617-84-5

Basic information

• Product Name: N,N-Diethylformamide
• Synonyms: n,n-diethyl-formamid;N-Formyldiethylamine;FORMYLDIETHYLAMINE;FORMIC ACID DIETHYLAMIDE;DIETHYL FORMAMIDE;N,N-DIETHYLFORMAMIDE;N,N-DIETHYLFORMYLAMIDE;N.N-Diethylformamide>99%
• CAS NO: 617-84-5
• Molecular Formula: C5H11NO
• Molecular Weight: 101.15
• EINECS: 210-533-2
• Product Categories: Amides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 617-84-5.mol
• Article Data: 106

Chemical Properties

• Melting Point: 176-177°C
• Boiling Point: 176-177 °C(lit.)
• Flash Point: 141 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.908 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.04mmHg at 25°C
• Refractive Index: n20/D 1.434(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: Miscible with acetone, benzene, alcohol and ether.
• PKA: -0.44±0.70(Predicted)
• BRN: 1209392
• CAS DataBase Reference: N,N-Diethylformamide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N-Diethylformamide(617-84-5)
• EPA Substance Registry System: N,N-Diethylformamide(617-84-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• RIDADR: UN 1993 3/PG 3
• WGK Germany: 1
• RTECS: LQ1925000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 617-84-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to pale yellow liquid

Uses

Different sources of media describe the Uses of 617-84-5 differently. You can refer to the following data:
1. N,N-Diethylformamide is used in the synthesis of metal-organic frameworks and Diethyltrifluoromethylamine. It is also used as solvent in the preparation of porous cubic-shaped zinc oxide particles. It is involved in the preparation of quinazoline-2,4(1H,3H)-dione by reacting with o-aminonitrile.
2. N,N-Diethylformamide was used in the synthesis of metal-organic frameworks. It was also used as solvent in the synthesis of porous cubic-shaped ZnO particles.

General Description

N,N-Diethylformamide undergoes condensation with aromatic o-aminonitriles in the presence of ZnCl2 in sealed reactor to yield quinazoline-2,4(1H,3H)-dione.

InChI:InChI=1/C5H11NO/c1-3-6(4-2)5-7/h5H,3-4H2,1-2H3

Synthetic route

carbon dioxide (124-38-9) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With C21H24N2; phenylsilane In tetrahydrofuran at 20℃; under 750.075 - 2250.23 Torr; for 1.5h; Solvent; Concentration; Reagent/catalyst; Temperature; Time; Inert atmosphere; Glovebox;	100%
With phenylsilane at 25℃; under 37503.8 Torr; for 12h; Pressure; Temperature; Autoclave;	100%
With Zn(salen); phenylsilane; tetrabutylammomium bromide at 25℃; under 3750.38 Torr; for 15h; Reagent/catalyst; Autoclave;	99%

formaldehyd (50-00-0) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With potassium tetrachloroaurate(III); potassium carbonate In water; acetonitrile at 40℃; for 12h;	98%
With sodium hydroxide In water at 25℃; for 6h;	91%
With potassium iodide In water Ambient temperature; electrolysis;	85%

N-<(trimethylsilyl)methyl>-N,N-diethylamine (10545-36-5) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With copper(I) bromide In acetonitrile at 25℃; for 4h; chemoselective reaction;	94%

formic acid (64-18-6) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With Thiamine hydrochloride at 80℃; for 0.5h;	90%
With sulfated polyborate In neat (no solvent) at 70℃; for 0.333333h;	86%
With silica gel for 0.0236111h; microwave irradiation;	80%

C10H20CuN2O2(1-)*Li(1+) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With hydrogenchloride; diethyl ether In diethyl ether at -78℃; for 0.5h;	85%

dihydroxyacetone (96-26-4) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With Cu/Al2O3; dihydrogen peroxide In water at 25℃; for 24h; Green chemistry;	83%

4-tert-butyl-2-(2-nitrophenylazo)phenol (27959-42-8) → 2-Methyl-1H-benzimidazole (615-15-6) + N-formyldiethylamine (617-84-5) + 2-(5-tert-butyl-2-hydroxyphenyl)benzotriazole (3147-76-0) + 2-nitro-aniline (88-74-4)

