544-16-1

Basic information

• Product Name: 1-Butyl nitrite
• Synonyms: N-BUTYL NITRITE;NITROUS ACID BUTYL ESTER;1-butylnitrite;Butyl ester of nitrous acid;butylnitrites;NBN;n-C4H9ONO;NCI-C56553
• CAS NO: 544-16-1
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.12
• EINECS: 208-862-1
• Product Categories: Organics;Carboxylic;Nitrogen Compounds;Organic Building Blocks;Organic Nitrates/Nitrites
• Mol File: 544-16-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 78 °C(lit.)
• Flash Point: 8 °F
• Appearance: Clear yellow liquid
• Density: 0.882 g/mL at 25 °C(lit.)
• Vapor Pressure: 760 mm Hg ( 78 °C)
• Refractive Index: n20/D 1.376(lit.)
• Storage Temp.: 0-6°C
• Solubility: alcohol: miscible(lit.)
• Water Solubility: SLIGHTLY SOLUBLE
• Merck: 14,1582
• BRN: 1701036
• CAS DataBase Reference: 1-Butyl nitrite(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butyl nitrite(544-16-1)
• EPA Substance Registry System: 1-Butyl nitrite(544-16-1)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/25
• Safety Statements: 16-24-45
• RIDADR: UN 2351 3/PG 2
• WGK Germany: 1
• RTECS: RA0780000
• F: 8-10-23
• TSCA: Yes
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 544-16-1(Hazardous Substances Data)

Usage

Chemical Properties

CLEAR YELLOW LIQUID

Uses

Different sources of media describe the Uses of 544-16-1 differently. You can refer to the following data:
1. In the manufacture of rare earth azides.
2. Butyl nitrite is used in the manufacture of rare earth azides. It is used as a recreational drug due its vasodilator property.
3. It is used as pharmaceutical intermediate.

General Description

A yellow oily liquid with a pleasant odor. A mixture of isomers (n-butyl, sec-butyl and tert-butyl). Slightly soluble in water. Slightly less dense than water. Vapors are much heavier than air. Flash point about 15°F. Toxic by ingestion, mildly toxic by inhalation. Used to make fuel for jet airplanes.

Reactivity Profile

1-Butyl nitrite si an oxidizing agent but can serve as a reducing agent. May begin a vigorous reaction that culminates in a detonation if mixed with reducing agents, including hydrides, sulfides, nitrides, ammonium salts, cyanides, and many fuels.

Health Hazard

May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Flammability and Explosibility

Notclassified

Safety Profile

A poison by ingestion and intraperitoneal routes. Mildly toxic by inhalation. An irritant. Human systemic effects by ingestion: methemoglobinemiacarboxyhemoglobinemia. Resembles amyl nitrite in causing fall in blood pressure, headache, pulse throbbing, and weakness. Mutation data reported. Flammable when exposed to heat or flame or by spontaneous chemical reaction. When heated to decomposition it emits toxic fumes of NOx. See also NITRITES, n-BUTYL ALCOHOL, and ESTERS

Environmental Fate

Butyl nitrite causes rapid S-nitrosyl glutathione formation and simultaneously reduces protein thiols, followed by marked adenosine triphosphate depletion. It also causes lipid peroxidation. It produces methemoglobinemia in which oxidized hemoglobin has no oxygen carrying capacity. Also, in the clinical state of methemoglobinemia, the unaltered hemoglobin shows an increased affinity for oxygen that results in symptoms of tissue hypoxia. Cyanosis occurs when methemoglobin levels are greater than 10%. Levels above 70% are potentially lethal.

Toxicity evaluation

It is an extremely flammable, insoluble liquid with vapor pressure of 62 mm Hg and boiling point of 75°C.

InChI:InChI=1/C4H9NO2/c1-2-3-4-7-5-6/h2-4H2,1H3

Synthetic route

butan-1-ol (71-36-3) → n-Butyl nitrite (544-16-1)

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 0℃; for 1h;	80%
With tert.-butylnitrite In chloroform at 26℃; Equilibrium constant;
With nitrosylchloride In tetrachloromethane; acetic acid at 5℃; Thermodynamic data; Equilibrium constant; Rate constant; Ea, ΔH, ΔG, ΔS; various temperatures and solvent composition; solvent-jump relaxation; mechanism;

1-bromo-butane (109-65-9) → n-Butyl nitrite (544-16-1) + 1-nitrobutane (627-05-4)

