| Identification | More | [Name]
Cyclohexylamine | [CAS]
108-91-8 | [Synonyms]
AKOS BBS-00003664
AMINOCYCLOHEXANE
AURORA KA-7609
CHA
CHA-60
CYCLOHEXYLAMINE
HEXAHYDROANILINE
1-Aminocyclohexane
1-Cyclohexylamine
aminocyclohexane[qr]
Aminohexahydrobenzene
aminohexahydrobenzene[qr]
Aniline, hexahydro-
Benzenamine, hexahydro-
benzenamine,hexahydro-[qr]
cha[qr]
cyclohexanamine[qr]
cyclohexane,amino-
cyclohexaneamine
hexahydro-anilin | [EINECS(EC#)]
203-629-0 | [Molecular Formula]
C6H13N | [MDL Number]
MFCD00001486 | [Molecular Weight]
99.17 | [MOL File]
108-91-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Cyclohexylamine is a colorless to yellow liquid (amines, primary aromatic). It has an unpleasant fishy odor.
| [Melting point ]
-17 °C | [Boiling point ]
134 °C(lit.)
| [density ]
0.867 g/mL at 25 °C(lit.)
| [vapor density ]
3.42 (vs air)
| [vapor pressure ]
10 mm Hg ( 22 °C)
| [refractive index ]
n20/D 1.459(lit.)
| [Fp ]
90 °F
| [storage temp. ]
Flammables area | [solubility ]
organic solvents: miscible | [form ]
Liquid | [pka]
10.66(at 24℃) | [color ]
Clear | [Odor]
strong fishy odor | [PH]
11.5 (100g/l, H2O, 20℃) | [explosive limit]
1.6-9.4%(V) | [Water Solubility ]
MISCIBLE | [FreezingPoint ]
-17.7℃ | [Sensitive ]
Air Sensitive | [Merck ]
14,2729 | [BRN ]
471175 | [Dielectric constant]
5.3（-21℃） | [Exposure limits]
TLV-TWA 10 ppm (～40 mg/m3) (ACGIH). | [InChIKey]
PAFZNILMFXTMIY-UHFFFAOYSA-N | [LogP]
3.7 at 25℃ | [CAS DataBase Reference]
108-91-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Cyclohexanamine(108-91-8) | [EPA Substance Registry System]
108-91-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R10:Flammable.
R21/22:Harmful in contact with skin and if swallowed .
R34:Causes burns. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S1/2:Keep locked up and out of the reach of children . | [RIDADR ]
UN 2357 8/PG 2
| [WGK Germany ]
1
| [RTECS ]
GX0700000
| [F ]
10-34 | [Autoignition Temperature]
559 °F | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29213000 | [Safety Profile]
A poison by ingestion,
skin contact, and intraperitoneal routes.
Experimental teratogenic and reproductive
effects. A severe human skin irritant. Can
cause dermatitis and convulsions. Human
mutation data reported. Questionable
carcinogen. Flammable liquid. Dangerous
fire hazard when exposed to heat, flame, or
oxidizers. To fight fire, use alcohol foam,
CO2, dry chemical. When heated to
decomposition it emits toxic fumes of NOx. | [Hazardous Substances Data]
108-91-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 0.71 ml/kg (Smyth) |
| Hazard Information | Back Directory | [General Description]
Cyclohexylamine(108-91-8) appears as a clear colorless to yellow liquid with an odor of ammonia. Flash point 90 °F. Irritates the eyes and respiratory system. Skin contact may cause burns. Less dense than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion. | [Reactivity Profile]
CYCLOHEXYLAMINE(108-91-8) 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. | [Air & Water Reactions]
Highly flammable. Sensitive to air and light. Soluble in water. | [Health Hazard]
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. | [Potential Exposure]
CHA is used in making dyes, chemi-
cals, dry cleaning chemicals; insecticides, plasticizers, rub-
ber chemicals; and as a chemical intermediate in the
production of cyclamate sweeteners. Used in water treat-
ment and as a boiler feedwater additive. It is also used in
rubber production to retard degradation. | [Fire Hazard]
When heated to decomposition, CYCLOHEXYLAMINE 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 acid; reacts vigorously with oxiding materials. Stable, avoid physical damage, storage with oxidizing material. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ-
ing resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medi-
cal attention. If victim is conscious, administer water or
milk. Do not induce vomiting. Medical observation is
recommended for 24 to 48 hours after breathing overexpo-
sure, as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy.
| [Shipping]
UN2357 Cyclohexylamine, Hazard class: 8;
Labels: 8-Corrosive material, 3-Flammable liquid. | [Incompatibilities]
May form explosive mixture with air.
Cyclohexylamine is a strong base: it reacts violently with
acid. Contact with strong oxidizers may cause fire and
explosion hazard. Incompatible with organic anhydrides;
isocyanates, vinyl acetate; acrylates, substituted allyls;
alkylene oxides; epichlorohydrin, ketones, aldehydes, alco-
hols, glycols, phenols, cresols, caprolactum solution; lead.
