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3637-31-8

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3637-31-8 Usage

Synthesis

4,4,5,5,5-Pentaflfluoropentanol (1.8 kg, 10.1 mol), tetraethylammonium hydrogen sulfate (18.1 g, 0.08 mole), and water (10.8 L) were added to a 50 L QVF vessel and heated with stirring to 70 °C. Sodium permanganate monohydrate (2.33 kg, 14.14 mol) was dissolved at 20 °C in water (10.8 L) and transferred to a measure vessel. Aqueous sodium permanganate was added in aliquots (approximately 10% at a time) to the stirred aqueous solution of pentaflfluoropentanol and tetraethylammonium hydrogen sulfate maintaining a temperature of 65?75 °C by the additions of permanganate. The total time taken to add the aqueous permanganate was 2 h 30 min. The reaction was stirred at 70 °C for 4 h when gas chromatography (GC) analysis showed conversion of pentaflfluoropentanol to pentaflfluoropentanoic acid to be complete. The reaction mixture was allowed to cool to ambient temperature overnight and screened through a Celite fifilter aid (500 g) to remove precipitated manganese dioxide. The isolated manganese dioxide was washed with hot water (60 °C, 18 L). The combined aqueous layers were extracted with methyl tert-butyl ether (5.4 L), and the upper organic layer was discarded. The aqueous layer was acidifified with concentrated sulfuric acid (320 mL) to pH 1. The lower organic layer which separated was retained. The aqueous layer was extracted with methyl tert-butyl ether (2 × 5.4 L), and the upper organic layers were combined with the initial, lower organic layer. The combined organic layers were washed with water (5.4 L) and dried with anhydrous sodium sulfate. The organic solvent was removed in vacuo at 50 °C and the residue distilled to give the acid as a pale pink, low-melting solid (1.49 kg, 77%). Reference: Mahmood, A.; Robinson, G. E.; Powell, L. Org. Proc. Res. Dev. 1999, 3, 363–364.

Check Digit Verification of cas no

The CAS Registry Mumber 3637-31-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,6,3 and 7 respectively; the second part has 2 digits, 3 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 3637-31:
(6*3)+(5*6)+(4*3)+(3*7)+(2*3)+(1*1)=88
88 % 10 = 8
So 3637-31-8 is a valid CAS Registry Number.

3637-31-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 4,4,5,5,5-Pentafluoropentanoic acid

1.2 Other means of identification

Product number -
Other names 2H,2H,3H,3H-Perfluoropentanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3637-31-8 SDS

3637-31-8Synthetic route

4,4,5,5,5-pentafluorpentan-1-ol
148043-73-6

4,4,5,5,5-pentafluorpentan-1-ol

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

Conditions
ConditionsYield
With Jones reagent In acetone at 0 - 20℃; for 1h;82%
With sodium permanganate monohydrate; tetraethylammonium hydrogen sulphate In water at 65 - 75℃; for 6.5h; Large scale;77%
With chromium(VI) oxide; acetic acid at 0 - 20℃; for 26h;63%
4,4,5,5,5-pentafluoropentyl acetate
148043-72-5

4,4,5,5,5-pentafluoropentyl acetate

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 92 percent / aq. NaOH / 1 h / Heating
2: 63 percent / CrO3, aq. AcOH / 26 h / 0 - 20 °C
View Scheme
4,4,5,5,5-pentafluoro-2-iodopentyl acetate
148043-71-4

4,4,5,5,5-pentafluoro-2-iodopentyl acetate

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / azoisobutyronitrile (AIBN), Bu3SnH / 55 - 65 °C
2: 92 percent / aq. NaOH / 1 h / Heating
3: 63 percent / CrO3, aq. AcOH / 26 h / 0 - 20 °C
View Scheme
tetra(n-butyl)ammonium hydrogensulfate
32503-27-8

tetra(n-butyl)ammonium hydrogensulfate

4,4,5,5,5-pentafluorpentan-1-ol
148043-73-6

4,4,5,5,5-pentafluorpentan-1-ol

A

3,3,4,4,4-pentafluorobutanoic acid
380-60-9

3,3,4,4,4-pentafluorobutanoic acid

B

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

C

butyric acid
107-92-6

butyric acid

Conditions
ConditionsYield
With potassium permanganate In water at 65 - 70℃;
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4,4,5,5,5-pentafluoropentanoyl chloride
3637-18-1

