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Chemical Structure| 16480-05-0 Chemical Structure| 16480-05-0
Chemical Structure| 16480-05-0

1-Methylcyclopropanecarbonyl chloride

CAS No.: 16480-05-0

4.5 *For Research Use Only !

Cat. No.: A582094 Purity: 98%

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Product Details of [ 16480-05-0 ]

CAS No. :16480-05-0
Formula : C5H7ClO
M.W : 118.56
SMILES Code : O=C(Cl)C1(C)CC1
MDL No. :MFCD11617014
InChI Key :GTDXPJJHRWOFDI-UHFFFAOYSA-N
Pubchem ID :12789939

Safety of [ 16480-05-0 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 16480-05-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 16480-05-0 ]

[ 16480-05-0 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 16480-05-0 ]
  • [ 15910-91-5 ]
YieldReaction ConditionsOperation in experiment
With ammonia; In methanol; dichloromethane; at 5 - 20℃; The solvent and excess oxalyl chloride were removed by evaporation, the residuedissolved in DCM and added to a solution of ammonia (excess) in MeOH cooled at 5 C. The mixture was allowed to warm to ambient temperature and the volatiles removed by evaporation to give the title compound. NMR: 0.29 (q, 2H), 0.71 (q, 2H), 1.02 (s, 3H), 6.62 (s, 1H), 6.85 (s, 1H).
With ammonia; In chloroform; (ii) Preparation of 1-methylcyclopropanecarboxamide. A solution of 1-methylcyclopropanecarboxylic acid chloride (49 g) in chloroform (300 cm3) was added gradually to a concentrated aqueous solution of ammonia (300 cm3), previously cooled to 0 C. by external cooling. The reaction mixture warmed spontaneously to 20 C. and a white solid precipitate was formed; the precipitate was redissolved by further addition of chloroform. The organic layer was separated, dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure. The residual solid was recrystallized from a mixture of chloroform and n-hexane to give 1-methylcyclopropanecarboxamide (17.6 g) as colourless crystal. Melting point: 148 C. Infra red (paraffin mull): 3390, 3200, 1660, 1615, 1405, 1245, 1110, 880 cm-1
With ammonia; In chloroform; (ii) Preparation of 1-methylcyclopropanecarboxamide. A solution of 1-methylcyclopropanecarboxylic acid chloride (49 g) in chloroform (300 cm3) was added gradually to a concentrated aqueous solution of ammonia (300 cm3), previously cooled to 0 C. by external cooling. The reaction mixture warmed spontaneously to 20 C. and a white solid precipitate was formed; the precipitate was redissolved by further addition of chloroform. The organic layer was separated, dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure. The residual solid was recrystallized from a mixture of chloroform and n-hexane to give 1-methylcyclopropanecarboxamide (17.6g) as colourless crystals. Melting point: 148 C. Infra red (paraffin mull): 3390, 3200, 1660, 1615, 1405, 1245, 1110, 880 cm-1.
With ammonia; In chloroform; (ii) Preparation of 1-methylcyclopropanecarboxamide A solution of 1-methylcyclopropanecarboxylic acid chloride (49g) in chloroform (300 cm3) was added gradually to a concentrated aqueous solution of ammonia (300 cm3), previously cooled to 0C by external cooling. The reaction mixture warmed spontaneously to 20C and a white solid precipitate was formed; the precipitate was redissolved by further addition of chloroform. The organic layer was separated, dried over anhydrous magnesium sulphate and the solvent evaporated under reduced pressure. The residual solid was recrystallized from a mixture of chloroform and n -hexane to give 1-methylcyclopropanecarboxamide (17.6g) as colourless crystal. Melting point: 148C. Infra red (paraffin mull): 3390, 3200, 1660, 1615, 1405, 1245, 1110, 880 cmmin1.
With ammonia; In chloroform-d1; Example 19.34: Preparation of 6-{ r-[3-(dimethylamino)-l,2,4-thiadiazol-5-yl]-4,4'-bipiperidin-l-yl}-N- ( 1 -methylcyclopropyOnicotinamide; Step 1: 1-methylcyclopropanecarboxamide; <n="121"/>v CO2H v CONH2I? I?A solution of 1-methylcyclopropane carboxylic acid (2.01g; 20.08mmol) in CDCI3 (4OmL) was treated with oxalyl chloride (2.29mL; 26.1mmol). The solution was stirred at 25AC for 48hr (progress followed by NMR). The reaction was permeated with excess gaseous ammonia. The mixture was filtered and the filtrate evaporated to give the title compound as a white solid.

  • 2
  • [ 16480-05-0 ]
  • [ 64628-73-5 ]
  • N-(3-chloro-4-trifluoromethoxyphenyl)-1-methylcyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; EXAMPLE 8 Production of N-(3-chloro-4-trifluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (Compound No. 6): To a solution of <strong>[64628-73-5]3-chloro-4-trifluoromethoxyaniline</strong> (2.1 g) in methylene chloride (50 ml), triethylamine (1.1 g) was added, and a solution of 1-methylcyclopropanecarbonyl chloride (1.2 g) in methylene chloride was dropwise added thereto while stirring and ice-cooling. After stirring at room temperature for 1 hour, the reaction mixture was washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated. The crude crystals (2.9 g) were recrystallized from ethanol to give N-(3-chloro-4-trifluoromethoxyphenyl)-1-methylcyclopropanecarboxamide (2.6 g). M.P., 101-102 C. Anal. Calcd. for C12 H11 ClF3 NO2: C, 49.08%; H, 3.78%; N, 4.77%; Cl, 12.07%. Found: C, 48.92%; H, 3.81%; N, 4.60%; Cl, 12.30%. NMR deltaCDCl 3 (ppm): 0.75 (2H, m), 1.30 (2H, m), 1.46 (3H, s), 7.3 (2H, m), 7.54 (1H, br. s), 7.76 (1H, d, J=2 Hz).
  • 3
  • [ 16480-05-0 ]
  • [ 90942-47-5 ]
  • [ 1427158-18-6 ]
YieldReaction ConditionsOperation in experiment
250 mg With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -50 - 26℃; for 2.0h; To a solution 1-methylcyclopropanecarboxylic acid (140 mg, 1.39 mmol) in dichloromethane (5.0 mL) were added oxalyl chloride (211 mg, 1.6 mmol) and a drop of DMF. The reaction mass was stirred at rt for 2 h and was added to the solution of methyl 5-(aminomethyl)-2- chlorobenzoate hydrochloride (200 mg, 0.911 mmol) and DIPEA (183 mg, 1.36 mmol) in CH2CI2 (3 mL) at -50C. The reaction mixture was stirred at rt for 2 h. The reaction mixture was quenched with water and was extracted with CHCI3. The organic layer was separated, dried and concentrated to afford 250 mg of the title product. XH NMR (300 MHz, DMSO d6): delta 8.19 (m, 1H), 7.65 (s, 1H), 7.52 (d, / = 8.1Hz, 1H), 7.41 (d, / = 8.1Hz, 1H), 4.26 (d, / = 5.7 Hz, 2H), 3.85 (s, 3H), 1.27 (s, 3H), 0.94 (m, 2H), 0.53 (m, 2H).
 

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