Product Name

  • Name

    (S)-(-)-1-(P-TOLYL)ETHYLAMINE

  • EINECS -0
  • CAS No. 27298-98-2
  • Article Data60
  • CAS DataBase
  • Density 0.945 g/cm3
  • Solubility
  • Melting Point <-20 °C
  • Formula C9H13N
  • Boiling Point 208.6 °C at 760 mmHg
  • Molecular Weight 135.209
  • Flash Point 84.2 °C
  • Transport Information UN 2619 8/PG 2
  • Appearance colorless to light yellow liquid
  • Safety 16-26-27-36/37/39-45
  • Risk Codes 20/21/22-34
  • Molecular Structure Molecular Structure of 27298-98-2 ((S)-(-)-1-(P-TOLYL)ETHYLAMINE)
  • Hazard Symbols CorrosiveC
  • Synonyms Benzenemethanamine,a,4-dimethyl-, (S)-;Benzylamine,p,a-dimethyl-, (S)-(-)- (8CI);(-)-1-(4-Methylphenyl)ethylamine;(-)-1-(p-Tolyl)ethylamine;(-)-p-Methyl-a-phenylethylamine;(1S)-(p-Tolyl)ethylamine;(1S)-1-(4-Methylphenyl)ethanamine;(S)-(-)-1-(4-Methylphenyl)ethylamine;(S)-(-)-p,a-Dimethylbenzylamine;(S)-1-(4-Methylphenyl)ethylamine;(S)-1-(p-Methylphenyl)ethylamine;(S)-1-(p-Tolyl)ethylamine;(S)-a-4-Dimethylbenzylamine;N-[(1S)-1-(4-Methylphenyl)ethyl]amine;
  • PSA 26.02000
  • LogP 2.71500

Synthetic route

para-methylacetophenone
122-00-9

para-methylacetophenone

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
With formate dehydrogenase; Arthrobacter citreus S9 ω-transaminase; ATA-113 ω-transaminase; sodium formate; isopropylamine; NADH; yeast alcohol dehydrogenase pH=7; aq. phosphate buffer; Enzymatic reaction; optical yield given as %ee;99%
Stage #1: para-methylacetophenone With ochrobactrum anthropi ω-transaminases W58L/R417A; isopropylamine In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 460 Torr; for 8h; pH=7; Enzymatic reaction;
Stage #2: With hydrogenchloride; perchloric acid In water; acetonitrile		92%
With pyridoxal 5'-phosphate; ω-transaminases from ochrobactrum anthropi mutant W58A; isopropylamine In aq. phosphate buffer; dimethyl sulfoxide at 37℃; under 300 Torr; for 7h; pH=7; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;n/a
(1R)-2-({[(1S)-1-(4-methylphenyl)ethyl]amino}oxy)-1-phenylethanol
757195-32-7

(1R)-2-({[(1S)-1-(4-methylphenyl)ethyl]amino}oxy)-1-phenylethanol

A

(R)-1-phenyl-1,2-ethanediol
16355-00-3

(R)-1-phenyl-1,2-ethanediol

B

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
With hexacarbonyl molybdenum In water; acetonitrile at 85℃; for 1h;A n/a
B 72%
1-(p-tolyl)ethylamine
42070-98-4

1-(p-tolyl)ethylamine

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
With 6-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranosyl) hydrogen phthalate In isopropyl alcohol Heating;A 65.7%
B n/a
Stage #1: 1-(p-tolyl)ethylamine With N-(1-(R)-phenylethyl)-malonamic acid In acetone Heating;
Stage #2: With hydrogenchloride		A 55%
B n/a
Stage #1: 1-(p-tolyl)ethylamine With 5-(1,2-O-C(CH3)2-3,6-anhydro-α-D-glucofuranose)-H-phthalate In methanol for 0.05h; Heating;
Stage #2: With hydrogenchloride
isopropyl methoxyacetate
17640-21-0

isopropyl methoxyacetate

1-(p-tolyl)ethylamine
42070-98-4

1-(p-tolyl)ethylamine

A

2-methoxy-N-[(1R)-1-(4-methylphenyl)ethyl]acetamide
296236-17-4

2-methoxy-N-[(1R)-1-(4-methylphenyl)ethyl]acetamide

B

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
With Novozym 435 at 23℃; for 3h; Molecular sieve; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;A 45%
B 45%
With Candida antacrtica lipase B at 20℃; Enzymatic reaction; optical yield given as %ee;
...Expand
1-(p-tolyl)ethylamine
42070-98-4

1-(p-tolyl)ethylamine

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
With D-(+)-camphoric acid
With N-Ac-Leu
(1S,2R)-1-Phenyl-2-[1-p-tolyl-eth-(E)-ylideneamino]-propan-1-ol

(1S,2R)-1-Phenyl-2-[1-p-tolyl-eth-(E)-ylideneamino]-propan-1-ol

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
With platinum(IV) oxide; sodium periodate; hydrogen 1.) C6H6, 2.) CH3OH, RT, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
(1R,2S)-1-Phenyl-2-[1-p-tolyl-eth-(E)-ylideneamino]-propan-1-ol