Conditions	Yield
With tetraphenylphosphonium nitrite (ionic form) Yield given. Yields of byproduct given;
With silver(I) nitrite; diethyl ether
With silver(I) nitrite; Petroleum ether
With tetraphenylphosphonium nitrite (ionic form) Yield given. Yields of byproduct given;

1-iodo-butane (542-69-8) → n-Butyl nitrite (544-16-1) + 1-nitrobutane (627-05-4)

Conditions	Yield
With tetraphenylphosphonium nitrite (ionic form) Yield given. Yields of byproduct given;
With silver(I) nitrite; Petroleum ether
With silver(I) nitrite; diethyl ether
With tetraphenylphosphonium nitrite (ionic form) Yield given. Yields of byproduct given;

sodium butanolate (2372-45-4) → n-Butyl nitrite (544-16-1)

Conditions	Yield
With dichloromethane; dinitrogen tetraoxide; butan-1-ol

1-Butoxy radical (19062-98-7) → n-Butyl nitrite (544-16-1) + butyraldehyde (123-72-8)

Conditions	Yield
With H2(15)NO at 175℃; Product distribution; ratios of disproportion to combination reactions; labeled by 15N;

dibutyl ether (142-96-1) → n-Butyl nitrite (544-16-1) + butyraldehyde (123-72-8)

Conditions	Yield
With Cu(NO3)2-SiO2 In tetrachloromethane for 1h; Heating; Yield given. Yields of byproduct given;

n-butane (106-97-8) → n-Butyl nitrite (544-16-1) + butyl nitrate (928-45-0) + sec-butyl nitrite (924-43-6) + 2-nitrobutane (600-24-8, 116783-22-3) + 2-butyl nitrate (924-52-7) + 1-nitrobutane (627-05-4)

Conditions	Yield
With dihydrogen peroxide; Nitrogen dioxide at 24.9℃; under 300.02 Torr; Rate constant; Product distribution; Mechanism; boric-acid-coated surface; various pressure and carrier-gas composition;	A 6 % Chromat. B 0.3 % Chromat. C 31 % Chromat. D 51 % Chromat. E 3 % Chromat. F 7 % Chromat.

1-bromo-butane (109-65-9) + silver nitrite → n-Butyl nitrite (544-16-1) + 1-nitrobutane (627-05-4)

1-iodo-butane (542-69-8) + silver nitrite → n-Butyl nitrite (544-16-1) + 1-nitrobutane (627-05-4)

valeric acid (109-52-4) + NaNO3 + natrium carbonate → n-Butyl nitrite (544-16-1) + butyl nitrate (928-45-0) + butyl valerate (591-68-4) + racbutanediol-(2.3)-dinitrate(?)

Conditions	Yield
Reaktion des Natriumsalzes; Produkt 5: Octan; Produkt 6: Octandioldinitrat.Electrolysis;

butan-1-ol (71-36-3) + nitrosyl tetrafluoroborate → n-Butyl nitrite (544-16-1)

Conditions	Yield
With sodium carbonate at -10℃;

tetrachloromethane (56-23-5) + dibutyl ether (142-96-1) + nitrogen dioxide → n-Butyl nitrite (544-16-1) + butyric acid (107-92-6)

n-Butyl nitrite (544-16-1) + PdCl2COOC4H9P(C6H5)3NO + ethene (74-85-1) → PdCl2(NO2)(P(C6H5)3)(NO)

Conditions	Yield
In neat (no solvent) stirring (60°C, 2 h, 0.6 MPa of C2H4); addn. of pentane; elem.anal.;	95%

acetylferrocene (1271-55-2) + n-Butyl nitrite (544-16-1) + sodium methylate (124-41-4) → methyl ferrocenecarboxylate + isonitrosoacetylferrocene (88787-91-1)

Conditions	Yield
In methanol to soln. of NaOCH3 added acetylferrocene; butyl nitrite added at 10°C; stirred for 10 h at 20°C; filtered, evapd.; sepd. chromatographically (aluminum oxide); (C5H5)Fe(C5H4COOCH3) eluted (hexane); (C5H5)Fe(C5H4COCHNOH) eluted (ethyl acetate);	A 94.1% B 3%

n-Butyl nitrite (544-16-1) → butyraldehyde (123-72-8)

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 4h; Ambient temperature;	93%
With dimethyl sulfoxide at 70℃; for 6h;	87.06%
With oxygen at 24.9℃; under 700 Torr; Rate constant; Product distribution; Irradiation; further reactio pressure;	20%

