Basic information
- Standard SMILES
CC(C)CNCC(C)C- InChIKey
NJBCRXCAPCODGX-UHFFFAOYSA-N- Molecular formula
- C8H19N
- Average molar mass
- 129.24 g/mol
- Monoisotopic mass
- 129.15174961
Overview
Diisobutylamine appears as a clear colorless liquid with an ammonia-like odor. Insoluble in water and less dense than water. Hence floats on water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.
Names & identifiers
- Preferred name
- Diisobutylamine
- IUPAC
- 2-methyl-N-(2-methylpropyl)propan-1-amine
- English name
- Diisobutylamine
- Molecular formula
- C8H19N
- Molecular weight
- 129.24
Names & synonyms
Show more names
Database identifiers
- CAS
110-96-3- PubChem CID
- 8085
- DTXSID
DTXSID5025079- ChEMBL
CHEMBL3187581- UNII
- T18Y0A819S
- EC Number
- 203-819-3
- Nikkaji
- J43.435C
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 4
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 49.6
Experimental & physicochemical properties
Chemical Classes
Nitrogen Compounds -> Amines, Aliphatic
Corrosives
LogP
2.63
2.67
Density
0.745 at 68 °F (USCG, 1999) - Less dense than water; will float
0.745 @ 20 °C
Relative density (water = 1): 0.75 (20 °C)
0.745 @ 20°C
Solubility
Slightly soluble (NTP, 1992)
Sol in ethanol, ether, acetone, benzene
In water, 2,200 mg/l @ 25 °C.
Solubility in water, g/100ml at 25 °C: 0.22 (slightly soluble)
Flash Point
85 °F (NTP, 1992)
29 °C (85 °F) (CLOSED CUP)
29 °C c.c.
Boiling Point
282 to 284 °F at 760 mmHg (NTP, 1992)
139.6 °C
139 °C
139 °C @760 [mm Hg]
Melting Point
-100.3 °F (NTP, 1992)
-73.5 °C
-74 °C
-70 °C
Vapor Density
4.46 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Relative vapor density (air = 1): 4.5
Physicochemical properties
- Melting point
- -77 °C · -77 °C (lit.)
- Boiling point
- 137 · 137-139 °C (lit.)
- Density
- 0.74 g/mL · 0.74 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.4081(lit.)
- Flash point
- 85 °F · 85 °F
- storage temp.
- Flammables area
- solubility
- insoluble to slightly soluble in water; soluble in ethanol, methanol, ethyl ether, ethyl acetate, acetone, benzene, aromatic and aliphatic hydrocarbons, fixed oils, mineral oil, oleic and stearic acids
- pka
- 11.07 · 11.07±0.28(Predicted)
- form
- Liquid
- color
- Clear
- Odor
- amine odor
- Water Solubility
- 5 g/L · 5 g/L (20 ºC)
- Sensitive
- Air Sensitive
- BRN
- 1209251 · 1209251
- Henry's Law Constant
- 1.8 · 1.8×10-2 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
- Dielectric constant
- 2.7 · 2.7(22℃)
- InChI
- 1S/C8H19N/c1-7(2)5-9-6-8(3)4/h7-9H,5-6H2,1-4H3
- InChIKey
- NJBCRXCAPCODGX-UHFFFAOYSA-N
- SMILES
- CC(C)CNCC(C)C
- LogP
- 2.383 · 2.383 (est)
- CAS DataBase Reference
- 110 · 110-96-3(CAS DataBase Reference)
- FDA UNII
- 18 Y0A819S · T18Y0A819S
- NIST Chemistry Reference
- 1 · 1-Propanamine, 2-methyl-N-(2-methylpropyl)-(110-96-3)
- EPA Substance Registry System
- Diisobutylamine (110-96-3)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 310 · H310+H330-H301-H314-H226
- Precautionary statements
- 501 · P501-P270-P262-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C
- Risk Statements
- 10 · 10-22-34-52/53
- Safety Statements
- 26 · 26-36/37/39-45-25-16-61
- RIDADR
- 2361 · UN 2361
- WGK Germany
- 1 · 1
- RTECS
- 1750000 · TX1750000
- F
- 34 · 34
- TSCA
- TSCA listed
- HazardClass
- 3 · 3
- PackingGroup
- III
- HS Code
- 29211990 · 29211990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 OralAquatic · Acute Tox. 3 OralAquatic Chronic 3Eye Dam. 1Flam. Liq. 3Skin Corr. 1B
- Hazardous Substances Data
- 110 · 110-96-3(Hazardous Substances Data)
- REACH Registrations
- Active
- Limited Quantities
- 5 L · 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Safety & regulation
GHS classification
GHS Classification
Danger
H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 166 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H226: Flammable liquid and vapor [Warning Flammable liquids]
Hazard information
Regulatory Information
Chemical: 1-Propanamine, 2-methyl-N-(2-methylpropyl)-
Status: Active Update: 25-08-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/26625
1-Propanamine, 2-methyl-N-(2-methylpropyl)-: HSNO Approval: HSR001251 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: May contain toxic NOx fumes.
