40652-40-2

Basic information

• Product Name: 1-FORMAMIDO-1-CYCLOHEXENE
• Synonyms: 1-FORMAMIDO-1-CYCLOHEXENE;N-(1-CYCLOHEXENYL)FORMAMIDE;N-CYCLOHEXENYLFORMAMIDE;N-CYCLOHEX-1-ENYL-FORMAMIDE;N-(Cyclohex-1-en-1-yl)forMaMide;cyclohexene formamide 97%
• CAS NO: 40652-40-2
• Molecular Formula: C₇H₁₁NO
• Molecular Weight: 125.17
• Mol File: 40652-40-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 58-63 °C
• Boiling Point: 282.3°C at 760 mmHg
• Flash Point: 158.8°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 0.00338mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: 2-8°C
• PKA: 15.62±0.20(Predicted)
• CAS DataBase Reference: 1-FORMAMIDO-1-CYCLOHEXENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-FORMAMIDO-1-CYCLOHEXENE(40652-40-2)
• EPA Substance Registry System: 1-FORMAMIDO-1-CYCLOHEXENE(40652-40-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 40652-40-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 3343, 1988 DOI: 10.1016/0040-4039(88)85157-8

InChI:InChI=1/C7H11NO/c9-6-8-7-4-2-1-3-5-7/h4,6H,1-3,5H2,(H,8,9)

Synthetic route

Cyclohexanone oxime (100-64-1) → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
With 1H-imidazole; titanium acetate; formyl acetic anhydride In N,N-dimethyl-formamide at 25℃; for 4h;	97%

C13H17NS (128828-05-7) + Acetic formic anhydride (2258-42-6) → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
With triphenylphosphine; methyloxirane In dichloromethane for 18h; Ambient temperature;	76%

cyclohexanone (108-94-1) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
With sulfuric acid In toluene for 12h; Condensation; Heating; Dean-Stark-conditions;	76%
With sulfuric acid In toluene	70%

1-cyano-1-formamidocyclohexane (1125-02-6) → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran for 6h; Heating;	74%
With potassium tert-butylate In tetrahydrofuran for 6h; Reflux; Inert atmosphere;	74%
at 590℃; under 14 Torr;

cyclohexanone (108-94-1) + 1.1'-dinitro-dicyclohexyl → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 61 percent / aq. NH4Cl / diethyl ether / 23 °C 2: 53 percent / Ac2O / 12 h / 23 °C 3: 74 percent / t-BuOK / tetrahydrofuran / 6 h / Heating View Scheme

1-amino-1-cyanocyclohexane (5496-10-6) → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 53 percent / Ac2O / 12 h / 23 °C 2: 74 percent / t-BuOK / tetrahydrofuran / 6 h / Heating View Scheme
Multi-step reaction with 2 steps 1: HCO2H 2: 590 °C / 14 Torr View Scheme

1-hydroxy-1-cyclohexanecarbonitrile (931-97-5) → N-(cyclohexen-1-yl)formamide (40652-40-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: liq. NH3 / methanol 2: HCO2H 3: 590 °C / 14 Torr View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 1-isocyanocyclohexene (1121-57-9)

Conditions	Yield
With pyridine; 1,3,5-trichloro-2,4,6-triazine In dichloromethane at 100℃; for 0.166667h; microwave irradiation;	96%
With benzene-1,3-disulfonyl chloride; triethylamine In dichloromethane at 110℃; for 1h;	94%
With Burgess Reagent In dichloromethane for 12h; Ambient temperature;	77%

N-(cyclohexen-1-yl)formamide (40652-40-2) → 1-isocyanocyclohexene (1121-57-9) + 1-Isocyano-7-oxa-bicyclo[4.1.0]heptane (128798-30-1)

