93-61-8

Basic information

• Product Name: N-Methylformanilide
• Synonyms: Formamide,N-methyl-N-phenyl-;Formanilide, N-methyl-;Methylphenylformamide;N-Methyl-N-formylaniline;n-methyl-n-phenyl-formamid;N-Phenyl-N-methylformamide;FORMIC ACID N-METHYLANILIDE;METHYLFORMANILIDE
• CAS NO: 93-61-8
• Molecular Formula: C₈H₉NO
• Molecular Weight: 135.16
• EINECS: 202-262-3
• Product Categories: Acids and Esters;organic chemical;Amides;Building Blocks;C8 to C20+;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks;aldehyde;Pyridines
• Mol File: 93-61-8.mol
• Article Data: 241

Chemical Properties

• Melting Point: 8-13 °C(lit.)
• Boiling Point: 243-244 °C(lit.)
• Flash Point: 260 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.095 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0329mmHg at 25°C
• Refractive Index: n20/D 1.561(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 10.3g/l
• PKA: 0.53±0.50(Predicted)
• Water Solubility: immiscible
• BRN: 636496
• CAS DataBase Reference: N-Methylformanilide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylformanilide(93-61-8)
• EPA Substance Registry System: N-Methylformanilide(93-61-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-43-38
• Safety Statements: 36/37
• WGK Germany: 2
• TSCA: Yes
• Hazardous Substances Data: 93-61-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 93-61-8 differently. You can refer to the following data:
1. Organic synthesis.
2. N-Methylformanilide is used as a formylating reagent for certain organometallics. It is in combination with phosphoryl chloride used for Vilsmeier-Haack reactions and in heterocycle syntheses. Further, it acts as a swelling agent in the dyeing process of meta-aramid fibers.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C8H9NO/c1-9(7-10)8-5-3-2-4-6-8/h2-7H,1H3

Synthetic route

formic acid (64-18-6) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With copper (II) carbonate hydroxide; phenylsilane; cyclohexyldiphenylphosphine In acetonitrile at 60℃; for 12h;	99%
In toluene for 0.0833333h; Reflux;	96%
In toluene at 88 - 108℃;	96%

N,N-dimethyl-formamide (68-12-2, 33513-42-7) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With zinc(II) phthalocyanine; carbon dioxide; phenylsilane at 25℃; under 3750.38 Torr; for 6h; Reagent/catalyst; Temperature; Pressure; Autoclave; chemoselective reaction;	99%
With 1H-imidazole; nickel oxinate at 150℃;	85%
With t-butyldimethylsiyl triflate at 20℃; for 24h;	82%
With 1,2,4-Triazole; 8-quinolinol; copper(II) choride dihydrate at 150℃;	74%
With methyl benzylphosphonic chloride at 130℃; for 3.5h;	59%

carbon dioxide (124-38-9) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With copper(II) acetate dihydrate; phenylsilane; 1,2-bis-(diphenylphosphino)ethane In toluene at 25℃; under 760.051 Torr; for 2h;	99%
With Zn(salen); phenylsilane at 25℃; under 3750.38 Torr; for 7h; Reagent/catalyst; Pressure; Temperature;	99%
With Al(salen); phenylsilane at 100℃; under 37503.8 Torr; for 3h; Reagent/catalyst; Pressure; Temperature; Autoclave;	99%

triethoxysilyl formate + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
In acetonitrile at 30℃;	99%

N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With formaldehyd; sodium hydroxide In ethanol; water at 27℃; for 9h;	97%
With ethanol; oxalic acid anschliessend man erhitzt das abgeschiedene Salz bis zur Beendung der Gasentwicklung auf 160-180grad;

N-phenylthioacetamide (36325-39-0) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 20℃; for 0.5h;	97%
With triphenyltin(IV) hydroxide In benzene-d6 at 90℃; for 3h;	50%

formaldehyd (50-00-0) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With sodium hydroxide In ethanol; water at 27℃; for 9h;	97%
With sodium hydroxide In water; toluene at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; chemoselective reaction;	94%
With sodium hydroxide In water at 25℃; for 6h;	93%

carbon monoxide (201230-82-2) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With phenylsilane; C19H37N2(1+)*Br(1-) In neat (no solvent) at 20℃; under 3750.38 Torr; for 6h; Autoclave;	95%
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 100℃; under 22502.3 Torr; for 20h; Autoclave;	70%
diethylzinc at 100℃; under 34200 Torr; for 18h;	30%
With Wilkinson's catalyst; copper diacetate; lithium carbonate In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; under 760.051 Torr; for 36h; Schlenk technique;