Conditions	Yield
With carbon monoxide; triethylamine In 1,2-dichloro-benzene at 200℃; under 60800 Torr; for 8h; Further byproducts given;	A n/a B n/a C 63% D 82%

bis(diethylamin)nickeldibromid (14873-98-4) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5) + N,N,N',N'-tetraethylurea (1187-03-7) + N,N,N',N'-tetraethyloxamide (14288-05-2) + diethylamine hydrobromide (6274-12-0) + tetracarbonyl nickel (13463-39-3, 71564-36-8)

Conditions	Yield
With carbon monoxide In tetrahydrofuran; diethyl ether reaction in THF/Et2O = 2/1 soln., room temp., under CO (1 bar);	A 7% B 0.5% C 80% D n/a E n/a

triethylamine (121-44-8) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With manganese(IV) oxide; oxygen In chlorobenzene at 100℃; under 4500.45 Torr; for 4h; Autoclave; Green chemistry;	80%
With Eosin Y In ethanol at 23℃; Irradiation;	16%
With pyridine; copper(II) bis(trifluoromethanesulfonate) In acetonitrile at 130℃; under 7500.75 - 30003 Torr; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave;

N-formylformamide (18197-22-3) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
Ambient temperature;	78%

N-formylbenzotriazole (72773-04-7) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.15h;	78%

trimethylsilyl formate (18243-21-5) + (diethylamino)triethylsilane (6022-10-2) → N-formyldiethylamine (617-84-5) + Hexamethyldisiloxane (107-46-0) + 1,1,1-triethyl-3,3,3-trimethyl-disiloxane (2652-41-7) + hexaethyl disiloxane (994-49-0)

Conditions	Yield
With N-Methylformamide at 20℃; for 2h;	A 72.5% B 13.6% C n/a D 23.8%
With N-Methylformamide at 20℃; for 2h; Product distribution; Mechanism; various amides as catalysts, other temperature, other time;	A 72.5% B 13.6% C n/a D 23.8%

trimethylsilyl formate (18243-21-5) → N-formyldiethylamine (617-84-5) + Hexamethyldisiloxane (107-46-0) + 1,1,1-triethyl-3,3,3-trimethyl-disiloxane (2652-41-7) + hexaethyl disiloxane (994-49-0)

Conditions	Yield
With N-Methylformamide; (diethylamino)triethylsilane at 20℃; for 2h;	A 72.5% B 13.6% C n/a D 23.8%

(diethylamino)triethylsilane (6022-10-2) → N-formyldiethylamine (617-84-5) + Hexamethyldisiloxane (107-46-0) + 1,1,1-triethyl-3,3,3-trimethyl-disiloxane (2652-41-7) + hexaethyl disiloxane (994-49-0)

Conditions	Yield
With N-Methylformamide; trimethylsilyl formate at 20℃; for 2h;	A 72.5% B 13.6% C n/a D 23.8%

diethylamine (109-89-7) + orthoformic acid triethyl ester (122-51-0) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With dioxo[bis(sulfato-κO)]molybdenum In ethanol for 5h; Reflux; Green chemistry;	70%

diethylamine (109-89-7) + 2,2-Dichloro-3-oxo-butyraldehyde (160663-31-0) → N-formyldiethylamine (617-84-5) + 1,1-Dichloroacetone (513-88-2)

Conditions	Yield
In tetrachloromethane for 12h; Ambient temperature;	A 68% B 60%

carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5) + N,N,N',N'-tetraethylurea (1187-03-7) + N,N,N',N'-tetraethyloxamide (14288-05-2)

Conditions	Yield
With (Et2NH)2CuBr; (Et2NH)2NiBr In tetrahydrofuran under 15001.2 Torr; for 16h; Ambient temperature;	A n/a B n/a C 66%

carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5) + N,N,N',N'-tetraethyloxamide (14288-05-2)

