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102-97-6

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102-97-6 Usage

Description

N-(1-Methylethyl)-benzenemethanamine, also known as N-Isopropylbenzylamine, is a structural isomer of methamphetamine and is commonly found as an adulterant due to its similar appearance and physical properties. It is a clear, very slightly yellow to yellow liquid that forms amine adducts with magnesocene at ambient temperature in toluene.

Uses

Used in Pharmaceutical Synthesis:
N-Isopropylbenzylamine is used as an intermediate in the synthesis of pharmaceutical compounds and as a precursor to the manufacture of some drugs. Its role in the pharmaceutical industry is crucial for the development of new medications and therapies.
Used in Chemical Research:
As a ligand, N-Isopropylbenzylamine was used in the preparation and characterization of bis(cyclopentadienyl)magnesium. This application highlights its importance in chemical research and the development of new compounds with potential applications in various fields.
Used in Synthesis of N-Benzylideneisopropylamine-N-Oxide:
N-Isopropylbenzylamine is also utilized in the synthesis of N-Benzylideneisopropylamine-N-Oxide, which may have its own set of applications in different industries.
Used in Law Enforcement and Regulatory Considerations:
Due to its similarity to methamphetamine, N-Isopropylbenzylamine has come under the consideration of the Drug Enforcement Administration (DEA). This use is more related to the monitoring and regulation of the compound to prevent its misuse in illegal activities.

Preparation

N-benzylisopropylamine is synthesized by the reduction reaction of N-isopropylbenzamide or prepared from benzylamine and acetone by reductive amination reaction.

Check Digit Verification of cas no

The CAS Registry Mumber 102-97-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 2 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 102-97:
(5*1)+(4*0)+(3*2)+(2*9)+(1*7)=36
36 % 10 = 6
So 102-97-6 is a valid CAS Registry Number.
InChI:InChI=1/C10H15N/c1-9(2)11-8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/p+1

102-97-6 Well-known Company Product Price

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  • Alfa Aesar

  • (B23243)  N-Isopropylbenzylamine, 97%   

  • 102-97-6

  • 100g

  • 375.0CNY

  • Detail
  • Alfa Aesar

  • (B23243)  N-Isopropylbenzylamine, 97%   

  • 102-97-6

  • 500g

  • 1137.0CNY

  • Detail

102-97-6SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Benzylisopropylamine

1.2 Other means of identification

Product number -
Other names N-Benzylpropan-2-amine

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:102-97-6 SDS

102-97-6Synthetic route

isopropyl alcohol
67-63-0

isopropyl alcohol

benzylamine
100-46-9

benzylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With C13H20N2O*Ir(1+); hydrogen at 80℃; under 3000.3 Torr; for 23h; Reagent/catalyst; Autoclave; Green chemistry;100%
With nickel at 20℃; for 26h;70%
Pt on TiO2 for 10h; Ambient temperature; Irradiation;36.32%
1-benzyl-2-(chloromethyl)aziridine

1-benzyl-2-(chloromethyl)aziridine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 6h; Reflux;98%
diisopropylamine
108-18-9

diisopropylamine

benzylamine
100-46-9

benzylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium) In 5,5-dimethyl-1,3-cyclohexadiene at 155℃; for 10h; Inert atmosphere;97%
With [(C5Me4)(CH2)3(C5Me4)(IrI2)2]m In 5,5-dimethyl-1,3-cyclohexadiene at 155℃; for 10h; Schlenk technique; Reflux;96%
N-isopropylbenzamide
5440-69-7

N-isopropylbenzamide

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
Stage #1: N-isopropylbenzamide With 2-fluoropyridine; trifluoromethylsulfonic anhydride In dichloromethane at 0℃; for 0.333333h;
Stage #2: With 1,1,3,3-Tetramethyldisiloxane In dichloromethane at 0 - 20℃; for 3.16667h;
Stage #3: With tris(pentafluorophenyl)borate In dichloromethane at 0 - 20℃;
94%
With lithium aluminium tetrahydride In diethyl ether for 5h; Heating;
With diphenylsilane; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In tetrahydrofuran at 20℃; for 48h;80 % Spectr.
(E)-N-benzylidenepropan-2-amine
27845-51-8

