609-31-4

Basic information

• Product Name: 2-NITRO-1-BUTANOL
• Synonyms: 2-NITRO-1-BUTANOL;1-Butanol, 2-nitro-;2-nitro-1-butano;2-nitrobutan-1-ol;2-Nitrobutanol
• CAS NO: 609-31-4
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• EINECS: 210-188-8
• Mol File: 609-31-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: -47°C
• Boiling Point: 247.38°C (rough estimate)
• Flash Point: 97.7 °C
• Appearance: /
• Density: 1.1332
• Vapor Pressure: 0.0343mmHg at 25°C
• Refractive Index: 1.4390
• PKA: 7.46±0.13(Predicted)
• Stability: Stable. Combustible.
• CAS DataBase Reference: 2-NITRO-1-BUTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITRO-1-BUTANOL(609-31-4)
• EPA Substance Registry System: 2-NITRO-1-BUTANOL(609-31-4)

Safety Data

• Hazardous Substances Data: 609-31-4(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Organic synthesis.

General Description

Colorless clear amber liquid. pH (0.1 molar solution) 4.51.

Air & Water Reactions

Soluble in water.

Reactivity Profile

Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

Fire Hazard

2-NITRO-1-BUTANOL is probably combustible.

InChI:InChI=1/C4H9NO3/c1-2-4(3-6)5(7)8/h4,6H,2-3H2,1H3

Synthetic route

formaldehyd (50-00-0) + 1-Nitropropane (108-03-2) → 2-nitro-1-butanol (609-31-4)

Conditions	Yield
Stage #1: 1-Nitropropane With sodium hydroxide In water at 30℃; Henry Nitro Aldol Condensation; Stage #2: formaldehyd In water at 30℃; for 2h; Solvent; Reagent/catalyst; Time; Henry Nitro Aldol Condensation;	91.5%
Stage #1: 1-Nitropropane With water; sodium hydroxide at 0 - 23℃; for 2h; Stage #2: formaldehyd at 0 - 23℃; for 1h;	76%
Stage #1: 1-Nitropropane With sodium hydroxide In water at 0 - 20℃; for 2.5h; Stage #2: formaldehyd In water at 20℃; for 7h;	55%

bis-(2-nitro-butoxy)-methane (73928-13-9) → 2-nitro-1-butanol (609-31-4)

Conditions	Yield
(i) BCl3, (ii) MeOH; Multistep reaction;

1-tert-butoxy-2-nitro-butane (90227-61-5) → 2-nitro-1-butanol (609-31-4)

Conditions	Yield
(i) BCl3, (ii) MeOH; Multistep reaction;

bis-(2-hydroxymethyl-2-nitro-butyl)-amine (99864-18-3) → 2-nitro-1-butanol (609-31-4) + 5-nitro-5-ethyl-tetrahydro-1.3-oxazine

Conditions	Yield
bei der Destillation unter vermindertem Druck;

2-ethyl-4-[(hydroxymethyl-amino)-methyl]-2,4-dinitro-hexan-1-ol (806635-31-4) → 2-nitro-1-butanol (609-31-4) + 5-nitro-5-ethyl-tetrahydro-1.3-oxazine

Conditions	Yield
Destillation unter vermindertem Druck;

2-nitro-1-butanol (609-31-4) → 2-aminobutanol (96-20-8, 13054-87-0)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol at 50 - 55℃; under 6000.6 - 7500.75 Torr; for 3h; Reagent/catalyst; Solvent; Temperature;	91%
In ethanol; toluene	78%
In ethanol	41%

2-nitro-1-butanol (609-31-4) + isoprene (78-79-5) → 1-methyl-4-ethyl-4-nitrocyclohexene + 2-methyl-4-ethylnitrocyclohexene

Conditions	Yield
In methanol	A 87% B n/a

2-nitro-1-butanol (609-31-4) + acetic anhydride (108-24-7) → 2-nitrobutyl acetate (2123-71-9)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 0 - 20℃; for 8h;	86%

2-nitro-1-butanol (609-31-4) + buta-1,3-diene (106-99-0) → 4-nitro-Δ'-cyclohexene (4883-68-5)

Conditions	Yield
In methanol	81%

2-nitro-1-butanol (609-31-4) → 2-nitrobutene (2783-12-2)

