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N-Methylbenzylamine, also known as N-Benzylmethylamine, is a colorless to light yellow liquid with a distinct amine odor. It is an organic compound belonging to the amine family, characterized by its chemical structure that includes a benzyl group attached to a methylamine group. N-Methylbenzylamine is known for its versatile applications across various industries due to its unique chemical properties.

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  • 103-67-3 Structure
  • Basic information

    1. Product Name: N-Methylbenzylamine
    2. Synonyms: Benzenemethanamine,N-methyl-;Benzylamine, N-methyl-;N-Methyl(phenyl)methanamine;n-methyl-benzenemethanamin;N-methyl-Benzenemethanamine;N-Methy-N-benzylamine;N-METHYLBENZYLAMINE;NMBA
    3. CAS NO:103-67-3
    4. Molecular Formula: C8H11N
    5. Molecular Weight: 121.18
    6. EINECS: 203-133-4
    7. Product Categories: PHARMACEUTICAL INTERMEDIATES;Amine;Amines;Aromatics;Miscellaneous Reagents;Building Blocks;C8;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
    8. Mol File: 103-67-3.mol
  • Chemical Properties

    1. Melting Point: -24 °C
    2. Boiling Point: 184-189 °C(lit.)
    3. Flash Point: 172 °F
    4. Appearance: Clear colorless to light yellow/Liquid
    5. Density: 0.939 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.893mmHg at 25°C
    7. Refractive Index: n20/D 1.522(lit.)
    8. Storage Temp.: Store below +30°C.
    9. Solubility: 65g/l
    10. PKA: 9.75±0.10(Predicted)
    11. Explosive Limit: 1.4-7.7%(V)
    12. Water Solubility: 65 g/L (20 ºC)
    13. Sensitive: Air Sensitive
    14. Stability: Stable, but may be air sensitive through reaction with carbon dioxide. Combustible. Incompatible with strong oxidizing agents, a
    15. BRN: 606221
    16. CAS DataBase Reference: N-Methylbenzylamine(CAS DataBase Reference)
    17. NIST Chemistry Reference: N-Methylbenzylamine(103-67-3)
    18. EPA Substance Registry System: N-Methylbenzylamine(103-67-3)
  • Safety Data

    1. Hazard Codes: C
    2. Statements: 34-42/43-22
    3. Safety Statements: 23-26-36/37/39-45
    4. RIDADR: UN 2735 8/PG 2
    5. WGK Germany: 1
    6. RTECS:
    7. F: 2-10
    8. TSCA: Yes
    9. HazardClass: 8
    10. PackingGroup: III
    11. Hazardous Substances Data: 103-67-3(Hazardous Substances Data)

103-67-3 Usage

Uses

Used in Dye Production:
N-Methylbenzylamine is used as a key intermediate in the production of dyes. Its chemical structure allows it to participate in various chemical reactions, enabling the synthesis of a wide range of dye compounds with different color properties and applications.
Used as a Catalytic Agent:
In the chemical industry, N-Methylbenzylamine is employed as a catalytic agent. Its ability to act as a catalyst stems from its amine functional group, which can facilitate various chemical reactions, such as esterification, transesterification, and hydrogenation processes. This makes it a valuable component in the production of various chemicals and pharmaceuticals.
Used as a Petrochemical Additive:
N-Methylbenzylamine is also utilized as an additive in the petrochemical industry. Its amine functionality can help improve the performance of fuels and lubricants by acting as a corrosion inhibitor, anti-oxidant, or detergent. This enhances the overall efficiency and longevity of the products, making it a valuable addition to the petrochemical formulations.

Synthesis Reference(s)

The Journal of Organic Chemistry, 16, p. 1434, 1951 DOI: 10.1021/jo50003a015Synthesis, p. 941, 1984 DOI: 10.1055/s-1984-31028

Check Digit Verification of cas no

The CAS Registry Mumber 103-67-3 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 3 respectively; the second part has 2 digits, 6 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 103-67:
(5*1)+(4*0)+(3*3)+(2*6)+(1*7)=33
33 % 10 = 3
So 103-67-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H11N/c1-9-7-8-5-3-2-4-6-8/h2-6,9H,7H2,1H3/p+1

103-67-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A13746)  N-Benzylmethylamine, 97%   

