Cyclohexylamin

CHA · Cyclohexylamin · AMINOCYCLOHEXANE · HEXAHYDROANILINE · cyclohexaneamine · 1-Aminocyclohexane · CHA-60 · cha[qr]

Identifikatoren & physikalische Daten

CAS No.	108-91-8
Summenformel	C6H13N
Durchschnittliche Molmasse	99,17 g/mol
Monoisotopische Masse	99,10479942 g/mol
SMILES	NC1CCCCC1
InChIKey	PAFZNILMFXTMIY-UHFFFAOYSA-N
PubChem CID	7965
ChEMBL	CHEMBL1794762
ChEBI	CHEBI:15773
EC No.	203-629-0
DTXSID	DTXSID1023996
Lokaler Name	Cyclohexylamin

Chemische & physikalische Eigenschaften

XLogP	1,5
Polarare Oberfläche (TPSA)	26
H-Brücken-Donoren	1
H-Brücken-Akzeptoren	1
Frei drehbare Bindungen	0
Schwere Atome	7
Formalladung	0
Komplexität	46,1
Stoffklassen	Nitrogen Compounds -> Amines, CyclicCorrosives
Arzneimittel	Pharmaceuticals -> Listed in ZINC15
Kosmetika	AnticorrosiveBuffering
pH	STRONG BASE11.5 (100g/l, H2O, 20℃)
SpringerMaterials Properties	Boiling point
Pestizide	Pesticide -> EPA IRIS
LogP (Verteilungskoeffizient)	log Kow = 1.49
Geruch	Strong, fishy, amine odor.
Lebensmittelzusatzstoffe	BOILER WATER ADDITIVE -> FDA Substance added to food
Dichte	0.8647 at 77 °F (EPA, 1998) - Less dense than waterwill float0.8647 @ 25 °C/25 °CRelative density (water = 1): 0.860.870.8647 @25 °C0.867 g/mL at 25 °C(lit.)
Viscosity	2.10 Pa*s at 20 °C
Color/Form	Colorless or yellow liquid.
Schmelzpunkt	-17 °C
Siedepunkt	134 °C(lit.)
Dampfdichte	3.42 (vs air)
Dampfdruck	10 mm Hg ( 22 °C)
Brechungsindex	n20/D 1.459(lit.)
Flammpunkt	90 °F
Lagerbedingungen	Store below +30°C.
Löslichkeit	organic solvents: miscible
pKa (Säurekonstante)	10.66(at 24℃)
Aggregatzustand	Liquid
Farbe	Clear
Geruch	strong fishy odor
Explosionsgrenze	1.6-9.4%(V)
Merck	14,2729
BRN	471175
Henry-Konstante	2.2×100 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielektrizitätskonstante	5.3(-21℃)
Kosmetik-Inhaltsstoffe Funktionen	BUFFERINGANTICORROSIVE
InChI	1S/C6H13N/c7-6-4-2-1-3-5-6/h6H,1-5,7H2
InChIKey	PAFZNILMFXTMIY-UHFFFAOYSA-N
SMILES	NC1CCCCC1
LogP (Verteilungskoeffizient)	3.7 at 25℃
CAS Datenbank	108-91-8(CAS DataBase Reference)
NIST chemische Informationen	Cyclohexanamine(108-91-8)
EPA chemische Informationen	Cyclohexylamine (108-91-8)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH226: Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P264, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P362+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)H226 (90.4%): Flammable liquid and vapor [Warning Flammable liquids]P203, P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P318, P321, P330, P361+P364, P362+P364, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Regulatorische Informationen	Chemical: CyclohexanamineCyclohexanamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Cyclohexanamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 24-08-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/13348Cyclohexanamine: HSNO Approval: HSR001532 Approved with controlsThe 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.)
Weitere Sicherheitsinformationen	IMAP assessments - Cyclohexanamine: Human health tier II assessment
DOT-Kennzeichnung	Corrosive Flammable Liquid
Brandgefahren	When heated to decomposition, it emits highly toxic fumes. Vapor may travel a considerable distance to source of ignition and flash back. Toxic oxides of nitrogen are produced during combustion. Nitric acidreacts vigorously with oxiding materials. Stable, avoid physical damage, storage with oxidizing material. (EPA, 1998)· Flammable/combustible material.Flammable. Above 28 °C explosive vapour/air mixtures may be formed.
Brandpotenzial	FLAMMABLE LIQUID...Dangerous fire hazard when exposed to heat, flame, or oxidizers.
Gesundheitsgefahren	This is classified as very toxic -- probable oral lethal dose is 50-500 mg/kg or between 1 teaspoon and 1 ounce for a 70 kg (150 lb.) person. It is considered a nerve poison. This is a weak methemoglobin-forming substance. (EPA, 1998)· May cause toxic effects if inhaled or ingested.