Conditions	Yield
With (Et2NH)2CuBr; (Et2NH)2NiBr In tetrahydrofuran under 15001.2 Torr; for 16h; Ambient temperature;	A n/a B 66%

2-aminopyridine (504-29-0) + triethylamine (121-44-8) → N-formyldiethylamine (617-84-5) + imidazo[1,2-a]pyridine-3-carbaldehyde

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; oxygen In dimethyl sulfoxide at 100℃; for 24h; Sealed tube;	A n/a B 66%

chloroform (67-66-3) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With sodium ethanolate at 50℃; Riemer-Tiemann reaction; Inert atmosphere;	62%
With potassium tert-butylate; water; benzene
With sodium hydroxide

Hex-1-en-2-yl formate (134965-38-1) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
In ethyl acetate for 1h; Ambient temperature;	62%

sec.-butyllithium (598-30-1) + N,N-diethylcarbamyl chloride (88-10-8) → N-formyldiethylamine (617-84-5) + 2-methyl-butyric acid diethylamide (59002-07-2)

Conditions	Yield
Stage #1: sec.-butyllithium With CuCN In tetrahydrofuran at -30℃; for 0.5h; Stage #2: N,N-diethylcarbamyl chloride In tetrahydrofuran at -30 - 0℃; for 2h;	A 11 % Chromat. B 62%

N,N-diethylthioformamide (13839-14-0) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With triphenyltin(IV) hydroxide In benzene-d6 at 90℃; for 8h;	60%

carbon monoxide (201230-82-2) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
With tetracarbonyl nickel In toluene at 180℃; for 24h;	55%
With 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In methanol at 0 - 130℃; under 22502.3 Torr; for 36h; Autoclave;	12.1%
In tetrahydrofuran under 760 Torr; for 24h; Product distribution; Mechanism; Ambient temperature; other conditions: other catalyst, other times, addition of complexing agents, addition of LiBr;

diethylamine (109-89-7) + (1-phenyl-2-methyl-4-phenyl-1-azabuta-1,3-diene)tricarbonyliron(0) → N-formyldiethylamine (617-84-5) + (1E,2E)-N,3-diphenylprop-2-en-1-imine (953-21-9)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 0℃; for 3h;	A 50% B n/a

carbon monoxide (201230-82-2) + bis(diethylamin)nickel bromid + acetylene (74-86-2) → 4-butanolide (96-48-0) + N-formyldiethylamine (617-84-5) + tetraethyl-butynediamide (25883-23-2) + N,N-diethylpropiolamide (51590-64-8)

Conditions	Yield
In tetrahydrofuran; diethyl ether under 750.06 Torr; Ambient temperature;	A 8.9 % Chromat. B 2.4 % Chromat. C 45% D 11%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
	12%

chloral (75-87-6) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

diethyl ether (60-29-7) + chloroacetylene (593-63-5) + diethylamine (109-89-7) → N-formyldiethylamine (617-84-5)

Conditions	Yield
durch folgendes Erwaermen;

N-formyldiethylamine (617-84-5) → 1,1-dichloromethyl-N,N-diethylamine (40416-60-2)

Conditions	Yield
With thionyl chloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	100%
With (pentachloroethyl)phosphorimidic trichloride In benzene

N-formyldiethylamine (617-84-5) + (tert-butyldimethylsilyl)(phenyl)methanone (132868-67-8) + N-(p-methoxybenzylidene)diphenylphosphinamide (119701-95-0) → N,N-diethyl-2-phenyl-2-((tert-butyldimethylsilyl)oxyl)-3-(4-methoxyphenyl)-3-((N’-diphenylphosphinyl)amido)propionamide

Conditions

Yield

Stage #1: N-formyldiethylamine; (tert-butyldimethylsilyl)(phenyl)methanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; Stage #2: N-(p-methoxybenzylidene)diphenylphosphinamide In tetrahydrofuran at -78℃; for 0.5h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; diastereoselective reaction;