Corrosive to copper alloys, zinc, or galvanized steel. | [Description]
Cyclohexylamine is a colorless to yellow liquid (amines, primary aromatic). It has an unpleasant fishyodor. Molecular weight=99.20; Specific gravity=0.87;Boiling point=134.4℃; Freezing/Melting point 52 -17.7℃; Vapor pressure=11 mmHg at 20℃; Flashpoint=31℃; Autoignition temperature=293℃. Explosivelimits: LEL=1.5%; UEL=9.4%. Hazard Identification(based on NFPA-704 M Rating System): Health 3,Flammability 3, Reactivity 0. Soluble in water. | [Chemical Properties]
Cyclohexylamine is a colorless to yellow liquid (amines, primary aromatic). It has an unpleasant fishy odor. | [Waste Disposal]
Incineration; incinerator
equipped with a scrubber or thermal unit to reduce nitrogen
oxides emissions. | [Uses]
Cyclohexylamine is used in the manufactureof a number of products, including plasticizers, drycleaning soaps, insecticides, andemulsifying agents. It is also used as a cor rosion inhibitor and in organic synthesis. | [Uses]
In organic synthesis, manufacture of insecticides, plasticizers, corrosion inhibitors, rubber chemicals, dyestuffs, emulsifying agents, dry-cleaning soaps, acid gas absorbents. | [Definition]
ChEBI: Cyclohexylamine is a primary aliphatic amine consisting of cyclohexane carrying an amino substituent. It has a role as a human xenobiotic metabolite and a mouse metabolite. It is a conjugate base of a cyclohexylammonium. | [Production Methods]
Cyclohexylamine is produced by the reaction of ammonia and cyclohexanol at
elevated temperature and pressure in the presence of a silica-alumina catalyst
(SRI 1985). It is also prepared by a similar process of catalytic hydrogenation of
aniline at elevated temperature and pressure. Fractionation of the product of this
reaction yields CHA, aniline, and a high-boiling residue containing n-phenylcyclohexylamine
and dicyclohexylamine (Carswell and Morrill 1937). In 1982,
U.S. production was 4.54 metric tons and 739.3 metric tons were imported into the
U.S. (SRI 1985). | [Reactions]
Cyclohexylamine reacts with chlorine to form N,N-dichlorocyclohexylamine. N-Cyclohexylidenecyclohexylamine reacts with chloramine to give 1-cyclohexyl-3,3-pentamethylenediaziridine, which can be hydrolyzed to give cyclohexylhydrazine [46]. Cyclohexylamine and formaldehyde together react with peracetic acid to give 2-cyclohexyloxaziridine. In addition to using alkyl halides, alkyl sulfates, or alkyl phosphates, cyclohexylamine can be alkylated with an alcohol in the presence of a catalyst, such as aluminum oxide, copper, nickel, cobalt, or platinum, or by the Leuckart – Wallach method. | [Flammability and Explosibility]
Flammable | [Industrial uses]
The primary use of cyclohexylamine is as a corrosion inhibitor in boiler water
treatment and in oil field applications (HSDB 1989). It is also a chemical
intermediate for rubber processing chemicals, dyes (acid blue 62, former use),
cyclamate artificial sweeteners and herbicides and a processing agent for nylon
fiber production (SRI 1985). Windholz et al (1983) reports its use in the manufacture
of insecticides, plasticizers, emulsifying agents, dry-cleaning soaps, and acid
gas absorbents. | [Synthesis]
Prepared by catalytic hydrogenation of aniline at elevated temp and pressures. Fractionation of crude reaction product yields cyclohexylamine, unchanged aniline, and high-boiling residue containing n-phenylcyclohexylamine (cyclohexylaniline) and dicyclohexylamine. | [Carcinogenicity]
According to the International Agency for Research of
Cancer (IARC) working group, there is no evidence that
cyclohexylamine is teratogenic or carcinogenic.
Price et al. reported the development
of bladder tumors in Charles River rats fed cyclohexylamine
sulfate for 2 years at doses of 0, 0.15, 1.5, and
15 mg/kg/day, 25 male and 25 female per dosage group.
During the first year, there was only a slight depression of
weight gain in the males of the high-dose group; no other
signs of toxicity were observed. At the end of 2 years (104
weeks) 13–16 animals were still alive in the 0.15- and 1.5-
mg/kg groups, and eight males and nine females in the 15-
mg/kg group. An invasive transitional-cell carcinoma of
the bladder was observed in one of eight male survivors of
the high-dose group. The author noted that spontaneous
bladder tumors were very rare in the strain of rats used.
No other relevant findings were noted. Gaunt used the same
dosages for a 2 year diet feeding study in Wistar rats. They
observed no evidence of carcinogenicity, slight anemia,
failure to produce normally concentrated urine, and an
increase in the number of animals with foamy macrophages
in the pulmonary alveoli at the highest dosage level.