  • 103-67-3

  • 100ml

  • 201.0CNY

  • Detail
  • Alfa Aesar

  • (A13746)  N-Benzylmethylamine, 97%   

  • 103-67-3

  • 250ml

  • 260.0CNY

  • Detail
  • Alfa Aesar

  • (A13746)  N-Benzylmethylamine, 97%   

  • 103-67-3

  • 1000ml

  • 938.0CNY

  • Detail

103-67-3SDS

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-Methylbenzylamine

1.2 Other means of identification

Product number -
Other names Benzenemethanamine, N-methyl-

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:103-67-3 SDS

103-67-3Synthetic route

N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With poly(p-aminostyrene)-palladium(II); hydrogen In N,N-dimethyl-formamide at 25℃; under 760 Torr;100%
With potassium hydroxide; isopropyl alcohol; chelating Rh(III) bis-carbene for 18h; Heating;98%
With bis(pentamethylcyclopentadienyl)zinc; hydrogen; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In benzene-d6 at 25℃; under 51005.1 Torr; for 24h; Reagent/catalyst; Inert atmosphere;98%
N-allyloxycarbonyl-N-methylbenzylamine
152507-72-7

N-allyloxycarbonyl-N-methylbenzylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water for 0.25h; Ambient temperature;100%
With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; deallylation;100 % Chromat.
N-allyl-N-α-methylbenzylamine
2520-97-0

N-allyl-N-α-methylbenzylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 0.416667h;100%
With Thiosalicylic acid; 1,4-di(diphenylphosphino)-butane; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 20℃; for 0.416667h;100%
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); diisobutylaluminium hydride In toluene for 1h; Ambient temperature;84%
Grubbs catalyst first generation In toluene at 110℃; for 1.5h;78%
Grubbs catalyst first generation In toluene for 1.5h; Heating;78%
(N-benzyl, N-methyl) 2,4-dinitrophenylsulfonamide
1352615-98-5

(N-benzyl, N-methyl) 2,4-dinitrophenylsulfonamide

A

S-(2,4-Dinitrophenyl)-cystein
3165-76-2

S-(2,4-Dinitrophenyl)-cystein

B

sulfur dioxide
7446-09-5

sulfur dioxide

C

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
In aq. phosphate buffer for 0.5h; pH=7.4;A n/a
B 100%
C n/a
Benzyl isocyanide
88333-03-3, 10340-91-7

Benzyl isocyanide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With Zr12(μ3-O)5[(μ3-O)CoCl]8[(μ2-O)2(μ3-O)CoCl]3Li3(triphenyldicarboxylate)9; hydrogen In toluene at 110℃; under 30003 Torr; for 42h; Catalytic behavior; Inert atmosphere; Schlenk technique;100%
(N-benzyl-N-methylamino)acetonitrile
14321-25-6

(N-benzyl-N-methylamino)acetonitrile

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In ethanol98%
N-benzyl-N-methyl-4-nitrobenzenesulfonamide

N-benzyl-N-methyl-4-nitrobenzenesulfonamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With potassium carbonate; mercaptoacetic acid In methanol at 0 - 25℃; Inert atmosphere; chemoselective reaction;98%
methyl N-benzyl,N-methyl carbamate
56475-82-2

methyl N-benzyl,N-methyl carbamate

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
Stage #1: methyl N-benzyl,N-methyl carbamate With 3-azapentane-1,5-diamine at 140℃; for 48h; Sealed tube;
Stage #2: With hydrogenchloride In diethyl ether at 0 - 20℃;
98%
benzaldehyde
100-52-7

benzaldehyde

methylamine
74-89-5

methylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
Stage #1: benzaldehyde; methylamine In methanol at 20℃;
Stage #2: With sodium tetrahydroborate In methanol for 6h;
96.6%
Stage #1: benzaldehyde; methylamine With titanium(IV) isopropylate In methanol at 20℃; for 5h;
Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 2h;
92%
With copper chromium spinel oxide; hydrogen; barium(II) oxide at 130℃; under 37503 Torr; for 1h;62%
N-allyloxycarbonyl-N-methylbenzylamine
152507-72-7

N-allyloxycarbonyl-N-methylbenzylamine

A

N-allyl-N-α-methylbenzylamine
2520-97-0

N-allyl-N-α-methylbenzylamine

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water at 20℃; for 0.0833333h;A n/a
B 96%
With diethylamine; palladium diacetate; trisodium tris(3-sulfophenyl)phosphine In water; acetonitrile for 0.0833333h; Ambient temperature;A 70%
B 30%
With tetrabutylammonium borohydride; tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 20℃; Product distribution; Further Variations:; Reagents; Decarboxylation; substitution;
tert-butyl N-benzyl-N-methylcarbamate
81616-14-0

tert-butyl N-benzyl-N-methylcarbamate

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With nitric acid In dichloromethane at 0℃; for 1h;96%
With methanol; Amberlyst 15; ammonia 1.) CH2Cl2, 25 deg C, 8 h, 2.) 50 min; Yield given. Multistep reaction;
With trifluoroacetic acid In dichloromethane at 20℃; for 16h; Inert atmosphere;
With 1,1,3,3-Tetramethyldisiloxane; pyrographite; palladium dichloride In 1,2-dimethoxyethane at 25 - 40℃; for 24h;>99 %Spectr.
formaldehyd
50-00-0

