Product Name

  • Name

    12-Methyltridecanal

  • EINECS
  • CAS No. 75853-49-5
  • Article Data11
  • CAS DataBase
  • Density 0.825 g/cm3
  • Solubility
  • Melting Point 25°C (estimate)
  • Formula C14H28O
  • Boiling Point 275.1 ºC at 760 mmHg
  • Molecular Weight 212.376
  • Flash Point 111.5 ºC
  • Transport Information
  • Appearance Almost colourless to very slightly yellow
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 75853-49-5 (12-Methyltridecanal)
  • Hazard Symbols
  • Synonyms 12-Methyltridecanal;12-Methyl tridecanal;
  • PSA 17.07000
  • LogP 4.74230

Synthetic route

12-methyl-1-tridecanol
21987-21-3

12-methyl-1-tridecanol

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane at 20℃; for 24h;98%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 0℃; for 4h;85%
With pyridinium chlorochromate In dichloromethane for 2h;84%
With dipyridinium dichromate; 3 A molecular sieve In dichloromethane for 2h; Ambient temperature;
With Dess-Martin periodane In dichloromethane at 20℃; for 1h;
13-methyltetradec-1-ene
107841-96-3

13-methyltetradec-1-ene

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
With ozone In dichloromethane at -55℃; Temperature;93.5%
1,2-epoxy-13-methyltetradecane
107841-97-4

1,2-epoxy-13-methyltetradecane

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
With periodic acid In tetrahydrofuran; diethyl ether for 4h;66.04%
methyl 12-methyltridecanoate
5129-58-8

methyl 12-methyltridecanoate

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 93 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
2: 98 percent / pyridinium chlorochromate / CH2Cl2 / 24 h / 20 °C
View Scheme
1-undecen-11-ylbromide
7766-50-9

1-undecen-11-ylbromide

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) Mg, 2.) dilithium tetrachlorocuprate / 1) THF, 2.) THF, -10 deg C, 4 h
2: 1.) NaBH4, Hg(OAc)2, 2.) aq. H2O2, aq. NaOH / 1) THF, 16 h, room temperature; 2) THF, 70 deg C, 1 h
3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h
View Scheme
12-methyltridec-1-ene
156991-32-1

12-methyltridec-1-ene

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaBH4, Hg(OAc)2, 2.) aq. H2O2, aq. NaOH / 1) THF, 16 h, room temperature; 2) THF, 70 deg C, 1 h
2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 2 h
View Scheme
ethyl 12-methyltridecanoate
88591-29-1

ethyl 12-methyltridecanoate

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / LiAlH4 / tetrahydrofuran
2: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature
View Scheme
ethyl E-12-methyltridec-2-enoate
157922-16-2

ethyl E-12-methyltridec-2-enoate

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 74 percent / H2 / 10percent Pd/C / ethanol / Ambient temperature
2: 100 percent / LiAlH4 / tetrahydrofuran
3: pyridinium dichromate (PDC), molecular sieves 3A / CH2Cl2 / 2 h / Ambient temperature
View Scheme
1,10-Decanediol
112-47-0

1,10-Decanediol

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogen bromide / water; toluene / 48 h / Reflux
2: dilithium tetrachlorocuprate / tetrahydrofuran / 20 h / -78 °C
3: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 4 h / -78 - 0 °C
View Scheme
1-bromo-10-decanol
53463-68-6

1-bromo-10-decanol

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dilithium tetrachlorocuprate / tetrahydrofuran / 20 h / -78 °C
2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 4 h / -78 - 0 °C
View Scheme
10-undecenoic acid
112-38-9

10-undecenoic acid

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: thionyl chloride / dichloromethane / 10 °C
2: dichloromethane / 5 - 10 °C
3: tetrahydrofuran / 25 - 50 °C
4: potassium hydroxide; hydrazine hydrate / diethylene glycol / 70 - 190 °C
5: ozone / dichloromethane / -55 °C
View Scheme
C21H34O

C21H34O

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: palladium on activated carbon; hydrogen / methanol / 3 h / 20 °C
2: Dess-Martin periodane / dichloromethane / 1 h / 20 °C
View Scheme
13-methyltetradecanoic acid
2485-71-4