Decreased food intake caused the lessened body weight
gain and organ weights as compared to the controls. Animals
that received 2000 or 6000 ppm showed testicular atrophy or
tubules with few spermatids. The no-untoward-effect
level in both of these studies was 600 ppm, equivalent to an
intake of about 30 mg/kg/day. | [Metabolism]
Cyclamate is metabolized
to cyclohexylamine by the gut flora in the rat (Renwick and Williams 1969;
Bickel et al 1974; Tesoriero and Roxon 1975) and is excreted in the urine after
cyclamate ingestion by rats, rabbits, dogs, monkeys, and humans (Asahina et al
1971; Coulston et al 1977; Kojima and Ichibagase 1968; Leahy et al 1967; Oser et
al 1968). There is individual variation in the ability to biotransform cyclamate to
cyclohexylamine, probably due to the presence or absence of the necessary
bacteria. Bacteria exposed to cyclamate seem to acquire the ability to convert
cyclamate. Those individuals that do produce cyclohexylamine have been categorized
by researchers as convertors. Rhesus monkeys fed cyclamate for eight years
converted 0.5% of the dose to cyclohexylamine which in turn was metabolized to
cyclohexanone and cyclohexanol to the extent of 1-2% (Coulston et al 1977).
Generally, cyclohexylamine is readily absorbed and rapidly excreted from the
body. After administration to rats, cyclohexylamine appears in body tissues with
the highest concentrations in the lungs, spleen, liver, adrenals, heart, gastrointes-
tinal tract and kidneys (Estep and Wiegand 1967 as reported by Bopp et al
1986).
After oral administration (0.2 g/kg) to rabbits, cyclohexylamine gave rise to
unchanged cyclohexylamine and 7V-hydroxycyclohexylamine in the urine (Elliott
et al 1968). When [14C]-labelled cyclohexylamine was administered, 68% of the
radioactivity was recovered in the urine after 60 h. A small amount (0.5%) was
eliminated in the breath and 45% of the administered dose was shown to be
excreted in the urine as unconjugated cyclohexylamine, 0.2% as JV-hydroxycyclohexylamine
in conjugated form, and 2.5% as cyclohexanone oxime. The authors
postulated the latter metabolite to be an artifact formed from the glucuronide of
TV-hydroxy cyclohexylamine during the hydrolysis procedure.
In contrast to rabbits, man, as well as rats and guinea pigs, excrete 90% or more
of a dose of [14C]-labelled cyclohexylamine unchanged in the urine (Renwick and
Williams 1972). Small amounts of radioactivity were found in the feces, 1% or
less in man, rat and rabbit, and 4-7% in the guinea pig. Only 4-5% of the dose was
metabolized in 24 h in the rat and guinea pig and 1-2% in man. The metabolites
identified indicated that in rats, the metabolism of cyclohexylamine was mainly
through hydroxylation of the cyclohexane ring, in man by deamination and in
guinea pigs and rabbits by ring hydroxylation and deamination. The metabolites to
cyclohexylamine were excreted in both free and conjugated forms.
When cyclohexylamine was administered orally to healthy adult humans at
doses of 2.5, 5, and 10 mg/kg body weight, 86-95% of the dose was excreted in
the urine in 48 h as unchanged cyclohexylamine (Eichelbaum et al 1974). Dose
dependency was shown by the plasma half-lives which ranged from 3.5 to 4.8 h.
A study by Roberts and Renwick (1985) showed other species and strain
differences in metabolism of cyclohexylamine. After administration of [14C]-
cyclohexylamine (35-500 mg/kg) to male mice and rats, 80% of the dose was
excreted in the urine 24 h after dosing. In Wistar rats, 14-19% of the 14C was
present as 3- and 4-aminocyclohexanols, while in the DA strain rat, aminocyclohexanols
accounted for only 1-2% of the activity, and in mouse, <1%. Dose or
route of administration did not significantly affect metabolism.
When [14C]-cyclohexylamine hydrochloride was administered to pregnant rhesus
monkeys by infusion into the antecubital vein, maternal and fetal levels of
radioactivity were virtually identical over a period of 6 h (Pitkin et al 1969)
indicating that cyclohexylamine freely crosses the hemochorial placenta.
Rabbit liver microsomes have been shown to deaminate cyclohexylamine to
cyclohexanone in the presence of NADPH and molecular oxygen (Kurebayashi et
al 1979). The hexanone was then reduced to the alcohol (approximately 75% of
the deaminated product). Carbon monoxide, SKF 525A, metyrapone, potassium
cyanide and mercuric chloride inhibited the deamination. These results suggest
that the deamination is catalyzed by a microsomal cytochrome P-450 monooxygenase
system. | [storage]
Cyclohexylamine can be stored and shipped in iron tanks. Nonferrous metals, particularly copper-containing materials, are attacked and are therefore unsuitable. The amine discolors on contact with air and therefore must be kept under nitrogen. | [Purification Methods]
Dry the amine with CaCl2 or LiAlH4, then distil it from BaO, KOH or Na, under N2. Also purify it by conversion to the hydrochloride (which is crystallised several times from water), then liberation of the amine with alkali and fractional distillation under N2. The hydrochloride has m 205-207o (dioxane/EtOH). [Lycan et al. Org Synth Coll Vol II 319 1943, Beilstein 12 III 10, 12 IV 8.] |
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