624-78-2

Basic information

• Product Name: N-Ethylmethylamine
• Synonyms: N-METHYLETHYLAMINE;N-ETHYLMETHYLAMINE;(CH3)(C2H5)NH;Ethylamine, N-methyl-;Ethylmethylamine;ethyl-methyl-amine;Methylaminoethane;Methylethylamine
• CAS NO: 624-78-2
• Molecular Formula: C₃H₉N
• Molecular Weight: 59.11
• EINECS: 210-862-1
• Mol File: 624-78-2.mol
• Article Data: 28

Chemical Properties

• Melting Point: -70.99°C (estimate)
• Boiling Point: 36-37 °C(lit.)
• Flash Point: <−30 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.688 g/mL at 25 °C(lit.)
• Vapor Pressure: 8.53 psi ( 20 °C)
• Refractive Index: n20/D 1.374(lit.)
• Storage Temp.: 0-6°C
• PKA: pK1:4.23(＋1) (25°C)
• Sensitive: Hygroscopic
• BRN: 1730786
• CAS DataBase Reference: N-Ethylmethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethylmethylamine(624-78-2)
• EPA Substance Registry System: N-Ethylmethylamine(624-78-2)

Safety Data

• Hazard Codes: F,C
• Statements: 11-20/21/22-35-34
• Safety Statements: 26-36/37/39-45-16
• RIDADR: UN 2733 3/PG 1
• WGK Germany: 2
• F: 3-10-23
• TSCA: Yes
• HazardClass: 3
• PackingGroup: I
• Hazardous Substances Data: 624-78-2(Hazardous Substances Data)

Usage

Chemical Properties

Ethylmethylamine, or N-methylethanamine, is a clear colorless to light yellow liquid with the chemical formula C3H9N. It is corrosive and highly flammable.

Uses

N-Ethylmethylamine has been used in the synthesis of N-ethyl-methyl acrylamide via reaction with acryloyl chloride.

General Description

Ethyl methylamine is part of a group of substances called dialkyl amines. Dialkylamines can be described as organic substances with the dialkylamine group and are which is distinguished by two alkyl groups joined to the amino nitrogen. Ethylmethylamine is insoluble (in the water) and is a very solid base chemical (based upon the pKa). Ethyl-methyl amine is found in many foods, including wild carrots, corn, and cabbage as well as carrots, making the compound of ethylmethylamine a biomarker for the consumption of these foods.

InChI:InChI=1/C3H9N/c1-3-4-2/h4H,3H2,1-2H3

Synthetic route

acetaldehyde (75-07-0) + methylamine (74-89-5) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With hydrogen; sodium hydroxide; Raney nickel at 65 - 67℃; under 22502.3 Torr; for 4.3h; Product distribution / selectivity; Autoclave; Industry scale;	90%
With potassium hydroxide; dipotassium hydrogenphosphate; phosphoric acid at 10 - 12℃; for 4h; electrochemical reductive amination, lead cathode, current density 0.05 A/cm2, pH 12; Yield given;
With imine reductase from Streptomyces ipomoeae; NADPH In water at 30℃; for 0.166667h; pH=9.5; Catalytic behavior; Reagent/catalyst; Enzymatic reaction;

N-ethylidenemethylamine (6898-67-5) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With hydrogen; platinum(IV) oxide In ethanol	80%

N-ethyl-N-hydroxy-ethanamine (3710-84-7) → formaldehyd (50-00-0) + N-Ethylmethylamine (624-78-2) + ethylamine (75-04-7) + acetaldehyde (75-07-0)

Conditions	Yield
With phosphorus pentachloride In toluene at 18 - 20℃; Mechanism; Product distribution; object of study: Stieglitz rearrangement (prototype);	A n/a B 1.4% C 76% D n/a

N-(benzylidene)ethylamine (6852-54-6) + (ethoxycarbonylmethyl)dimethylsulfonium bromide (5187-82-6) → N-Ethylmethylamine (624-78-2) + 1-methylthio-3-phenyl-1,2-cyclopropanedicarboxylic acid diethyl ester (94117-87-0)

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride In tetrahydrofuran at 20℃; for 4h;	A n/a B 50%

pyridine (110-86-1) + N,N-diethylnmethylamine (616-39-7) + dibenzoyl peroxide (94-36-0) → formaldehyd (50-00-0) + N-Ethylmethylamine (624-78-2) + acetaldehyde (75-07-0) + diethylamine (109-89-7)

diethyl ether (60-29-7) + N-chloromethylamine (6154-14-9) + diethylzinc (557-20-0) → N-Ethylmethylamine (624-78-2) + methylamine (74-89-5)

