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111-36-4

Basic Information
CAS No.: 111-36-4
Name: Butane, 1-isocyanato-
Article Data: 81
Cas Database
Molecular Structure:
Molecular Structure of 111-36-4 (Butane, 1-isocyanato-)
Formula: C5H9NO
Molecular Weight: 99.1326
Synonyms: n-Butylisocyanate;Isocyanicacid, butyl ester (6CI,8CI);1-Isocyanatobutane;
EINECS: 203-862-8
Density: 0.87 g/cm3
Melting Point: 85.5 °C
Boiling Point: 115 °C at 760 mmHg
Flash Point: 17.8 °C
Solubility: N/A
Appearance: Colorless to faintly yellow liquid
Hazard Symbols: FlammableF,VeryT+
Risk Codes: 11-21/22-26-34-37-42/43
Safety: 23-26-28-36/37/39-45
Transport Information: UN 2485 6.1/PG 1
PSA: 29.43000
LogP: 1.12230
Synthetic route
41891-17-2

N-butylcarbamoyl chloride

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With triethylamine In toluene for 10h; Solvent; Reagent/catalyst; Reflux;95%
With N,N-dimethyl-aniline; 1,2-dichloro-benzene
In 1,2-dichloro-ethane
With triethylamine In Dimethyldisulphide at 0 - 5℃; pH=8 - 8.5;
591-62-8

N-(ethoxycarbonyl)butylamine

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With Phenyltrichlorosilane at 120 - 165℃; for 0.5h;88.9%
With boron trichloride; triethylamine In benzene for 0.5h; Heating;86 % Chromat.
29262-59-7

2-(n-butylamino)-2-oxoacetic acid

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate; copper(II) sulfate In hexane; water at 40℃; for 3h;83%
With ammonium peroxydisulfate; copper diacetate; silver nitrate In hexane; water at 40℃; for 3h;83%
124-38-9

carbon dioxide

109-73-9

N-butylamine

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at -78 - 20℃; under 760 Torr;63%
With di-isopropyl azodicarboxylate; triphenylphosphine 1.) dichloromethane, -5 deg C to -10 deg C, 2.) dichloromethane, -78 deg C, ambient temp.; Yield given; Multistep reaction;
29262-59-7

2-(n-butylamino)-2-oxoacetic acid

A

14040-75-6

N,N'-bis(n-butyl)oxamide

B

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With ammonium peroxydisulfate; silver nitrate In dichloromethane; water at 40℃; for 3h;A 22%
B 49%

diethyl 2-amino-6-[(hydroxycarbamoyl)-methyl]-azulene-1,3-dicarboxylate

A

diethyl 2-amino-6-{[(N-n-butylamino)-carbonyloxy-carbamoyl]-methyl}-azulene-1,3-dicarboxylate

B

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
A 47%
B n/a
106-48-9

4-chloro-phenol

A

17576-37-3

(p-chlorophenyl)methylcarbamate

B

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With sodium iodide; N-butylamineA n/a
B 14%
75-44-5

phosgene

3858-78-4

n-butylamine hydrochloride

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With 1,2-dichloro-benzene at 120 - 140℃;
With 1,2-dichloro-benzene at 120 - 140℃;
590-28-3

potassium cyanate

126-73-8

phosphoric acid tributyl ester

111-36-4

n-butyl isocyanide

591-62-8

N-(ethoxycarbonyl)butylamine

A

846-74-2

1,3,5-tributyl-[1,3,5]triazinane-2,4,6-trione

B

111-36-4

n-butyl isocyanide

Conditions
ConditionsYield
With calcium oxide at 150 - 200℃;
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Consensus Reports

Reported in EPA TSCA Inventory.

Standards and Recommendations

DOT Classification:  3; Label: Flammable Liquid, Poison; DOT Class: 6.1; Label: Poison; DOT Class: 6.1; Label: Poison, Flammable Liquid; DOT Class: 3; Label: Flammable Liquid, Poison

Specification

The N-Butyl isocyanate, with the CAS registry number 111-36-4 and EINECS registry number 203-862-8, has the systematic name of 1-isocyanatobutane. And the molecular formula of this chemical is C5H9NO. It is a kind of colorless to faintly yellow liquid, and belongs to the following product categories: Pharmaceutical Intermediates; Isocyanate; Organics; Isocyanates; Nitrogen Compounds; Organic Building Blocks. In addition, it should be stored at 2-8°C.

The physical properties of N-Butyl isocyanate are as following: (1)ACD/LogP: 2.42; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.42; (4)ACD/LogD (pH 7.4): 2.42; (5)ACD/BCF (pH 5.5): 40.95; (6)ACD/BCF (pH 7.4): 40.95; (7)ACD/KOC (pH 5.5): 496.18; (8)ACD/KOC (pH 7.4): 496.18; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 29.43 Å2; (13)Index of Refraction: 1.429; (14)Molar Refractivity: 29.3 cm3; (15)Molar Volume: 113.6 cm3; (16)Polarizability: 11.61×10-24cm3; (17)Surface Tension: 29.6 dyne/cm; (18)Density: 0.87 g/cm3; (19)Flash Point: 17.8 °C; (20)Enthalpy of Vaporization: 35.34 kJ/mol; (21)Boiling Point: 115 °C at 760 mmHg; (22)Vapour Pressure: 19.4 mmHg at 25°C.

Preparation and uses of N-Butyl isocyanate: It can be prepared by N-butylamine and phosgene. Add N-butylamine and o-dichlorohenzene to the reactor, and pass hydrogen chloride gas till it is saturated. Pass excess phosgene in the temperature of 110-160°C till the solution becomes clear. Distill and collect the distillation cut before 160°C. Distill again, and collect the distillation cut between 106-120°C. Add anhydrous potassium sulfite, and then filter, the product desired is obtained. In addition, it is used as intermediate in organic systhesis, and it is also used in the production of bactericide Benlate.

You should be cautious while dealing with this chemical. It is a kind of highly flammable chemcial whcih is harmful in contact with skin and if swallowed. It is very toxic by inhalation and irritating to the respiratory system. Besides, it may also cause sensitization by inhalation and skin contact. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer); After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer); In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C=N/CCCC
(2)InChI: InChI=1/C5H9NO/c1-2-3-4-6-5-7/h2-4H2,1H3
(3)InChIKey: HNHVTXYLRVGMHD-UHFFFAOYAO

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LD50 oral 250mg/kg (250mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(3), Pg. 53, 1976.
guinea pig LD50 skin > 1gm/kg (1000mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" National Technical Information Service. Vol. OTS0528347,
mouse LC50 inhalation 680mg/m3 (680mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(3), Pg. 53, 1976.
mouse LD50 intravenous 1mg/kg (1mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#05701,
mouse LD50 oral 150mg/kg (150mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(3), Pg. 53, 1976.
rabbit LDLo skin 6gm/kg (6000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
National Technical Information Service. Vol. OTS0528441,
rat LC50 inhalation 3gm/m3(3000mg/m3) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(3), Pg. 53, 1976.
rat LD50 oral 600mg/kg (600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 20(3), Pg. 53, 1976.

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