13-methyltetradecanoic acid

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

Conditions
ConditionsYield
With α‑dioxygenase from Crocosphaera subtropica In aq. phosphate buffer pH=7.5; Enzymatic reaction;
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

(+/-)-2-trimethylsilyloxy-13-methyltetradecanonitrile
671756-90-4

(+/-)-2-trimethylsilyloxy-13-methyltetradecanonitrile

Conditions
ConditionsYield
With triethylamine In dichloromethane at 25℃; for 2h;96%
C18H33NO3Si

C18H33NO3Si

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

A

C26H47NO4

C26H47NO4

B

C26H47NO4

C26H47NO4

Conditions
ConditionsYield
With titanium tetrachloride In dichloromethane at -78℃; for 42h;A n/a
B 87%
...Expand
N,N-dimethylthioacetamide
631-67-4

N,N-dimethylthioacetamide

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

(S)-3-hydroxy-N,N,14-trimethylpentadecanethioamide
1402050-26-3

(S)-3-hydroxy-N,N,14-trimethylpentadecanethioamide

Conditions
ConditionsYield
With 2,2,5,7,8-pentamethylchroman-6-ol; mesitylcopper(I); (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In tetrahydrofuran; N,N-dimethyl-formamide at -60℃; for 40h; Inert atmosphere;69%
ethyl bromide
74-96-4

ethyl bromide

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

14-methylpentadecan-3-ol
107841-98-5

14-methylpentadecan-3-ol

Conditions
ConditionsYield
With magnesium 1) ether, 2) ether, a) 0 deg C to rt, 4 h, b) overnight; Yield given. Multistep reaction;
ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

14-methylpentadecan-3-ol
107841-98-5

14-methylpentadecan-3-ol

Conditions
ConditionsYield
In tetrahydrofuran
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

methyl (triphenylphosphoranylidene)acetate
21204-67-1

methyl (triphenylphosphoranylidene)acetate

methyl E-14-methylpentadec-2-enoate

methyl E-14-methylpentadec-2-enoate

Conditions
ConditionsYield
In benzene Ambient temperature; Yield given;
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

(+/-)-2-hydroxy-13-methyltetradecanoic acid
22226-24-0

(+/-)-2-hydroxy-13-methyltetradecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 96 percent / Et3N / CH2Cl2 / 2 h / 25 °C
2: aq. HCl / 1,2-dimethoxy-ethane / 24 h / 90 °C
3: aq. NaOH / 1,2-dimethoxy-ethane / 2 h / 90 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

2-hydroxy-13-methyl-tetradecanoic acid amide

2-hydroxy-13-methyl-tetradecanoic acid amide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / Et3N / CH2Cl2 / 2 h / 25 °C
2: aq. HCl / 1,2-dimethoxy-ethane / 24 h / 90 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

14-methylpentadecan-3-one
90965-32-5

14-methylpentadecan-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrahydrofuran
2: pyridinium chlorochromate / CH2Cl2
View Scheme
Multi-step reaction with 2 steps
1: 1) Mg / 1) ether, 2) ether, a) 0 deg C to rt, 4 h, b) overnight
2: 83.33 percent / pyridinium chlorochromate / CH2Cl2 / 3 h
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

C35H58NOSSi(1+)*CF3O3S(1-)

C35H58NOSSi(1+)*CF3O3S(1-)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere
2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C
3: diethyl ether / 4.5 h / 0 - 20 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

A

(S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal
1402050-29-6

(S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanal

B

C32H50O2Si

C32H50O2Si

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere
2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C
3: diethyl ether / 4.5 h / 0 - 20 °C
4: Li(1+)*AlH4(1-)*3C4H10O / tetrahydrofuran; dichloromethane / 4 h / -78 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

(S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanoic acid
1402050-38-7

(S)-3-((tert-butyldiphenylsilyl)oxy)-14-methylpentadecanoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere
2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C
3: diethyl ether / 4.5 h / 0 - 20 °C
4: Li(1+)*AlH4(1-)*3C4H10O / tetrahydrofuran; dichloromethane / 4 h / -78 °C
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 5 h / 0 - 20 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

