Diallylamine
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Diallylamine
structure -
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CAS No:
124-02-7
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Formula:
C6H11N
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Chemical Name:
Diallylamine
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Synonyms:
2-Propen-1-amine,N-2-propen-1-yl-;Diallylamine;2-Propen-1-amine,N-2-propenyl-;N-2-Propen-1-yl-2-propen-1-amine;Di-2-propenylamine;N-2-propenyl-2-propen-1-amine;NSC 20948;Bisallylamine;N,N-Bis(allyl)amine;Bis-allylamine;1263263-74-6
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CAS No:
Description
CLEAR COLOURLESS TO YELLOW LIQUID Diallylamine is a flammable liquid. Diallylamine can be detected, but it is not unpleasant at 2–9 ppm and is not intolerable at 70 ppm.A liquid with a disagreeable odor. Less dense than water. Flash point 70°F. May be toxic by inhalation and skin absorption. Irritates skin and eyes. Used to make other chemicals.
Diallylamine appears as a liquid with a disagreeable odor. Less dense than water. May be toxic by inhalation and skin absorption. Irritates skin and eyes. Used to make other chemicals.|Liquid|COLOURLESS LIQUID WITH CHARACTERISTIC ODOUR.
Diallylamine appears as a liquid with a disagreeable odor. Less dense than water. May be toxic by inhalation and skin absorption. Irritates skin and eyes. Used to make other chemicals.
Diallylamine Basic Attributes
97.15820
97.16
204-671-2
N18EXB6V6P
0866
20948
2359
DTXSID1024918
Liquid
2921300090
Characteristics
12.03000
1.33890
Diallylamine appears as a liquid with a disagreeable odor. Less dense than water. May be toxic by inhalation and skin absorption. Irritates skin and eyes. Used to make other chemicals.
0.7889 g/cm3 @ Temp: 20 °C
-88.4 °C
111 °C
7ºC
1.4395-1.4415
H2O: 8.6 g/100mL
Flammables area
18 mm Hg ( 20 °C)
3.35 (vs air)
LD50 orally in rats: 0.65 g/kg (Smyth)
vol% in air: 2.22
RECOGNIZABLE BUT REFRESHING ODOR @ 4-9 PPM
SWEETISH TASTE
pKa= 9.29 (conjugate acid)|pKb = 4.87 @ 25 °C
Conversion units: 1 mg/l= 252 ppm, 1 ppm= 3.97 mg/cu m
Highly flammable. Soluble in water.
Amines, Phosphines, and Pyridines
Highly Flammable
DIALLYLAMINE 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.
273 °C
The vapour mixes well with air, explosive mixtures are easily formed. As a result of flow, agitation, etc., electrostatic charges can be generated.
4.86X10+7 J/Kmol @ 184.75 K
Critical temperature: 556.0 K; Critical pressure: 3.32X10+6 Pa
Safety Information
II
3
UN 2359
3
R11; R20/22; R24; R34
S16-S26-S28-S36/37/39-S45
UC6650000
F
Provision to contain effluent from fire extinguishing. Fireproof. Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Store in an area without drain or sewer access.
P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P309+P311, P310, P312, P321, P322, P330, P361, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
H225
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.
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Flammable/combustible material. May be 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water. (ERG, 2016)|Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Vapour/air mixtures are explosive.|Flammable - 3rd degree, Reactive - 2nd degree
|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501|Aggregated GHS information provided by 153 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P309+P311, P310, P312, P321, P322, P330, P361, P363, P370+P378, P403+P233, P403+P235, P405, and P501
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Some of these materials may react violently with water. SMALL FIRE: Dry chemical, CO2, water spray or alcohol-resistant foam. LARGE FIRE: Water spray, fog or alcohol-resistant foam. Move containers from fire area if you can do it without risk. Dike fire-control water for later disposal; do not scatter the material. Do not get water inside containers. FIRE INVOLVING TANKS OR CAR/TRAILER LOADS: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. (ERG, 2016)|Use water spray, foam, powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Fully encapsulating, vapor-protective clothing should be worn for spills and leaks with no fire. ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb with earth, sand or other non-combustible material and transfer to containers (except for Hydrazine). Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. (ERG, 2016)
Explosive limits , vol% in air: 2.2-22
/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Fire or Explosion: Flammable/combustible material. May be 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. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Health: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to 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.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 132: FLAMMABLE LIQUIDS - CORROSIVE/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.|For more DOT Emergency Guidelines (Complete) data for DIALLYLAMINE (8 total), please visit the HSDB record page.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
/IN EXPTL HUMAN EXPOSURES/... MUCOUS MEMBRANE IRRITATION & CHEST DISCOMFORT IN A FEW SUBJECTS @ 22 PPM, NOT INTOLERABLE @ 70 PPM.
Remove all ignition sources. Evacuate danger area! Consult an expert! Personal protection: gas-tight chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.
Provision to contain effluent from fire extinguishing. Fireproof. Separated from strong oxidants, strong acids and food and feedstuffs. Well closed. Store in an area without drain or sewer access.
No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
The substance is corrosive to the eyes, skin and respiratory tract. Corrosive on ingestion. Inhalation of fumes may cause lung oedema. Exposure could cause severe swelling of the throat. The substance may cause effects on cardiovascular system and nervous system. This may result in cardiac disorders and impaired functions. The effects may be delayed. Medical observation is indicated.
Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the respiratory tract and lungs. This may result in chronic inflammation and impaired functions.