(E)-N-benzylidenepropan-2-amine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With titanocene dichloride; butyl magnesium bromide In diethyl ether at 25℃; for 15h; Mechanism; var. aldimine and cyclic ketimine substr.; var. quant. of catalyst;94%
With titanocene dichloride; butyl magnesium bromide In diethyl ether at 25℃; for 15h;94%
N-benzylideneisopropylamine
6852-56-8

N-benzylideneisopropylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With sodium tetrahydroborate; (-) In ethanol at 20℃; for 72h;92%
With ammonia borane at 20℃; for 12h;75%
With sodium tetrahydroborate In methanol at 20℃; for 1h;
benzaldehyde
100-52-7

benzaldehyde

isopropylamine
75-31-0

isopropylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; hydrogen; 2,2′‐biquinoline‐4,4′‐dicarboxylic acid dipotassium salt at 100℃; under 10343 Torr; for 24h;90%
With sodium tetrahydroborate In 2,2,2-trifluoroethanol at 35 - 40℃; for 0.0333333h;90%
Stage #1: benzaldehyde; isopropylamine In tetrahydrofuran; methanol for 6h; Molecular sieve;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0 - 20℃; for 2h;
85%
acetone
67-64-1

acetone

benzylamine
100-46-9

benzylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With iridium bromide; sulfuric acid; zinc In 1,4-dioxane; water at 30℃; for 72h;88%
With sodium hydrogen telluride In ethanol for 20h; Ambient temperature;80%
With sodium tris(acetoxy)borohydride In dichloromethane at 30℃;70%
benzyldiisopropylamine
34636-09-4

benzyldiisopropylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With iodine; sodium carbonate In chloroform at 60℃; for 24h;86%
benzyl chloride
100-44-7

benzyl chloride

isopropylamine
75-31-0

isopropylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With copper(l) chloride In ethanol at 40℃; Reagent/catalyst; Solvent; Temperature;85.3%
With sodium carbonate In glycerol
N-benzyl-2-(bromomethyl)aziridine
25662-24-2

N-benzyl-2-(bromomethyl)aziridine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether Reflux;82%
benzaldehyde
100-52-7

benzaldehyde

Isopropylamine hydroperchlorate
15576-36-0

Isopropylamine hydroperchlorate

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With tri-n-butyl-tin hydride In N,N-dimethyl-formamide at 20℃; for 4h; Reductive amination;73%
benzyldiisopropylamine
34636-09-4

benzyldiisopropylamine

methylphenylsilane
766-08-5

methylphenylsilane

A

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

B

methyl(phenyl)(1-propyl)silane

methyl(phenyl)(1-propyl)silane

Conditions
ConditionsYield
With tris(pentafluorophenyl)borate In chlorobenzene at 130℃; for 36h; Inert atmosphere; Glovebox;A 70%
B 36%
(Z)‑N‑isopropyl‑1‑phenylmethanimine oxide
10229-64-8, 143957-81-7, 300802-10-2

(Z)‑N‑isopropyl‑1‑phenylmethanimine oxide

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride In tetrahydrofuran at 20℃; for 6h;67%
N-benzyl-4-methylbenzenesulfinamide
6873-90-1

N-benzyl-4-methylbenzenesulfinamide

isopropyl alcohol
67-63-0

isopropyl alcohol

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With nickel at 20℃; for 6h;65%
acetone
67-64-1

acetone

Benzaldoxime
932-90-1

Benzaldoxime

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With hydrogen; magnesium oxide; copper at 220℃; under 11250.9 Torr;61%
diisopropylamine
108-18-9

diisopropylamine

dibenzylamine
103-49-1

dibenzylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With μ-diiodo-di((η5-pentamethylcyclopentadienyl)(iodo)iridium) In 5,5-dimethyl-1,3-cyclohexadiene at 155℃; for 10h; Inert atmosphere;60%
(E)-N-benzylidenepropan-2-amine
27845-51-8