N,N-dichloromethylamine (7651-91-4) + diethylzinc (557-20-0) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With Petroleum ether

N-nitrosomethylethylamine (10595-95-6) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With hydrogenchloride

N-ethyl-N-methylbenzylamine (4788-37-8) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With platinum(IV) oxide; acetic acid at 65 - 75℃; under 2206.5 Torr; durch Hydrogenolyse;

ethylamine (75-04-7) + methyl iodide (74-88-4) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With ethanol at 100℃;

1-Ethyl-1-methylpyrrolidinium iodide (4186-68-9) + ethanolamine (141-43-5) → 1-Methylpyrrolidine (120-94-5) + 1-ethylpyrrolidine (7335-06-0) + 1-pyrrolidineethanol (2955-88-6) + N-Ethylmethylamine (624-78-2)

ethyl isocyanate (109-90-0) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With lithium aluminium tetrahydride; 3,6,9-trioxaundecane
With hydrogen; nickel at 180 - 190℃;

acetic anhydride (108-24-7) + (RS)-disinomenine (596-58-7, 70630-96-5, 70630-97-6, 70680-98-7) → N-Ethylmethylamine (624-78-2) + 3.7.3'.7'-Tetramethoxy-4.6.4'.6'-tetraacetoxy-diphenanthryl-(1.1')

Conditions	Yield
at 180℃; isomer(ic) I;

MORPHIN (57-27-2) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With potassium hydroxide at 180℃;

N-Diphenylmethylen(ethyl)amin (27126-11-0) + methyl iodide (74-88-4) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
Kochen des endstandenen Jodmethylats mit Alkohol;

methyl bromide (74-83-9) + diethyl N-ethylphosphoramidate (1946-09-4) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
(i) aq. NaOH, HSO4, (ii) HCl; Multistep reaction;

N-(benzylidene)ethylamine (6852-54-6) + dimethyl sulfate (77-78-1) → N-Ethylmethylamine (624-78-2)

ethyl bromide (74-96-4) + methylamine (74-89-5) → N-Ethylmethylamine (624-78-2)

Conditions	Yield
In ethanol at 100℃; under 3677.5 Torr;

1,3,5-triethyl-1,3,5-triazacyclohexane (7779-27-3) + mono-trimethylsilylphosphite (91076-68-5) → N,N-dimethyl-ethanamine (598-56-1) + N-Ethylmethylamine (624-78-2)

N-Ethyl,N-methylacetamide (38806-26-7) → N-Ethylmethylamine (624-78-2) + acetate (71-50-1)

Conditions	Yield
With sodium hydroxide In water at 100℃; Rate constant; Mechanism;

triphenylmethane (519-73-3) + lithium ethylmethyl amide (57018-31-2) → N-Ethylmethylamine (624-78-2) + trityllithium (733-90-4)

Conditions	Yield
In tetrahydrofuran at 30℃; Equilibrium constant;

N-Methyl-N-ethylamino-triphenyl-phosphonium-jodid → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With water; hydroxide

nitrogen mustard (51-75-2) → ethanol (64-17-5) + N-Ethylmethylamine (624-78-2) + N,N-diethylnmethylamine (616-39-7)

Conditions	Yield
With potassium hydroxide; aluminum nickel In methanol Product distribution; degradation under various conditions with preparation of nonmutagenic reaction mixtures of products;

propiononitrile (107-12-0) + Devarda's's alloy → N-Ethylmethylamine (624-78-2) + methyl-n-propylamine (627-35-0) + ethylamine (75-04-7) + propionaldehyde (123-38-6)

Conditions	Yield
weiteres Produkt:Ammoniak;

propiononitrile (107-12-0) + magnesium copper → N-Ethylmethylamine (624-78-2) + methyl-n-propylamine (627-35-0) + ethylamine (75-04-7) + propionaldehyde (123-38-6)

Conditions	Yield
weiteres Produkt:Ammoniak;

ethyl isocyanate (109-90-0) + hydrogen + nickel → N-Ethylmethylamine (624-78-2) + ammonia (7664-41-7) + ethylamine (75-04-7) + diethylamine (109-89-7)

