Home Cart 0 Sign in  
X

[ CAS No. 58644-54-5 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

type HazMat fee
Excepted Quantity Free
Inaccessible (Haz class 6.1), Domestic USD 41.00
Inaccessible (Haz class 6.1), International USD 64.00
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 83.00
Accessible (Haz class 3, 4, 5 or 8), International USD 133.00
Chemical Structure| 58644-54-5
Chemical Structure| 58644-54-5
Structure of 58644-54-5 * Storage: {[proInfo.prStorage]}

Quality Control of [ 58644-54-5 ]

Related Doc. of [ 58644-54-5 ]

SDS
Alternatived Products of [ 58644-54-5 ]
Alternatived Products of [ 58644-54-5 ]

Product Details of [ 58644-54-5 ]

CAS No. :58644-54-5 MDL No. :MFCD07774134
Formula : C4H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :85.10 g/mol Pubchem ID :-
Synonyms :

Safety of [ 58644-54-5 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P273-P243-P403 UN#:1993
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 58644-54-5 ]

  • Downstream synthetic route of [ 58644-54-5 ]

[ 58644-54-5 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 58644-54-5 ]
  • [ 58644-53-4 ]
YieldReaction ConditionsOperation in experiment
With tributyl-amine; p-toluenesulfonyl chloride
With p-toluenesulfonyl chloride at 100℃;
With isocyanate de chlorosulfonyle; triethylamine In methanol; dichloromethane; toluene at 0 - 40℃; for 5.5h;
With triethylamine; trichlorophosphate In dichloromethane for 0.0666667h; Cooling with ice; Green chemistry;

  • 2
  • [ 765-30-0 ]
  • [ 109-94-4 ]
  • [ 58644-54-5 ]
YieldReaction ConditionsOperation in experiment
100% for 4h; Heating;
84% at 50℃; for 5h; Synthesis of CAP-004-43-1 A mixture of cyclopropanamine (5.00 g, 0.088 mol) and ethyl formate (13.00 g, 0.180 mol) was stirred at 50 oc for 5 h. The solvent was removed in vacuo to afford CAP-004-43-1(7.02 g, 84 %) as a pale yellow oil.
59% With sodium carbonate In ethanol for 20h; Ambient temperature;
Heating;
at 60℃; for 5h; 1 8-(Cyclopropyl-methyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate (125) In a sealed tube, a solution of 1.14 g (20 mmol) of cyclopropylamine in 5 mL of ethylformate is heated at 60° C. for 5 hours. The solvents are evaporated and the residue is added in portions to a solution of 1.07 g (28 mmol) of lithium aluminium hydride in 100 mL of anhydrous tetrahydrofuran. The reaction mixture is stirred at room temperature for 18 hours. Methanol is added and the reaction mixture is filtered on celite. 10 mL (20 mmol) of a 2M solution of hydrochloric acid in diethyl ether is added to the filtrate. The solvents are evaporated to give 1.5 g (74%) of N-methylcyclopropylamine hydrochloride in the form of an oil.
With sodium carbonate In ethanol at 0 - 20℃;