4,4,5,5,5-pentafluoropentanoyl chloride

Conditions
ConditionsYield
With thionyl chloride for 2h; Heating / reflux;54%
(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)methanethiol
1333236-67-1

(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)methanethiol

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

S-(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)-methyl 4,4,5,5,5-pentafluoropentanethioate
1333236-78-4

S-(2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)-methyl 4,4,5,5,5-pentafluoropentanethioate

Conditions
ConditionsYield
Stage #1: 4,4,5,5,5-pentafluoropentanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h;
Stage #2: (2,3-dihydrothieno[3,4-b][1,4]oxathiin-3-yl)methanethiol In dichloromethane at 50℃; for 24h;
25%
pivaloyl chloride
3282-30-2

pivaloyl chloride

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

C10H13F5O3

C10H13F5O3

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at -78 - 0℃; for 0.333333h;
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

(-)-(S)-2-azido-4,4,5,5,-pentafluoropentanoic acid
148043-92-9

(-)-(S)-2-azido-4,4,5,5,-pentafluoropentanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / tetrahydrofuran / 0.33 h / -78 - 0 °C
2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 20 min
3: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h
4: tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C
5: 70 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

(4R)-3-(4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone
148043-77-0

(4R)-3-(4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Et3N / tetrahydrofuran / 0.33 h / -78 - 0 °C
2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 20 min
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

(2RS,4R)-3-(2-bromo-4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone

(2RS,4R)-3-(2-bromo-4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / tetrahydrofuran / 0.33 h / -78 - 0 °C
2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 20 min
3: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

(2S,4R)-3-(2-azido-4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone
148043-87-2

(2S,4R)-3-(2-azido-4,4,5,5,5-pentafluoro-1-oxopentyl)-4-(phenylmethyl)-2-oxazolidinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Et3N / tetrahydrofuran / 0.33 h / -78 - 0 °C
2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 20 min
3: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h
4: tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

(-)-(S)-4,4,5,5-pentafluoronorvaline

(-)-(S)-4,4,5,5-pentafluoronorvaline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / tetrahydrofuran / 0.33 h / -78 - 0 °C
2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 20 min
3: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h
4: tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C
5: 70 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C
6: H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

(R)-4,4,5,5-pentafluoronorvaline

(R)-4,4,5,5-pentafluoronorvaline

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: Et3N / tetrahydrofuran / 0.33 h / -78 - 0 °C
2: 1.) BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, -78 deg C, 20 min
3: 1.) (i-Pr)2NEt, Bu2BOTf, 2.) NBS / 1.) CH2Cl2, from -78 deg C to 0 deg C, 75 min, 2.) CH2Cl2, -78 deg C, 1.25 h
4: tetramethylguanidinium azide / CH2Cl2 / 3 h / 0 °C
5: 70 percent / aq. H2O2, LiOH / tetrahydrofuran / 0.5 h / 0 °C
6: H2, aq. AcOH / 10percent Pd/C / 23 h / 2068.6 Torr
View Scheme
Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;
N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4,4,5,5,5-pentafluoro-N-methoxy-N-methylpentanamide
1350856-28-8

4,4,5,5,5-pentafluoro-N-methoxy-N-methylpentanamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 25℃; Inert atmosphere;
methyl-2-bromo-5-chlorobenzoate
27007-53-0

methyl-2-bromo-5-chlorobenzoate

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

1-(2-bromo-5-chlorophenyl)-4,4,5,5,5-pentafluoropentan-1-one
1350855-82-1

1-(2-bromo-5-chlorophenyl)-4,4,5,5,5-pentafluoropentan-1-one

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; Inert atmosphere;
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
1350853-32-5