100%

N-formyldiethylamine (617-84-5) + N-(p-methoxybenzylidene)diphenylphosphinamide (119701-95-0) + tert-butyldimethylsilyl 4-fluorophenyl ketone → N,N-diethyl-2-(4-fluorophenyl)-2-((tert-butyldimethylsilyl)oxyl)-3-(4-methoxyphenyl)-3-((N’-diphenylphosphinyl)amido)propionamide

Conditions

Yield

Stage #1: N-formyldiethylamine; tert-butyldimethylsilyl 4-fluorophenyl ketone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; Stage #2: N-(p-methoxybenzylidene)diphenylphosphinamide In tetrahydrofuran at -78℃; for 0.5h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; diastereoselective reaction;

100%

N-formyldiethylamine (617-84-5) + C17H28OSi + N-(p-methoxybenzylidene)diphenylphosphinamide (119701-95-0) → N,N-diethyl-2-(4-tert-butylphenyl)-2-((tert-butyldimethylsilyl)oxyl)-3-(4-methoxyphenyl)-3-((N’-diphenylphosphinyl)amido)propionamide

Conditions	Yield
Stage #1: N-formyldiethylamine; C17H28OSi With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; Stage #2: N-(p-methoxybenzylidene)diphenylphosphinamide In tetrahydrofuran at -78℃; for 0.5h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; diastereoselective reaction;	100%

N-formyldiethylamine (617-84-5) + C15H24OSi + N-(p-methoxybenzylidene)diphenylphosphinamide (119701-95-0) → N,N-diethyl-2-(3,4-dimethylphenyl)-2-((tert-butyldimethylsilyl)oxyl)-3-(4-methoxyphenyl)-3-((N’-diphenylphosphinyl)amido)propionamide

Conditions	Yield
Stage #1: N-formyldiethylamine; C15H24OSi With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; Stage #2: N-(p-methoxybenzylidene)diphenylphosphinamide In tetrahydrofuran at -78℃; for 0.5h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; diastereoselective reaction;	100%

N-formyldiethylamine (617-84-5) + ethyl acetoacetate (141-97-9) → 3-diethylcarbamoyloxybut-2-enoic acid ethyl ester (1416425-91-6)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In water at 20 - 70℃; for 0.75h; Green chemistry; stereoselective reaction;	99%
With tert.-butylhydroperoxide; copper nanoparticles on black carbon In water; N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;	80%
With tert.-butylhydroperoxide In water at 80℃; for 4h; Inert atmosphere; stereoselective reaction;	70%
With tert.-butylhydroperoxide; copper(ll) bromide In water at 80℃; for 3h; stereoselective reaction;	68%
With tert.-butylhydroperoxide; copper(II) oxide In water at 20℃; for 4h; Sonication;

N-formyldiethylamine (617-84-5) + o-hydroxyacetophenone (118-93-4) → diethylcarbamic acid 2-acetylphenyl ester (211449-24-0)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In water at 20 - 70℃; for 0.75h; Green chemistry;	99%
With tert.-butylhydroperoxide at 70℃; for 0.5h;	95%
With tert.-butylhydroperoxide; copper diacetate In water at 80℃; for 3h;	84%

N-formyldiethylamine (617-84-5) + ethyl 3-oxo-3-phenylpropionate (94-02-0) → 3-diethylcarbamoyloxy-3-phenylacrylic acid ethyl ester (1416425-90-5)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In water at 20 - 70℃; for 0.75h; Green chemistry; stereoselective reaction;	99%
With tert.-butylhydroperoxide; copper(ll) bromide In water at 80℃; for 3h; stereoselective reaction;	80%

N-formyldiethylamine (617-84-5) + acetoacetic acid methyl ester (105-45-3) → 3-diethylcarbamoyloxybut-2-enoic acid methyl ester (1416425-92-7)

Conditions	Yield
With tert.-butylhydroperoxide; copper(l) chloride In water at 20 - 70℃; for 0.5h; Green chemistry; stereoselective reaction;	99%
With tert.-butylhydroperoxide; copper nanoparticles on black carbon In water; N,N-dimethyl-formamide at 80℃; for 5h; Inert atmosphere;	84%
With tert.-butylhydroperoxide; copper(ll) bromide In water at 80℃; for 3h; stereoselective reaction;	66%
With tert.-butylhydroperoxide; copper(II) oxide In water at 20℃; for 4h; Sonication;