  • 3
  • [ 58644-54-5 ]
  • methylcyclopropylamine hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; dimethylsulfide borane complex 1.) THF, reflux, 14 h, 2.) THF, 80 deg C, 3 h; Multistep reaction;
Stage #1: N-cyclopropylformamide With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 18h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; diethyl ether 1 8-(Cyclopropyl-methyl-sulfamoyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-propyl carboxylate (125) In a sealed tube, a solution of 1.14 g (20 mmol) of cyclopropylamine in 5 mL of ethylformate is heated at 60° C. for 5 hours. The solvents are evaporated and the residue is added in portions to a solution of 1.07 g (28 mmol) of lithium aluminium hydride in 100 mL of anhydrous tetrahydrofuran. The reaction mixture is stirred at room temperature for 18 hours. Methanol is added and the reaction mixture is filtered on celite. 10 mL (20 mmol) of a 2M solution of hydrochloric acid in diethyl ether is added to the filtrate. The solvents are evaporated to give 1.5 g (74%) of N-methylcyclopropylamine hydrochloride in the form of an oil.
  • 4
  • [ 64-18-6 ]
  • [ 765-30-0 ]
  • [ 58644-54-5 ]
YieldReaction ConditionsOperation in experiment
In water Heating;
  • 5
  • [ 58644-54-5 ]
  • [ 100-39-0 ]
  • [ 246257-66-9 ]
YieldReaction ConditionsOperation in experiment
96% With sodium hydride In benzene at 40℃; for 10h;
90% With sodium hydride at 20℃; for 10h; Synthesis of CAP-004-43-2 To a mixture of sodium hydride (13.70 g, 0.36 mol) and CAP-004-43-1 (15.21 g, 0.18 mol)in 100 ml of anhydrous benzene was added benzyl bromide (29.7 ml, 0.25 mol). Themixture was stirred at room temperature for 10 h. Water (200 ml) was added and the10 resultant was extracted with ethyl acetate. The organic phase was dried and concentratedto give CAP-004-43-2 (28.21 g, 90 %) as a colorless oil.
  • 7
  • [ 107-31-3 ]
  • [ 765-30-0 ]
  • [ 58644-54-5 ]
YieldReaction ConditionsOperation in experiment
for 12h; Heating / reflux; 228 Cyclopropylamine (5.0 ml, 72 mmol) and methyl formate (4.5 ml, 72 mmol) were added together and heated to reflux. After 12 h, the excess starting materials were removed under reduced pressure and the material was utilized directly
6.92 g (93%) 17 Preparation of Cyclopropyl Formamide EXAMPLE 17 Preparation of Cyclopropyl Formamide A mixture of cyclopropylamine (5.00 g, 87.6 mmole) and methylformate (5.26 g, 87.6 mmole) is stirred at 25° C., for 2 hours. (an initial exotherm is noted). The mixture is then placed on the rotary evaporator to remove the MeOH formed in the reaction. The remaining material is distilled through a short path head to yield 6.92 g (93%) of the desired N-cyclopropyl formamide as a colorless oil, n.m.r. (CDCl3) δ8.1 (1H, br S), 6.8-8.5 (1H, br), δ2.4-3.0 (1H, m), δ0.4-1.0 (4H,m).
6.92 g (93%) 25 Preparation of Cyclopropyl Formamide EXAMPLE 25 Preparation of Cyclopropyl Formamide A mixture of cyclopropylamine (5.00 g, 87.6 mmole) and methylformate (5.26 g, 87.6 mmole) is stirred at 25° C., for 2 hours. (an initial exotherm is noted). The mixture is then placed on the rotary evaporator to remove the MeOH formed in the reaction. The remaining material is distilled through a short path head to yield 6.92 g (93%) of the desired N-cyclopropyl formamide as a colorless oil, n.m.r. (CDCl3) δ 8.1 (1H, br S), 6.8-8.5 (1H, br), δ 2.4-3.0 (1H, m), δ 0.4-1.0 (4H, m).
6.92 g (93%) 25 Preparation of Cyclopropyl Formamide EXAMPLE 25 Preparation of Cyclopropyl Formamide A mixture of cyclopropylamine (5.00 g, 87.6 mmole) and methylformate (5.26 g, 87.6 mmole) is stirred at 25° C., for 2 hours. (an initial exotherm is noted). The mixture is then placed on the rotary evaporator to remove the MeOH formed in the reaction. The remaining material is distilled through a short path head to yield 6.92 g (93%) of the desired N-cyclopropyl formamide as a colorless oil, n.m.r. (CDCl3) δ8.1 (1H, br S), 6.8-8.5 (1H, br), δ2.4-3.0 (1H, m), δ0.4-1.0 (4H,m).