formaldehyd

benzylamine
100-46-9

benzylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With butyl triphenylphosphonium tetraborate at 20℃; for 0.166667h;96%
Stage #1: formaldehyd; benzylamine In methanol at 20℃; for 1h;
Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;
60%
With formic acid In dimethyl sulfoxide for 0.0166667h; Eschweiler-Clarke methylation; microwave irradiation;
Stage #1: formaldehyd; benzylamine In tetrahydrofuran at 120℃; for 9h; Autoclave;
Stage #2: With hydrogen In tetrahydrofuran at 140℃; under 3750.38 Torr; for 9h; Autoclave;
N-benzyl-N-methyl-2-nitrobenzenesulfonamide
42060-39-9

N-benzyl-N-methyl-2-nitrobenzenesulfonamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With polystyrene-thiophenol; caesium carbonate; triphenylphosphine In tetrahydrofuran at 20℃; for 24h;96%
N-methylbenzamide
88070-48-8

N-methylbenzamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With triethyl borane; phenylsilane; sodium methylate In tetrahydrofuran at 50℃; Reagent/catalyst; Inert atmosphere; Schlenk technique; Sealed tube; chemoselective reaction;95%
With triethyl borane; phenylsilane; sodium methylate In tetrahydrofuran at 50℃; Inert atmosphere; Schlenk technique; Glovebox; Sealed tube;95%
Stage #1: N-methylbenzamide With triethyl borane; phenylsilane; sodium methylate In tetrahydrofuran; tert-butyl methyl ether at 20 - 50℃; for 48h; Sealed tube;
Stage #2: With hydrogenchloride In tetrahydrofuran; tert-butyl methyl ether; ethyl acetate at 20℃; for 6h;
95%
N-benzyl-N-methylacetamide
29823-47-0

N-benzyl-N-methylacetamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With ammonium bromide; ethylenediamine at 80℃; for 10h; Microwave irradiation; Inert atmosphere; neat (no solvent);95%
4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine
383865-57-4

4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine

A

1-Benzyl-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-urea

1-Benzyl-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-urea

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
A 94%
B n/a
4-(Methylthio)-N-methylbenzenemethanamine
84212-03-3

4-(Methylthio)-N-methylbenzenemethanamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With sodium tetrahydroborate; nickel dichloride91%
With sodium tetrahydroborate; nickel dichloride In methanol for 18h; Ambient temperature;
N-benzyl-2,2,2,-trifluoro-N-methylacetamide
68464-36-8

N-benzyl-2,2,2,-trifluoro-N-methylacetamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 60℃; for 15h;90%
(R,S)-N,N'-dimethyl-1,2-diphenylethylenediamine
60509-62-8, 1219814-39-7

(R,S)-N,N'-dimethyl-1,2-diphenylethylenediamine

(+/-)-N,N'-dimethyl-1,2-diphenyl-1,2-ethylenediamine
22751-68-4, 60508-97-6, 60509-62-8, 70749-06-3, 118628-68-5

(+/-)-N,N'-dimethyl-1,2-diphenyl-1,2-ethylenediamine

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With lithium; isoprene In tetrahydrofuran at 35℃; for 1h; Yields of byproduct given;A 89%
B n/a
methanol
67-56-1

methanol

N-methyl-N-benzylformamide
17105-71-4

N-methyl-N-benzylformamide

β-naphthol
135-19-3

β-naphthol

A

1-methyl-2-naphthol
1076-26-2

1-methyl-2-naphthol

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With pyrrolidine; tris(2,4-pentanedionato)ruthenium(III); [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; for 20h;A 89%
B 10%
N-benzyl-N-methyl-p-toluenesulfonamide
3695-02-1

N-benzyl-N-methyl-p-toluenesulfonamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With sodium tetrahydroborate; 1,2-dimethoxybenzene In ethanol for 1h; Irradiation;87%
With sodium tetrahydroborate; 1,2-dimethoxybenzene In ethanol Irradiation;87%
With titanium tetrachloride In tetrahydrofuran for 6h; Heating;45%
N-benzyl-N-methylbenzenesulfonamide
42060-55-9

N-benzyl-N-methylbenzenesulfonamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 3h; Heating;86%
With hydrogenchloride at 160 - 180℃;
N-benzyl-N-methylpyridine-2-sulfonamide

N-benzyl-N-methylpyridine-2-sulfonamide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With magnesium In methanol at 0℃; for 1.5h;86%
N-Benzylidenemethylamine
622-29-7