N,N-dimethyl-aniline (121-69-7) + triethyl phosphite (122-52-1) → triethyl phosphate (78-40-0) + N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; oxygen In 1,2-dichloro-ethane; acetonitrile at 25℃; for 24h; Schlenk technique; Irradiation;	A n/a B 95%

dihydroxyacetone (96-26-4) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With Cu/Al2O3; dihydrogen peroxide In water at 50℃; for 12h; Green chemistry;	95%

methanol (67-56-1) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8) + Formanilid (103-70-8)

Conditions	Yield
With lithium hydroxide In water for 4h; Air; Reflux;	A 94% B 5%

N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8) + Formanilid (103-70-8)

Conditions	Yield
With methanol; lithium hydroxide In water at 80℃; for 4h;	A 94% B 5%

carbon dioxide (124-38-9) + N-methylaniline (100-61-8) → N,N-dimethyl-aniline (121-69-7) + N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With phenylsilane In N,N-dimethyl acetamide at 60℃; for 4h; Time; Sealed tube;	A 94% B 8%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 110℃; under 760.051 Torr; for 48h; Mechanism; Solvent; Reagent/catalyst; Schlenk technique;	A 92% B 8%
With phenylsilane; C23H23O2P In acetonitrile at 100℃; under 15001.5 Torr; for 24h;	A 8% B 91%

chloroform (67-66-3) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 20℃; for 18h;	93%
With sodium ethanolate at 50℃; Riemer-Tiemann reaction; Inert atmosphere;	65%

Glyoxilic acid (298-12-4) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With copper(II) acetate dihydrate; nickel(II) chloride hexahydrate; sodium perchlorate; caesium carbonate In dimethyl sulfoxide at 20℃; Reagent/catalyst; Solvent; Electrolysis;	93%

dimethyl(phenyl)silyl formate + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
at 60℃; for 15h; Inert atmosphere;	92%

4-methoxy-benzoyl chloride (100-07-2) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	91.2%

lithium bis(N-methyl-N-phenylcarbamoyl)cuprate → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With hydrogenchloride; diethyl ether In diethyl ether at -78℃; for 0.5h;	91%

Methyl formate (107-31-3) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 25℃; for 48h;	91%
at 50℃;	80%

(formyloxy)(acetoxy)phenylmethane (113388-44-6) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
In neat (no solvent) at 20℃; for 1h;	91%

N-methylaniline (100-61-8) + formic acid ethyl ester (109-94-4) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With Silphos at 20℃; for 12h;	90%
With N1-(3-(trimethoxysilyl)propyl)ethane-1,2-diamine-sulfamic acid supported on mesoporous silica SBA-15 In neat (no solvent) at 50℃; Green chemistry;	90%
With immobilized H2SO4 on activated charcoal at 54℃; for 1.33333h;	90%

3-phenyl-2-azido-N-(2-iodophenyl)-N-methylpropanamide (1029963-89-0) → 3-benzyl-1-methyl-2(1H)-quinoxalinone (132346-18-0) + N-methyl-N-phenyl-carbamoyl cyanide (99839-93-7) + phenylacetonitrile (140-29-4) + N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃;	A n/a B n/a C 80% D 89%

α,α,α-iodinefluoroacetophenone (150542-06-6) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With water; sodium hydroxide In acetonitrile at 20℃; for 0.166667h;	89%

chloroform (67-66-3) + N-(3-methylbut-2-enyl)-N-methylaniline (10229-37-5) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide at 20℃; for 4h;	88%

N,N-dimethyl-aniline (121-69-7) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With air In 1,2-dimethoxyethane at 20℃; under 760.051 Torr; Solvent; Irradiation;	87%
With FeIII(meso-tetrakis(o,o,m,m-tetrafluoro-p-(dimethylamino)phenyl)porphyrinato)OTf; dihydrogen peroxide; acetic acid In methanol; water at 20℃; for 2h; Reagent/catalyst; chemoselective reaction;	82%
With benzyl(triethyl)ammoniumpermanganate In dichloromethane	78%

2-(1-adamantyl)-2-azido-N-(2-iodophenyl)-N-methylacetamide (1029963-87-8) → 3-((1s,3s)-adamantan-1-yl)-1-methylquinoxalin-2(1H)-one (1029963-99-2) + 1-adamantanecarbonitrile (23074-42-2) + N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃;	A n/a B 86% C 84%

