13310-75-3

Basic information

• Product Name: 2-PROPYLVALERONITRILE
• Synonyms: PENTANENITRILE, 2-PROPYL-;2-PROPYLVALERONITRILE;2-Propylpentanenitrile;Ai3-18232;Einecs 236-338-2;Sodium Valproate Impurity I
• CAS NO: 13310-75-3
• Molecular Formula: C₈H₁₅N
• Molecular Weight: 125.21
• EINECS: 236-338-2
• Mol File: 13310-75-3.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 193 °C at 760 mmHg
• Flash Point: 82.3 °C
• Appearance: /
• Density: 0.811 g/cm³
• Vapor Pressure: 0.475mmHg at 25°C
• Refractive Index: 1.419
• CAS DataBase Reference: 2-PROPYLVALERONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-PROPYLVALERONITRILE(13310-75-3)
• EPA Substance Registry System: 2-PROPYLVALERONITRILE(13310-75-3)

Safety Data

• Hazardous Substances Data: 13310-75-3(Hazardous Substances Data)

Usage

Uses

2-Propylvaleronitrile, is an impurity of Valproic Acid (V094750), an antiepileptic; anticonvulsant that also acts as a mood stabilizer for those with bipolar disorder.

InChI:InChI=1/C8H15N/c1-3-5-8(7-9)6-4-2/h8H,3-6H2,1-2H3

Synthetic route

4-chloroheptane (998-95-8) + sodium cyanide (143-33-9) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With tetrakis[tris(dimethylamino)phosphoranylideneamino] phosphonium bromide; tris phosphate In DMF (N,N-dimethyl-formamide) at 110℃; for 6h;	89%

pentanonitrile (110-59-8) + 4-Cyan-4-propylheptan (5340-48-7) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
	83.82%
	78.2%

1-<4-(4-Cyanoheptyl)>-2-carbomethoxyhydrazine (124243-25-0) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With sodium cyanide In methanol at 17℃; for 4.7h; electrolysis;	79%

pentanonitrile (110-59-8) + propyl bromide (106-94-5) → di-N-propyl acetonitrile (13310-75-3) + 4-Cyan-4-propylheptan (5340-48-7)

Conditions	Yield
With sodium In toluene for 2h; Irradiation;	A 78% B 2%

1-Methoxycarbonyl-2-(4-heptylidene)hydrazine (14978-96-2) + sodium cyanide (143-33-9) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
In methanol at 17℃; for 4.7h; after standing for seven days before electrolysis;	77%

methyl 2-cyano-2-propylpentanoate (66546-92-7) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With lithium chloride In water; dimethyl sulfoxide at 150℃; Inert atmosphere;	77%

pentanonitrile (110-59-8) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
	65.2%

propyl bromide (106-94-5) + acetonitrile (75-05-8) → pentanonitrile (110-59-8) + di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With sodium In toluene for 2h; Irradiation;	A 44% B 20%

4-bromoheptane (998-93-6) + potassium cyanide (151-50-8) → di-N-propyl acetonitrile (13310-75-3)

pentanonitrile (110-59-8) + propyl bromide (106-94-5) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With sodium amide

4-heptanone (123-19-3) + [(p-methylphenyl)sulfonylmethyl]isonitrile (38622-91-2, 36635-61-7) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With potassium tert-butylate In 1,2-dimethoxyethane; ethanol

valpromide (2430-27-5) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
With pyridine; trichlorophosphate
With triethylamine; trifluoroacetic anhydride In 1,4-dioxane at 0℃;

4-heptanone trisylhydrazone (63883-82-9) + potassium cyanide (151-50-8) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
In methanol for 3h; Heating; Yield given;

1-Acetyl-2-(4-heptylidene)hydrazine (124243-19-2) + sodium cyanide (143-33-9) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
In methanol at 17℃; for 4.7h; electrolysis;	27 % Chromat.