(E)-N-benzylidenepropan-2-amine

A

N,N'-diisopropyl-1,2-diphenyl-1,2-ethanediamine
55079-98-6

N,N'-diisopropyl-1,2-diphenyl-1,2-ethanediamine

B

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With sodium hydroxide; zinc In water for 5.2h; Ambient temperature;A 20%
B 53%
With samarium diiodide In tetrahydrofuran at 180℃; under 8250.66 - 10500.8 Torr; for 0.0833333h; Product distribution; Further Variations:; Reagents; time; microwave irradiation;
benzyl bromide
100-39-0

benzyl bromide

isopropylamine
75-31-0

isopropylamine

A

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

B

N-isopropyl-N,N-dibenzylamine
55578-14-8

N-isopropyl-N,N-dibenzylamine

Conditions
ConditionsYield
With sodium hydroxideA 51%
B 27%
N-isopropyl-N-ethylbenzylamine
68723-26-2

N-isopropyl-N-ethylbenzylamine

A

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

B

N-ethylbenzylamine
14321-27-8

N-ethylbenzylamine

Conditions
ConditionsYield
With iodine; sodium carbonate In chloroform at 60℃; for 24h;A 34%
B 41%
isopropylamine
75-31-0

isopropylamine

benzyl alcohol
100-51-6

benzyl alcohol

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
Pt on TiO2 for 20h; Ambient temperature; Irradiation;4.9%
benzyl bromide
100-39-0

benzyl bromide

isopropylamine
75-31-0

isopropylamine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

isopropyl phenyl ketoxime
72846-70-9, 72846-71-0, 6668-39-9

isopropyl phenyl ketoxime

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
(i) PCl5, benzene, Et2O, (ii) LiAlH4; Multistep reaction;
Diisopropoxycarbenium-tetrafluoroborat

Diisopropoxycarbenium-tetrafluoroborat

benzonitrile
100-47-0

benzonitrile

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
(i) CH2Cl2, (ii) EtOH, (iii) NaBH4; Multistep reaction;
C28H29NP(1+)*I(1-)

C28H29NP(1+)*I(1-)

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With water; hydroxide
Isopropyl-[2,2,2-trichloro-1-phenyl-eth-(E)-ylidene]-amine
76757-59-0

Isopropyl-[2,2,2-trichloro-1-phenyl-eth-(E)-ylidene]-amine

A

1-isopropyl-2-phenyl-aziridine
4164-23-2

1-isopropyl-2-phenyl-aziridine

B

N-isopropyl-(+/-)-α-methylbenzylamine
19302-16-0

N-isopropyl-(+/-)-α-methylbenzylamine

C

N-isopropyl-N-(2-phenylethyl)amine
52007-97-3

N-isopropyl-N-(2-phenylethyl)amine

D

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

E

N-(2-hydroxy-1-phenylethyl)-N-isopropylamine
68058-02-6

N-(2-hydroxy-1-phenylethyl)-N-isopropylamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether for 7h; Product distribution; Heating; various molar ratios, solvents, time. Other N-alkyl- and N-aryltrichloroacetophenone imines;A 5 % Chromat.
B 4 % Chromat.
C 64 % Chromat.
D 15 % Chromat.
E 9 % Chromat.
(E)-N-benzylidenepropan-2-amine
27845-51-8

(E)-N-benzylidenepropan-2-amine

A

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

B

(R,S)-N,N'-di(1-methylethyl)-1,2-diphenyl-1,2-ethylenediamine
55079-98-6

(R,S)-N,N'-di(1-methylethyl)-1,2-diphenyl-1,2-ethylenediamine

(R*,R*)-N,N'-di(1-methylethyl)-1,2-diphenyl-1,2-ethylenediamine

(R*,R*)-N,N'-di(1-methylethyl)-1,2-diphenyl-1,2-ethylenediamine

Conditions
ConditionsYield
With ammonium hydroxide; chloro-trimethyl-silane; water; ammonium chloride; ethylene dibromide; zinc 1.) CH3CN, 35 deg C, 1 h, 2.) CH3CN, 0 deg C; Yield given. Multistep reaction. Yields of byproduct given;
isopropyl alcohol
67-63-0

isopropyl alcohol

benzylamine
100-46-9

benzylamine

A

benzyldiisopropylamine
34636-09-4

benzyldiisopropylamine

B

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With γ-Al2O3 In gaseous matrix at 230℃; Yield given; Yields of byproduct given;
benzaldehyde isopropylimine

benzaldehyde isopropylimine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Conditions
ConditionsYield
With ethanol; nickel Hydrogenation;
phenylacetic acid
103-82-2

phenylacetic acid

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-benzyl-N-isopropyl-2-phenylacetamide