Conditions	Yield
With phthalic anhydride Heating;	79%
With phthalic anhydride at 150 - 200℃;	44%
With phthalic anhydride at 180℃; under 75 Torr;
With phthalic anhydride

2-nitro-1-butanol (609-31-4) → 2-nitropropene (4749-28-4)

Conditions	Yield
With phthalic anhydride at 150 - 200℃;	52%

2-nitro-1-butanol (609-31-4) + hexafluoropropene-diethylamine adduct (309-88-6) → 2-nitrobutyl 2,3,3,3-tetrafluoropropionate

Conditions	Yield
In dichloromethane Ambient temperature;	51%

2-nitro-1-butanol (609-31-4) + phenyllead(IV) triacetate (3076-54-8) → 2-nitro-2-phenylbutan-1-ol

Conditions	Yield
In dimethyl sulfoxide at 40℃; for 30h;	42%

phosgene (75-44-5) + 2-nitro-1-butanol (609-31-4) → chlorocarbonic acid-(2-nitro-butyl ester)

N-carbamoylmaleimide (3345-50-4) + 2-nitro-1-butanol (609-31-4) → maleic acid-(2-nitro-butyl ester)-ureide (114960-76-8)

Conditions	Yield
With zinc(II) chloride

N-carbamoylmaleimide (3345-50-4) + 2-nitro-1-butanol (609-31-4) → fumaric acid-(2-nitro-butyl ester)-ureide (114698-92-9)

Conditions	Yield
With aluminium trichloride

formaldehyd (50-00-0) + 2-nitro-1-butanol (609-31-4) → 1-chloromethoxy-2-nitro-butane

Conditions	Yield
With hydrogenchloride

formaldehyd (50-00-0) + 2-nitro-1-butanol (609-31-4) → bis-(2-nitro-butoxy)-methane (73928-13-9)

Conditions	Yield
With toluene; benzenesulfonic acid
With toluene-4-sulfonic acid; toluene
With toluene-4-sulfonic acid; toluene
With toluene; benzenesulfonic acid

formic acid (64-18-6) + 2-nitro-1-butanol (609-31-4) → formic acid-(2-nitro-butyl ester) (89417-50-5)

Conditions	Yield
With sulfuric acid; benzene

carbon suboxide (504-64-3) + 2-nitro-1-butanol (609-31-4) → malonic acid bis-(2-nitro-butyl ester) (100051-92-1)

Conditions	Yield
With aluminium trichloride; diethyl ether at -78℃;

crotonic acid methyl ester (623-43-8) + 2-nitro-1-butanol (609-31-4) → trans-crotonic acid-(2-nitro-butyl ester) (5390-56-7)

Conditions	Yield
With sulfuric acid

ketenedivinylacetal (69814-53-5) + 2-nitro-1-butanol (609-31-4) → orthoacetic acid-(2-nitro-butyl ester)-divinyl ester

Conditions	Yield
With hydrogenchloride

1-nitrobutane (627-05-4) + 2-nitro-1-butanol (609-31-4) → 4,6-dinitro-nonane (856578-83-1)

Conditions	Yield
With chloroform; diethylamine

2-nitro-1-butanol (609-31-4) + (4-bromophenyl)diazonium chloride (2028-85-5) → 2-(4-bromo-phenylazo)-2-nitro-butan-1-ol

Conditions	Yield
With sodium hydroxide; water schnellen Ansaeuern des Reaktionsgemisches;

2-nitro-1-butanol (609-31-4) + p-chlorobenzenediazonium chloride (2028-74-2) → 2-(4-chloro-phenylazo)-2-nitro-butan-1-ol

Conditions	Yield
With sodium hydroxide; water schnellen Ansaeuern des Reaktionsgemisches;

2-nitro-1-butanol (609-31-4) → sulfuric acid mono-(2-nitro-butyl ester) (25000-81-1)

Conditions	Yield
With 1,4-dioxane; chlorosulphuric acid

2-nitro-1-butanol (609-31-4) → 1-chloro-2-nitro-butane (54113-40-5)

Conditions	Yield
With pyridine; tetrachloromethane; thionyl chloride
With pyridine; thionyl chloride

2-nitro-1-butanol (609-31-4) → 2-nitro-butane-1-sulfonic acid (745717-45-7)

Conditions	Yield
With potassium bisulfite; water
With potassium bisulfite; water

2-nitro-1-butanol (609-31-4) + chloroformic acid ethyl ester (541-41-3) → carbonic acid ethyl ester-(2-nitro-butyl ester)