N-methyl-N-phenacylaniline (32119-53-2) → benzoic acid (65-85-0) + N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With TEMPO; oxygen In acetonitrile at 50℃; under 760.051 Torr; for 12h;	A 71% B 86%

2-azido-N-(2-iodophenyl)-N-methyltridecanamide (1029963-84-5) → 1-methyl-3-undecyl-2(1H)-quinoxalinone (1029964-01-9) + N-methyl-N-phenylformamide (93-61-8) + undecyl cyanide (2437-25-4)

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 110℃;	A 13% B 80% C 85%

Ethyl bromodifluoroacetate (667-27-6) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With copper (I) acetate; caesium carbonate; XPhos In water; N,N-dimethyl-formamide at 110℃; for 12h; Reagent/catalyst; Solvent; Schlenk technique;	85%
With water In N,N-dimethyl-formamide at 110℃; for 6h; Mechanism; Solvent; Time; Temperature; Reagent/catalyst; Schlenk technique;	84%
With copper (I) acetate; caesium carbonate; XPhos In N,N-dimethyl-formamide at 110℃; for 12h; Reagent/catalyst; Solvent;	82%

formamide (77287-34-4, 77287-35-5, 60100-09-6) + N-methylaniline (100-61-8) → N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With sulfated tungstate at 100℃; for 60h; Green chemistry;	84%
With [Mn((N'1E,N'2E)-N'1,N'2-bis(phenyl(pyridin-2-yl)methylene)oxalohydrazide(-H))(OAc)(H2O)]2*6H2O In neat (no solvent) at 120℃; for 24h;	83%
With 1-(3-sulfopropyl)pyridinium phosphotungstate In neat (no solvent) at 100℃; for 1.5h; Microwave irradiation;	75%

2-carbethoxyindole (3770-50-1) + N-methyl-N-phenylformamide (93-61-8) → ethyl 3-formyl-1H-indole-2-carboxylate (18450-27-6)

Conditions	Yield
With trichlorophosphate In 1,2-dichloro-ethane for 1.5h; Heating / reflux;	100%
With trichlorophosphate In 1,2-dichloro-ethane Vilsmeier-Haack reaction; Heating;	86%
Stage #1: N-methyl-N-phenylformamide With chlorophosphonic acid at 20℃; for 0.25h; Stage #2: 2-carbethoxyindole In 1,2-dichloro-ethane for 1.5h; Heating / reflux;	66%
With 1,2-dichloro-ethane; trichlorophosphate Behandeln des Reaktionsgemisches mit wss. Natriumacetat;

6,7,8-trimethoxy-1,4-dimethylcarbazole (129819-66-5) + N-methyl-N-phenylformamide (93-61-8) → 3-formyl-6,7,8-trimethoxy-1,4-dimethylcarbazole (129819-67-6)

Conditions	Yield
With trichlorophosphate for 3.5h; Heating;	100%
With trichlorophosphate In Trichloroethylene for 3.5h; Heating;	99%

3-fluorobromobenzene (1073-06-9) + N-methyl-N-phenylformamide (93-61-8) → 2-bromo-6-fluorobenzaldehyde (360575-28-6)

Conditions	Yield
Stage #1: 3-fluorobromobenzene With hydrogenchloride; n-butyllithium; diisopropylamine In tetrahydrofuran; hexanes at -78 - -70℃; for 2.5h; Stage #2: N-methyl-N-phenylformamide In tetrahydrofuran; hexanes at -78 - -70℃; for 2h;	100%

N-methyl-N-phenylformamide (93-61-8) + p-aminoethylbenzoate (94-09-7) → N-(4-ethoxycarbonylphenyl)-N'-methyl-N'-phenylformamidine (57834-33-0)

Conditions	Yield
With thionyl chloride In toluene at 20℃; for 19.5h; Reagent/catalyst;	99.4%
In water; toluene for 5h; Solvent; Reflux;	92.2%

2-butylthiophene (1455-20-5) + N-methyl-N-phenylformamide (93-61-8) → 5-butylthiophene-2-carboxaldehyde (98954-25-7)

Conditions	Yield
With trichlorophosphate	99%
With trichlorophosphate

carbon dioxide (124-38-9) + N-methyl-N-phenylformamide (93-61-8) → N,N-dimethyl-aniline (121-69-7)

Conditions	Yield
With phenylsilane; triphenylphosphine In tetrahydrofuran at 120℃; under 3750.38 Torr; for 24h; Autoclave; Green chemistry;	99%

toluene-4-sulfonamide (70-55-3) + N-methyl-N-phenylformamide (93-61-8) → (E)-N-methyl-N-phenyl-N'-tosylformimidamide