N-benzyl-N-isopropyl-2-phenylacetamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;100%
2,6-dichloropyridine
2402-78-0

2,6-dichloropyridine

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

2-(N-benzylisopropylamino)-6-chloropyridine
464170-02-3

2-(N-benzylisopropylamino)-6-chloropyridine

Conditions
ConditionsYield
Stage #1: Benzyl-isopropyl-amin With n-butyllithium In hexane; toluene at -64 - 0℃;
Stage #2: 2,6-dichloropyridine In hexane; toluene at 4 - 20℃;
99%
With n-butyllithium
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

Glyoxilic acid
298-12-4

Glyoxilic acid

phenylboronic acid
98-80-6

phenylboronic acid

N-benzyl-N-isopropyl-α-phenylglycine

N-benzyl-N-isopropyl-α-phenylglycine

Conditions
ConditionsYield
In dichloromethane for 48h; Petasis reaction;99%
carbon disulfide
75-15-0

carbon disulfide

nickel(II) chloride hexahydrate

nickel(II) chloride hexahydrate

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

(benzylisopropyldithiocarbamate)2 nickel(II)
82421-76-9

(benzylisopropyldithiocarbamate)2 nickel(II)

Conditions
ConditionsYield
In ethanol; water mixing amine and CS2 in EtOH, standing for 15 min, addn. of warm H2O soln. of Ni-salt, standing for 1 h; collection (filtration), washing (warm H2O), drying (IR-lamp); elem. anal.;99%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

A

(Z)‑N‑isopropyl‑1‑phenylmethanimine oxide
10229-64-8, 143957-81-7, 300802-10-2

(Z)‑N‑isopropyl‑1‑phenylmethanimine oxide

B

benzaldehyde
100-52-7

benzaldehyde

Conditions
ConditionsYield
With dihydrogen peroxide; PCWP In chloroform at 40℃; for 2h;A 98%
B 2%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

N-isopropyl-N-(phenylmethyl)-2-bromoacetamide
100140-99-6

N-isopropyl-N-(phenylmethyl)-2-bromoacetamide

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 1h;98%
With triethylamine In dichloromethane Ambient temperature;
With triethylamine In chloroform at 0 - 20℃; for 24h;
With triethylamine In dichloromethane at 0 - 20℃;52.2 g
tert-butyl acetoacetate
1694-31-1

tert-butyl acetoacetate

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-(1-methylethyl)-3-oxo-N-(phenylmethyl)butanamide

N-(1-methylethyl)-3-oxo-N-(phenylmethyl)butanamide

Conditions
ConditionsYield
at 100 - 115℃; under 100 Torr;97%
3-bromocycloheptene
36291-49-3

3-bromocycloheptene

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

(RS)-3-(N-Benzyl-N-isopropylamino)cyclohept-1-ene
1393659-10-3

(RS)-3-(N-Benzyl-N-isopropylamino)cyclohept-1-ene

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 50℃; for 16h; Kinetics;96%
carbon disulfide
75-15-0

carbon disulfide

Pentafluorobenzonitrile
773-82-0

Pentafluorobenzonitrile

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

4-cyano-2,3,5,6-tetrafluorophenyl-N-benzyl-N-isopropylcarbamodithioate

4-cyano-2,3,5,6-tetrafluorophenyl-N-benzyl-N-isopropylcarbamodithioate

Conditions
ConditionsYield
Stage #1: carbon disulfide; Benzyl-isopropyl-amin With potassium phosphate In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry;
Stage #2: Pentafluorobenzonitrile In dimethyl sulfoxide at 20℃; for 2h; Schlenk technique; Green chemistry; regioselective reaction;
96%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-benzylideneisopropylamine N-oxide
10229-64-8, 143957-81-7, 300802-10-2