N-formyldiethylamine (617-84-5) + 1-Chloromethylnaphthalene (86-52-2) → 1-<(N,N-diethylamino)methyl>naphthalene (35693-45-9)

Conditions	Yield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;	99%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;	85%

N-formyldiethylamine (617-84-5) + P,P-diphenyl-N-(phenylmethylene)phosphinic amide (98837-46-8, 67764-52-7) + (tert-butyldimethylsilyl)(phenyl)methanone (132868-67-8) → N,N-diethyl-2-phenyl-2-((tert-butyldimethylsilyl)oxyl)-3-phenyl-3-((N’-diphenylphosphinyl)amido)propionamide

Conditions

Yield

Stage #1: N-formyldiethylamine; (tert-butyldimethylsilyl)(phenyl)methanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; Stage #2: P,P-diphenyl-N-(phenylmethylene)phosphinic amide In tetrahydrofuran at -78℃; for 0.5h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; diastereoselective reaction;

99%

N-formyldiethylamine (617-84-5) + toluene-4-sulfonamide (70-55-3) → (E)-N'-((4-methylphenyl)sulfonyl)-N,N-diethylformimidamide (29397-20-4)

Conditions	Yield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;	99%
With thionyl chloride In chloroform at 60℃; for 3h;	96%

N-formyldiethylamine (617-84-5) + 4-chlorobenzo[d]thiazol-2-amine (19952-47-7) → N,N-diethyl-N',N''-bis(4-chloro-2-benzothiazolyl)triaminomethane (112446-70-5)

Conditions	Yield
With benzenesulfonyl chloride In pyridine	98%

N-formyldiethylamine (617-84-5) + m-methoxybenzyl chloride (824-98-6) → N,N-diethyl-3-(methoxyl)benzenemethanamine (27958-95-8)

Conditions	Yield
With NHC-Pd(II)-Im; sodium hydroxide In water at 50℃; for 3h; Inert atmosphere; Schlenk technique;	98%
With potassium hydroxide In water at 50℃; for 3h; Green chemistry;	92%

N-formyldiethylamine (617-84-5) + diphenylcyclopropenone (886-38-4) → 5-(diethylamino)-3,4-diphenyl-2(5H)-furanone

Conditions	Yield
With silver trifluoromethanesulfonate at 130℃; for 2h; Inert atmosphere; Schlenk technique;	98%
With silver hexafluoroantimonate In N,N-dimethyl-formamide at 80℃; for 20h; Inert atmosphere;	86%

N-formyldiethylamine (617-84-5) + trimethylsilyl cyanide (7677-24-9) + phenylacetylene (536-74-3) → 1-ethyl-5-methyl-3-phenyl-1H-pyrrole-2-carbonitrile

Conditions	Yield
With ammonium iodide at 90℃; for 0.25h; Reagent/catalyst; Temperature; Time; Microwave irradiation;	97%
With iodine In neat (no solvent) at 80℃; for 2h; Schlenk technique; Green chemistry;	80%

N-formyldiethylamine (617-84-5) + 1-((5-phenylpent-1-en-2-yl)oxy)pyridin-1-ium bis((trifluoromethyl)sulfonyl)amide → 2-oxo-5-phenylpentyl formate

Conditions	Yield
With water In dichloromethane at 60℃; for 24h;	97%

N-formyldiethylamine (617-84-5) + 2-(2-methylbenzyl)benzoic acid (80716-36-5) → N,N-diethyl-2-(2-methylbenzyl)benzamide (80716-39-8)

Conditions	Yield
With thionyl chloride for 20h;	96%

cobalt(II) trifluoromethanesulfonate + 4,4'-benzene-1,4-diylbis(1H-pyrazole) (1036248-62-0) + N-formyldiethylamine (617-84-5) → Co(1,4-benzenedi(4'-pyrazolyl)(2-))*2(N,N-diethylformamide)*H2O