Benzoic acid N'-(1-cyano-1-propyl-butyl)-hydrazide (128721-94-8) → 4-heptanone (123-19-3) + di-N-propyl acetonitrile (13310-75-3) + 2-benzoyl-2-n-propylpentanenitrile (135664-51-6)

Conditions	Yield
With air; sodium cyanide; acetic acid; Aliquat 336 In hexane; water for 3h; Product distribution; Ambient temperature; other reagents, other solvents, other catalysts;

sodium cyanide (143-33-9) + 4-Heptanone benzoylhydrazone (124243-15-8) → benzoic acid methyl ester (93-58-3) + di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
In methanol at 17℃; for 4.7h; electrolysis;	A 45 % Chromat. B 44 % Chromat.

dipropylcyanoacetic acid → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
langsame Destillieren;

4-heptanone (123-19-3) + sodium → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 2 h / Ambient temperature 2: methanol / 3 h / Heating View Scheme

4-heptanone (123-19-3) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH / methanol / 6 h / Heating 2: 77 percent / methanol / 4.7 h / 17 °C / after standing for seven days before electrolysis View Scheme
Multi-step reaction with 3 steps 1: AcOH / methanol / 6 h / Heating 2: AcOH / methanol / Ambient temperature 3: 79 percent / NaCN / methanol / 4.7 h / 17 °C / electrolysis View Scheme
Multi-step reaction with 2 steps 1: AcOH / methanol / 6 h / Heating 2: 44 percent Chromat. / methanol / 4.7 h / 17 °C / electrolysis View Scheme
Multi-step reaction with 2 steps 1: AcOH / methanol / 6 h / Heating 2: 27 percent Chromat. / methanol / 4.7 h / 17 °C / electrolysis View Scheme

1-Methoxycarbonyl-2-(4-heptylidene)hydrazine (14978-96-2) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH / methanol / Ambient temperature 2: 79 percent / NaCN / methanol / 4.7 h / 17 °C / electrolysis View Scheme

20%-hydrochloric acid + pentanonitrile (110-59-8) + propyl bromide (106-94-5) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
In di-isopropyl ether; water

ethyl 2-cyano-2-propylpentanoate (66546-90-5) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide 2: toluene / Reflux View Scheme

2-cyano-2-propyl-valeric acid (66546-91-6) → di-N-propyl acetonitrile (13310-75-3)

Conditions	Yield
In toluene Reflux;

di-N-propyl acetonitrile (13310-75-3) + propyl bromide (106-94-5) → 4-Cyan-4-propylheptan (5340-48-7)

Conditions	Yield
	94.5%
With sodium amide; toluene

di-N-propyl acetonitrile (13310-75-3) + (3-phenylpropane-1,1-diyl)bis(phenylsulfane) (58749-30-7) → 1-phenyl-5-propyl-octan-4-one

Conditions	Yield
Stage #1: (3-phenylpropane-1,1-diyl)bis(phenylsulfane) With titanocene(II) triethylphosphite complex In tetrahydrofuran at 20℃; for 0.25h; complexation; Stage #2: di-N-propyl acetonitrile In tetrahydrofuran at 20℃; for 1h; Alkylation; Stage #3: With sodium hydroxide Hydrolysis;	85%

di-N-propyl acetonitrile (13310-75-3) → valproic acid (99-66-1)

Conditions	Yield
With sodium perborate at 240℃; for 1h;	82.5%
With benzene-1,2-dicarboxylic acid at 240℃; under 3040 Torr; for 1h;	74%
With sodium hydroxide

di-N-propyl acetonitrile (13310-75-3) → 2-propylpentan-1-amine (40755-20-2)

Conditions	Yield
With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 20℃; for 1h; Inert atmosphere;	77%
With ethanol; sodium
With hydrogen; nickel
With lithium aluminium tetrahydride In tetrahydrofuran at 70℃; for 24h;

di-N-propyl acetonitrile (13310-75-3) → 5-(heptan-4-yl)-1H-tetrazole

Conditions	Yield
With sodium azide; ammonium chloride In N,N-dimethyl-formamide Reflux;	34%

di-N-propyl acetonitrile (13310-75-3) → 2-bromo-2-propyl-valeronitrile

Conditions	Yield
With bromine

n-butyl magnesium bromide (693-03-8) + di-N-propyl acetonitrile (13310-75-3) → 4-propyl-nonan-5-one (51864-95-0)

Conditions	Yield
In diethyl ether

triethylsilane (617-86-7) + di-N-propyl acetonitrile (13310-75-3) → (2-Propyl-pent-1-enyl)-triethylsilanyl-amine (35289-16-8)

Conditions	Yield
With triethylamine; zinc(II) chloride at 170℃;

methyl bromide (74-83-9) + di-N-propyl acetonitrile (13310-75-3) → 3-propyl-2-hexanone (40239-27-8)

Conditions	Yield
(i) Mg, Et2O, (ii) /BRN= 1744050/; Multistep reaction;

ethanol (64-17-5) + di-N-propyl acetonitrile (13310-75-3) → Ethyl di-n-propyl-acetimidat (57554-21-9)