2,3-dimethyl-4-methanesulfonyl-1-bromobenzene (128277-66-7) + n-Butyl nitrite (544-16-1) → 3-bromo-2-methyl-6-methylsulfonylbenzaldoxime

Conditions	Yield
With potassium tert-butylate In N-methyl-acetamide; ice-water; water; acetic acid	90%
With sodium ethanolate; sodium hydrogencarbonate In ice-water; acetic acid; N,N-dimethyl-formamide	331 g (75%)

1,1'-diacetylferrocene (1273-94-5) + n-Butyl nitrite (544-16-1) + sodium t-butanolate (865-48-5) → 1-acetyl-1'-[(hydroxyimino)acetyl]ferrocene sodium salt

Conditions	Yield
In tert-butyl alcohol addn. of the ferrocene compd. to t-BuONa in t-BuOH, addn. of butyl nitrite at 10°C and stirring at this temp. for 20 h; filtration, washing with acetone and ether; elem. anal.;	90%

4-bromo-2-(4,5-dihydroisoxazol-3-yl)-3-methylaniline (250592-93-9) + n-Butyl nitrite (544-16-1) + Dimethyldisulphide (624-92-0) + copper (12775-96-1, 15158-11-9, 15721-63-8, 16941-75-6, 17493-86-6, 19498-52-3, 20499-83-6, 20499-84-7, 20499-85-8, 20499-86-9, 20573-10-8, 20573-11-9, 21595-51-7, 21595-52-8, 22206-52-6, 26445-28-3, 28959-95-7, 37362-93-9, 39417-05-5, 54603-16-6, 54603-23-5, 54603-32-6, 54603-40-6, 54603-48-4, 54603-81-5, 54603-89-3, 56316-56-4, 95985-91-4, 122297-32-9, 7440-50-8) → 4-methylthio-3-(4,5-dihydroisoxazol-3-yl)-2-methylbromobenzene (250592-92-8)

Conditions	Yield
With hydrogenchloride In water	89%

n-Butyl nitrite (544-16-1) + 4-bromo-N,N-dimethylaniline (586-77-6) → di-n-butyloxymethane (2568-90-3) + 4-bromo-N-nitroso-N-methylaniline (937-23-5)

Conditions	Yield
With water; ammonium chloride for 0.25h; Product distribution; Heating; also PTSA instead of NH4Cl;	A n/a B 88%

1-ferrocenyl-1,3-butanedione + n-Butyl nitrite (544-16-1) + sodium butanolate (2372-45-4) → (C5H5)Fe(C5H4C(O)OCH2CH2CH2CH3) + [2-(hydroxyimino)-3-oxobutyryl]ferrocene

Conditions	Yield
In butan-1-ol to soln. of NaOC4H9 added (3-oxobutyryl)ferrocene; butyl nitrite added at 10°C; stirred for 10 h at 20°C; filtered, evapd.; sepd. chromatographically (aluminum oxide); (C5H5)Fe(C5H4COOC4H9) eluted (hexane); (C5H5)Fe(C5H4COC(COCH3)NOH) eluted (ethyl acetate);	A 88% B 7%

1,1'-diacetylferrocene (1273-94-5) + n-Butyl nitrite (544-16-1) + sodium ethanolate (141-52-6) → 1,1'-bis[(hydroxyimino)acetyl]ferrocene disodium salt

Conditions	Yield
In ethanol addn. of the ferrocene compd. to EtONa in EtOH, addn. of butyl nitrite at 10°C and stirring at this temp. for 20 h; filtration, washing with acetone and ether; elem. anal.;	87%

1-ferrocenyl-1,3-butanedione + n-Butyl nitrite (544-16-1) + sodium ethanolate (141-52-6) → ferrocenecarboxylic acid ethyl ester + [2-(hydroxyimino)-3-oxobutyryl]ferrocene

Conditions	Yield
In ethanol to soln. of NaOC2H5 added (3-oxobutyryl)ferrocene; butyl nitrite added at 10°C; stirred for 10 h at 20°C; filtered, evapd.; sepd. chromatographically (aluminum oxide); (C5H5)Fe(C5H4COOC2H5) eluted (hexane); (C5H5)Fe(C5H4COC(COCH3)NOH) eluted (ethyl acetate);	A 87% B 11%

tetrachlorosilane (10026-04-7, 53609-55-5) + n-Butyl nitrite (544-16-1) → tetra(n-butoxy)silane (4766-57-8)

Conditions	Yield
at 20-25°C;;	85%
at 20-25°C;;	85%

n-Butyl nitrite (544-16-1) + 1,3,5-tris(2'-fluorophenyl)-hexahydro-1,3,5-triazine (83734-38-7) → C11H15FN2O2