4-amino-2-[6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridin-1-yl]-5-(4-fluorophenyl)-5-methyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 18 - 25 °C / Inert atmosphere
2.1: trichlorophosphate / 1,2-dichloro-ethane / 18 h / Inert atmosphere; Reflux
3.1: N-iodo-succinimide / dichloromethane / 18 h / 18 - 25 °C / Inert atmosphere
4.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide; water / 18 h / 120 °C / Inert atmosphere
5.1: ammonium chloride; trimethylaluminum / toluene / 18 h / 100 °C / Inert atmosphere
5.2: 0.5 h / 18 - 25 °C / silica gel
6.1: potassium tert-butylate / tert-butyl alcohol / 0.67 h / 110 °C / Inert atmosphere; sealed tube
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine
1350855-92-3

6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 18 - 25 °C / Inert atmosphere
2: trichlorophosphate / 1,2-dichloro-ethane / 18 h / Inert atmosphere; Reflux
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

6-chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine
1350855-93-4

6-chloro-1-iodo-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 18 - 25 °C / Inert atmosphere
2: trichlorophosphate / 1,2-dichloro-ethane / 18 h / Inert atmosphere; Reflux
3: N-iodo-succinimide / dichloromethane / 18 h / 18 - 25 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carbonitrile
1350855-94-5

6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 18 - 25 °C / Inert atmosphere
2: trichlorophosphate / 1,2-dichloro-ethane / 18 h / Inert atmosphere; Reflux
3: N-iodo-succinimide / dichloromethane / 18 h / 18 - 25 °C / Inert atmosphere
4: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide; water / 18 h / 120 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carboximidamide
1350855-95-6

6-chloro-3-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-1-carboximidamide

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 2 h / 18 - 25 °C / Inert atmosphere
2.1: trichlorophosphate / 1,2-dichloro-ethane / 18 h / Inert atmosphere; Reflux
3.1: N-iodo-succinimide / dichloromethane / 18 h / 18 - 25 °C / Inert atmosphere
4.1: 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0) / N,N-dimethyl-formamide; water / 18 h / 120 °C / Inert atmosphere
5.1: ammonium chloride; trimethylaluminum / toluene / 18 h / 100 °C / Inert atmosphere
5.2: 0.5 h / 18 - 25 °C / silica gel
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentan-1-one
1350856-29-9

4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentan-1-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 25 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere
2.2: 25 °C
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentan-1-amine
1350856-30-2

4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentan-1-amine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 25 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere
2.2: 25 °C
3.1: hydroxylamine / methanol / 25 °C / Inert atmosphere
4.1: trifluoroacetic acid; zinc / 3 h / 25 °C / Inert atmosphere
4.2: pH 10 / Cooling with ice
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

C10H9F5N2O
1350856-44-8

C10H9F5N2O

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 25 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere
2.2: 25 °C
3.1: hydroxylamine / methanol / 25 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

methyl oxo{[4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentyl]amino}acetate
1350856-31-3

methyl oxo{[4,4,5,5,5-pentafluoro-1-(pyridin-2-yl)pentyl]amino}acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 25 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere
2.2: 25 °C
3.1: hydroxylamine / methanol / 25 °C / Inert atmosphere
4.1: trifluoroacetic acid; zinc / 3 h / 25 °C / Inert atmosphere
4.2: pH 10 / Cooling with ice
5.1: triethylamine / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

methyl 1-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-3-carboxylate
1350856-32-4

methyl 1-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-3-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 25 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere
2.2: 25 °C
3.1: hydroxylamine / methanol / 25 °C / Inert atmosphere
4.1: trifluoroacetic acid; zinc / 3 h / 25 °C / Inert atmosphere
4.2: pH 10 / Cooling with ice
5.1: triethylamine / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
6.1: trichlorophosphate / 1,2-dichloro-ethane / 120 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

1-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-3-carboximidamide
1350856-33-5

1-(3,3,4,4,4-pentafluorobutyl)imidazo[1,5-a]pyridine-3-carboximidamide

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 25 °C / Inert atmosphere
2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 25 °C / Inert atmosphere
2.2: 25 °C
3.1: hydroxylamine / methanol / 25 °C / Inert atmosphere
4.1: trifluoroacetic acid; zinc / 3 h / 25 °C / Inert atmosphere
4.2: pH 10 / Cooling with ice
5.1: triethylamine / dichloromethane / 3 h / 0 - 25 °C / Inert atmosphere
6.1: trichlorophosphate / 1,2-dichloro-ethane / 120 °C / Inert atmosphere
7.1: amino(methyl)aluminum chloride / toluene / 3 h / 107 °C / Inert atmosphere
7.2: 0.5 h / 18 - 25 °C / silica gel
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4-amino-2-[5-chloro-3-(3,3,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
1350852-32-2