N-Benzylidenemethylamine

allyl bromide
106-95-6

allyl bromide

A

N-methyl-α-2-propenylbenzemethanamine
49603-23-8

N-methyl-α-2-propenylbenzemethanamine

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With bismuth; tetrabutylammomium bromide In acetonitrile for 0.166667h; Ambient temperature;A 85%
B n/a
β,β,β-Trichloroethyl Benzylmethylaminoformate
107292-20-6

β,β,β-Trichloroethyl Benzylmethylaminoformate

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With chloro-trimethyl-silane; mischmetal (50 percent Ce, 25 percent La, 16 percent Nd, 6 percent Pr) In tetrahydrofuran for 2h; Heating;85%
C14H25NO3Si

C14H25NO3Si

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With water In ethanol at 60℃; for 48h;84%
N-benzyl-N-methyltritylamine

N-benzyl-N-methyltritylamine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
Stage #1: N-benzyl-N-methyltritylamine With naphthalene; lithium In tetrahydrofuran at 0℃; for 1h;
Stage #2: With water In tetrahydrofuran at 0 - 20℃;
84%
methanol
67-56-1

methanol

benzylamine
100-46-9

benzylamine

A

N-methyl-N-benzylformamide
17105-71-4

N-methyl-N-benzylformamide

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); hydrogen at 120℃; under 30003 Torr; for 24h; Temperature; Reagent/catalyst; Glovebox;A 6%
B 82%
methanol
67-56-1

methanol

N-benzyl-N,4-dimethylbenzenesulfinamide
436850-67-8

N-benzyl-N,4-dimethylbenzenesulfinamide

A

methyl p-toluene sulfinate
672-78-6

methyl p-toluene sulfinate

B

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Conditions
ConditionsYield
With tetraethylammonium tosylate Electrochemical reaction; reticulated vitreous carbon anode; Pt cathode;A 80%
B n/a
phosgene
75-44-5

phosgene

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

benzyl(methyl)carbamic chloride
32366-02-2

benzyl(methyl)carbamic chloride

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 3h; Inert atmosphere;100%
With triethylamine In tetrahydrofuran at 0℃;74%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-(N-benzyl-N-methyl)amino-1-ethanol
101-98-4

2-(N-benzyl-N-methyl)amino-1-ethanol

Conditions
ConditionsYield
In acetonitrile Heating;100%
With potassium carbonate; potassium iodide In acetonitrile for 48h; Heating / reflux;63%
With toluene
at 110℃; im Rohr;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-benzyl-N-methylhydroxylamine
3555-72-4

N-benzyl-N-methylhydroxylamine

Conditions
ConditionsYield
With 4-hydroperoxy-5-ethyl-3-methyllumiflavine In tert-butyl alcohol at 30℃; Rate constant;100%
Stage #1: benzyl-methyl-amine With REM resin In N,N-dimethyl-formamide at 20℃; for 20h; Michael addition;
Stage #2: With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃; for 12h; Cope elimination;
47%
With dihydrogen peroxide
Multi-step reaction with 2 steps
1: tetrahydrofuran / 25 °C
2: mCPBA; DBU / methanol; H2O / 25 °C
View Scheme
Multi-step reaction with 2 steps
1: dipotassium hydrogenphosphate; dicyclohexyl phthalate / N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere
2: diisobutylaluminium hydride / dichloromethane; hexane / 0.25 h / 0 °C / Inert atmosphere
View Scheme
acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

methyl 3-propanoate
17946-01-9

methyl 3-propanoate

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 24h;100%
imidazolium-based polymer supported Gd(OTf)3 at 20℃; for 1h; Michael addition;96%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 4h; aza-Michael addition;95%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

phenylacetyl chloride
103-80-0

phenylacetyl chloride

N-benzyl-N-methyl-2-phenylacetamide
34317-22-1

N-benzyl-N-methyl-2-phenylacetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;100%
In diethyl ether
With sodium hydroxide In dichloromethane for 1h; Yield given;
With TEA; N-methylglycine potassium salt 1.) DMF, 4 h; 2.) DMF, 0.5 h; Yield given. Multistep reaction;
formaldehyd
50-00-0

formaldehyd

potassium cyanide
151-50-8

potassium cyanide

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

(N-benzyl-N-methylamino)acetonitrile
14321-25-6

(N-benzyl-N-methylamino)acetonitrile

Conditions
ConditionsYield
With hydrogenchloride for 16h; Ambient temperature;100%
isopropyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate
104272-89-1

isopropyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

propan-2-yl benzyl(methyl)carbamate
104272-97-1

propan-2-yl benzyl(methyl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile for 0.166667h; Ambient temperature;100%
isobutyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate
104272-90-4

isobutyl S-3,6-diisopropylpyrazin-2-ylthiolcarbonate

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

isobutyl benzyl(methyl)carbamate
104272-98-2

isobutyl benzyl(methyl)carbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile for 0.166667h; Ambient temperature;100%
2-t-butoxycarbonyloxy-3,6-diisopropylpyrazine
104272-92-6

