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Chemical Structure| 67305-24-2 Chemical Structure| 67305-24-2

Structure of 67305-24-2

Chemical Structure| 67305-24-2

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Product Details of [ 67305-24-2 ]

CAS No. :67305-24-2
Formula : C5H4ClNO2
M.W : 145.54
SMILES Code : O=C(Cl)C1=C(C)ON=C1
MDL No. :MFCD03411599
InChI Key :ZKAQPVQEYCFRTK-UHFFFAOYSA-N
Pubchem ID :2759917

Safety of [ 67305-24-2 ]

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 [ 67305-24-2 ]

* 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 [ 67305-24-2 ]

[ 67305-24-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 42831-50-5 ]
  • [ 67305-24-2 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; In toluene; b) A mixture of <strong>[42831-50-5]5-methylisoxazole-4-carboxylic acid</strong> (5 g, 39.4 mm), SOCl2 (15 ml, 205.8 mm) and toluene (15 ml) was heated to 79+-1 C. and stirred for about 4-5 h. Excess SOCl2 and toluene were evaporated under vacuum (50 torr) at 70 C. to give the title compound (>=99% purity) as a pale yellow liquid residue identical to that of Example 1(a).
96% With thionyl chloride; at 50℃; 5-Methyl isoxazole-4-carboxylic acid (1 g, 7.86 mmol) was dissolved in SOCl2 (3 mL) and stirred at 50 C. After the reaction was completed, the mixture was cooled to room temperature, and then distilled under reduced pressure to obtain 5-methylisoxazole-4-carbonyl chloride (1098 mg, 96%).
With thionyl chloride; at 26 - 89℃; for 1h; Thionyl chloride (4.3 ml, 39.5 mmol) was added dropwise to <strong>[42831-50-5]5-methylisoxazole-4-carboxylic acid</strong> (0.44 g, 3.4 mmol) at 26C. The mixture was heated at 89C for 1 hr and allowed to cool. Excess thionyl chloride was evaporated under reduced pressure to give an acid chloride as a brown oil, which was used in the next reaction.
With thionyl chloride; sodium carbonate; In chloroform; EXAMPLE 1 2-Cyano-3-hydroxythiocrotonic acid-S-phenyl ester A 72 ml. portion of thionyl chloride is added dropwise to a mixture of 70.24 g. of <strong>[42831-50-5]5-methylisoxazole-4-carboxylic acid</strong> [H. Yasuda, Yakugaku Zasshi, 79, 836-838 (1959); C. A. 53, 21885d] and 64.44 g. of sodium carbonate in 250 ml. of chloroform. The mixture is heated gently on a steam bath for 4 hours, then the solid is filtered and the filtrate is evaporated to an oil. This oil is distilled at 4.5 mm. and the material boiling at 68-70 C. is collected, giving 65.23 g. of 5-methylisoxazole-4-carbonyl chloride.
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 5h; Preparation 4 N-(6-Amino-5-chloropyrazin-2-yl)-5-methylisoxazole-4-carboxamide Oxalyl chloride (0.8 ml, 10.3 mmol) was added to a solution of 5-Methyl-isoxazole-4-carboxylic acid (1 g, 6.9 mmol) in dichloromethane (30 ml) followed by 1 drop of dimethylformamide. The mixture was stirred at room temperature for 5 hours before concentrating in vacuo and azeotroping with dichloromethane. The residue was taken up in pyridine (3 ml) and added to a solution of 3-chloro-pyrazine-2,6-diamine (Preparation 1) (0.65 g, 4.6 mmol) in anhydrous pyridine (30 ml) and the mixture heated at 50 C. for 3 hours before cooling to room temperature and concentrating in vacuo. The residue was purified by silica gel column chromatography, eluding with ethyl acetate:heptane 1:1, to afford the product as a white solid (360 mg). 1H-NMR (d6-DMSO): 2.51 (s, 3H), 6.71 (br, s, 2H), 8.35 (s, 1H), 9.12 (s, 1H), 10.63 (br, s, 1H). MS m/z 254 [MH]+
With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 2.25h;Product distribution / selectivity; Step 5: To generate the acid chloride a suspension of 5-methyl-1 ,2-oxazole-4-carboxylic acid (39 mg, 0.30 mmol) in CH2CI2 (0.5 mL) at 0 C was added oxalyl chloride (50 muIota_, 1.2 mmol) and DMF (1 drop). The suspension was allowed to stir for a further 15 min at 0 C followed by 2 h at room temperature. The resulting mixture was concentrated in vacuo to give a dark oil. The oil was twice suspended in n-hexanes (2 x 1 mL) and concentrated in vacuo. A solution of 7-acetyl-10a-(4-chlorophenyl)-2,3, 10, 10a-tetrahydro-1 H,5H-imidazo[1 ,2- a]pyrrolo[1 ,2-c ]pyrazin-5-one (20 mg, 61 muetaetaomicronIota) in pyridine (0.5 mL) was added to a suspension of the acid chloride (generated as above; 0.30 mmol) in pyridine (0.5 mL) and CH2CI2 (0.5 mL) at 0 C . The resultant mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was diluted with a saturated aqueous solution of NaHC03 (25 mL) and extracted with CH2CI2 containing 20% of propan-2-ol (3 x 25 mL). The organic layers were combined, dried and concentrated in vacuo to yield a crude brown residue that was partially purified using flash chromatography (Biotage SP4, 12 g cartridge, 0-10%MeOH gradient in CH2CI2) to give a mixture (10 mg) containing the desired product which was further purified by flash chromatography (2 x Biotage SP4, 12 g cartridge, C18 phase, 20-40% acetonitrile gradient in water) to give 7-acetyl-10a-(4-chlorophenyl)-1-[(5-methyl-1 ,2- oxazol-4-yl)carbonyl]-2,3, 10, 10a-tetrahydro-1 H,5H-imidazo[1 ,2-a]pyrrolo[1 ,2-c ]pyrazin-5-one (24) as a solid (3.5 mg, yield 14%).
