5921-80-2

Basic information

• Product Name: Butane, 1,1-dibutoxy-
• Synonyms: Butane, 1,1-dibutoxy-;1,1-dibutoxybutane;Butyraldehyde Dibutyl Acetal
• CAS NO: 5921-80-2
• Molecular Formula: C₁₂H₂₆O₂
• Molecular Weight: 202.33
• Mol File: 5921-80-2.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 214°C(lit.)
• Flash Point: 51°C
• Appearance: /
• Density: 0.844g/cm³
• Vapor Pressure: 0.213mmHg at 25°C
• Refractive Index: 1.4140-1.4180
• CAS DataBase Reference: Butane, 1,1-dibutoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Butane, 1,1-dibutoxy-(5921-80-2)
• EPA Substance Registry System: Butane, 1,1-dibutoxy-(5921-80-2)

Safety Data

• RIDADR: 1993
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 5921-80-2(Hazardous Substances Data)

Usage

General Description

1,1-dibutoxybutane is a chemical compound with the molecular formula C10H22O2. It is a colorless liquid with a faint odor, and is commonly used as a solvent in various industrial applications. It is also used in the production of plasticizers, hydraulic fluids, and as a fuel additive. It is considered to have low toxicity and is not known to be carcinogenic. However, it can be irritating to the eyes, skin, and respiratory system, and should be handled with care. It is important to follow proper safety precautions when working with 1,1-dibutoxybutane to minimize potential health risks.

InChI:InChI=1/C12H26O2/c1-4-7-10-13-12(9-6-3)14-11-8-5-2/h12H,4-11H2,1-3H3

Synthetic route

butyraldehyde (123-72-8) + butan-1-ol (71-36-3) → lageracetal (5921-80-2)

Conditions	Yield
With hydrogenchloride In diethyl ether at 20℃; for 0.333333h;	91%
With sulfur dioxide In benzene for 6h; Heating;	54%
With hydrogenchloride at 25℃; Gleichgewicht und Geschwindigkeit der Reaktion;

butan-1-ol (71-36-3) → lageracetal (5921-80-2)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; C18H17N2O2P In tetrahydrofuran at 130℃; for 24h; Inert atmosphere; Schlenk technique;	74%
With tetrabutylammonium tetrafluoroborate (electrolysis);
With Ru(PPh3)2(NCCH3)2(η2-SO4) at 118℃; for 48h; Inert atmosphere; chemoselective reaction;	47 %Chromat.

meso-galactaric acid (526-99-8, 1213827-87-2) + butan-1-ol (71-36-3) → lageracetal (5921-80-2) + (2E,4E)-hexa-2,4-dienedioic acid dibutyl ester (98330-95-1)

Conditions	Yield
With per-rhenic acid In water at 170℃; for 7.5h; Time; Inert atmosphere;	A n/a B 71%

gluconic acid (526-95-4) + butan-1-ol (71-36-3) → lageracetal (5921-80-2) + C14H24O3

Conditions	Yield
With per-rhenic acid In water at 170℃; for 15h;	A 50% B 47%

dibutyl acetal (871-22-7) + butyraldehyde (123-72-8) → lageracetal (5921-80-2)

Conditions	Yield
With hydrogenchloride unter Abdestillieren von Acetaldehyd;

dibutyl ether (142-96-1) → lageracetal (5921-80-2)

Conditions	Yield
With tert-Butyl peroxybenzoate; copper(l) chloride In benzene

2-methyl-propan-1-ol (78-83-1) + butyraldehyde (123-72-8) + butan-1-ol (71-36-3) → lageracetal (5921-80-2) + n-butyraldehyde diisobutyl acetal (13002-16-9) + 1-butoxy-1-isobutoxy butane (20266-12-0)

Conditions	Yield
hydrogenchloride In dichloromethane Heating;

butan-1-ol (71-36-3) → 3-methyl-1,4-heptanediol (7748-38-1) + lageracetal (5921-80-2) + octane-4,5-diol (22607-10-9) + 2-ethyl-1,3-hexane diol (94-96-2)

Conditions	Yield
With hydrogen; mercury under 760 Torr; Heating; Irradiation; Yield given. Yields of byproduct given;

n-Butyl nitrite (544-16-1) + 4-tert-Butylaniline (769-92-6) → tert-butylbenzene (253185-03-4, 253185-04-5) + lageracetal (5921-80-2) + 4-tert-butyl-2-nitrophenol (3279-07-0) + 4-tert-butylphenyl-n-butyl-ether (5891-68-9) + 4-(tert-butyl)chlorobenzene (3972-56-3) + 1,2-bis(4-(tert-butyl)phenyl)diazene (7775-81-7)

Conditions	Yield
With tetrachloromethane for 0.5h; Product distribution; other time, other temp., also without CCl4;

n-Butyl nitrite (544-16-1) → lageracetal (5921-80-2)

Conditions	Yield
With tetrachloromethane; 4-chloro-aniline at 60℃; for 1h;

4-chloro-aniline (106-47-8) → para-dichlorobenzene (106-46-7) + lageracetal (5921-80-2) + 3,4'-dichlorobiphenyl (2974-90-5) + 4,4'-dichlorobiphenyl (2050-68-2) + chlorobenzene (108-90-7)

Conditions	Yield
With tetrachloromethane; n-Butyl nitrite at 60℃; for 1h; Product distribution; other time, other temp., also without CCl4;

butan-1-ol (71-36-3) → lageracetal (5921-80-2) + 1-butanethiol (109-79-5) + Dibutyl sulfide (544-40-1) + butyraldehyde (123-72-8)

Conditions	Yield
With iron sulfide In ethanol at 350℃; under 760 Torr; for 1h; Product distribution; var. temp., parial pressure of alcohol vapour, reaction period and contact time;

crotonaldehyde (123-73-9) + nickel → lageracetal (5921-80-2) + butyraldehyde (123-72-8) + butan-1-ol (71-36-3)