  • 8
  • [ 58644-54-5 ]
  • [ 541-41-3 ]
  • [ 64222-04-4 ]
YieldReaction ConditionsOperation in experiment
18 Preparation of Ethyl N-Cyclopropyl Formimidate EXAMPLE 18 Preparation of Ethyl N-Cyclopropyl Formimidate Ethylchloroformate (4.078 g, 37.58 mmole) is added by syringe to N-cyclopropylformamide (3.194 g, 37.58 mmole) in a dry flask under N2. After an induction period of 30 sec., a rapid evolution of gas begins. The resulting reaction mixture is stirred at 25° C. until no further evolution of gas can be detected (~4 hr), then the viscous product is subjected to a vacuum of 0.5 mm for 1 hr to remove any unreacted ethyl chloroformate. NMR analysis of the product shows the formyl proton at 9.37 as a broad singlet. (CDCl3 solution).
26 Preparation of Ethyl N-Cyclopropyl Formimidate EXAMPLE 26 Preparation of Ethyl N-Cyclopropyl Formimidate Ethylchloroformate (4.078 g, 37.58 mmole) is added by syringe to N-cyclopropylformamide (3.194 g, 37.58 mmole) in a dry flask under N2. After an induction period of 30 sec., a rapid evolution of gas begins. The resulting reaction mixture is stirred at 25° C. until no further evolution of gas can be detected (~4 hr), then the viscous product is subjected to a vacuum of 0.5 mm for 1 hr to remove any unreacted ethyl chloroformate. NMR analysis of the product shows the formyl proton at δ 9.37 as a broad singlet. (CDCl3 solution).
26 Preparation of Ethyl N-Cyclopropyl Formimidate EXAMPLE 26 Preparation of Ethyl N-Cyclopropyl Formimidate Ethylchloroformate (4.078 g, 37.58 mmole) is added by syringe to N-cyclopropylformamide (3.194 g, 37.58 mmole) in a dry flask under N2. After an induction period of 30 sec., a rapid evolution of gas begins. The resulting reaction mixture is stirred at 25° C. until no further evolution of gas can be detected (~4 hr), then the viscous product is subjected to a vacuum of 0.5 mm for 1 hr to remove any unreacted ethyl chloroformate. NMR analysis of the product shows the formyl proton at δ9.37 as a broad singlet. (CDCl3 solution).
  • 9
  • [ 58644-54-5 ]
  • [ 64-19-7 ]
  • [ 160801-74-1 ]
  • [ 856707-38-5 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 1.J A solution of aldehyde 1m (1.8 g) in 100 mL of dry dichloromethane was treated with isonitrile (1.1 eq, 680 mg) and acetic acid (2 eq, 1.02 mL, d 1.0149). The mixture was stirred overnight. All the volatiles were removed under vacuum and the residue was chromatographed on silica gel (gradient: ethyl acetate/hexanes; 2:8 to 6:4) to afford the product 1n as a white solid.
  • 10
  • [ 1262043-89-9 ]
  • [ 58644-54-5 ]
  • [ 765-30-0 ]
  • [ 1262043-90-2 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid In toluene at 100℃; for 24h; Sealed tube; 1.A.3 Step 3: Preparation of benzyl 6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-ylcarbamate To a sealable flask containing benzyl 6-(hydrazinecarbonyl)pyridin-2-ylcarbamate (1.97 g, 6.89 mmol, 1.0 eq) was added N-cyclopropyl formamide (1.8 mL, 20.7 mmol, 3.0 eq), cyclopropylamine (1.4 mL, 20.7 mmol, 3.0 eq), toluene (0.2 M), and trifluoracetic acid (0.511 mL, 6.89 mmol, 1.0 eq). The flask was sealed and heated to 100° C. for 24 hours. The reaction mixture was concentrated under reduced pressure to provide a yellow oil, which was purified by flash chromatography (Rf=0.44 in 10% methanol/ethyl acetate, gradient flash: 3%→10% methanol in ethyl acetate). The product, which consisted of a mixture of the desired compound with cyclopropyl formamide, was suspended in acetonitrile, sonicated, and the resultant suspension filtered to provide benzyl 6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-ylcarbamate (680 mg).
  • 11
  • [ 33513-42-7 ]
  • [ 765-30-0 ]
  • [ 58644-54-5 ]
YieldReaction ConditionsOperation in experiment