Conditions	Yield
With hydrogenchloride for 336h;

di-N-propyl acetonitrile (13310-75-3) + methylmagnesium bromide (75-16-1) → 3-propyl-2-hexanone (40239-27-8)

di-N-propyl acetonitrile (13310-75-3) + ethylmagnesium bromide (925-90-6) → 4-propyl-heptan-3-one (40239-34-7)

Conditions	Yield
In diethyl ether

di-N-propyl acetonitrile (13310-75-3) + n-propylmagnesium bromide (927-77-5) → 5-propyl-octan-4-one (40239-43-8)

Conditions	Yield
In diethyl ether

Upstream product

• 110-59-8 pentanonitrile 
• 106-94-5 propyl bromide 
• 143-33-9 sodium cyanide 
• 124243-15-8 4-Heptanone benzoylhydrazone 
• 75-05-8 acetonitrile 
• 66546-92-7 methyl 2-cyano-2-propylpentanoate 
• 66546-91-6 2-cyano-2-propyl-valeric acid 
• 66546-90-5 ethyl 2-cyano-2-propylpentanoate 
• 5340-48-7 4-Cyan-4-propylheptan 
• 123-19-3 4-heptanone 
• 124243-25-0 1-<4-(4-Cyanoheptyl)>-2-carbomethoxyhydrazine 
• 128721-94-8 Benzoic acid N'-(1-cyano-1-propyl-butyl)-hydrazide 
• 124243-19-2 1-Acetyl-2-(4-heptylidene)hydrazine 
• 63883-82-9 4-heptanone trisylhydrazone 

Downstream Products

• 5340-48-7 4-Cyan-4-propylheptan 
• 40239-27-8 3-propyl-2-hexanone 
• 85508-57-2 5-(heptan-4-yl)-1H-tetrazole 
• 51864-93-8 4-Propyl-4-nonanol 
• 51864-92-7 5-Propyl-4-octanol 
• 51864-91-6 3-Propyl-2-hexanol 
• 40755-41-7 1-(3-Chloro-phenyl)-3-(2-propyl-pentyl)-urea 
• 40755-40-6 1-(2-Propyl-pentyl)-3-p-tolyl-urea 
• 40755-39-3 1-Phenyl-3-(2-propyl-pentyl)-urea 
• 40755-38-2 1-Cyclohexyl-3-(2-propyl-pentyl)-urea 
• 40755-27-9 2-Propyl-pentanoic acid (2-propyl-pentyl)-amide 
• 40755-37-1 1-Allyl-3-(2-propyl-pentyl)-urea 
• 40755-28-0 2-Chloro-N-(2-propyl-pentyl)-acetamide 
• 40755-25-7 N-(2-Propyl-pentyl)-acetamide 

Relevant articles and documents

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Synthesis of new N-glycosides based on Valproic acid analogs tetrazole derivatives

New N-glycosides based on valproic acid analogs tetrazole derivatives were synthesized. The bis-tetrazole derived from 1,6-hexandiol was also connected to acetylated glucose and formed bis-N-glycoside. Structures characterizations have been performed using FT IR, 1H and 13C NMR spectroscopy.

Method for producing organic compounds by substituting halogen atoms

The invention pertains to a method in which a halogen atom of an organic compound is replaced with a group derived from a nucleophilic agent, at high yield and high efficiency, by the following method which includes a step of reacting the nucleophilic agent with an organic material having a halogen atom bonded to a carbon atom having four σ bonds, more specifically: a method for producing an organic compound having Q, the method including a step of reacting a compound represented by general formula (2) with an organic starting material having at least one halogen atom bonded to a carbon atom having four σ bonds so as to replace the halogen atom in the organic starting material with Q:MQa (wherein M represents an alkali metal atom, an alkali earth metal atom, or a rare earth metal atom; Q represents a moiety of an inorganic acid or an active hydrogen compound derived by eliminating a proton, wherein Q is a halogen atom different from the halogen atom in the organic starting material having the halogen atom bonded to the carbon atom having the four σ bonds; and a represents an integer of 1 to 3) in the presence of a compound represented by general formula (1) (wherein Z- represents an anion derived by eliminating a proton from an inorganic acid or an active hydrogen compound; R2 is the same or different; R2 each independently represent a C1-C10 hydrocarbon group or two R2 on the same nitrogen atom may be bonded with each other to form a ring with the nitrogen atom).