Conditions	Yield
In further solvent(s) mixt. Co(OTf)2, 1,4-benzenedipyridyl and HCONEt2 in sealed evacuated tube was heated at 150°C for 6 days; ppt. was filtered, washed with HCONEt2 and dried in vacuo for 30 min; elem. anal.;	95%
In further solvent(s) react. in N,N-diethylformamide at 130°C;

N-formyldiethylamine (617-84-5) + indium(III) nitrate hydrate + benzene-1,3,5-tricarboxylic acid (554-95-0) + tetraethylammonium bromide (71-91-0) → (tetraethylammonium)3[In3(1,3,5-benzenetricarboxylate)4]*N,N-diethylformamide

Conditions	Yield
In further solvent(s) C6H3(COOH)3, (C2H5)4NBr, In(NO3)3*xH2O in N,N-diethylformamide was heated at 120°C for 4 days, cooled to room temp.; washed with ethanol; elem. anal.;	95%

N-formyldiethylamine (617-84-5) + Dimethylphenylsilane (766-77-8) → phenyldimethylsilyloxymethyldiethylamine (1366432-35-0)

Conditions	Yield
With CpMn(CO)3 for 16h; Irradiation;	95%

N-formyldiethylamine (617-84-5) + (tert-butyldimethylsilyl)(naphthalen-2-yl)methanone + N-(p-methoxybenzylidene)diphenylphosphinamide (119701-95-0) → N,N-diethyl-2-(2-naphthyl)-2-((tert-butyldimethylsilyl)oxyl)-3-(4-methoxyphenyl)-3-((N’-diphenylphosphinyl)amido)propionamide

Conditions

Yield

Stage #1: N-formyldiethylamine; (tert-butyldimethylsilyl)(naphthalen-2-yl)methanone With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; Stage #2: N-(p-methoxybenzylidene)diphenylphosphinamide In tetrahydrofuran at -78℃; for 0.5h; Brook Silaketone Rearrangement; Inert atmosphere; Schlenk technique; diastereoselective reaction;

95%

N-formyldiethylamine (617-84-5) + cyclohexanone (108-94-1) → N,N-diethyl-1-hydroxycyclohexanecarboxamide

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at 25℃; for 0.0166667h;	95%

1,3-Benzothiazole (95-16-9) + N-formyldiethylamine (617-84-5) → N,N-diethylbenzo[d]thiazol-2-amine (24255-48-9)

Conditions	Yield
With silver(I) acetate; sodium t-butanolate In neat (no solvent) at 120℃; for 5h; Inert atmosphere;	95%

N-formyldiethylamine (617-84-5) + 3-Phenylpropionic acid (501-52-0) → N,N-diethyl-3-phenylpropanamide (18859-19-3)

Conditions	Yield
With sulfur trioxide pyridine complex at 160℃; Schlenk technique; Inert atmosphere;	95%

N-formyldiethylamine (617-84-5) + N-(1-phenyl)sulfamide (15959-53-2) → (E)-N,N-diethyl-N'-(N-phenylsulfamoyl)formimidamide

Conditions	Yield
With trichlorophosphate In dichloromethane at 40℃; for 9h;	95%

4,4'-bis-(1H-imidazol-1-yl)biphenyl (855766-92-6) + N-formyldiethylamine (617-84-5) + cobalt(II) nitrate hexahydrate + 2′,3′,5′,6′-tetramethyl(1,1′:4′,1″-terphenyl)-4,4″-dicarboxylic acid (1394899-62-7) → 2Co(2+)*2C24H20O4(2-)*2C5H11NO*C18H14N4

Conditions	Yield
at 120℃; for 24h; Sealed tube;	95%

Upstream product

• 64-18-6 formic acid 
• 109-89-7 diethylamine 
• 60-29-7 diethyl ether 
• 593-63-5 chloroacetylene 
• 64-17-5 ethanol 
• 107-31-3 Methyl formate 
• 74-90-8 hydrogen cyanide 
• 67-66-3 chloroform 
• 1493-02-3 formyl fluoride 
• 5411-58-5 ethyl N,N-diethyloxamate 
• 18243-21-5 trimethylsilyl formate 
• 6022-10-2 (diethylamino)triethylsilane 
• 77287-34-4 formamide 
• 1630-73-5 N-ethyloxazolidine 