Conditions	Yield
In dichloromethane for 1h; Heating;	80%

n-Butyl nitrite (544-16-1) + thallium (I) ethoxide (20398-06-5) + methylhydrazine (60-34-4) → thallium(I) (E)-methanediazotate (113925-83-0)

Conditions	Yield
In diethyl ether byproducts: N2O, n-BuOH, EtOH; Peroxide free anhydrous Et2O, stirred in absence of air overnight, crystn.; Recrystn. from CH2Cl2 or CH2Cl2/CH3CN, elem. anal.;	80%

n-Butyl nitrite (544-16-1) + dichlorobis(α-benzyl oximato)ruthenium(III) (75400-19-0) → RuC28H20N3O5Cl (174094-71-4)

Conditions	Yield
In methanol stirring (298 K, 1 h), cooling; filtration, soln. evapn. (red. pressure), pptn., washing (ether), redissoln. (methanol-water), soln. evapn., pptn., drying (vac.); IR monitoringat 1900 cm**-1, elem. anal.;	80%

n-Butyl nitrite (544-16-1) + 1,3,5-tri-p-bromophenyl-hexahydro-1,3,5-triazine (102310-99-6) → C11H15BrN2O2

Conditions	Yield
In dichloromethane for 1h; Heating;	79%

acetylferrocene (1271-55-2) + n-Butyl nitrite (544-16-1) + sodium ethanolate (141-52-6) → ferrocenecarboxylic acid ethyl ester + isonitrosoacetylferrocene (88787-91-1)

Conditions	Yield
In ethanol to soln. of NaOC2H5 added acetylferrocene; butyl nitrite added at 10°C; stirred for 10 h at 20°C; filtered, evapd.; sepd. chromatographically (aluminum oxide); (C5H5)Fe(C5H4COOCH2CH3) eluted (hexane); (C5H5)Fe(C5H4COCHNOH) eluted (ethyl acetate);	A 78.6% B 20%

2-(pyridin-2-yl)-2,3,4,5-tetrahydro-1-benzoxepin-5-one + diethyl ether (60-29-7) + n-Butyl nitrite (544-16-1) → 4-hydroxyimino-2-(2-pyridyl)2,3,4,5-tetrahydro-1-benzoxepin-5-one

Conditions	Yield
With hydrogenchloride; sodium hydroxide In tetrahydrofuran; dichloromethane; water	78.4%

n-Butyl nitrite (544-16-1) + 4-bromo-N,N-dimethylaniline (586-77-6) → formaldehyd (50-00-0) + di-n-butyloxymethane (2568-90-3) + Tributyl orthoformate (588-43-2) + 2,4-dibromo-N,N-dimethylaniline (64230-27-9) + 4-Bromo-N,N-di(n-butoxymethyl)benzeneamine (130717-78-1) + 4-bromo-N-nitroso-N-methylaniline (937-23-5)

Conditions	Yield
for 60h; Product distribution; Heating;	A n/a B 30 % Chromat. C 7 % Chromat. D n/a E 10 % Chromat. F 78%

(2R,3R,4S,5S)-2-(2-amino-6-chloro-9H-purin-9-yl)-4-(benzoyloxy)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate + diiodomethane (75-11-6) + n-Butyl nitrite (544-16-1) → (2R,3R,4S,5S)-4-(benzoyloxy)-2-(6-chloro-2-iodo-9H-purin-9-yl)-5-[(ethylamino)carbonyl]-tetrahydro-3-furanyl benzoate (355144-97-7)

Conditions	Yield
With iodine; copper(I) iodide In tetrahydrofuran	78%

n-Butyl nitrite (544-16-1) + 2,3-dimethylnitrobenzene (83-41-0) → 2-methyl-6-nitrobenzaldoxime

Conditions	Yield
With potassium tert-butylate In N-methyl-acetamide; ice-water; water; acetic acid; toluene	77%
With potassium tert-butylate In N-methyl-acetamide; ice-water; water; acetic acid; toluene	77%

1-ferrocenyl-1,3-butanedione + n-Butyl nitrite (544-16-1) + sodium methylate (124-41-4) → methyl ferrocenecarboxylate + [2-(hydroxyimino)-3-oxobutyryl]ferrocene