N-benzylideneisopropylamine N-oxide

Conditions
ConditionsYield
With dihydrogen peroxide; trichloroacetonitrile In methanol; water at 0 - 25℃; for 8h;95%
With sodium tungstate; dihydrogen peroxide In methanol; water at 20℃;48%
With α-D-glucose 6-phosphate; oxygen; NADP; cyclohexanone monooxygenase at 25℃; for 24h; pH=8.6; Enzymatic reaction;
With air; cyclohexanone monooxygenase from Escherichia coli; NADPH In water at 25℃; pH=8.6; Enzyme kinetics;
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-benzyl-N-isopropylnitrous amide
20689-97-8

N-benzyl-N-isopropylnitrous amide

Conditions
ConditionsYield
With N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide; water; silica gel; sodium nitrite In dichloromethane at 20℃; for 0.05h; Reagent/catalyst;95%
With sodium nitrite In dichloromethane at 20℃; for 0.0833333h;89%
With acetic acid; sodium nitrite In water at 0 - 20℃; for 1h; Inert atmosphere;
2-thiophenylcarboxylic acid
527-72-0

2-thiophenylcarboxylic acid

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-benzyl-N-isopropylthiophene-2-carboxamide

N-benzyl-N-isopropylthiophene-2-carboxamide

Conditions
ConditionsYield
Stage #1: 2-thiophenylcarboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃; for 0.166667h;
Stage #2: Benzyl-isopropyl-amin at 20℃; for 1h;
95%
styrene oxide
96-09-3

styrene oxide

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

(+/-)-benzylisopropyl(α-hydroxyphenethyl)amine
87040-39-9

(+/-)-benzylisopropyl(α-hydroxyphenethyl)amine

Conditions
ConditionsYield
In water; toluene for 3h; Heating;94%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-benzylideneisopropylamine
6852-56-8

N-benzylideneisopropylamine

Conditions
ConditionsYield
With oxygen In para-xylene at 110℃; for 1.5h;94%
With 5,10,15,20-tetrakisphenylporphyrin; oxygen In ethyl acetate at 20℃; under 760.051 Torr; for 9h; Molecular sieve; Irradiation; regioselective reaction;92%
With 5,15,10,20-tetraphenylporphyrin In acetonitrile at 30℃; for 1h; Irradiation;80%
5-methyl-imidazo[5,1-b][1,3,4]thiadiazole-2-carboxylic acid hydrochloride

5-methyl-imidazo[5,1-b][1,3,4]thiadiazole-2-carboxylic acid hydrochloride

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

5-methylimidazo[5,1-b][1,3,4]thiadiazole-2-carboxylic acid benzylisobutylamide

5-methylimidazo[5,1-b][1,3,4]thiadiazole-2-carboxylic acid benzylisobutylamide

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h;94%
3-methoxy-4-methyl-3-cyclobutene-1,2-dione
29769-77-5

3-methoxy-4-methyl-3-cyclobutene-1,2-dione

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

3-(benzyl(isopropyl)amino)-4-methylcyclobut-3-ene-1,2-dione

3-(benzyl(isopropyl)amino)-4-methylcyclobut-3-ene-1,2-dione

Conditions
ConditionsYield
In methanol at 20℃; for 4h;94%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

trifluoroacetic acid
76-05-1

trifluoroacetic acid

N-benzyl-N-(2,2,2-trifluoroethyl)propan-2-amine

N-benzyl-N-(2,2,2-trifluoroethyl)propan-2-amine

Conditions
ConditionsYield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 4h; Glovebox; Molecular sieve; Schlenk technique;94%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

allyl bromide
106-95-6

allyl bromide

N-benzyl-N-isopropylallylamine
247033-00-7

N-benzyl-N-isopropylallylamine

Conditions
ConditionsYield
With sodium hydroxide In N,N-dimethyl-formamide for 1h; Ambient temperature;93%
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

allyl alcohol
107-18-6

allyl alcohol

N-benzyl-N-isopropylallylamine
247033-00-7

N-benzyl-N-isopropylallylamine

Conditions
ConditionsYield
With ammonium hexafluorophosphate; [Pt(η3-C3H5)(DPP-Xantphos)]PF6 In toluene; acetonitrile at 50℃; for 8h; Inert atmosphere;93%
1-fluorodecane
334-56-5