Conditions	Yield
With sodium hydroxide

2-nitro-1-butanol (609-31-4) + propionic acid (802294-64-0) → propionic acid-(2-nitro-butyl ester) (4003-81-0)

Conditions	Yield
With sulfuric acid; benzene unter Abdestillieren des Reaktionswassers;

2-nitro-1-butanol (609-31-4) + benzonitrile (100-47-0) → benzimidic acid-(2-nitro-butyl ester); hydrochloride

Conditions	Yield
With hydrogenchloride

chloroform (67-66-3) + 1-nitrobutane (627-05-4) + 2-nitro-1-butanol (609-31-4) + diethylamine (109-89-7) → 4,6-dinitro-nonane (856578-83-1)

2-nitro-1-butanol (609-31-4) + ethyl vinyl ether (109-92-2) → (2-nitro-butoxy)-ethene (64566-31-0)

Conditions	Yield
With mercury(II) diacetate

2-nitro-1-butanol (609-31-4) + acrylic acid methyl ester (292638-85-8) → 2-nitrobutyl acrylate (5390-54-5)

Conditions	Yield
With toluene-4-sulfonic acid; xylene

Upstream product

• 99864-18-3 bis-(2-hydroxymethyl-2-nitro-butyl)-amine 
• 806635-31-4 2-ethyl-4-[(hydroxymethyl-amino)-methyl]-2,4-dinitro-hexan-1-ol 
• 90227-61-5 1-tert-butoxy-2-nitro-butane 
• 73928-13-9 bis-(2-nitro-butoxy)-methane 
• 50-00-0 formaldehyd 
• 108-03-2 1-Nitropropane 

Downstream Products

• 73928-13-9 bis-(2-nitro-butoxy)-methane 
• 96-20-8 2-aminobutanol 
• 4749-28-4 2-nitropropene 
• 597-09-1 2-nitro-2-ethyl-1,3-propanediol 
• 4883-68-5 4-nitro-Δ'-cyclohexene 
• 2123-71-9 2-nitrobutyl acetate 
• 28367-35-3 2-(benzylidene-oxy-amino)-butan-1-ol 
• 55381-39-0 2-(5-Dimethylamino-naphthalene-1-sulfonylamino)-5-guanidino-pentanoic acid 2-nitro-butyl ester; compound with toluene-4-sulfonic acid 
• 6526-60-9 2-Nitro-1-butyl-N-Phenylcarbamat 
• 2783-12-2 2-nitrobutene 
• 5077-67-8 1-Hydroxy-2-butanone 
• 3857-75-8 butyric acid-(2-nitro-butyl ester) 
• 5390-39-6 isobutyric acid-(2-nitro-butyl ester) 
• 23531-32-0 2-nitro-1-(toluene-4-sulfonyloxy)-butane 

Relevant articles and documents

CONTINUOUS FLOW PROCESS AND APPARATUS FOR MANUFACTURE OF DL-2-NITRO-1-BUTANOL

A continuous process(200) for manufacture of dl-2-nitro-1-butanol from 1-nitropropane is disclosed. The process mixes aqueous solution of sodium hydroxide (A) and a solution of 1-nitropropane (B) dissolved in alcohol(203) at a first molar ratio in a first tubular reactor to form a mixture. The mixture is pumped(205) with an aqueous solution of formaldehyde at a second predetermined molar ratio to a second tubular reactor for a second residence time to form a product stream. The product stream is quenched(207) in glacial acetic acid to obtain quench liquor having dl-2-nitro-1-butanol. The first(130) and the second(150) tubular reactors are maintained at a temperature of 35° C or less. The method produces conversion of at least 89% dl-2-nitro-1-butanol with residence time of 30 minutes or less. Apparatus for continuous production of dl-2-nitro-1-butanol from 1-nitropropane is further disclosed. A method of obtaining dl-2-amino-1-butanol by hydrogenation of the dl-2-nitro-1-butanol is further disclosed.

Novel electrophilic ipso acylation - Detosylation reaction of pyrroles

A pyrrole and two pyrroloindoles that are substituted with a p-toluenesulfonyl group undergo an ipso acylation - detosylation reaction with acid chlorides and aluminum chloride to afford the corresponding acyl-substituted pyrroles and pyrroloindoles.