4-tetrahydro-isoquinoline

: 15574-49-9
mecarbinate

: ethyl 5-hydroxy-4-((6-methoxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl)-1,2-dimethyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
With acetic acid In water at 90℃; for 0.5h;	63%

...Expand

: 15574-49-9
mecarbinate

: C13H14FNO5S

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; triethylamine In 1,4-dioxane at 20℃; under 760.051 Torr; for 24h;	57%

: 50-00-0
formaldehyd

: 15574-49-9
mecarbinate

: ethyl 4-formyl-5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: formaldehyd With triethylamine; magnesium chloride In tetrahydrofuran for 0.166667h; Stage #2: mecarbinate In tetrahydrofuran at 75℃; for 24h;	50%

: 15574-49-9
mecarbinate

: 64-19-7
acetic acid

: ethyl 4-formyl-5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
With hexamethylenetetramine at 90℃; for 6h;	12%

: 50-00-0
formaldehyd

: 15574-49-9
mecarbinate

: 124-40-3
dimethyl amine

: 6-dimethylaminomethyl-5-hydroxy-1,2-dimethyl-indole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With acetic acid

...Expand

: 15574-49-9
mecarbinate

: 79-11-8
chloroacetic acid

: 64199-47-9
5-carboxymethoxy-1,2-dimethyl-indole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With 1,4-dioxane; sodium hydroxide

: 15574-49-9
mecarbinate

: 77-78-1
dimethyl sulfate

: 40963-98-2
ethyl 5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate

Conditions

Conditions	Yield
With 1,4-dioxane; sodium hydroxide

: 50-00-0
formaldehyd

: 15574-49-9
mecarbinate

: 593-51-1
methylamine hydrochloride

: 2,7,8-trimethyl-1,2,3,7-tetrahydro-[1,3]oxazino[5,6-e]indole-9-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In 1,4-dioxane; water

...Expand

: 50-00-0
formaldehyd

: 15574-49-9
mecarbinate

: 3858-78-4
n-butylamine hydrochloride

: 2-butyl-7,8-dimethyl-1,2,3,7-tetrahydro-[1,3]oxazino[5,6-e]indole-9-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In 1,4-dioxane; water

...Expand

: 51-80-9
bis-(dimethylamino)methane

: 15574-49-9
mecarbinate

: 88461-90-9
1,2-Dimethyl-3-ethoxycarbonyl-4,6-bis(dimethylaminomethyl)-5-hydroxyindole

Conditions

Conditions	Yield
In acetic acid Heating; Yield given;

: 15574-49-9
mecarbinate

: 106-49-0
p-toluidine

: 76921-18-1
5-Hydroxy-1,2-dimethyl-4-p-tolylazo-1H-indole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite 1.)-5 to 0 deg C 2.)dioxane, 0 deg C, 3 h; Yield given. Multistep reaction;

: 15574-49-9
mecarbinate

: 106-47-8
4-chloro-aniline

: 76921-20-5
4-(4-Chloro-phenylazo)-5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite 1.)-5 to 0 deg C 2.)dioxane, 0 deg C, 3 h; Yield given. Multistep reaction;

Mecarbinate Chemical Properties

IUPAC Name: ethyl 5-hydroxy-1,2-dimethylindole-3-carboxylate
Synonyms of 1H-Indole-3-carboxylicacid, 5-hydroxy-1,2-dimethyl-, ethyl ester (CAS NO.15574-49-9): Mecarbinate [INN] ; 4-22-00-02229 (Beilstein Handbook Reference) ; 5-Hydroxy-1,2-dimethylindol-3-carbonsaeureethylester ; BA 2676 ; BRN 0193275 ; Dimecarbin ; Dimecarbine ; Dimekarbin ; Ethyl 5-hydroxy-1,2-dimethyl-1H-indole-3-carboxylate ; Mecarbinate ; Mecarbinato ; Mecarbinato [INN-Spanish] ; Mecarbinatum ; Mecarbinatum [INN-Latin] ; UNII-Z927X3UJ2W ; 1,2-Dimethyl-3-carbethoxy- 5-hydroxyindole ; Ethyl 5-hydroxy-1,2-dimethylindole-3-carboxylate
CAS NO: 15574-49-9
Classification Code: Drug / Therapeutic Agent
Molecular Formula of 1H-Indole-3-carboxylicacid, 5-hydroxy-1,2-dimethyl-, ethyl ester (CAS NO.15574-49-9): C₁₃H₁₅NO₃
Molecular Weight: 233.2631
Molecular Structure:

H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 40.46 Å²
Index of Refraction: 1.571
Molar Refractivity: 63.85 cm³
Molar Volume: 194.1 cm³
Surface Tension: 40.1 dyne/cm
Density of 1H-Indole-3-carboxylicacid, 5-hydroxy-1,2-dimethyl-, ethyl ester (CAS NO.15574-49-9): 1.2 g/cm³
Flash Point: 195.6 °C
Enthalpy of Vaporization: 67.6 kJ/mol
Boiling Point: 399.8 °C at 760 mmHg
Vapour Pressure: 5.77E-07 mmHg at 25°C

Mecarbinate Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
mouse	LD	intraperitoneal	> 10gm/kg (10000mg/kg)	Toksikologicheskii Vestnik. Vol. (1), Pg. 29, 1994.
mouse	LD	oral	> 10gm/kg (10000mg/kg)	Toksikologicheskii Vestnik. Vol. (1), Pg. 29, 1994.
rat	LD	oral	> 10gm/kg (10000mg/kg)	Toksikologicheskii Vestnik. Vol. (1), Pg. 29, 1994.

Mecarbinate Safety Profile

Hazard Codes: Xi
HazardClass: IRRITANT

Product Name

Mecarbinate

Synthetic route

Mecarbinate Chemical Properties

Mecarbinate Toxicity Data With Reference

Mecarbinate Safety Profile

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