1-fluorodecane

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

N-benzyl-N-isopropyl-1-decylamine

N-benzyl-N-isopropyl-1-decylamine

Conditions
ConditionsYield
With tris(bis(trimethylsilyl)amido)lanthanum(III) In dichloromethane at 20℃; for 7h; Inert atmosphere; chemoselective reaction;93%
2-hydroxycyclobutanone
99440-99-0

2-hydroxycyclobutanone

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

2-(benzyl(isopropyl)amino)cyclobutanone

2-(benzyl(isopropyl)amino)cyclobutanone

Conditions
ConditionsYield
With dmap In toluene at 20℃; for 15h;93%
With dmap In 1,4-dioxane at 20℃; for 1h;
Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

1,1'-carbonyldiimidazole
530-62-1

1,1'-carbonyldiimidazole

N-benzyl-N-isopropyl-1H-imidazole-1-carboxamide
55245-48-2

N-benzyl-N-isopropyl-1H-imidazole-1-carboxamide

Conditions
ConditionsYield
In tetrahydrofuran for 16h; Heating;92%
C15H13ClFN3O2

C15H13ClFN3O2

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

4-(2-fluoro-phenyl)-2-morpholin-4-yl-pyrimidine-5-carboxylic acid benzyl-isopropyl-amide

4-(2-fluoro-phenyl)-2-morpholin-4-yl-pyrimidine-5-carboxylic acid benzyl-isopropyl-amide

Conditions
ConditionsYield
In toluene at 0 - 20℃; for 1.5h;92%
methyl (RS)-5-tris(phenylthio)methylcyclopent-1-enecarboxylate
1046427-59-1

methyl (RS)-5-tris(phenylthio)methylcyclopent-1-enecarboxylate

Benzyl-isopropyl-amin
102-97-6

Benzyl-isopropyl-amin

methyl (1RS,2SR,5SR)-2-(N-benzyl-N-isopropylamino)-5-tris(phenylthio)methylcyclopentanecarboxylate

methyl (1RS,2SR,5SR)-2-(N-benzyl-N-isopropylamino)-5-tris(phenylthio)methylcyclopentanecarboxylate

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;92%

102-97-6Relevant articles and documents

Selective hydrogenation of nitriles to secondary amines catalyzed by a pyridyl-functionalized and alkenyl-tethered NHC-Ru(II) complex

Saha, Sayantani,Kaur, Mandeep,Singh, Kuldeep,Bera, Jitendra K.

, p. 87 - 94 (2016)

A set of Co(III) and Ru(II) compounds are synthesized bearing pyridyl-functionalized and alkenyl-tethered N-heterocyclic carbene (NHC) ligand (L1). [CoIII(L1)3](PF6)3 (1) was synthesized by the reaction of [L1H]PF6, Co(OAc)2.4H2O, K2CO3 in tetrahydrofuran (THF) under refluxing condition. [RuIIL1(η6-p-cymene)Cl]PF6 (2) was synthesized via transmetallation method. For both compounds, the NHC ligand chelates the metal through carbene carbon and pyridyl nitrogen whereas the butenyl unit remains free. Compound 2 hydrogenates organic nitriles efficiently providing selectively secondary amines. In the presence of external amines, unsymmetrical secondary amines are also obtained.

Design of a bifunctional Ir-Zr based metal-organic framework heterogeneous catalyst for the N-alkylation of amines with alcohols

Rasero-Almansa,Corma,Iglesias,Sanchez

, p. 1794 - 1800 (2014)

The direct N-alkylation of amines with alcohols was performed with an Ir-Zr-based metal-organic framework multifunctional heterogeneous catalyst. This system is efficient and environmentally benign for the synthesis of various organic amines in air in the absence of a base. The catalyst was recovered and reused without significant loss of activity, and only water was produced as a byproduct. Better be direct than elusive: The direct N-alkylation of amines with alcohols is performed with an Ir-Zr-based metal-organic framework multifunctional heterogeneous catalyst. This system is efficient and environmentally benign for the synthesis of various organic amines in air in the absence of a base. The catalyst is recovered and reused without significant loss of activity, and only water is produced as a byproduct.