Conditions	Yield
In methanol to soln. of NaOCH3 added (3-oxobutyryl)ferrocene; butyl nitrite added at 10°C; stirred for 10 h at 20°C; filtered, evapd.; sepd. chromatographically (aluminum oxide); (C5H5)Fe(C5H4COOCH3) eluted (hexane); (C5H5)Fe(C5H4COC(COCH3)NOH) eluted (ethyl acetate); elem. anal.;	A 21.8% B 77%

n-Butyl nitrite (544-16-1) + 2-amino-3-chloropyridine (39620-04-7) + succinic acid diethyl ester (123-25-1) → ethyl 2-(3-chloropyridin-2-yl)-5-hydroxy-3-pyrazolidinecarboxylate

Conditions	Yield
Stage #1: n-Butyl nitrite; 2-amino-3-chloropyridine With acetic acid; sodium nitrite In butan-1-ol at -5 - 10℃; Stage #2: succinic acid diethyl ester With ammonium hydroxide; nitrogen; ammonia In butan-1-ol at -5 - 95℃; under 37.5038 - 75.0075 Torr; for 2h; pH=4 - 10.5;	75.89%

n-Butyl nitrite (544-16-1) + 1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane (32752-37-7) → C12H18N2O3

Conditions	Yield
In dichloromethane for 1h; Heating;	73%

acetylferrocene (1271-55-2) + n-Butyl nitrite (544-16-1) + sodium butanolate (2372-45-4) → isonitrosoacetylferrocene (88787-91-1) + (C5H5)Fe(C5H4C(O)OCH2CH2CH2CH3)

Conditions	Yield
In butan-1-ol to soln. of NaOC4H9 added acetylferrocene; butyl nitrite added at 10°C; stirred for 10 h at 20°C; filtered, evapd.; sepd. chromatographically (aluminum oxide); (C5H5)Fe(C5H4COO(CH2)3CH3) eluted (hexane); (C5H5)Fe(C5H4COCHNOH) eluted (ethyl acetate); elem. anal.;	A 71% B 25.7%

n-Butyl nitrite (544-16-1) + 1-(4-(phenylthio)phenyl)-1-octanone (17792-67-5) → C20H23NO2S

Conditions	Yield
With hydrogenchloride In tetrahydrofuran at 20℃; for 5h; Concentration;	71%

n-Butyl nitrite (544-16-1) + carbon monoxide (201230-82-2) → Dibutyl carbonate (542-52-9)

Conditions	Yield
With auphen; potassium iodide In butan-1-ol at 80℃; under 22502.3 Torr; for 5h; Autoclave;	70.3%

n-Butyl nitrite (544-16-1) + C24H18N6 (109423-11-2) → C12H15N3O2

Conditions	Yield
In dichloromethane for 20h; Heating;	70%

n-Butyl nitrite (544-16-1) + 1,3,5-tris(2-chlorophenyl)-1,3,5-triazine (83734-36-5) → N-nitroso-N-(n-butoxymethyl)-2-chlorophenylamine

Conditions	Yield
In dichloromethane for 2h; Heating;	70%

Upstream product

• 109-65-9 1-bromo-butane 
• 71-36-3 butan-1-ol 
• 142-96-1 dibutyl ether 
• 106-97-8 n-butane 
• 56-23-5 tetrachloromethane 
• 109-52-4 valeric acid 
• 542-69-8 1-iodo-butane 
• 19062-98-7 n-butoxy radical 
• 2372-45-4 sodium butanolate 

Downstream Products

• 950-17-4 1,1-diphenyl-2-chloroethan-1-ol 
• 134-81-6 benzil 
• 66553-34-2 2,3-dimethyl-1-nitro-butane 
• 34075-28-0 2,3-dimethyl-2-nitrobutane 
• 16529-56-9 2-METHYL-3-BUTENENITRILE 
• 107649-71-8 2-hydroxyimino-3-oxo-octadecanoic acid methyl ester 
• 859080-85-6 1-p-tolyl-butane-1,2-dione-2-oxime 
• 24623-36-7 4,7-dimethyl-2-(hydroxyimino)-1-indanone 
• 38847-67-5 1-(4-chloro-phenyl)-butane-1,2-dione-2-oxime 
• 92040-89-6 1-phenyl-heptane-1,2-dione-2-oxime 
• 133168-49-7 1-[4-(2-dimethylamino-ethoxy)-phenyl]-propane-1,2-dione-2-oxime ; hydrochloride 
• 7214-61-1 (1-nitroethyl)benzene 
• 4358-06-9 bis-(2-chloro-2-phenyl-cyclohexyl)-diazene-N,N'-dioxide 
• 101708-94-5 1-phenyl-pentane-1,2-dione-2-oxime 

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