Conditions	Yield
at 180 - 190℃; Produkt 5: Triaethylamin;

1.3.5-triethyl-hexahydro-1.3.5-triazine → N-Ethylmethylamine (624-78-2)

Conditions	Yield
With hydrogenchloride; zinc zuletzt bei Siedetemperatur;

N-Ethylmethylamine (624-78-2) + indole-2,3-dione (91-56-5) → (2-Amino-phenyl)-oxo-acetic acid; compound with ethyl-methyl-amine

Conditions	Yield
In water Heating;	100%

N-Ethylmethylamine (624-78-2) + 4-[phenyl(endo-8-methyl-8-azabicyclo[3.2.1]octan-3-yl)amino]benzoic acid (287721-05-5) → N-ethyl-N-methyl-4-[(8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-phenyl-amino]-benzamide (287720-97-2)

Conditions	Yield
With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate Acylation;	100%

C16H20N2O5S + N-Ethylmethylamine (624-78-2) → ethyl-methyl-{3-[3-(4-methyl-piperidin-1-yl)-4-nitro-phenyl]-prop-2-ynyl}-amine (954424-88-5)

Conditions	Yield
In dichloromethane for 0.333333h; Heating / reflux;	100%

3-[3-(phenylsulfonyl)-1H-indol-4-yl]propyl 4-methylbenzenesulfonate (945001-04-7) + N-Ethylmethylamine (624-78-2) → N-ethyl-N-methyl-3-[3-(phenylsulfonyl)-1H-indol-4-yl]propan-1-amine hydrochloride

Conditions	Yield
Stage #1: 3-[3-(phenylsulfonyl)-1H-indol-4-yl]propyl 4-methylbenzenesulfonate; N-Ethylmethylamine In tetrahydrofuran at 65℃; for 16h; Stage #2: With sodium hydroxide; water In tetrahydrofuran	100%
Stage #1: 3-[3-(phenylsulfonyl)-1H-indol-4-yl]propyl 4-methylbenzenesulfonate; N-Ethylmethylamine In tetrahydrofuran at 65℃; for 16h; Stage #2: With hydrogenchloride In ethanol	69%

N-Ethylmethylamine (624-78-2) + 2,4-dichloro-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidine (1263868-77-4) → 2-chloro-N-ethyl-N-methyl-8-phenyl-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine (1263868-83-2)

Conditions	Yield
In methanol at 20℃; for 1h;	100%
In methanol at 20℃; for 1h;	100%

N-Ethylmethylamine (624-78-2) + 2,4-dichloro-8-(4-fluorophenyl)-5,6,7,8-tetrahydroquinazoline (1263870-09-2) → 2-chloro-N-ethyl-8-(4-fluorophenyl)-N-methyl-5,6,7,8-tetrahydroquinazolin-4-amine (1263870-13-8)

Conditions	Yield
In methanol at 20℃; for 0.5h;	100%
In methanol at 20℃; for 0.5h;	100%

N-Ethylmethylamine (624-78-2) + 2,4-dichloro-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (1263868-24-1) → 2-chloro-N-ethyl-N-methyl-7-phenyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-amine (1263868-27-4)

Conditions	Yield
In methanol at 20℃; for 1h;	100%
In methanol at 20℃; for 1h;	100%

N-Ethylmethylamine (624-78-2) + 3-methoxy-4-methyl-3-cyclobutene-1,2-dione (29769-77-5) → 3-(ethyl(methyl)amino)-4-methylcyclobut-3-ene-1,2-dione

Conditions	Yield
In methanol at 20℃; for 4h;	100%

carbon disulfide (75-15-0) + N-Ethylmethylamine (624-78-2) → lithium N-ethyl-N-methyldithiocarbamate

Conditions	Yield
Stage #1: N-Ethylmethylamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: carbon disulfide In tetrahydrofuran; hexane at 20℃; for 3h;	100%

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + N-Ethylmethylamine (624-78-2) → N-[N-(tert-butyloxycarbonyl)-L-isoleucyl]-N-ethyl-N-methylamine

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In triethylamine; N,N-dimethyl-formamide Ambient temperature;	99%

4-(2-ethyl-3-chloropyridyl-4-oxy)-2,5-xylidine + N-Ethylmethylamine (624-78-2) + trimethyl orthoformate (149-73-5) → N-ethyl-N-methyl-N'-[4-(2-ethyl-3-chloropyridyl-4-oxy)-2,5-xylyl]formamidine