2-t-butoxycarbonyloxy-3,6-diisopropylpyrazine

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

tert-butyl N-benzyl-N-methylcarbamate
81616-14-0

tert-butyl N-benzyl-N-methylcarbamate

Conditions
ConditionsYield
With triethylamine In acetonitrile for 0.166667h; Ambient temperature;100%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

2-phenyl-1-(2-thioxothiazolidin-3-yl)ethan-1-one
65439-58-9

2-phenyl-1-(2-thioxothiazolidin-3-yl)ethan-1-one

N-benzyl-N-methyl-2-phenylacetamide
34317-22-1

N-benzyl-N-methyl-2-phenylacetamide

Conditions
ConditionsYield
In dichloromethane for 0.0166667h; Ambient temperature;100%
4-(bromomethyl)benzene-1-sulfonyl chloride
66176-39-4

4-(bromomethyl)benzene-1-sulfonyl chloride

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-benzyl-4-(bromomethyl)-N-methylbenzenesulfonamide
125734-38-5

N-benzyl-4-(bromomethyl)-N-methylbenzenesulfonamide

Conditions
ConditionsYield
With triethylamine In diethyl ether at 20℃; for 3h; Substitution;100%
In dichloromethane at 20℃;20%
chloroacetonitrile
107-14-2

chloroacetonitrile

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

(N-benzyl-N-methylamino)acetonitrile
14321-25-6

(N-benzyl-N-methylamino)acetonitrile

Conditions
ConditionsYield
100%
Stage #1: benzyl-methyl-amine With triethylamine In acetone at 20℃; for 0.166667h;
Stage #2: chloroacetonitrile In acetone at 20℃; Inert atmosphere;
99%
With potassium carbonate; potassium iodide In acetone at 20℃; for 24h; Reflux;93%
hydratropic acid
492-37-5, 2328-24-7

hydratropic acid

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-Benzyl-N-methyl-2-phenylpropanamide

N-Benzyl-N-methyl-2-phenylpropanamide

Conditions
ConditionsYield
With O,O'-di(2-pyridyl) thiocarbonate; dmap In diethyl ether at 20℃;100%
With dmap; 2-methyl-6-nitrobenzoic anhydride In dichloromethane at 20℃;93%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

N-benzyl-N-methyl-3-phenylpropionamide
61751-42-6

N-benzyl-N-methyl-3-phenylpropionamide

Conditions
ConditionsYield
With 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride In methanol at 20℃; for 3h;100%
With tetrakis(2-methylimidazol-1-yl)silane In tetrahydrofuran at 20℃; for 12h;99%
Stage #1: 3-Phenylpropionic acid With 1,1'-carbonyldioxydi[2(1H)-pyridone] In dichloromethane at 20℃; for 1h;
Stage #2: benzyl-methyl-amine In dichloromethane at 20℃;
97%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

5-bromomethyl-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
174073-49-5

5-bromomethyl-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
174071-70-6

5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N-methyl-acetamide100%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide100%
With N-ethyl-N,N-diisopropylamine In N-methyl-acetamide100%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

wortmannin
19545-26-7

wortmannin

acetic acid 4-[(benzylmethylamino)methylene]-6-hydroxy-1α-methoxymethyl-10β,13β-dimethyl-3,7,17-trioxo-1,3,4,7,10,11β,12,13,14α,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester

acetic acid 4-[(benzylmethylamino)methylene]-6-hydroxy-1α-methoxymethyl-10β,13β-dimethyl-3,7,17-trioxo-1,3,4,7,10,11β,12,13,14α,15,16,17-dodecahydro-2-oxa-cyclopenta[a]phenanthren-11-yl ester

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃;100%
crotonic acid methyl ester
623-43-8

crotonic acid methyl ester

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

methyl 3-(N-benzyl-N-methylamino)-3-methylpropionate
40871-09-8

methyl 3-(N-benzyl-N-methylamino)-3-methylpropionate

Conditions
ConditionsYield
100%
100%
100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 14h; aza-Michael addition;77%
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

Chloroacetic anhydride
541-88-8

Chloroacetic anhydride

N-benzyl-N-methyl-α-chloroacetamide
73685-56-0

N-benzyl-N-methyl-α-chloroacetamide

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃; for 0.166667h;100%
6-(2-hydroxyethyl)-2-(methylthio)-4-pyrimidinyl 4-methyl-1-benzenesulfonate
920490-05-7