(1R,2S)-1-Phenyl-2-[1-p-tolyl-eth-(E)-ylideneamino]-propan-1-ol

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
With platinum(IV) oxide; sodium periodate; hydrogen 1.) C6H6, 2.) CH3OH, RT, 5 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
para-methylacetophenone
122-00-9

para-methylacetophenone

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
Stage #1: para-methylacetophenone With [((R)-tol-binap)RuCl2(DMF)x]; ammonia; ammonium formate In methanol at 85℃; for 21h; Leuckart-Wallach reaction;
Stage #2: With hydrogenchloride In ethanol for 1h; Heating; Title compound not separated from byproducts;
Stage #1: para-methylacetophenone With ammonium acetate; sodium cyanoborohydride In methanol at 20℃; reductive amination;
Stage #2: racemate resolution; Further stages.;
Stage #1: para-methylacetophenone With 2-Hydroxybenzylamine; C24H34N2O2 In toluene at 110℃; for 72h;
Stage #2: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 24h; Overall yield = 52 %;		A n/a
B n/a
1-p-tolylethanone oxime
54582-23-9

1-p-tolylethanone oxime

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
Stage #1: 1-p-tolylethanone oxime With diphenylsilane; silver trifluoromethanesulfonate In 1,2-dimethoxyethane at 20℃; for 40h;
Stage #2: With hydrogenchloride In methanol; 1,2-dimethoxyethane Further stages. Title compound not separated from byproducts.;
(E)-1-(4-methylphenyl)ethanone O-benzyl oxime
937371-81-8

(E)-1-(4-methylphenyl)ethanone O-benzyl oxime

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
With sodium tetrahydroborate; borane; enantiopure spiroborate ester In 1,4-dioxane for 36h;
1-p-tolylethanone oxime
54582-23-9

1-p-tolylethanone oxime

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaH / dimethylformamide / 20 °C
2: borane; NaBH4 / enantiopure spiroborate ester / dioxane / 36 h
View Scheme
4-methylbenzaldehyde O-[(2R)-2-hydroxy-2-phenylethyl]oxime
757195-21-4

4-methylbenzaldehyde O-[(2R)-2-hydroxy-2-phenylethyl]oxime

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene; diethyl ether / 0.42 h / -20 °C
2: 72 percent / Mo(CO)6 / acetonitrile; H2O / 1 h / 85 °C
View Scheme
4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / TsOH / toluene / 0.5 h / Heating
2: toluene; diethyl ether / 0.42 h / -20 °C
3: 72 percent / Mo(CO)6 / acetonitrile; H2O / 1 h / 85 °C
View Scheme
para-methylacetophenone
122-00-9

para-methylacetophenone

KOH

KOH

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 4 Angstroem molecular sieves / benzene / 24 h / Ambient temperature
2: 1.) H2, PtO2, 2.) NaIO4 / 1.) C6H6, 2.) CH3OH, RT, 5 h
View Scheme
Multi-step reaction with 2 steps
1: 4 Angstroem molecular sieves / benzene / 24 h / Ambient temperature
2: 1.) H2, PtO2, 2.) NaIO4 / 1.) C6H6, 2.) CH3OH, RT, 5 h
View Scheme
4-methylacethophenone oxime
2089-33-0

4-methylacethophenone oxime

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ethanol; sodium
2: (1R)-cis-camphoric acid
View Scheme

A

B

C

Conditions
ConditionsYield
With Candida antarctica lipase B; hydrogen; nickel In toluene at 70℃; under 75.0075 Torr; for 72h; Autoclave; Enzymatic reaction; optical yield given as %ee;
...Expand

para-methylacetophenone
122-00-9

para-methylacetophenone

A

(R)-1-phenyl-ethyl-amine

(R)-1-phenyl-ethyl-amine

B

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

C

3-Carboxyphenol

3-Carboxyphenol

Conditions
ConditionsYield
With Chromobacterium violaceum ω-transaminase variant W60C at 37℃; for 12h; pH=7; Reagent/catalyst; pH-value; enantioselective reaction;A n/a
B n/a
C n/a
...Expand
para-methylacetophenone
122-00-9

para-methylacetophenone

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-N-[1-(4-methylphenyl)ethyl]acetamide

(R)-N-[1-(4-methylphenyl)ethyl]acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: formamide / water / 10 h / 210 °C
1.2: 1 h / 100 °C / Reflux
2.1: Candida antarctica B lipase CAL-B acrylic resin / toluene / 72 h / 50 °C / Enzymatic reaction
View Scheme
1-(p-tolyl)ethylamine
42070-98-4

1-(p-tolyl)ethylamine

ethyl acetate
141-78-6

ethyl acetate

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-N-[1-(4-methylphenyl)ethyl]acetamide