Conditions	Yield
Stage #1: 4-(2-ethyl-3-chloropyridyl-4-oxy)-2,5-xylidine; trimethyl orthoformate With toluene-4-sulfonic acid for 3h; Heating / reflux; Stage #2: N-Ethylmethylamine In dichloromethane at 20℃; for 16h;	99%

N-Ethylmethylamine (624-78-2) + methyl 2-(methylthio)benzo[d]oxazole-6-carboxylate (1160490-11-8) → C12H14N2O3 (1160490-12-9)

Conditions	Yield
In tetrahydrofuran at 70℃;	99%
In tetrahydrofuran at 70℃;

carbon disulfide (75-15-0) + N-Ethylmethylamine (624-78-2) → C2H5CH3NC(S)SSC(S)NCH3C2H5 (155722-99-9)

Conditions	Yield
With oxygen In isopropyl alcohol at 50℃; under 1275.13 Torr; for 2h; Autoclave;	98.6%

N-Ethylmethylamine (624-78-2) → N,N-chloromethylethylamine (36260-79-4)

Conditions	Yield
With N-chloro-succinimide under 0.004 Torr; Ambient temperature; stored at t<-20 deg C;	98%
With N-chloro-succinimide under 1E-05 Torr; Ambient temperature; Yield given;
With sodium hypochlorite; sodium perchlorate In water at 24.85℃; Kinetics; Further Variations:; Temperatures; Chlorination;

N-Ethylmethylamine (624-78-2) + m-anisoyl chloride (1711-05-3) → N-ethyl-3-methoxy-N-methylbenzamide (207558-42-7)

Conditions	Yield
In dichloromethane at 0℃; for 2h;	98%

N-Ethylmethylamine (624-78-2) + 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-chloroethanone (942035-74-7) → 1-(6-bromo-3,4-dihydroquinolin-1(2H)-yl)-2-(ethyl(methyl)amino)ethanone (1063408-94-5)

Conditions	Yield
With potassium iodide In tetrahydrofuran at 20 - 65℃; for 3h;	98%
With potassium iodide In tetrahydrofuran at 20 - 65℃; for 3h; Inert atmosphere;	98%

N-Ethylmethylamine (624-78-2) + triisopropylchlorogermane (2816-54-8) → ethylmethylaminotriisopropylgermane (1147551-48-1)

Conditions	Yield
Stage #1: N-Ethylmethylamine With n-butyllithium In diethyl ether at 0℃; for 2h; Cooling with ice; Stage #2: triisopropylchlorogermane In diethyl ether at 0 - 20℃;	98%

N-Ethylmethylamine (624-78-2) + 6-Chloropurine riboside (2004-06-0) → (2R,3R,4S,5R)-2-(6-(ethyl(methyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Conditions	Yield
With triethylamine In ethanol at 60℃; for 18h;	98%
With triethylamine In ethanol Reflux;	0.93 g

N-Ethylmethylamine (624-78-2) + 4-isocyanobenzenesulfonyl chloride → N-ethyl-4-isocyano-N-methylbenzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 25℃; for 1h;	98%

N-hydroxyphthalimide (524-38-9) + N-Ethylmethylamine (624-78-2) → N-ethyl-2-(3-ethyl-3-methylureido)-N-methylbenzamide

Conditions	Yield
With triethyl phosphite In toluene at 50℃; for 12h;	98%

3-(1-hydroxy-1-phenyl-methylene)-6-carboxy-2-indolinone + N-Ethylmethylamine (624-78-2) → 3-(1-hydroxy-1-phenyl-methylene)-6-(N-ethyl-methylcarbamoyl)-2-indolinone

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	97%

2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate (945000-91-9) + N-Ethylmethylamine (624-78-2) → N-ethyl-N-methyl-N-{2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl}amine hydrochloride

Conditions	Yield
Stage #1: 2-[3-(phenylsulfonyl)-1H-indol-4-yl]ethyl 4-methylbenzenesulfonate; N-Ethylmethylamine In tetrahydrofuran at 71℃; for 24h; Stage #2: With ammonia In ethanol; dichloromethane Stage #3: With hydrogenchloride; water In diethyl ether	97%

N-Ethylmethylamine (624-78-2) + (Z)-3-(hydroxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid (1253768-91-0) → (Z)-3-(hydroxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid N-methyl-N-ethylamide (1253768-93-2)