With thionyl chloride; at 50℃; The <strong>[42831-50-5]5-methylisoxazole-4-carboxylic acid</strong> (1) (1 g, 7.86 mmol) inSOCl2 (3 mL) was heated at 50 C until compound 1 disappeared inTLC. After reaction was terminated, the mixture was cooled toambient temperature and solvent was evaporated under reducedpressure. 5-methylisoxazole-4-carbonyl chloride, a crude yellow oil(2) (96%)was used for the next step without additional purification;1H NMR (400 MHz, DMSO) d 8.77 (1H, s), 2.64 (3H, s).
With thionyl chloride; In toluene; for 3h;Reflux; To a solution of <strong>[42831-50-5]5-methylisoxazole-4-carboxylic acid</strong> SM (500 mg, 4.0 mmol) in toluene(10 mL) was added SOd2 (720 mg, 6.0 mmol). The mixture was heated to reflux for 3 hours. Thereaction mixture was concentrated under reduced pressure to obtain 5-methylisoxazole-4-carbonyl chloride compound 1 (550 mg, crude) without further purification.
With thionyl chloride; N,N-dimethyl-formamide; In dichloromethane; for 12h;Reflux; Thionylchloride (3.53 g, 0.0278 mol) was added to a solutionof 5-Methylisoxazole-4-carboxylic acid (2.7 g, 0.0185 mol) in anhydrous dichloromethane (50 ml) with catalytic drops of DMF. The reaction was heated under reflux for 12 h then followed by removing the solvent under reduced pressure. DCM (20 ml) was added and evaporated 3 times to produce a brown oil that was used directly in the next step.
With thionyl chloride; at 50℃; 5-Methylisoxazole-4-carboxylic acid (1 g, 7.86 mmol) was added to SOCl 2 (3 mL) and stirred at 50 C. After completion of the reaction, the reaction mixture was cooled and then distilled under reduced pressure to remove volatile materials to obtain crude yellow oil (96%)
0.59 mol With thionyl chloride; at 45℃; A round bottomed flask equipped with a mechanical stiner, condenser, thermometer pocket and a stopper were added 5-Methylisoxazole-4-carboxylic acid (3.00 g, 0.02 mol) and Thionyl chloride (14.66 g, 0.12 mol) and the reaction mixture was gradually heated to 45±5C and stined at same temperature for 2 to 3 h. The progress of the reaction was monitored by TLC (Acid chloride was analyzed as corresponding methyl ester by quenching the samplein methanol). After the completion of reaction, the reaction mixture was concentrated under reduced pressure at 45±5C to afford 5-Methylisoxazole-4-carbonyl chloride as a liquid (0.59 mol).
With thionyl chloride; In N-methyl-acetamide; (iv) 5-Methylisoxazol-4-yl carbonyl chloride Thionyl chloride (118 g) was added to <strong>[42831-50-5]5-methylisoxazol-4-yl carboxylic acid</strong> (42 g) and stirred at room temperature as dimethylformamide (0.2 ml) was added. The solution was heated under reflux for 2 hours with stirring. Excess thionyl chloride was removed in vacuo at 50C, then the residue was distilled through a 15 cm Vigreaux column at reduced pressure to give an oil, b.p. 32-34C/0.1 mm Hg.
With thionyl chloride; In N-methyl-acetamide; (iv) 5-Methylisoxazol-4-yl carbonyl chloride Thionyl chloride (118 g) was added to <strong>[42831-50-5]5-methylisoxazol-4-yl carboxylic acid</strong> (42 g) and stirred at room temperature as dimethylformamide (0.2 ml) was added. The solution was heated under reflux for 2 hours with stirring. Excess thionyl chloride was removed in vacuo at 50 C., then the residue was distilled through a 15 cm Vigreaux column at reduced pressure to give an oil, b.p. 32-34 C./0.1 mm Hg.
With thionyl chloride; In N-methyl-acetamide; (iv) 5-Methylisoxazol-4-yl carbonyl chloride Thionyl chloride (118 g) was added to <strong>[42831-50-5]5-methylisoxazol-4-yl carboxylic acid</strong> (42 g) and stirred at room temperature as dimethylformamide (0.2 ml) was added. The solution was heated under reflux for 2 hours with stirring. Excess thionyl chloride was removed in vacuo at 50 C., then the residue was distilled through a 15 cm Vigreux column at reduced pressure to give an oil, b.p. 32-34 C./0.1 mmHg.

  • 3
  • [ 42831-50-5 ]
  • of toluene [ No CAS ]
  • [ 67305-24-2 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; Stage b) 5-Methylisoxazole-4-carbonyl chloride 127.1 g (1.0 mol) of <strong>[42831-50-5]5-methylisoxazole-4-carboxylic acid</strong> are initially introduced into 1 I of toluene, 129.8 g (1.1 mol) of thionyl chloride are added dropwise and the mixture is then heated at 80 C. for 6 h. The volume is concentrated under reduced pressure to approximately one half and the toluene solution is used directly for further reactions.
  • 4
  • ammonium thiocyanate [ No CAS ]
  • [ 67305-24-2 ]
  • [ 828-81-9 ]
  • [ 1023696-95-8 ]
 

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