4-amino-2-[5-chloro-3-(3,3,4,4-pentafluorobutyl)-1H-indazol-1-yl]-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
2: boron trifluoride diethyl etherate / methanol / 3 h / 100 °C / Inert atmosphere
3: sodium hydrogencarbonate / methanol / 0.67 h / 135 °C / Inert atmosphere; microwave irradiation
4: copper(l) iodide; N,N`-dimethylethylenediamine / N,N-dimethyl-formamide / 0.5 h / 18 - 25 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

2-[1-(2-bromo-5-chlorophenyl)-4,4,5,5,5-pentafluoropentylidene]hydrazinecarboximidamide

2-[1-(2-bromo-5-chlorophenyl)-4,4,5,5,5-pentafluoropentylidene]hydrazinecarboximidamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
2: boron trifluoride diethyl etherate / methanol / 3 h / 100 °C / Inert atmosphere
View Scheme
4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

4-amino-2-{(2E)-2-[1-(2-bromo-5-chlorophenyl)-4,4,5.5,5-pentarluoropentylidene]hydrazinyl}-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one
1350855-84-3

4-amino-2-{(2E)-2-[1-(2-bromo-5-chlorophenyl)-4,4,5.5,5-pentarluoropentylidene]hydrazinyl}-5-methyl-5-phenyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hexamethyldisilazane / tetrahydrofuran / -78 - 0 °C / Inert atmosphere
2: boron trifluoride diethyl etherate / methanol / 3 h / 100 °C / Inert atmosphere
3: sodium hydrogencarbonate / methanol / 0.67 h / 135 °C / Inert atmosphere; microwave irradiation
View Scheme
(5-chloropyridin-2-yl)methanamine hydrochloride

(5-chloropyridin-2-yl)methanamine hydrochloride

4,4,5,5,5-pentafluoropentanoic acid
3637-31-8

4,4,5,5,5-pentafluoropentanoic acid

N-[(5-chloropyridin-2-yl)methyl]-4,4.5,5.5-pentafluoropentanamide
1350855-91-2

N-[(5-chloropyridin-2-yl)methyl]-4,4.5,5.5-pentafluoropentanamide

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 18 - 25℃; for 2h; Inert atmosphere;

3637-31-8Relevant articles and documents

SOLUBLE GUANYLATE CYCLASE ACTIVATORS

-

Page/Page column 50, (2015/06/25)

A compound of Formula I or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate (" cGMP") and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of Formula I, or a pharmaceutically acceptable salt thereof, for their use in the therapy and prophylaxis of the abovementioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of Formula I or a pharmaceutically acceptable salt thereof.

SOLUBLE GUANYLATE CYCLASE ACTIVATORS

-

Page/Page column 70; 71, (2011/12/14)

A compound of Formula (I): or a pharmaceutically acceptable salt thereof, are capable of modulating the body's production of cyclic guanosine monophosphate ("cGMP") and are generally suitable for the therapy and prophylaxis of diseases which are associated with a disturbed cGMP balance. The invention furthermore relates to processes for preparing compounds of Formula I , or a pharmaceutically acceptable salt thereof, for their use in the therapy and prophylaxis of the above mentioned diseases and for preparing pharmaceuticals for this purpose, and to pharmaceutical preparations which comprise compounds of Formula (I) or a pharmaceutically acceptable salt thereof

An improved oxidation of an alcohol using aqueous permanganate and phase-transfer catalyst

Mahmood, Arshed,Robinson, Graham E.,Powell, Lyn

, p. 363 - 364 (2013/09/08)

The oxidation of a primary alcohol to the corresponding carboxylic acid via permanganate and phase-transfer catalyst has been modified to circumvent impurity formation incurred during the reaction. A safe, simple, and efficient process was developed which gave the required carboxylic acid in 77% isolated yield using sodium permanganate in the presence of tetraethylammonium hydrogen sulphate.

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