Gefahrenübersicht	Cyclohexylamine has moderate skin sensitizing potential and is a weak methemoglobin inducer. Listed in the table Examples of Industrial Chemicals for Which Methemoglobin Formation is NOT the Principal Cause of Toxicity[ACGIH] Merck Index # 2729Causes second and third degree burns after short skin exposure[CHRIS] Corrosive to skin[Quick CPC] Corrosive to the skin, eyes, and respiratory tractInhalation of high concentrations may cause CNS effects[ICSC] No apparent effects in workers exposed to 4-10 ppmInhalation of high concentrations could cause pulmonary edemaA 25% solution produced severe irritation of the skin in humansMay cause permanent eye injuryTransient visual effects (blue haze or halo vision) occur at low concentrations[CHEMINFO]
DOT-Nummer und Handbuch	2357 132
Reaktive Gruppe	Amines, Phosphines, and Pyridines
EG-Einstufung	Symbol: CR: 10-21/22-34S: (1/2)-36/37/39-45
UN-Einstufung	UN Hazard Class: 8UN Subsidiary Risks: 3UN Pack Group: II
Special Reports	Bopp BA et alToxicological Aspects of Cyclamate and CyclohexylamineCrit Rev Toxicol 16 (3): 213-306 (1986)
Brandbekämpfung	Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. Use dry chemical, alcohol foam or carbon dioxidewater may be ineffective. Move container from fire area if you can do it without risk. Stay away from ends of tanks. Cool containers that are exposed to flames with water from the side until well after fire is out. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire. Keep unnecessary people awayisolate hazard area and deny entry. Isolate for one-half mile in all directions if tank car or truck is involved in fire. Stay upwindkeep out of low areas. (EPA, 1998)Use water in large amounts, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.
Erste-Hilfe-Maßnahmen	Fresh air, rest. Half-upright position. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Refer for medical attention . Give one or two glasses of water to drink.
Freisetungsmaßnahmen	· 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.
Erste Hilfe	Warning: Cyclohexylamine is an alkaline-corrosive agent. Contact with eyes may result in severe damage to the cornea, conjunctiva, and blood vessels. Caution is advised.General First Aid:(General first aid procedures)
Sichere Lagerung	Fireproof. Separated from acids, oxidants, aluminium, copper, zinc and food and feedstuffs. Well closed.
Firefighting Hazards	VAPORS ARE HEAVIER THAN AIR AND MAY TRAVEL TO A SOURCE OF IGNITION & FLASH BACK.
Expositionsschutz und Persönliche Schutzausrüstung	· Wear positive pressure self-contained breathing apparatus (SCBA).2.0 [ppm]
Brandbekämpfungsverfahren	Use water spray, dry chemical, "alcohol resistant" foam, or carbon dioxide. Use water spray to keep fire-exposed containers cool. Solid streams of water may be ineffective and spread material.
Lagerbedingungen	Outside or detached storage is preferred. Avoid oxidizing materials, acid, and sources of halogen. Store in a cool, dry well-ventilated location.
Reinigungsverfahren	Stop or control the leak, if this can be done without undue risk. Eliminate all ignition sources. Use water spray to cool and disperse vapors, protect personnel, and dilute spills to form nonflammable mixtures. Approach release from upwind. Absorb in noncombustible material for proper disposal.
Freisetung ohne Brand	Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]:
Entsorgungsverfahren	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.
Zielorgane	ReproductiveEyes, skin, respiratory system, central nervous system