(R)-N-[1-(4-methylphenyl)ethyl]acetamide

Conditions
ConditionsYield
With Candida antarctica B lipase CAL-B acrylic resin In toluene at 50℃; for 72h; Enzymatic reaction; enantioselective reaction;A n/a
B 50 %Chromat.
...Expand
1-(p-tolyl)ethylamine
42070-98-4

1-(p-tolyl)ethylamine

3-Methyl-2,4-pentanedione
815-57-6

3-Methyl-2,4-pentanedione

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R,Z)-3-methyl-4-((1-(p-tolyl)ethyl)amino)pent-3-en-2-one

(R,Z)-3-methyl-4-((1-(p-tolyl)ethyl)amino)pent-3-en-2-one

C

(S,Z)-3-methyl-4-((1-(p-tolyl)ethyl)amino)pent-3-en-2-one

(S,Z)-3-methyl-4-((1-(p-tolyl)ethyl)amino)pent-3-en-2-one

D

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
With C74H89O4P In diethyl ether at -78 - -5℃; for 20h; Inert atmosphere; Molecular sieve; Resolution of racemate;A n/a
B n/a
C n/a
D n/a
...Expand
2-amino-5-methylhexane
28292-43-5

2-amino-5-methylhexane

3-Methyl-2,4-pentanedione
815-57-6

3-Methyl-2,4-pentanedione

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R,Z)-3-methyl-4-((5-methylhexan-2-yl)amino)pent-3-en-2-one

(R,Z)-3-methyl-4-((5-methylhexan-2-yl)amino)pent-3-en-2-one

C

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

Conditions
ConditionsYield
With C74H89O4P In diethyl ether at -78 - -5℃; for 20h; Inert atmosphere; Molecular sieve; Resolution of racemate;A n/a
B n/a
C n/a
...Expand
1-(p-tolyl)ethylamine
42070-98-4

1-(p-tolyl)ethylamine

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

para-methylacetophenone
122-00-9

para-methylacetophenone

Conditions
ConditionsYield
With (R)-amine dehydrogenase In dimethyl sulfoxide at 37℃; pH=8.5; Catalytic behavior; Resolution of racemate; Microbiological reaction; Enzymatic reaction; enantioselective reaction;
4-methylethylbenzene
622-96-8

4-methylethylbenzene

A

(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

B

(R)-4'-methyl-1-phenylethylamine
586-70-9, 4187-38-6, 27298-98-2, 42070-98-4

(R)-4'-methyl-1-phenylethylamine

C

4-ethylbenzylamine
7441-43-2

4-ethylbenzylamine

Conditions
ConditionsYield
With C5H11NO*CHF3O3S In ethanol; water at 10℃; for 12h; pH=7.4; Inert atmosphere; Sealed tube; Enzymatic reaction; Overall yield = 48 percent; enantioselective reaction;A n/a
B n/a
C n/a
...Expand
(S)-1-(4-methylphenyl)ethylamine
27298-98-2

(S)-1-(4-methylphenyl)ethylamine

2-oxopropanal
78-98-8

2-oxopropanal

N-[(S)-1-(4-methylphenyl)ethyl]-2-oxopropan-1-imine

N-[(S)-1-(4-methylphenyl)ethyl]-2-oxopropan-1-imine

Conditions
ConditionsYield
100%

(S)-(-)-1-(4-Methylphenyl)ethylamine Specification

The (S)-(-)-1-(p-Tolyl)ethylamine, with the CAS registry number 27298-98-2, is also known as (S)-(-)-alpha,4-Dimethylbenzylamine. It belongs to the product categories of Chiral; API intermediates; Amines (Chiral); Asymmetric Synthesis; Chiral Building Blocks; For Resolution of Acids; Optical Resolution; Synthetic Organic Chemistry; Amines; Chiral Building Blocks; Organic Building Blocks. This chemical's molecular formula is C9H13N and molecular weight is 135.21. Its systematic name is called (1S)-1-(4-methylphenyl)ethanamine.

Physical properties of (S)-(-)-1-(p-Tolyl)ethylamine: (1)ACD/LogP: 1.90; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.18; (4)ACD/LogD (pH 7.4): -0.48; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1.08; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.53; (13)Molar Refractivity: 44.16 cm3; (14)Molar Volume: 142.9 cm3; (15)Surface Tension: 35.6 dyne/cm; (16)Density: 0.945 g/cm3; (17)Flash Point: 84.2 °C; (18)Enthalpy of Vaporization: 44.48 kJ/mol; (19)Boiling Point: 208.6 °C at 760 mmHg; (20)Vapour Pressure: 0.212 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may destroy living tissue on contact. It is harmful by inhalation, in contact with skin and if swallowed. In addition, it may cause burns. You should keep it away from sources of ignition - No smoking. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: N[C@H](c1ccc(cc1)C)C
(2)InChI: InChI=1/C9H13N/c1-7-3-5-9(6-4-7)8(2)10/h3-6,8H,10H2,1-2H3/t8-/m0/s1
(3)InChIKey: UZDDXUMOXKDXNE-QMMMGPOBBK

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