· Flammable/combustible material.
Flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 29 °C explosive vapour/air mixtures may be formed. Risk of fire and explosion on contact with strong oxidizing agents.
Fire Potential
FLAMMABLE, MODERATE FIRE RISK
A dangerous fire hazard when exposed to heat or flame ...
Health Hazards
Inhalation of high concentrations of vapor will cause irritation of the respiratory tract and the lungs. Contact with liquid may result in severe skin and eye irritation. Exposure to concentrated vapors may result in corneal edema. Poisonous if swallowed. (USCG, 1999)
· May cause toxic effects if inhaled or ingested.
Hazards Summary
A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause pulmonary edema; Can be absorbed through skin; [ICSC] Not mutagenic in five strains of Salmonella typhimurium; Emergency treatment: Corrosives-alkaline; [HSDB] Sensitive to heat and air; A severe skin and eye irritant; A respiratory tract irritant; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation of high concentrations may cause pulmonary edema; May be absorbed through skin; [CHEMINFO]
Reactivity Profile
DIISOBUTYLAMINE can react vigorously with oxidizing materials (NTP, 1992). Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Chemical Dangers
Decomposes on burning. This produces toxic fumes including nitrogen oxides. The substance is a medium strong base. Reacts violently with strong oxidants. This generates fire and explosion hazard. Attacks many metals and some plastics. Solutions in water slowly etch glass.
Safety & protection
Fire Fighting
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Use alcohol-resistant foam, water, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
First Aid Measures
Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer immediately for medical attention.
Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse skin with plenty of water or shower for at least 15 minutes. Refer immediately for medical attention .
Rinse with plenty of water for several minutes (remove contact lenses if easily possible). Refer immediately for medical attention.
Rinse mouth. Give nothing to drink. Do NOT induce vomiting. Refer immediately for medical attention.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
General First Aid:
Fire Fighting Procedures
Alcohol foam. Water may be ineffective.
To fight fire, use alcohol foam, carbon dioxide, dry chemical.
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Spillage Disposal
Remove all ignition sources. Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Wash away remainder with plenty of water.
Isolation and Evacuation
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Immediate precautionary measure
Toxicology
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 640(SRC) from an estimated log Kow of 2.63(2) and a regression derived equation(3) indicates that diisobutylamine is expected to have low mobility in soil(SRC). A pKa value of 10.91(4) indicates that the protonated form of diisobutylamine will be the dominant species in moist soil surfaces and cations generally adsorb strongly to soils. Volatilization of diisobutylamine from moist soil surfaces is not expected to be an important fate process since the cation will not volatilize. Diisobutylamine may volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.27 mm Hg at 25 °C(5). 63 to 87% of the theoretical BOD was achieved for diisobutylamine using activated sludges over a 4 week incubation period(6), which suggests that biodegradation in soil is expected to be important(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 640(SRC) from an estimated log Kow of 2.63(2) and a regression derived equation(3) indicates that diisobutylamine is expected to adsorb to suspended solids and sediment in water(SRC). A pKa value of 10.91(4) indicates that the protonated form of diisobutylamine will be the predominant species in water. Volatilization from water surfaces is not expected to be an important fate process(SRC) since the protonated form will not volatilize. According to a classification scheme(5), an estimated BCF of 21(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 63 to 87% of the theoretical BOD was achieved for diisobutylamine using activated sludges over a 4 week incubation period(7), which suggests that biodegradation in water is expected to be important(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diisobutylamine, which has a vapor pressure of 7.27 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase diisobutylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), from its rate constant of 9X10-11 cu cm/molecule-sec at 25 °C(3). Diisobutylamine is not expected to directly photolyze due to the lack of absorption in the environmental UV spectrum(SRC).