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a measured log Kow of 1.49(2) and a regression-derived equation(3), indicates that cyclohexylamine as the free base is expected to have high mobility in soil(SRC). A pKa value of 10.6(4) indicates that the protonated form of cyclohexylamine will be the dominant species in moist soil surfaces and cations generally adsorb more strongly to soils than their neutral counterparts. Volatilization of cyclohexylamine from moist soil surfaces is not an important fate process since the cation will not volatilize. The potential for volatilization of cyclohexylamine from dry soil surfaces may exist(SRC) based upon a vapor pressure of 10.1 mm Hg(5). Biodegradation is expected to occur in soils based on standard biodegradability tests conducted with activated sludge and sewage inocula(6-8).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 150(SRC), determined from a measured log Kow of 1.49(2) and a regression-derived equation(3), indicates that cyclohexylamine as the free base is not expected to adsorb to suspended solids and sediment(SRC). A pKa value of 10.6(4) indicates that the protonated form of cyclohexylamine will be the predominant species in water and cations generally adsorb more strongly than their neutral counterparts. Volatilization from water surfaces is not an important fate process(SRC) since the protonated form will not volatilize. According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of 1.49(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low. Biodegradation is expected to occur in aquatic environments based on standard biodegradability tests conducted with activated sludge and sewage inocula(7-9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cyclohexylamine, which has a vapor pressure of 10.1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cyclohexylamine 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 7 hours(SRC), calculated from its rate constant of 5.5X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).
Unerwünschte Wirkungen	Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect
Expositionspfade	The substance can be absorbed into the body by inhalation, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contact
Signs and Symptoms	Burning sensation. Cough. Laboured breathing. Nausea. Vomiting.Redness. Pain. Skin burns.Redness. Pain. Severe deep burns.Dizziness. Abdominal cramps. Burning sensation. Vomiting. Abdominal pain. Shock or collapse. Nausea.irritation eyes, skin, mucous membrane, respiratory systemeye, skin burnsskin sensitizationcough, pulmonary edemadrowsiness, dizzinessdiarrhea, nausea, vomiting
Effluent Concentrations	Cyclohexylamine was detected, not quantified, in the leachate of 2 low-level radioactive disposal facilities located in Maxey Flats, Kentucky and West Valley, New York(1). Effluent from a tire manufacturing plant contained cyclohexylamine at approximately 0.01 ppm(2).
ICSC Environmental Data	The substance is harmful to aquatic organisms.
EPA IRIS Information	CyclohexylamineReproductive2 x 10 ^-1 mg/kg-day
Soil Adsorption/Mobility	The Koc of cyclohexylamine is estimated as 150(SRC), using a measured log Kow of 1.49(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that cyclohexylamine is expected to have very high mobility in soil. The pKa of cyclohexylamine is 10.6(4), indicating that the protonated form will be the predominant species in moist soils and cations are expected to adsorb strongly to soil surfaces.
TSCA Test Submissions	Cyclohexylamine (CAS # 108-91-8) was evaluated for acute dermal toxicity in solitary male and female New Zealand albino rabbits alternately administered single undiluted dermal applications of 398, 631, 1000, and 1580 mg/kg bodyweight for 24 hours. Clinical signs were observed at all dose levels and included reduced appetite and activity, increasing weakness and collapse. The 1000 mg/kg male and the 1580 mg/kg female both died within 16 hours of treatment, while solitary male and female rabbits of the 398 and 631 mg/kg doses, respectively, saw resolution of all pharmacotoxic signs within 5-7 days. Upon necropsy, the high dose study lethalities were found with lung and liver hyperemia, dark spleen and kidneys, and enlarged gall bladder, while the viscera of the male and female surviving 14-day post-treatment observation appeared normal.Cyclohexylamine (CAS # 108-91-8) was evaluated for acute inhalation toxicity in 6 male Sprague-Dawley albino rats exposed in a 35 L inhalation chamber to an atmospheric concentration of 13.7 mg/L for 6 hours. During the exposure, rats exhibited nasal and ocular discharge, labored