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2-Methyl-1-propanol
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Name

2-Methyl-1-propanol

 EINECS 201-148-0
CAS No. 78-83-1 Density 0.802 g/cm3
PSA 20.23000 LogP 0.63470
Solubility 95 g/L (20 °C) in water Melting Point -108 °C
Formula C4H10O Boiling Point 105.039 °C at 760 mmHg
Molecular Weight 74.1228 Flash Point 27.778 °C
Transport Information UN 1212 3/PG 3 Appearance colorless liquid
Safety 13-26-37/39-46-7/9 Risk Codes 10-37/38-41-67
Molecular Structure Molecular Structure of 78-83-1 (2-Methyl-1-propanol) Hazard Symbols IrritantXi
Synonyms

2-Methylpropyl alcohol;1-propanol, 2-methyl-;Isobutylalkohol [Czech];Alcool isobutylique [French];Alcool isobutylique;Isopropylcarbinol;Aluminium 2-methylpropanolate;1-Propanol,2-methyl-;2-Methylpropanol-1;2-Methyl propanol;Isobutanol or isobutyl alcohol [UN1212] [Flammable liquid];2-Methylpropan-1-ol;Isobutyl alcohol (natural);Iso-butyl alcohol;FEMA No. 2179;1-Hydroxymethylpropane;4-01-00-01588 (Beilstein Handbook Reference);Isobutylalkohol;Natural Isobutyl Alcohol;iso-Butyl Alcohol, Reagent;Isobutyl Alcohol;Isobutanol;

Article Data 362

2-Methyl-1-propanol Synthetic route

558-30-5

2-methyl-1,2-epoxypropane

A

78-83-1

2-methyl-propan-1-ol

B

78-84-2

isobutyraldehyde

Conditions
ConditionsYield
With hydrogen; chromium(III) oxide; copper at 140℃; under 26252.1 Torr; for 0.666667h;A 98.1%
B 1.9%
18269-50-6

isobutoxytrimethylsilane

78-83-1

2-methyl-propan-1-ol

Conditions
ConditionsYield
With methanol; 1,3-disulfonic acid imidazolium hydrogen sulfate at 20℃; for 0.0666667h; Green chemistry;97%
75-65-0

tert-butyl alcohol

A

78-83-1

2-methyl-propan-1-ol

B

7732-18-5

water

C

115-11-7

isobutene

Conditions
ConditionsYield
aluminum oxide at 315.546℃; under 11103.3 Torr;A 1.4%
B 1.1%
C 96.4%
71412-40-3

N,N'-(4-methyl-m-phenylene)-bis-carbamic acid diisobutyl ester

A

78-83-1

2-methyl-propan-1-ol

B

584-84-9

2,4-Toluene diisocyanate

Conditions
ConditionsYield
In 1,2,4-Trichlorobenzene at 120 - 350℃; under 7500.75 Torr; Product distribution / selectivity; Industry scale;A n/a
B 92.9%
97-72-3

2-Methylpropionic anhydride

78-83-1

2-methyl-propan-1-ol

Conditions
ConditionsYield
With [Zn(BH4)2(py)] In tetrahydrofuran for 2.5h; Heating;92%
78-84-2

isobutyraldehyde

78-83-1

2-methyl-propan-1-ol

Conditions
ConditionsYield
With sodium tetrahydroborate; Dowex1-x8 In tetrahydrofuran at 20℃; for 0.3h;90%
gadolinium(III) isopropoxide In isopropyl alcohol at 30℃; for 2h;74%
With PEG-bound sodium benzoyloxyborohydride In toluene at 21 - 23℃; for 2h;66%
187737-37-7

propene

201230-82-2

carbon monoxide

A

78-83-1

2-methyl-propan-1-ol

B

71-36-3

butan-1-ol

Conditions
ConditionsYield
Stage #1: propene; carbon monoxide With hydrogen; triphenylphosphine; acetylacetonatodicarbonyl triphenylphosphine Rhodium (ROPAC) at 89℃; for 240h; Inert atmosphere;
Stage #2: With hydrogen; Raney-nickel at 110℃; under 18751.9 Torr; for 90h; Product distribution / selectivity; Inert atmosphere;		A 8.6%
B 87.1%
Stage #1: propene; carbon monoxide With carbonyl-2,4-pentanedionato(triphenylphosphine)rhodium(I); hydrogen; triphenylphosphine at 89℃; under 11251.1 - 13501.4 Torr; for 240h; Industrial scale;
Stage #2: With hydrogen at 110℃; under 18751.9 Torr; for 90h; Industrial scale;		A 8.6%
B 87.1%
Stage #1: propene; carbon monoxide With (acetylacetonato)dicarbonylrhodium (l); tris(triphenylphosphine)ruthenium(II) chloride; hydrogen; triphenylphosphine In toluene at 19.84 - 49.84℃; under 23289.8 Torr; for 4h; Autoclave;
Stage #2: With hydrogen In toluene at 49.84 - 99.84℃; under 25877.6 Torr; for 4h; Autoclave;
73198-21-7