Stereodynamics of 2-(diethylamino)propane and 2-(dibenzylamino)propane. 1H and 13C{1H} DNMR studies. Molecular mechanics calculations

Brown, Jay H.,Bushweller, C. Hackett

, p. 12567 - 12577 (1995)

2-(Diethylamino)propane (DEAP) and 2-(dibenzylamino)propane (DBAP) possess similar molecular symmetries. Interconversion among the stable equilibrium conformations occurs by inversion-rotation at the pyramidal nitrogen and by isolated rotation about carbon-nitrogen bonds. In DEAP and DBAP, the fact that stable equilibrium conformations cannot have destabilizing syn-1,5 interactions between methyl or phenyl groups limits the number of equilibrium conformations that will be present at concentrations high enough to be NMR detectable. The 1H and 13C{1H} NMR spectra of DEAP at 100 K show two diastereomeric pairs of enantiomeric conformations. One pair of enantiomers has the isopropyl methine proton and both ethyl methyl groups gauche to the lone pair (75%). The other pair has the methine proton anti to the lone pair with the ethyl methyl groups respectively gauche and anti to the lone pair (25%). The barrier to inversion-rotation in DEAP (ΔG? = 6.4 kcal/mol) is higher than barriers to isolated rotation about carbon-nitrogen bonds (ΔG? = 5.3-5.7 kcal/mol). The 1H and 13C{1H} NMR spectra of DBAP at 100 K show just one pair of enantiomeric conformations that have the isopropyl methine proton and both phenyl groups gauche to the lone pair. There is no evidence in the NMR spectrum at 100 K for those conformations of DBAP that have a phenyl group anti to the lone pair. The barrier to inversion-rotation in DBAP (ΔG? = 6.4 kcal/mol) is higher than the barrier to racemization via isolated rotation about carbon-nitrogen bonds (ΔG? = 5.5 kcal/mol). Molecular mechanics calculations of conformational energies are in good agreement with the observed conformational preferences.

Additive-free selective methylation of secondary amines with formic acid over a Pd/In2O3 catalyst

Benaissa, Idir,Cantat, Thibault,Genre, Caroline,Godou, Timothé,Pinault, Mathieu

, p. 57 - 61 (2022/01/19)

Formic acid is used as the sole carbon and hydrogen source in the methylation of aromatic and aliphatic amines to methylamines. The reaction proceeds via a formylation/transfer hydrogenation pathway over a solid Pd/In2O3 catalyst without the need for any additive.

Imine reduction with me2s-bh3

Kamal, Mohammad M.,Liu, Zhizhou,Vidovi?, Dragoslav,Zhai, Siyuan

, (2021/09/13)

Although there exists a variety of different catalysts for hydroboration of organic substrates such as aldehydes, ketones, imines, nitriles etc., recent evidence suggests that tetra-coordinate borohydride species, formed by activation, redistribution, or decomposition of boron reagents, are the true hydride donors. We then proposed that Me2S-BH3 could also act as a hydride donor for the reduction of various imines, as similar compounds have been observed to reduce carbonyl substrates. This boron reagent was shown to be an effective and chemoselective hydroboration reagent for a wide variety of imines.

Poisoning effect of N-containing compounds on performance of Raney nickel in transfer hydrogenation

Martyanov, Oleg N.,Philippov, Alexey A.

, (2021/10/19)

The effect of amines, imines and heterocycle compounds on conversion has been studied in transfer hydrogenation of camphor and 2-PrOH catalyzed by Raney nickel. Small amount (5 mol% to nickel) of N-containing compound significantly decreases catalyst activity. It has been shown that the poisoning effect mostly depends on molecular size of amines and heterocyclic compounds. For aniline and cyclohexylamine the dependence of camphor conversion on poison/nickel ratio was obtained. Additionally, benzaldehyde, cinnamaldehyde demonstrated higher reactivity compared corresponding imines under transfer hydrogenation conditions. Obtained data explain low activity of nickel-based catalysts when N-containing compounds are presented in reaction mixture.

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