Conditions	Yield
With trifluoromethylsulfonic anhydride; i-PrNEt; 3,3-dimethyldioxirane 1.) CH2Cl2, -40 deg C; 2.) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;
With trifluoromethylsulfonic anhydride; 3,3-dimethyldioxirane; N-ethyl-N,N-diisopropylamine 1.) CH2Cl2, -40 deg C; 2.) -78 deg C; Yield given. Multistep reaction. Yields of byproduct given;

N-(cyclohexen-1-yl)formamide (40652-40-2) → rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-(2-thymin-methyl-benzoyl)-amino]-3,3-dimethyl-butyric acid-(cyclohexen-1-yl)-amide (255736-71-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / phosgene; NEt3 / CH2Cl2 / 1 h / 0 °C 2: 52 percent / methanol / 48 h / 20 °C View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → rac-2-[(2-isobutyryl-aminophenyl)-thyminacetyl-amino]-biphenyl-4-yl-acetic acid-(cyclohexen-1-yl)-amide (255735-94-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / phosgene; NEt3 / CH2Cl2 / 1 h / 0 °C 2: 51 percent / methanol / 48 h / 20 °C View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 2-[(2-tert-butyloxycarbonyl-aminoethyl)-(2-thyminhexanoyl)-amino]-ortho-chlorophenyl-acetic acid-(cyclohexen-1-yl)-amide

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / phosgene; NEt3 / CH2Cl2 / 1 h / 0 °C 2: 39 percent / methanol / 48 h / 20 °C View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-(2-amino-6-benzyloxy-N-9-purinacetyl)-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / phosgene; NEt3 / CH2Cl2 / 1 h / 0 °C 2: 31 percent / methanol / 48 h / 20 °C View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N6-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide (255735-96-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 71 percent / phosgene; NEt3 / CH2Cl2 / 1 h / 0 °C 2: 78 percent / methanol / 48 h / 20 °C View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 2-[Acetyl-(4-methoxy-benzyl)-amino]-N-cyclohex-1-enyl-3-methyl-butyramide (171070-14-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 2-(Acetyl-decyl-amino)-N-cyclohex-1-enyl-2-phenyl-acetamide

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → (R,S)-N-(1-cylohexenyl)-2-(N'-(4-methoxybenzyl)formamido)phenylacetamide (171070-16-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: 72 percent / methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → N-Cyclohex-1-enyl-2-(cyclohexyl-phenylacetyl-amino)-3-methyl-butyramide

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 2-[Acetyl-(4-methoxy-benzyl)-amino]-N-cyclohex-1-enyl-2-phenyl-acetamide (171070-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 1-[Acetyl-(4-methoxy-benzyl)-amino]-cyclohexanecarboxylic acid cyclohex-1-enylamide (171070-17-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → Dodecanoic acid [(cyclohex-1-enylcarbamoyl)-phenyl-methyl]-(4-methoxy-benzyl)-amide

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → N-Cyclohex-1-enyl-2-phenyl-2-piperidin-1-yl-acetamide (175606-30-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → N-Butyl-N-[(cyclohex-1-enylcarbamoyl)-phenyl-methyl]-benzamide (175606-32-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → (R,S)-N-(1-cyclohexenyl)-2-(N'-(4-methoxybenzyl)-2-aminobenzamido)-3-methylbutanamide (175606-21-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: 1.) 4 A molecular sieves / 1.) CH3OH, 23 deg C, 1 h, 2.) CH3OH, hexane, 23 deg C, 18 h View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 2-Amino-N-butyl-N-[(cyclohex-1-enylcarbamoyl)-phenyl-methyl]-5-iodo-benzamide (175606-23-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: 1.) 4 A molecular sieves / 1.) CH3OH, 23 deg C, 1 h, 2.) CH3OH, hexane, 23 deg C, 18 h View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → (3R,4S)-2-[Acetyl-(4-methoxy-benzyl)-amino]-3,4-bis-benzyloxy-N-cyclohex-1-enyl-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyramide

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / diazabicyclo<2.2.2>octane, triethylenediamine, triphosgene / CH2Cl2 / 0.5 h / 0 °C 2: 85 percent / methanol / 12 h / Ambient temperature View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → C27H35N3O4 (1354014-33-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: triethylamine; trichlorophosphate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere 2.1: methanol / 0.25 h / 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → 1-cyclohexenyl 3,4,5,7-tetra-O-benzyl-2,6-dideoxy-2,6-(pent-4-enimido)-D-glycero-D-idoheptonamide (1426550-76-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; trichlorophosphate / dichloromethane / 1 h / -30 °C / Inert atmosphere 2: methanol / 0 - 5 °C / Inert atmosphere View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → C16H27N3O4

Conditions	Yield
Multi-step reaction with 2 steps 1: Burgess Reagent / acetonitrile / 0.17 h / 50 °C / Microwave irradiation 2: ammonia / 2,2,2-trifluoroethanol / 0.17 h / 80 °C / Microwave irradiation View Scheme

N-(cyclohexen-1-yl)formamide (40652-40-2) → C16H27N3O5

Conditions	Yield
Multi-step reaction with 2 steps 1: Burgess Reagent / acetonitrile / 0.17 h / 50 °C / Microwave irradiation 2: ammonia / 2,2,2-trifluoroethanol / 0.17 h / 80 °C / Microwave irradiation View Scheme

Upstream product

• 1125-02-6 1-cyano-1-formamidocyclohexane 
• 100-64-1 cyclohexanone-oxime 
• 128828-05-7 C₁₃H₁₇NS 
• 2258-42-6 formyl acetic anhydride 
• 108-94-1 cyclohexanone 
• 77287-34-4 formamide 
• 5496-10-6 1-amino-1-cyanocyclohexane 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 

Downstream Products

• 1121-57-9 1-isocyanocyclohexene 
• 128798-30-1 1-Isocyano-7-oxa-bicyclo[4.1.0]heptane 
• 255736-71-1 rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-(2-thymin-methyl-benzoyl)-amino]-3,3-dimethyl-butyric acid-(cyclohexen-1-yl)-amide 
• 255735-94-5 rac-2-[(2-isobutyryl-aminophenyl)-thyminacetyl-amino]-biphenyl-4-yl-acetic acid-(cyclohexen-1-yl)-amide 
• 255735-96-7 rac-2-[(2-tert-butyloxycarbonyl-aminoethyl)-N⁶-benzyloxycarbonyl-adeninacetyl-amino]-ortho-chlorophenylacetic acid-(cyclohexen-1-yl)-amide 
• 171070-14-7 2-[Acetyl-(4-methoxy-benzyl)-amino]-N-cyclohex-1-enyl-3-methyl-butyramide 
• 171070-16-9 (R,S)-N-(1-cylohexenyl)-2-(N'-(4-methoxybenzyl)formamido)phenylacetamide 
• 171070-15-8 2-[Acetyl-(4-methoxy-benzyl)-amino]-N-cyclohex-1-enyl-2-phenyl-acetamide 
• 171070-17-0 1-[Acetyl-(4-methoxy-benzyl)-amino]-cyclohexanecarboxylic acid cyclohex-1-enylamide 
• 175606-30-1 N-Cyclohex-1-enyl-2-phenyl-2-piperidin-1-yl-acetamide 
• 175606-32-3 N-Butyl-N-[(cyclohex-1-enylcarbamoyl)-phenyl-methyl]-benzamide 
• 175606-21-0 (R,S)-N-(1-cyclohexenyl)-2-(N'-(4-methoxybenzyl)-2-aminobenzamido)-3-methylbutanamide 
• 175606-23-2 2-Amino-N-butyl-N-[(cyclohex-1-enylcarbamoyl)-phenyl-methyl]-5-iodo-benzamide 
• 1354014-33-7 C₂₇H₃₅N₃O₄ 

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