Downstream Products

• 91-65-6 diethyl-cyclohexyl-amine 
• 772-54-3 N,N-diethylbenzylamine 
• 102-53-4 bis-(diethylamino)methane 
• 59313-90-5 N,N-diethyl-1-methyl-2-phenylethylamine 
• 29665-24-5 N¹,N¹-diethyl-N²-phenylsulfonylformamidine 
• 1783-39-7 N-(p-Chlorphenyl)-N'.N'-diaethyl-formamidin 
• 46708-03-6 2-(piperidin-1-yl)quinoline 
• 92940-24-4 5-[N,N-bis(ethyl)amino]-1,4-thiazole-2-carboxaldehyde 
• 30451-38-8 1,9-dimethylcarbazole-3-carboxaldehyde 
• 78153-07-8 1,2,3,4-tetrahydro-9-methylcarbazole-7-carboxaldehyde 
• 1485-19-4 9-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 102237-53-6 9-benzyl-1,2,3,4-tetrahydrocarbazole-7-carbaldehyde 
• 87167-61-1 9-benzyl-1-methyl-9H-carbazole-3-carbaldehyde 
• 87167-64-4 (9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)carboxaldehyde 

Relevant articles and documents

Mesoporous Sn(IV) Doping DFNS Supported BaMnO3 Nanoparticles for Formylation of Amines Using Carbon Dioxide

Abstract: In the present paper, Sn(IV) doping DFNS (SnD) supported nanoparticles of BaMnO3 (BaMnO3/SnD) and using as a catalyst for the N-formylation of amines by CO2 hydrogenation. In this catalyst, the SnD with the ratios of Si/Sn in the range of from 6 to 50 were obtained with method of direct hydrothermal synthesis (DHS) as well as the nanoparticles of BaMnO3 were on the surfaces of SnD in situ reduced. Scanning electron microscope (SEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), X-ray energy dispersive spectroscopy (EDS), and transmission electron microscopy (TEM) were utilized for characterizing the nanostructures BaMnO3/SnD. It is found that the nanostructures of BaMnO3/SnD can be a nominate due to its effective and novel catalytic behavior in N-formylation of amines through hydrogenation of CO2. Graphic Abstract: [Figure not available: see fulltext.]

A N-Phosphinoamidinato NHC-Diborene Catalyst for Hydroboration

The use of the N-phosphinoamidinato NHC-diborene catalyst 2 for hydroboration is described. The N-phosphinoamidine tBu2PN(H)C(Ph)= N(2,6-iPr2C6H3) was reacted with nBuLi in Et2O to afford the lithium derivative, which was then treated with B2Br4(SMe2)2 in toluene to form the N-phosphinoamidinate-bridged diborane 1. It was reacted with the N-heterocyclic carbene IMe (:C{N(CH3)C(CH3)}2) and excess potassium graphite at room temperature in toluene to give the N-phosphinoamidinato NHC-diborene compound 2. It can stoichiometrically activate ammonia-borane and carbon dioxide. It also showed catalytic capability. A 2 mol % portion of 2 catalyzed the hydroboration of carbon dioxide (CO2) with pinacolborane (HBpin) in deuterated benzene (C6D6) at 110 °C (conversion >99%), which afforded the methoxyborane [pinBOMe] (yield 97.8%, TOF 33.3 h-1) and the bis(boryl) oxide [(pinB)2O]. In addition, 5 mol % of 2 catalyzed the N-formylation of secondary and primary amines by carbon dioxide and pinacolborane to yield the N-formamides (average yield 91.6%, TOF 25.9 h-1). Moreover, 2 showed chemoselectivity toward catalytic hydroboration of carbonyl compounds. In mechanistic studies, the B= B double bond in compound 2 activated the substrates, the intermediates of which then underwent hydroboration with pinacolborane to yield the products and regenerate catalyst 2.