breathing, roughened fur and lethargy. Reduced appetite and activity lasted for one day after treatment. Post-treatment responses were primarily marked by ocular signs of toxicity including near blindness due to corneal cloudiness for 2-6 days. Two of 6 rats had complete loss of sight with corneal blistering upon the final 14th day observation, while all other (4/6) rats were cleared of any clinical signs of toxicity. Upon terminal necropsy on Day 14, all viscera appeared normal.Cyclohexylamine (CAS # 108-91-8) was evaluated for acute oral toxicity in groups of 10 female Swiss-Webster mice administered single peroral doses of 5.0, 6.0, 6.5, 7.5, and 10.0 cc/kg bodyweight (1:10 in 0.5% methylcellulose). Study mortality was comprised of 1/10, 2/10, 4/10, 6/10, and 8/10 of successive incremental dosage groups, respectively, consistent with a LD50 of 730 mg/kg (95% C.L. = 640-830). Death occurred from 1/4 to 2 hours after treatment. Clinical signs of a systemic toxicity included hypokinesis, dyspnea, hyperpnea, diarrhea, diuresis, ptosis, piloerection, salivation, lacrimation, occult blood in urine and feces, cyanosis, somnolence, cachexia, weight loss, and hyperkinesis, random biting and chewing, ataxia, jerking, tremors, opisthotonos, irritability, limb abduction, paralysis, tail erection, hypothermia, clonic convulsions, tonic convulsions, increased and/or decreased muscle tone. Treatment was also associated with vocalization, tissue irritation to necrosis, writhing, self-decimation, and quiet death.Cyclohexylamine (CAS # 108-91-8) was evaluated for acute oral toxicity in groups of 10 female Swiss-Webster mice administered single peroral cyclohexylamine.HCl (10% solution in 0.5% methylcellulose) at doses of 400, 500, 600, 750, 850, 1250, and 1500 mg/kg. Treatment was associated with mortality in 0/10, 3/10, 6/10, 8/10, 9/10, 9/10, and 10/10 of successive incremental dosage groups, respectively, consistent with a LD50 of 530 mg/kg (95% C.L. 441-637). At doses of 400 mg/kg, mice exhibited clinical signs of toxicity including increased activity, increased respiration, tail erection, salivation, irritability, jerking, clonic convulsions, and death at 1-18 hours following treatment.For more TSCA Test Submissions (Complete) data for CYCLOHEXYLAMINE (10 total), please visit the HSDB record page.
Natural Pollution Sources	Cyclohexylamine is not known to occur as a natural product(1).
Atmospheric Concentrations	INDOOR AIR: The average concentration of cyclohexylamine was measured as 0.7 ppb in the indoor air of a building in Columbus Ohio where cyclohexylamine is used as a corrosion inhibitor in the boiler system of the building(1).
Luftstandards	This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Cyclohexylamine is produced, as an intermediate or a final product, by process units covered under this subpart.
CERCLA-Meldepflichtmengen	Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Cyclohexylamine is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 10,000 lbs.
DHS Chemicals of Interest (COI)	Cyclohexylamine115000Toxic chemical that can be released at a facility.
Landesrichtlinien für Trinkwasser	(FL) FLORIDA 5,000 ug/l
F	10-34
Berufliche Expositionsstufe (OEB)	A
Arbeitsplatzgrenzwert (OEL)	TWA: 10 ppm (40 mg/m3)
Wassergefährdungsklasse (WGK)	1
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 2357
Zollcode	2921 30 10
RTECS-Nr.	GX0700000
R-Sätze (R)	10-21/22-34-62-24-22
Toxizität	LD50 orally in rats: 0.71 ml/kg (Smyth)
Gefahrensymbole	C,T
Sicherheitshinweise (S)	36/37/39-45-1/2-26
Gefahrenklasse	8Acute Tox. 3 DermalAcute Tox. 3 OralEye Dam. 1Flam. Liq. 3Repr. 2Skin Corr. 1B
Verpackungsgruppe	II
Lagerklasse	3 - Flammable liquids
Gefahrstoffdaten	108-91-8(Hazardous Substances Data)
Selbstentzündungstemperatur	559 °F

Anwendungen & Verwendung

Verwenden

Cyclohexylamine is used in the manufacture of a number of products, including plasticizers, drycleaning soaps, insecticides, and emulsifying agents. It is also used as a corrosion inhibitor and in organic synthesis.