(S)-3-((tert-butyldiphenylsilyl)oxy)-N,N,14-trimethylpentadecanethioamide
1402050-28-5

(S)-3-((tert-butyldiphenylsilyl)oxy)-N,N,14-trimethylpentadecanethioamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2,5,7,8-pentamethylchroman-6-ol; (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane; mesitylcopper(I) / tetrahydrofuran; N,N-dimethyl-formamide / 40 h / -60 °C / Inert atmosphere
2: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C
View Scheme
N,N-diallylmethylmethanethioamide
1182707-33-0

N,N-diallylmethylmethanethioamide

12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

A

(S)-N,N-diallyl-3-hydroxy-14-methylpentadecanethioamide
1402050-25-2

(S)-N,N-diallyl-3-hydroxy-14-methylpentadecanethioamide

B

C22H41NOS

C22H41NOS

Conditions
ConditionsYield
With 2,2,5,7,8-pentamethylchroman-6-ol; mesitylcopper(I); (R,R)-1,2-bis(2,5-diphenylphospholanyl)ethane In tetrahydrofuran; N,N-dimethyl-formamide at -60℃; for 40h; Concentration; Solvent; Inert atmosphere; Overall yield = 92 %; Overall yield = 67.6 mg;A n/a
B n/a
...Expand
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

C26H49NO4

C26H49NO4

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: titanium tetrachloride / dichloromethane / 42 h / -78 °C
2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

C35H65N2O9P

C35H65N2O9P

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: titanium tetrachloride / dichloromethane / 42 h / -78 °C
2: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C
3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C
4: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

C35H65N2O11P

C35H65N2O11P

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C
2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C
4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C
5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C
5.2: 20 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

C40H78N3O12PSi

C40H78N3O12PSi

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C
2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C
4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C
5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C
5.2: 20 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C
7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C
View Scheme
12-methyltridecan-1-al
75853-49-5

12-methyltridecan-1-al

C36H65N3O8Si

C36H65N3O8Si

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: titanium tetrachloride / dichloromethane / 42 h / -78 °C
2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 19 h / 20 °C
3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 15 h / 20 °C
4.1: triethylamine; fluoro-N,N,N',N'-tetramethylformamidinium hexafluorophosphate; dmap / dichloromethane / 17 h / 20 °C
5.1: osmium(VIII) oxide; pyridine / 2.5 h / 20 °C
5.2: 20 h / 20 °C
6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 75 °C
7.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
8.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 21 h / 20 °C
9.1: Dess-Martin periodane / dichloromethane / 4 h / 20 °C
10.1: triethylamine; zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 19 h / 20 °C
View Scheme

12-Methyltridecanal Chemical Properties

Molecular Structure of 12-Methyltridecanal (CAS No.75853-49-5):

Molecular Formula: C14H28O 
Molecular Weight: 212.3715
CAS No: 75853-49-5
IUPAC Name: 12-Methyltridecanal
Product Categories: Aldehyde Flavor
H bond acceptors: 1
H bond donors: 0
Freely Rotating Bonds: 11
Polar Surface Area: 17.07 Å2
Index of Refraction: 1.434
Molar Refractivity: 67.05 cm3
Molar Volume: 257.3 cm3
Surface Tension: 28.6 dyne/cm
Density: 0.825 g/cm3
Flash Point: 111.5 °C
Enthalpy of Vaporization: 51.35 kJ/mol
Boiling Point: 275.1 °C at 760 mmHg
Vapour Pressure: 0.0052 mmHg at 25°C
InChI: InChI=1/C14H28O/c1-14(2)12-10-8-6-4-3-5-7-9-11-13-15/h13-14H,3-12H2,1-2H3
InChIKey: OQWNKUAZQSLNSR-UHFFFAOYAC
Std. InChI: InChI=1S/C14H28O/c1-14(2)12-10-8-6-4-3-5-7-9-11-13-15/h13-14H,3-12H2,1-2H3
Std. InChIKey: OQWNKUAZQSLNSR-UHFFFAOYSA-N

12-Methyltridecanal Specification

  12-Methyltridecanal (CAS No.75853-49-5), its synonyms are Tridecanal, 12-methyl- ; 12-MT Aldehyde .

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