6-(2-hydroxyethyl)-2-(methylthio)-4-pyrimidinyl 4-methyl-1-benzenesulfonate

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

C15H19N3OS

C15H19N3OS

Conditions
ConditionsYield
In tetrahydrofuran at 70℃; for 48h;100%
1,2,3-Benzotriazole
95-14-7

1,2,3-Benzotriazole

formaldehyd
50-00-0

formaldehyd

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-methyl-1-phenylmethanamine
57684-27-2

N-((1H-benzo[d][1,2,3]triazol-1-yl)methyl)-N-methyl-1-phenylmethanamine

Conditions
ConditionsYield
In methanol; diethyl ether; water Reflux;100%
In methanol; water at 50℃; for 15h;85%
In water
8-bromooctanol
50816-19-8

8-bromooctanol

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

8-(N-Benzyl-N-methylamino)octan-1-ol
808757-04-2

8-(N-Benzyl-N-methylamino)octan-1-ol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 35℃; for 7h;100%
With potassium carbonate In acetonitrile at 35 - 40℃; for 5h;79%
With potassium carbonate In acetonitrile at 35 - 40℃; for 5h;79%
Stage #1: 8-bromooctanol; benzyl-methyl-amine With potassium carbonate In acetonitrile at 35℃; for 7h;
Stage #2: With 2-pyrrolidinon In tert-butyl methyl ether
3-benzyl-6-bromo-2-methoxyquinoline
654655-69-3

3-benzyl-6-bromo-2-methoxyquinoline

3-chloro-1-(naphthalen-1-yl)-propan-1-one
345949-37-3

3-chloro-1-(naphthalen-1-yl)-propan-1-one

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

2-(N-methylbenzyl)aminoethyl-1-naphthylketone
654655-75-1

2-(N-methylbenzyl)aminoethyl-1-naphthylketone

Conditions
ConditionsYield
In acetonitrile at 80℃; for 2h;100%
1H-pyrazole-1-carboximidamide hydrochloride
4023-02-3

1H-pyrazole-1-carboximidamide hydrochloride

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-benzyl-N-methylguanidine hydrochloride
330-69-8

N-benzyl-N-methylguanidine hydrochloride

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;100%
With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃;100%
3-chloro-1-(naphthalen-1-yl)-propan-1-one
345949-37-3

3-chloro-1-(naphthalen-1-yl)-propan-1-one

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

2-(N-methylbenzyl)aminoethyl-1-naphthylketone
654655-75-1

2-(N-methylbenzyl)aminoethyl-1-naphthylketone

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 2h;100%
With potassium carbonate In acetonitrile at 80℃; for 2h;100%
In acetonitrile at 80℃; for 2h;
In acetonitrile at 80℃; for 2h;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
101385-93-7

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

tert-butyl 3-(benzyl(methyl)amino)pyrrolidine-1-carboxylate
862906-27-2

tert-butyl 3-(benzyl(methyl)amino)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: benzyl-methyl-amine; 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With sodium tris(acetoxy)borohydride In dichloromethane at 0 - 20℃; for 2h;
Stage #2: With water; sodium hydrogencarbonate In dichloromethane
100%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Inert atmosphere;76%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 25℃;
benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

5-bromomethyl-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
174073-49-5

5-bromomethyl-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

A

IR(KBr][hydrochloride]

IR(KBr][hydrochloride]

B

5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
174071-70-6

5-(N-benzyl-N-methylaminomethyl)-1-(2,6-difluorobenzyl)-6-(4-nitrophenyl)-3-phenylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Conditions
ConditionsYield
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In N-methyl-acetamideA n/a
B 100%
With sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine In N-methyl-acetamideA n/a
B 100%
benzaldehyde
100-52-7

benzaldehyde

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

N-methyldibenzylamine
102-05-6

N-methyldibenzylamine

Conditions
ConditionsYield
With dirhodium tetraacetate; carbon monoxide In tetrahydrofuran; water at 140℃; under 15001.5 Torr; for 12h; Autoclave;100%
With formic acid; 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; sodium formate In water at 80℃; for 2h; pH=4.8; Sealed tube; Inert atmosphere;98%
With cobalt(II) phthalocyanine; diphenylsilane In ethanol at 70℃; for 12h; chemoselective reaction;93%

103-67-3Relevant articles and documents

Formylation of amines through catalyst- and solvent-free transamidation reaction

Lebleu, Thomas,Kotsuki, Hiyoshizo,Maddaluno, Jacques,Legros, Julien

, p. 362 - 364 (2014)

The transamidation between formamide and various amines proceeds under heating, without any catalyst nor solvent, providing thus green and neutral conditions for the formylation of primary and secondary amines. The resulting amide product can be directly transformed, in a one pot sequence, into monomethylamine.