99% Stage #1: N,N-dimethyl-formamide With bis(2-chlorophenyl)borinic acid; acetic acid at 65℃; for 0.25h; Inert atmosphere; Stage #2: Cyclopropylamine at 65℃; for 12h; Inert atmosphere; Sealed tube;
  • 12
  • [ 58644-54-5 ]
  • [ 86483-51-4 ]
  • [ 86483-53-6 ]
YieldReaction ConditionsOperation in experiment
95.2% Stage #1: ethyl 2,4-dichloro-5-fluoro-benzoyl-acetate With triethylamine In toluene at 50℃; for 0.5h; Stage #2: N-cyclopropylformamide In toluene at 50℃; for 3h; 3 Example 3 27.7 g (0.1 mol) of 2,4-dichloro-5-fluorobenzoylacetic acid ethyl ester (II-1) was added to 80 ml of toluene with stirring, 10 ml of triethylamine was added and the temperature was raised to 50 DEG C and stirred for half an hour. 8.5g (0.1mol) of formamide derivative (III-2) was added in batches. The reaction was incubated at 50°C for 3 hours after completion of the dropwise addition. The reaction was completed by TLC. The solid salt was filtered off, and the organic phase was washed with water (50ml×3). After drying over magnesium sulfate and concentrating, 32.8 g of the compound (I-2) was obtained in a yield of 95.2% and the purity was 99.5% by HPLC.
  • 13
  • [ 1262043-89-9 ]
  • [ 58644-54-5 ]
  • [ 1262043-90-2 ]
YieldReaction ConditionsOperation in experiment
With Cyclopropylamine; trifluoroacetic acid In toluene at 100℃; for 18h; 3 Step 3: Benzyl (6-(4-cyclopropyl-4H-l,2,4-triazol-3-yl)pyridin-2-yl)carbamate (C-4) [00266] To a stirred mixture of C-3 (570 mg, 2.0 mmol), N-cyclopropylformamide (0.51 mg, (0841) 6.0 mmol), cyclopropylamine (0.42 mL, 6.0 mmol), and anhydrous toluene (10 mL), was added (0842) TFA (0.15 mL, 2.0 mmol). The mixture was heated at 100 °C for 18 h. The mixture was cooled to rt and concentrated under reduced pressure. The residue was purified (silica; eluting with 0- (0843) 20%) MeOH in DCM) to afford compound C-4 (460 mg) as an oil which was taken on to the next step without further purification. LCMS Mass: 336.0 (M++l).
  • 14
  • [ 118-48-9 ]
  • [ 58644-54-5 ]
  • [ 100-52-7 ]
  • [ 1508262-65-4 ]
YieldReaction ConditionsOperation in experiment
45% at 120℃; for 12h; Sealed tube; Typical experimental procedure for the synthesis of 4a General procedure: The mixture of isatoic anhydride 1a (41 mg, 0.25 mmol), benzaldehyde 2a (40 mg, 0.375 mmol), p-TSA/C (12 wt %, 90 mg, 25 mol % based on p-TSA content), and N-methylformamide 3a (1 mL) were added successively to a Schlenk tube (50 mL) equipped with a magnetic stirrer bar, the Schlenk tube was then closed and the resulting reaction mixture was heated at 120 °C for 12 h under air atmosphere. After cooling to room temperature, the reaction mixture was filtrated and then concentrated under vacuum. The residue was directly purified by preparative TLC on silica, eluting with petroleum ether (60-90°C): ethyl acetate (6:1) to give 3-methyl-2-phenylquinazolin-4(3H)-one (4a) as a white solid (52 mg, 89%).
  • 15
  • [ 124-38-9 ]
  • [ 765-30-0 ]
  • [ 58644-54-5 ]
YieldReaction ConditionsOperation in experiment
88% With 1,3-dimethylbenzimidazolium-2-carboxylate; phenylsilane In acetonitrile at 25℃; for 24h;
Historical Records

Related Functional Groups of
[ 58644-54-5 ]

Amines

Chemical Structure| 1403483-62-4

[ 1403483-62-4 ]

N-Cyclopropyl-N-methylformamide

Similarity: 0.85

Chemical Structure| 246257-70-5

[ 246257-70-5 ]

N,N-Dicyclopropylformamide

Similarity: 0.81

Aliphatic Cyclic Hydrocarbons

Chemical Structure| 1403483-62-4

[ 1403483-62-4 ]

N-Cyclopropyl-N-methylformamide

Similarity: 0.85

Chemical Structure| 246257-70-5

[ 246257-70-5 ]

N,N-Dicyclopropylformamide

Similarity: 0.81

Aldehydes

Chemical Structure| 1403483-62-4

[ 1403483-62-4 ]

N-Cyclopropyl-N-methylformamide

Similarity: 0.85

Chemical Structure| 246257-70-5

[ 246257-70-5 ]

N,N-Dicyclopropylformamide

Similarity: 0.81