Conditions	Yield
Stage #1: (Z)-3-(hydroxy-phenyl-methylene)-2-oxo-2,3-dihydro-1H-indole-6-carboxylic acid With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: N-Ethylmethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	97%

N-Ethylmethylamine (624-78-2) + ethyl 2-chloro-5-methyloxazole-4-carboxylate (1144520-57-9) → ethyl 2-(N-ethylmethylamino)-5-methyloxazole-4-carboxylate

Conditions	Yield
at 20℃; for 13.5h;	97%

N-Ethylmethylamine (624-78-2) + ethyl 8-bromo-2-chloroimidazo[1,2-b]pyridazine-7-carboxylate → ethyl 2-chloro-8-(ethyl(methyl)amino)imidazo[1,2-b]pyridazine-7-carboxylate

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	96.7%

N-Ethylmethylamine (624-78-2) + (R,E)-2-((4-(3,5-dimethoxystyryl)phenoxy)methyl)oxirane → (R,E)-1-(4-(3,5-dimethoxystyryl)phenoxy)-3-(ethyl(methyl)amino)propan-2-ol

Conditions	Yield
In methanol at 65℃; Inert atmosphere; Darkness;	96.3%

[2-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-benzyl]-carbamic acid phenyl ester + N-Ethylmethylamine (624-78-2) → 1-ethyl-3-[2-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-benzyl]-1-methyl-urea (745827-35-4)

Conditions	Yield
Stage #1: [2-(3-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-6-ylsulfanyl)-benzyl]-carbamic acid phenyl ester; N-Ethylmethylamine In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: In water	96%

methyl 5-chloro-7-[(3-methylphenyl)amino]-1-[2-(2,2,2-trifluoroethoxy)ethyl]-1H-pyrazolo[4,3-d]pyrimidine-3-carboxylate + N-Ethylmethylamine (624-78-2) → C21H25F3N6O3

Conditions	Yield
With cesium fluoride In dimethyl sulfoxide at 120℃; for 12h;	96%

N-Ethylmethylamine (624-78-2) + phenylacetylene (536-74-3) → C11H15N

Conditions	Yield
With C18H17N3Ni In toluene at 75℃; for 6h;	96%
With C17H15N3Pd In toluene at 75℃; for 6h;	93%

6-(methoxycarbonyl)pyridine-2-carboxylic acid (7170-36-7) + N-Ethylmethylamine (624-78-2) → 6-(ethyl(methyl)carbamoyl)picolinic acid methyl ester

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 5h;	96%

Upstream product

• 110-86-1 pyridine 
• 616-39-7 N,N-diethylnmethylamine 
• 94-36-0 dibenzoyl peroxide 
• 60-29-7 diethyl ether 
• 6154-14-9 N-chloromethylamine 
• 557-20-0 diethylzinc 
• 7651-91-4 N,N-dichloromethylamine 
• 10595-95-6 N-nitrosomethylethylamine 
• 4186-68-9 1-Ethyl-1-methylpyrrolidinium iodide 
• 141-43-5 ethanolamine 
• 109-90-0 ethyl isocyanate 
• 57-27-2 MORPHIN 
• 27126-11-0 N-Diphenylmethylen(ethyl)amin 
• 74-88-4 methyl iodide 

Downstream Products

• 2893-43-8 2-(N-ethyl-N-methylamino)ethanol 
• 691412-31-4 5-(ethyl-methyl-amino)-pentan-2-one 
• 74805-36-0 N-ethyl-N-methyl benzenesulfonamide 
• 13223-76-2 N-ethyl-N-methyl-2,4-dinitroaniline 
• 49642-03-7 3-(ethylmethylamino)-propan-1-ol 
• 51-93-4 ethyltrimethylammonium iodide 
• 2746-07-8 N-ethyl-N-methyl-2-chloroacetamide 
• 36612-75-6 1-Ethyl-1-methyl-3-[4-(4-nitro-phenoxy)-phenyl]-thiourea 
• 56570-67-3 (E)-3-(Ethyl-methyl-amino)-1-phenyl-propenone 
• 55412-81-2 2-Acetamino-N-ethyl-5-bromo-N,3-dimethyl-benzylamine 
• 77200-12-5 2-N-methylethylaminopyridine 
• 59708-19-9 C₁₀H₁₄N₄O 

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