Mechanism of α-Amino Acids decomposition in the gas phase. Experimental and theoretical study of the elimination kinetics of N-Benzyl Glycine Ethyl Ester

Tosta, Maria,Oliveros, Jhenny C.,Mora, Jose R.,Cordova, Tania,Chuchani, Gabriel

, p. 2483 - 2488 (2010)

The gas-phase elimination kinetics of N-benzylglycine ethyl ester was examined in a static system, seasoned with allyl bromide, and in the presence of the free chain radical suppressor toluene. The working temperature and pressure range were 386.4-426.7 °C and 16.7-40.0 torr, respectively. The reaction showed to be homogeneous, unimolecular, and obeys a first-order rate law. The elimination products are benzylglycine and ethylene. However, the intermediate benzylglycine is unstable under the reaction conditions decomposing into benzyl methylamine and CO2 gas. The variation of the rate coefficients with temperature is expressed by the following Arrhenius equation: log k1 (s-1) = (11.83 ± 0.52) - (190.3 ± 6.9) kJ mol -1 (2.303RT)-1. The theoretical calculation of the kinetic parameters and mechanism of elimination of this ester were performed at B3LYP/6-31G*, B3LYP/6-31+G**, MPW1PW91/6-31G*, and MPW1PW91/6-31+G** levels of theory. The calculation results suggest a molecular mechanism of a concerted nonsynchronous six-membered cyclic transition state process. The analysis of bond order and natural bond orbital charges implies that the bond polarization of C(=O)O-C, in the sense of C(=O)Oδ-...Cδ+, is rate determining. The experimental and theoretical parameters have been found to be in reasonable agreement.

New catalyst systems for iron-catalyzed hydrosilane reduction of carboxamides

Tsutsumi, Hironori,Sunada, Yusuke,Nagashima, Hideo

, p. 6581 - 6583 (2011)

A heptanuclear iron carbonyl cluster, [Fe3(CO) 11(μ-H)]2Fe(DMF)4 (4), is found to be a highly efficient catalyst for the reduction of various carboxamides by 1,2-bis(dimethylsilyl)benzene (BDSB), which makes possible reducing the amount of the catalyst, shortening the reaction time, and lowering the reaction temperatures.

Methylthio Activating Groups in the Synthesis of Isoquinolines

Euerby, Melvin R.,Waigh, Roger D.

, p. 127 - 128 (1984)

Methylthio activating groups have been found to improve the yields in six different isoquinoline syntheses: in four cases the improvement was from zero, in the unactivated system, to between 54 and 94percent.

Reactions of N-Halobenzylalkylamines with Sodium Methoxide in Methanol

Cho, Bong Rae,Yoon, Jong Chan,Bartsch, Richard A.

, p. 4943 - 4946 (1985)

Reactions of N-halobenzylmethylamines 1 and 2 (X = Cl and Br) with MeONa-MeOH have been investigated.Eliminations from 1 were quantitative, producing only benzylidenemethylamines.Reaction of 2 with MeONa-MeOH produced benzylidenemethylamines and benzylmethylamines.The yield of benzylidenemethylamine increased with electron-withdrawing aryl substituents and increased base concentration and became quantitative when pentane was used as a solvent.The results are interpreted as competing bimolecular elimination and nucleophilic substitution by methoxide on bromine.Product studies for reaction of N-halobenzyl-tert-butylamines with MeONa-MeOH and EtSNa-MeOH establish that the substitution reaction is a general reaction pathway available for the N-haloamines.Transition states for eliminations from 1 and 2 are characterized by Hammett ρ and primary deuterium isotope effect values.

Organolanthanide-catalyzed imine hydrogenation. Scope, selectivity, mechanistic observations, and unusual byproducts

Obora, Yasushi,Ohta, Tetsuo,Stern, Charlotte L.,Marks, Tobin J.