Isobutylmethyl(p-nitrophenyl)sulfonium perchlorate

A

67-56-1

methanol

B

78-83-1

2-methyl-propan-1-ol

C

701-57-5

1-methylthio-4-nitro-benzene

D

Isobutyl p-nitrophenyl sulfide

Conditions
ConditionsYield
With water Mechanism; Product distribution;A n/a
B n/a
C 15%
D 85%
79-31-2

isobutyric Acid

78-83-1

2-methyl-propan-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In diethyl ether at 0℃; for 6h;80%
With diphenylamine borane In dichloromethane 1.) 0 deg C, 1 h, 2.) 20 deg C, 1 h;72%
With hydrogen In n-heptane at 123℃; under 41372.9 Torr; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Time; Pressure; Autoclave;
With hydrogen In hexane at 130℃; under 15001.5 Torr; for 18h; Molecular sieve; chemoselective reaction;83 %Chromat.
With methanol; CuO on mesoporous silica at 360℃; Reagent/catalyst;
84110-40-7

Dihydroxy-isobutyl-boran

acetonitrile complex of hypofluorous acid

78-83-1

2-methyl-propan-1-ol

Conditions
ConditionsYield
In dichloromethane at 20℃;80%

2-Methyl-1-propanol Consensus Reports

Reported in EPA TSCA Inventory.

2-Methyl-1-propanol Standards and Recommendations

OSHA PEL: TWA 50 ppm
ACGIH TLV: TWA 50 ppm
DFG MAK: 100 ppm (310 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

2-Methyl-1-propanol Analytical Methods

For occupational chemical analysis use NIOSH: Alcohols II, 1401.

2-Methyl-1-propanol Specification

Isobutanol, also known as Isobutyl alcohol, is colorless, flammable liquid with a characteristic smell has three isomers including n-butanol, 2-butanol, and tert-butanol. Isobutanol  is miscible with ethanol and ether. What's more, it is mainly used as a solvent. Compared to ethanol, isobutanol is better candidates for gasoline replacement because it has an energy density.

Preparation: Isobutanol can be obtained by many methods.

1. Carbonyl synthesis: Use propylene and syngas as raw material. Firstly, n-butyraldehyde and iso-butyraldehyde is synthesized by carbonyl synthesis. Secondly, take off the catalyst and be hydrogenated to get n-butanol and isobutanol. Finally, separate the n-butanol and isobutanol by dehydration.

Preparation of Isobutanol

2. Isobutyraldehyde hydrogenation: Isobutyraldehyde goes through liquid-phase hydrogenation reaction in the presence of nickel, then the isobutanol is obtained.

3. Recovered from the byproduct isobutyl oil from production of methanol: isobutyl oil is the byproduct of rectification in the production of methanol. After removal of methanol, salting out, dehydration, and azeotropic distillation, the isobutanol is obtained.

4. Use industrial isobutanol as raw material. Add calcium oxide to dehydrate and dry. Then steam out of isobutanol after 5h. Distillate goes through rectification to get pure product. Azeotropic distillation with cyclohexane, anhydrous isobutanol can be obtained.

Uses: Isobutanol is widely used in technology and industry.

1. Isobutanol is used as a cosolvent of cellulose nitrate and solvent of ethyl cellulose, polyvinyl butyral, a variety of oils, rubber, natural resin.

2. Isobutanol is mainly used as raw material in the production of diisobutyl phthalate which is used as plasticiser and isobutyl acetate which is used in the manufacture of lacquer and similar coatings, in the food industry as a flavouring agent and as diluent of adhesive. There is a small part for the production of isobutyl butyrate, isobutyl lactate, etc.

3. Isobutanol is used as reagent in the determination of calcium, strontium, barium, sodium, potassium, lithium, silver, chlorine and phosphite. It is also used as chemical extractant in production of organic compounds, as mobile phase in thin layer chromatography.

4. In addition, isobutanol is used as paint solvent, varnish remover and ink ingredient.

Safty: Isobutanol is not only irritating to respiratory system and skin, but also has serious damage to the eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If swallowed, seek medical advice immediately and show this container or label. Vapours may cause drowsiness and dizziness. Keep it away from food, drink and animal foodstuffs. The Canadian government announced a ban on isobutanol use in cosmetics in March 2009.

Structure Descriptors:
1. Smiles:C(CO)(C)C
2. InChI:InChI=1/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3

Toxicity:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 725mg/kg (725mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 16, Pg. 1, 1920.
guinea pig LD50 intraperitoneal 1201mg/kg (1201mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
hamster LD50 intraperitoneal 1401mg/kg (1401mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
mouse LD50 intraperitoneal 544mg/kg (544mg/kg) LIVER: OTHER CHANGES Research Communications in Chemical Pathology and Pharmacology. Vol. 26, Pg. 75, 1979.
mouse LD50 intravenous 417mg/kg (417mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rabbit LD50 intraperitoneal 323mg/kg (323mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rabbit LD50 skin 3400mg/kg (3400mg/kg)   Raw Material Data Handbook, Vol.1: Organic Solvents, 1974. Vol. 1, Pg. 11, 1974.
rabbit LDLo oral 3750mg/kg (3750mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Journal of Laboratory and Clinical Medicine. Vol. 10, Pg. 985, 1925.
rat LCLo inhalation 8000ppm/4H (8000ppm)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.
rat LD50 intraperitoneal 720mg/kg (720mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rat LD50 intravenous 340mg/kg (340mg/kg)   EHP, Environmental Health Perspectives. Vol. 61, Pg. 321, 1985.
rat LD50 oral 2460mg/kg (2460mg/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 10, Pg. 61, 1954.

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