Signs and Symptoms
Cough. Sore throat. Burning sensation behind the breastbone. Shortness of breath. Laboured breathing.
Redness. Pain. Serious skin burns.
Redness. Pain. Severe burns. Blurred vision.
Burns in mouth and throat. Burning sensation. Abdominal pain. Vomiting. Shock or collapse.
Soil Adsorption/Mobility
The Koc of diisobutylamine was estimated as 640(SRC), using an estimated log Kow of 2.63(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diisobutylamine is expected to have low mobility in soil(SRC). The pKa of diisobutylamine is 10.91(4), indicating that the protonated form will be the predominant species in moist soils and cations are expected to adsorb strongly to soil surfaces.
Environmental Bioconcentration
An estimated BCF of 21 was calculated for diisobutylamine(SRC), using an estimated log Kow of 2.63(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Volatilization from Water/Soil
With a pKa of 10.91(1), diisobutylamine will exist predominantly in its protonated form in the environment and the protonated form of diisobutylamine will not volatilize from water or moist soil surfaces(2). Diisobutylamine may volatilize from dry soil surfaces(SRC) based on its vapor pressure of 7.27 mm Hg at 25 °C(3).
Non-Human Toxicity Excerpts
MORTALITY RATE OF 75 PPM INHALED BY RATS FOR 4 HR WAS 4/6; NO DEATHS OCCURRED WHEN INHALING SATURATED VAPOR FOR 50 MIN. /FROM TABLE/
Diisobutylamine was found to be negative when tested for mutagenicity using the Salmonella/ microsome preincubation assay, using the standard protocol approved by the National Toxicology Program (NTP). Diisobutylamine was tested in as many as 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of rat and hamster liver S-9, at doses of 0.100, 0.333, 1.000, 3.333, and 10.000 mg/plate. The highest ineffective dose tested in any S. typhimurium strain was 10.000 mg/plate.
Safety data
- F
- 34
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- TX1750000
- ridadr
- UN 2361
- hs_code
- 29211990
- risk_code
- 10-22-34-52/53
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS06
- hazard_code
- C
- safety_code
- 26-36/37/39-45-25-16-61
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- III
- Hazard statements
- H310+H330-H301-H314-H226
- Limited Quantities
- 5.0 L (1.3 gallons) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 3 OralAquatic Chronic 3Eye Dam. 1Flam. Liq. 3Skin Corr. 1B
- Precautionary statements
- P501-P270-P262-P240-P260-P210-P233-P243-P241-P242-P271-P264-P280-P284-P370+P378-P361+P364-P303+P361+P353-P301+P330+P331-P301+P310+P330-P304+P340+P310-P305+P351+P338+P310-P403+P233-P403+P235-P405
- Hazardous Substances Data
- 110-96-3(Hazardous Substances Data)
Chemistry & industry
Uses & manufacturing
Uses
Used as an intermediate; [Hawley] Used to make agrochemicals and other organic chemicals; [CHEMINFO]
As an intermediate
Applications
UsesDiisobutylamine was used to study the effect of achiral amine on hydrogenation of ethyl pyruvate over cinchonidine-Pt/Al2O3 catalyst system. Diisobutylamine is the principal starting material for the herbicide Butylate (Zeneca).
General DescriptionDiisobutylamine appears as a clear colorless liquid with an ammonia-like odor. Insoluble in water and less dense than water. Hence floats on water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.
Upstream & downstream products
Downstream products
Related reactions
Linked notes
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