, p. 3745 - 3755 (1997)

In this paper we report the Cp'2LnMe2SiCp''2Ln-catalyzed (Cp' = η5-Me5C5; Cp'' = η5-Me4C5) hydrogenation of acyclic imines to yield the corresponding amines. At 190 psi of H2, the observed turnover frequencies (h-1) (100:1 substrate:catalyst ratio, Cp'2Ln, temperature (°C)) are (1) (N-benzylidene(methyl)amine, Ln = La, 50) 0.03; (Ln = Sm, 90) 1.0; (Ln = Sm + PhSiH3, 90) 2.2; (Ln = Lu, 90) 0.60; (2) (N-benzylideneaniline, Ln = Sm, 90) 0.10; (3) (N-benzylidene(trimethylsilyl)amine, Ln = Sm, 90) 0.40; (4) (N-(α-methylbenzylidene)(methyl)amine, Ln = Sm, 90) 0.20; (5) (N-(α-methylbenzylidene)(benzyl)amine, Ln = Sm, 90) 0.70. The stoichiometric reaction of N-benzylidene(methyl)amine with Cp'2SmCH(SiMe3)2 or (Cp'2SmH)2 yields an orthometalated Cp'2Sm-substrate complex which undergoes either hydrogenolysis/hydrogenation or competing C=N insertion of a second substrate molecule to yield a Cp'2Sm-imine-amido complex with a seven-membered chelate ring. The stoichiometric reaction of 2-methyl-1-pyrroline with Cp'2SmCH(SiMe3)2 or (Cp'2SmH)2 yields a Cp'2Sm-imine-amido complex in which two substrate molecules have been coupled to form a six-membered chelate ring (characterized by X-ray diffraction). The stoichiometric reaction of N-benzylidene(trimethylsilyl)amine with (Cp'2SmH)2 yields a desilylated Cp'2Sm-imine-amido complex with a four-membered Sm(NSiMe3)(CPh)N=CHPh chelate ring (characterized by X-ray diffraction). Additional heating of this product under H2 yields S6-symmetric (Cp'2SmCN)6, which contains an unusual chairlike 18-membered (SmCN)6 ring (characterized by X-ray diffraction).

Reactions of N-Chlorobenzylmethylamines with Secondary Amines in Acetonitrile. Effect of Base Strength upon the Imine-Forming Transition State

Cho, Bong Rae,Namgoong, Sung Keon,Bartsch, Richard A.

, p. 1320 - 1324 (1986)

Reactions of N-chlorobenzylmethylamines 1 with R2NH in MeCN have been investigated kinetically.Eliminations from 1 were quantitative and regiospecific, producing only benzylidenemethylamines.For the elimination reaction of 1 with Bu2NH, kH/kD = 8.8, ρ = 0.96, ΔH(excit.) = 7.6 kcal/mol, and ΔS(excit.) = -45.1 eu were determined.The transition state structure is assessed as being highly symmetrical with similar extents of Cβ-H and Nα-Cl bond cleavage, little carbanionic character, and significant ? bond formation.The kH/kD and ρ values first increase and then decrease with enhancing amine base strength.Comparison of these results with those for related olefin-forming eliminations provides insight into the transition state differences between imine- and olefin-forming eliminations.

Reduction of amides with NaBH4 in diglyme at 162°C

Zhu, Hua-Jie,Lu, Kai-Tao,Sun, Guang-Ri,He, Jin-Bao,Li, Hai-Qing,Pittman Jr., Charles U.

, p. 409 - 413 (2003)

High temperature (162°C) reductions of aromatic amides were studied to extend the useful range of functional group transformations by NaBH4. Primary aromatic amides were reduced to the amines with NaBH4-diglyme at 162°C. Reduction proceeds via fast initial loss of hydrogen, followed by formation of the corresponding nitrile, which is then more slowly reduced to the amine. N-Methylbenzamide is not reduced under these conditions, but it is reduced to benzylmethylamine when LiCl is added to NaBH4-diglyme at 162°C. LiCl addition raised the rate of primary aromatic amide and aromatic nitrile conversions to both the nitrile, first, and the amine. An intermediate was isolated from the reaction of N-benzylformamide with NaBH4-LiCl in diglyme at 162°C. It was examined by 1H NMR, atomic absorption, IR and thermal decomposition. Possible structures are proposed. A mechanism for the reduction of primary aromatic amides is proposed based on the initial evolution of one mole equivalent of hydrogen and formation of the nitrile prior to further reduction to amine.

A mild method for cleavage of N-Tos protected amines using mischmetal and TiCl4

Vellem?e, Eerold,Lebedev, Oleg,M?eorg, Uno

, p. 1373 - 1375 (2008)

The para-toluenesulfonyl (Tos) protecting group is removed efficiently and quickly under neutral conditions from the corresponding protected primary and secondary amines using mischmetal in moderate to excellent yields.

Chelating bis-carbene rhodium(III) complexes in transfer hydrogenation of ketones and imines

Albrecht, Martin,Crabtree, Robert H.,Mata, Jose,Peris, Eduardo

, p. 32 - 33 (2002)

Chelating rhodium(III) carbene complexes are accessible via a simple synthesis and are catalytically active for hydrogen transfer from alcohols to ketones and imines.

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