Conditions	Yield
With diazoacetic acid ethyl ester; zinc trifluoromethanesulfonate In cyclohexane for 12h; Reflux; stereoselective reaction;	99%

7-Methyl-imidazo[1,2-a]pyridine (874-39-5) + N-methyl-N-phenylformamide (93-61-8) → 7-methylimidazo<1,2-a>pyridine-3-carboxaldehyde (30384-94-2)

Conditions	Yield
With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In ethanol at 80℃; for 11h; Reagent/catalyst;	98.8%

8-methyl-2-phenylimidazo[1,2-a]pyridine (885-89-2) + N-methyl-N-phenylformamide (93-61-8) → 8-methyl-2-phenylimidazo[1,2-a]pyridine-3-carbaldehyde (524724-72-9)

Conditions	Yield
With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In chlorobenzene at 80℃; for 10h; Reagent/catalyst;	98.6%

2-methylimidazo[1,2-a]pyridine (934-37-2) + N-methyl-N-phenylformamide (93-61-8) → 2-Methylimidazo<1,2-a>pyridin-3-carboxaldehyd (30384-93-1)

Conditions	Yield
With tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2]; N-butylpyridine p-toluenesulfonate In toluene at 70℃; for 12h; Reagent/catalyst;	98.3%

N-methyl-N-phenylformamide (93-61-8) + 1,4-Dimethoxy-2-[(3-methoxybenzyl)thio]benzol (648956-90-5) → 2,5-Dimethoxy-4-[(3-methoxybenzyl)thio]benzaldehyd (648957-13-5)

Conditions	Yield
Stage #1: N-methyl-N-phenylformamide; 1,4-Dimethoxy-2-[(3-methoxybenzyl)thio]benzol With trichlorophosphate at 15 - 60℃; Vilsmeier-formylation; Stage #2: With water for 0.5h;	98%

N-methyl-N-phenylformamide (93-61-8) + methyl 4-methyl-1H-indole-2-carboxylate (136831-13-5) → methyl 3-formyl-4-methylindole-2-carboxylate (691362-81-9)

Conditions	Yield
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 20℃; for 0.25h; Stage #2: methyl 4-methyl-1H-indole-2-carboxylate In 1,2-dichloro-ethane for 2.5h; Heating; Further stages.;	98%

ferrocene (102-54-5) + N-methyl-N-phenylformamide (93-61-8) → ferrocenecarboxaldehyde (12093-10-6)

Conditions	Yield
Stage #1: N-methyl-N-phenylformamide With trichlorophosphate at 0℃; for 0.25h; Stage #2: ferrocene at 20℃; Inert atmosphere;	98%
With phosphorus oxychloride In neat (no solvent) anilide and P-compd. stirring at room temp. for 30 min, Fe-compd. addn.,mixt. stirring at room temp. for 3 d, quenching by pouring onto ice, aq . layer extn. after 2 h with Et2O, org. layer drying (MgSO4), vac. concn.; residue flash column chromy. (SiO2, petrol/E2O 7:3 to 5:5), recrystn. (hot petroleum);	87%
With trichlorophosphate In neat (no solvent) Vilsmeyer formylation; double mol amt. of formylation mixt., few days at ambient temp.;;	81%

2-isopropoxynaphthalene (15052-09-2) + N-methyl-N-phenylformamide (93-61-8) → 2-iso-Propoxynaphthalin-1-carbaldehyd (885-24-5)

Conditions	Yield
Stage #1: 2-isopropoxynaphthalene; N-methyl-N-phenylformamide With trichlorophosphate at 0 - 75℃; for 12h; Vilsmeier-Haack reaction; Stage #2: With water; sodium hydroxide Vilsmeier-Haack reaction;	98%

p-methoxybenzyl chloride (824-94-2) + N-methyl-N-phenylformamide (93-61-8) → 4-methoxy-N-methyl-N-phenylbenzenemethanamine (37931-52-5)

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;	80%

C12H16N2 + N-methyl-N-phenylformamide (93-61-8) → 2-tert-butyl-6-methylimidazo[1,2-a]pyridine-3-carbaldehyde

Conditions	Yield
With 1-(4-sulfonylbutyl)pyridinium p-toluenesulfonate; tert.-butylhydroperoxide; cyclopentadienyltricarbonyliron; [copper(II)(trifluoroacetylacetonate)2] In 1-methyl-pyrrolidin-2-one at 100℃; for 8h; Reagent/catalyst;	97.9%