Conditions	Yield
at 130℃; Hydrogenation;

crotonaldehyde (123-73-9) → lageracetal (5921-80-2) + butyl alcohol,butyraldehyde

Conditions	Yield
With hydrogen; nickel at 130℃;

(E/Z)-2-butenyl butyl ether (18409-02-4) + palladium (7440-05-3) + butan-1-ol (71-36-3) → lageracetal (5921-80-2)

(E/Z)-2-butenyl butyl ether (18409-02-4) + 1-decanoic acid (334-48-5) + butan-1-ol (71-36-3) → lageracetal (5921-80-2)

Conditions	Yield
With triphenylphosphine

glucaric acid di-n-butyl ester + butan-1-ol (71-36-3) → lageracetal (5921-80-2) + (2E,4E)-hexa-2,4-dienedioic acid dibutyl ester (98330-95-1) + (2Z,4E)-dibutyl hexa-2,4-dienedioate (1314026-05-5)

Conditions	Yield
With per-rhenic acid In water at 170℃; for 15h;	A 87.4 mg B n/a C n/a

tetrachloromethane (56-23-5) + butan-1-ol (71-36-3) → lageracetal (5921-80-2) + chloroform (67-66-3) + hexachloroethane (67-72-1)

Conditions	Yield
With iron(III) chloride hexahydrate at 20℃; for 4h; Reagent/catalyst; UV-irradiation;

crotonaldehyde (123-73-9) → lageracetal (5921-80-2) + dibutyl ether (142-96-1) + (E/Z)-2-butenyl butyl ether (18409-02-4) + butyraldehyde (123-72-8) + butan-1-ol (71-36-3)

Conditions	Yield
With hydrogen at 150℃; under 30003 Torr; for 6h;

lageracetal (5921-80-2) → butyl butyrate (109-21-7) + butyric acid (107-92-6) + butan-1-ol (71-36-3)

Conditions	Yield
With oxygen; cobalt(II) acetate at 90℃; under 750.06 Torr; Mechanism; Rate constant; other oxygen pressure;	A 8% B 2% C 14%

1,6-hexanediol (629-11-8) + lageracetal (5921-80-2) → hexamethylene glycol-mono-buten-(1)-yl ether

lageracetal (5921-80-2) → (Z)-1-butenyl butyl ether (22617-94-3) + (E)-1-butenyl butyl ether (22617-95-4)

Conditions	Yield
With quinoline; diisopropyl sulfate at 350℃;

lageracetal (5921-80-2) → 2-ethyl-3-butoxy-hexanal-dibutylacetal

Conditions	Yield
With zinc(II) chloride

lageracetal (5921-80-2) + toluene-4-sulfonic acid (104-15-4) + acetic acid (64-19-7) → acetic acid butyl ester (123-86-4) + butyraldehyde (123-72-8)

lageracetal (5921-80-2) → 2-chloro-n-butyraldehyde di-n-butyl acetal (68139-04-8)

Conditions	Yield
With sodium persulfate; sulfuric acid; lithium chloride; hexan-1-ol In water for 4h; Heating;	0.003 mol

lageracetal (5921-80-2) → butyl butyrate (109-21-7) + butan-1-ol (71-36-3)

Conditions	Yield
With ozone In tetrachloromethane at 25℃; Rate constant; k= 4.1 liter/mole.sec;

lageracetal (5921-80-2) + boric acid-asbestos → 1-butyloxy-butene-(1)

Conditions	Yield
at 370 - 390℃;

lageracetal (5921-80-2) + water (7732-18-5) + toluene-4-sulfonic acid (104-15-4) → butyraldehyde (123-72-8) + butan-1-ol (71-36-3)

Conditions	Yield
at 105℃;

Upstream product

• 123-72-8 butyraldehyde 
• 71-36-3 butan-1-ol 
• 142-96-1 dibutyl ether 
• 78-83-1 2-methyl-propan-1-ol 
• 544-16-1 n-Butyl nitrite 
• 769-92-6 4-tert-Butylaniline 
• 123-73-9 crotonaldehyde 
• 18409-02-4 (E/Z)-2-butenyl butyl ether 
• 7440-05-3 palladium 
• 334-48-5 1-decanoic acid 
• 56-23-5 tetrachloromethane 
• 526-95-4 gluconic acid 
• 526-99-8 meso-galactaric acid 
• 106-47-8 4-chloro-aniline 

Downstream Products

• 22617-94-3 buten-1-yl butyl ether 
• 22617-95-4 (E)-1-butenyl butyl ether 
• 123-86-4 acetic acid butyl ester 
• 123-72-8 butyraldehyde 
• 109-21-7 butyl butyrate 
• 107-92-6 butyric acid 
• 71-36-3 butan-1-ol 

Relevant articles and documents

Chemical structure of a new component 'Lageracetal' from the leaves of Lagerstroemia speciosa (L.) Pers. (Japanese)

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Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates

A preparative method for obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.

Photocatalytic Conversion of a FeCl3–CCl4–ROH System

The photocatalytic transformations of carbon tetrachloride and aliphatic primary alcohols in the presence of iron trichloride and a molar ratio of components FeCl3: CCl4: ROH = 1: 300: 2550 were studied. CCl4 is transformed into chloroform and hexachloroethane after exposure to a mercury lamp (250 W) to the FeCl3–CCl4–ROH system at 20°C, whereas the primary ROH alcohols are selectively oxidized into acetals (1,1-dialkoxyalkanes). The maximum conversion of CCl4 reaches 80%. The kinetics and mechanism of the photocatalytic conversion of the FeCl3–CCl4–ROH system are considered.