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Basic Information

Molecular Structure:
CAS No.:	15574-49-9
Name:	Mecarbinate
Article Data:	23

Formula:	C₁₃H₁₅NO₃
Molecular Weight:	233.267
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;
EINECS:	605-026-1
Density:	1.2 g/cm³
Melting Point:	208-212oC
Boiling Point:	399.8 °C at 760 mmHg
Flash Point:	195.6 °C
Appearance:	Off-white crystalline powder
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	26-36
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

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Chemistry

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

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.

Safety Profile

Hazard Codes: Xi
HazardClass: IRRITANT