N-methyl-N-phenylformamide (93-61-8) → N-methylaniline (100-61-8)

Conditions	Yield
With 1,3-Dimethoxybenzene; trichlorophosphate In dichloromethane at 40℃; for 24h; Product distribution; other carboxamides, var. solvents, var. temp., var. time, var. reagents mole ratio;	97%
With C18H37ClMoNO2P2; hydrogen; sodium triethylborohydride In tetrahydrofuran; toluene at 100℃; under 37503.8 Torr; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Pressure; Temperature; Autoclave; Glovebox;	94%
With aluminum oxide; potassium fluoride for 0.333333h; microwave irradiation;	80%

1,4-dimethoxy-2,3-methylenedioxybenzene (23731-75-1) + N-methyl-N-phenylformamide (93-61-8) → 4,7-dimethoxy-benzo[1,3]dioxole-5-carbaldehyde (17055-09-3)

Conditions	Yield
With trichlorophosphate at 0 - 20℃; for 3h; Vilsmeier-Haack Formylation;	97%
With trichlorophosphate for 48h; Ambient temperature;	87%

Upstream product

• 62-53-3 aniline 
• 149-73-5 trimethyl orthoformate 
• 64-18-6 formic acid 
• 100-61-8 N-methylaniline 
• 64-17-5 ethanol 
• 16694-46-5 ethyl formimidate hydrochloride 
• 109-94-4 formic acid ethyl ester 
• 60-29-7 diethyl ether 
• 55948-95-3 formanilide; silver (I)-compound 
• 74-88-4 methyl iodide 
• 109-99-9 tetrahydrofuran 
• 121-69-7 N,N-dimethyl-aniline 
• 100-07-2 4-methoxy-benzoyl chloride 
• 107-31-3 Methyl formate 

Downstream Products

• 98-03-3 thiophene-2-carbaldehyde 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 5928-48-3 4,5-dimethylthiophene-2-carboxaldehyde 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 343268-79-1 3,4-dimethylthiophene-2-carbaldehyde 
• 36880-33-8 5-ethyl-thiophene-2-carbaldehyde 
• 63826-44-8 2,4,5-trimethyl-thiophene-3-carbaldehyde 
• 35250-76-1 5-n-propylthiophene-2-carbaldehyde 
• 24445-35-0 5-(methylthio)thiophene-2-carboxaldehyde 
• 104804-16-2 5-isobutylthiophene-2-carbaldehyde 
• 3541-37-5 benzothiophene-2-carboxaldehyde 
• 877-03-2 5-bromo-1H-indole-3-carboxaldehyde 
• 25365-68-8 1-Formyl-2,3-dimethylindolizin 
• 25932-48-3 N‐methyl‐N‐phenylquinolin‐2‐amine 

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The invention relates to an olefin functionalized IPr.HCl monomer, a preparation method thereof, a method for preparing an N-heterocyclic carbene functionalized organic polymer (PS-IPr-x) by using the olefin functionalized IPr.HCl monomer, and application of the N-heterocyclic carbene functionalized organic polymer as a heterogeneous catalyst for catalyzing reduction N-formylation of carbon dioxide and amine. A heterogeneous catalyst is prepared by using cheap and easily available DVB as a polymerization cross-linking agent through an AIBN-initiated olefin polymerization method, and has the advantages of low preparation cost and simple preparation method. Meanwhile, the catalytic activity of the catalyst is obviously higher than that of reported catalysts, and the catalyst has a wide practical application prospect.

Germyliumylidene: A Versatile Low Valent Group 14 Catalyst

Bis-NHC stabilized germyliumylidenes [RGe(NHC)2]+ are typically Lewis basic (LB) in nature, owing to their lone pair and coordination of two NHCs to the vacant p-orbitals of the germanium center. However, they can also show Lewis acidity (LA) via Ge?CNHC σ* orbital. Utilizing this unique electronic feature, we report the first example of bis-NHC-stabilized germyliumylidene [MesTerGe(NHC)2]Cl (1), (MesTer=2,6-(2,4,6-Me3C6H2)2C6H3; NHC= IMe4=1,3,4,5-tetramethylimidazol-2-ylidene) catalyzed reduction of CO2 with amines and arylsilane, which proceeds via its Lewis basic nature. In contrast, the Lewis acid nature of 1 is utilized in the catalyzed hydroboration and cyanosilylation of carbonyls, thus highlighting the versatile ambiphilic nature of bis-NHC stabilized germyliumylidenes.