NO open flames, NO sparks and NO smoking. Closed system, ventilation, explosion-proof electrical equipment and lighting. Do NOT use compressed air for filling, discharging, or handling. Prevent build-up of electrostatic charges (e.g., by grounding).
STRICT HYGIENE! IN ALL CASES CONSULT A DOCTOR!
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
Toxicity
Diallylamine's production and use as an intermediate in the production of pharmaceuticals and resins(1) and in crop protection, as an auxiliary in paper making(2), and as a solvent(3) may result in its direct release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 96(SRC), determined from a log Kow of 1.11(2) and a regression-derived equation(3), indicates that diallylamine is expected to have high mobility in soil(SRC). However, a pKa of 9.29(6), indicates that this compound will exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts, thus reducing mobility. Volatilization of diallylamine from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 20.2 mm Hg(5), and water solubility, 8.6X10+4 mg/l(4). The potential for volatilization of diallylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 20.2 mm Hg(5). However, adsorption to soil is expected to attenuate volatilization when the compound is in the cation form(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 96(SRC), determined from a log Kow of 1.11(2) and a regression-derived equation(3), indicates that diallylamine is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 3.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 20.2 mm Hg(7), and water solubility, 8.6X10+4 mg/l(8). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 20 hrs and 13 days, respectively(SRC). A pKa of 9.29(4) indicates diallylamine will exist almost entirely in the protonated form in aqueous environments and the protonated form of diallylamine is not expected to volatilize from water surfaces. According to a classification scheme(5), an estimated BCF of 1.4(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low.|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), diallylamine, which has a vapor pressure of 20.2 mm Hg at 25 °C(2), will exist solely in the vapor phase in the ambient atmosphere. Vapor-phase diallylamine 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 11 hrs(SRC), calculated from its rate constant of 1.33X10-10 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).
The rate constant for the vapor-phase reaction of diallylamine with photochemically-produced hydroxyl radicals has been estimated as 1.33X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 11 hours(SRC) at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1).
An estimated BCF of 1.4 was calculated for diallylamine(SRC), using a log Kow of 1.11(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.
The Koc of diallylamine is estimated as 96(SRC), using a log Kow of 1.11(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that diallylamine is expected to have high mobility in soil. The pKa of diallylamine is 9.29(4), indicating that this compound will exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts.
The Henry's Law constant for diallylamine is estimated as 3.0X10-5 atm-cu m/mole(SRC), derived from its vapor pressure, 20.2 mm Hg(1), and water solubility, 8.6X10+4 mg/l(2). This Henry's Law constant indicates that diallylamine is expected to volatilize from water surfaces(3). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(3) is estimated as 20 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(3) is estimated as 13 days(SRC). Diallylamine's estimated Henry's Law constant(1,2) indicates that volatilization from moist soil surfaces may occur(SRC). The potential for volatilization of diallylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 20.2 mm Hg(1). However, adsorption to soil is expected to attenuate volatilization when the compound is in the cation form(SRC).
Occupational exposure to diallylamine may occur through inhalation and dermal contact with this compound at workplaces where diallylamine is produced or used. (SRC)
Drug Information
Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to 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. (ERG, 2016)
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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
Fresh air, rest. Half-upright position. Refer immediately for medical attention.
First rinse with plenty of water for at least 15 minutes, then remove contaminated clothes and rinse again. Refer immediately for medical attention.
Rinse with plenty of water (remove contact lenses if easily possible). Refer immediately for medical attention.
/IN EXPTL HUMAN EXPOSURES/...RECOGNIZABLE BUT NOT UNPLEASANT @ 2 TO 9 PPM, MUCOUS MEMBRANE IRRITATION & CHEST DISCOMFORT IN A FEW SUBJECTS @ 22 PPM, NOT INTOLERABLE @ 70 PPM.
The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion. Serious local effects by all routes of exposure.
Cough. Headache. Nausea. Sore throat. Laboured breathing. Shortness of breath. Symptoms may be delayed.
Redness. Pain. Serious skin burns.
Watering of the eyes. Redness. Pain. Blurred vision. Severe burns. Loss of vision.
Diallylamine Use and Manufacturing
Prepared from allylamine and allyl bromide: Ladenburg, Ber. 14, 1879 (1881); from allylamine and allyl chloride: Liebermann, Hagen, Ber. 16, 1641 (1883); from diallylcyanamide by refluxing with dil sulfuric acid: Vliet, J. Am. Chem. Soc. 46, 1307 (1924); Org. Syn. coll. vol. I (2nd ed., 1941) p 201.|Prepared from allyl chloride plus ammonia (amine formation; coproduced with allylamine/triallylamine)
Diallylamine is manufactured from allyl chloride and ammonia. It is used as a solvent and in organic syntheses.
Intermediates
polymer for the paper industry
All other basic organic chemical manufacturing|2-Propen-1-amine, N-2-propen-1-yl-: ACTIVE|/PREPN OF THE CHLOROACETAMIDE HERBICIDE N,N-DIALLYL-2-CHLOROACETAMIDE (CDAA)/...BY THE REACTION OF CHLOROACETYL CHLORIDE WITH...DIALLYLAMINE...
Fire Hazards -> Flammable - 3rd degree, Reactive - 2nd degree
Computed Properties
Molecular Weight:97.16
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:97.089149355
Monoisotopic Mass:97.089149355
Topological Polar Surface Area:12
Heavy Atom Count:7
Complexity:49.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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